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A Lifestyle Worth Coming Home To! Winchester on the Severn is one of Annapolis area's most desirable water-privileged communities, offering residents an exceptional opportunity to enjoy the Chesapeake Bay lifestyle. This home is located within walking distance to community amenities which include a private sandy beach on the Severn River, a pier, kayak and paddleboard storage, waterfront pavilion, playground, and dog-friendly beach. Whether spending summer afternoons by the water, enjoying a sunset along the river, heading out for a day of boating, or exploring the nearby B&A Trail, there is something for everyone. Combine these wonderful amenities with convenient access to historic downtown Annapolis, waterfront dining, shopping, major commuter routes, proximity to desirable public and private schools and it's easy to understand why Winchester on the Severn is such a special place. Offering five bedrooms, four bathrooms, and an additional adjoining lot, this exceptional property encompasses nearly ¾ of an acre in a private, elevated setting with beautiful views of the Severn River. Enjoy the scenic views from multiple rooms throughout the home or while relaxing and entertaining on the expansive rear deck. The inviting interior features an open-concept main-level floor plan, hardwood flooring, gas fireplace, an updated kitchen, along with two bedrooms, including a primary suite with a full bathroom and direct access to the rear deck. The lower level provides three additional bedrooms and two full bathrooms, including a second primary suite with a beautifully updated private bath. With its generous living space, versatile bedroom accommodations, additional lot, and picturesque water views, this property offers a wonderful opportunity to enjoy the Annapolis waterfront lifestyle.

1607 Riverside Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$825,000

Enjoy comfortable living in the desirable waterfront community of Southaven! Tucked away on a cul-de-sac, this is a well-maintained home with 3 bedrooms, 2 full baths and 2 half baths. The inviting main level features an open floor plan connecting the kitchen, dining area and living room, creating a natural flow for everyday living and entertaining. Hardwood floors bring warmth to the main living spaces, while newly installed carpeting adds a fresh touch to the bedrooms and lower level. The kitchen offers ample counter space, an island with seating, a separate breakfast nook and generous pantry. Just off the kitchen, the living room features a gas fireplace, providing a welcoming spot to gather. The upper level includes a primary bedroom suite with a soaking tub and separate shower, two additional bedrooms, hall bath and laundry. The lower level offers flexible space for a family room, recreation area or home office, with sliding doors leading to an outdoor terrace and accessible from garage. Two separate HVAC systems (new units installed 2022) distribute temperature comfort throughout! New water heater also in 2022. An attached two-car garage and driveway provide convenient parking. Enjoy the added appeal of Southaven's waterfront setting, with nearby river access/community waterfront area and playground just one property over. Ideally located for commuters with easy access to Routes 50 and 97, and just a short drive to Downtown Annapolis, Annapolis Town Center, shopping and restaurants. A wonderful opportunity to enjoy this sought after community living in a convenient Annapolis location!

Enjoy comfortable living in the desirable waterfront community of Southaven! Tucked away on a cul-de-sac, this is a well-maintained home with 3 bedrooms, 2 full baths and 2 half baths. The inviting main level features an open floor plan connecting the kitchen, dining area and living room, creating a natural flow for everyday living and entertaining. Hardwood floors bring warmth to the main living spaces, while newly installed carpeting adds a fresh touch to the bedrooms and lower level. The kitchen offers ample counter space, an island with seating, a separate breakfast nook and generous pantry. Just off the kitchen, the living room features a gas fireplace, providing a welcoming spot to gather. The upper level includes a primary bedroom suite with a soaking tub and separate shower, two additional bedrooms, hall bath and laundry. The lower level offers flexible space for a family room, recreation area or home office, with sliding doors leading to an outdoor terrace and accessible from garage. Two separate HVAC systems (new units installed 2022) distribute temperature comfort throughout! New water heater also in 2022. An attached two-car garage and driveway provide convenient parking. Enjoy the added appeal of Southaven's waterfront setting, with nearby river access/community waterfront area and playground just one property over. Ideally located for commuters with easy access to Routes 50 and 97, and just a short drive to Downtown Annapolis, Annapolis Town Center, shopping and restaurants. A wonderful opportunity to enjoy this sought after community living in a convenient Annapolis location!

2937 Broad Ct, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$2,695,000

Life along Broad Creek unfolds at a different pace, where peaceful waters, wooded surroundings, and the ever-changing beauty of the seasons create an extraordinary setting for a truly distinctive home. This remarkable Acorn Deck home has been comprehensively transformed with over $875,000 in improvements by renowned builder GYC Group. Thoughtfully enhanced and updated throughout for effortless modern living, the home beautifully preserves its architectural character while introducing sophisticated finishes and modern conveniences. Soaring wood ceilings, exposed beams, dramatic walls of glass, and sweeping water views create an unforgettable connection to the surrounding landscape. Adding to its appeal is the rare trifecta of public water, public sewer, and natural gas, providing an added measure of peace of mind and ease to everyday living. At the heart of the residence, a spectacular two-story glass solarium brings the outdoors in, offering a stunning setting to appreciate the changing seasons. Warm wood finishes and abundant natural light carry throughout the inviting living spaces, including a beautifully appointed family room with a striking fireplace and custom built-ins. The completely redesigned kitchen features quartz countertops, an expansive island, custom cabinetry, and a welcoming breakfast area, creating an effortless flow for everyday living and entertaining. An elegant dining room provides another inviting gathering space. The upper-level primary suite is a peaceful sanctuary featuring vaulted wood ceilings, expansive windows framing the water, a private balcony, and a beautifully renovated spa-inspired bath with a freestanding soaking tub and walk-in shower. Additional bedrooms offer comfortable accommodations for family and guests, while the lower-level recreation room with wet bar opens to a private patio. Outside, multiple decks and patios invite you to experience waterfront living from every perspective. Morning coffee overlooking the creek, afternoon gatherings surrounded by nature, and evenings watching the sunset become part of the everyday experience. A private tram provides convenient access to approximately 60 feet of shoreline and a 70-foot long deep-water pier with approximately 10 feet MLW, two boat slips, two boat lifts, two jet ski lifts and waterfront shed, an exceptional setting for boating enthusiasts. Extensive improvements to the home's interior, exterior, and landscaping complement its remarkable transformation. Offering four bedrooms, three full baths, a powder room, and 2 car garage, this extraordinary property captures the essence of waterfront living, where architectural beauty, thoughtful enhancements, and endless adventures on the water come together. Conveniently located in the coveted Broadview Estates community with easy access to Riva Road quickly leading to shopping, restaurants and commuter roads. Welcome Home!

Life along Broad Creek unfolds at a different pace, where peaceful waters, wooded surroundings, and the ever-changing beauty of the seasons create an extraordinary setting for a truly distinctive home. This remarkable Acorn Deck home has been comprehensively transformed with over $875,000 in improvements by renowned builder GYC Group. Thoughtfully enhanced and updated throughout for effortless modern living, the home beautifully preserves its architectural character while introducing sophisticated finishes and modern conveniences. Soaring wood ceilings, exposed beams, dramatic walls of glass, and sweeping water views create an unforgettable connection to the surrounding landscape. Adding to its appeal is the rare trifecta of public water, public sewer, and natural gas, providing an added measure of peace of mind and ease to everyday living. At the heart of the residence, a spectacular two-story glass solarium brings the outdoors in, offering a stunning setting to appreciate the changing seasons. Warm wood finishes and abundant natural light carry throughout the inviting living spaces, including a beautifully appointed family room with a striking fireplace and custom built-ins. The completely redesigned kitchen features quartz countertops, an expansive island, custom cabinetry, and a welcoming breakfast area, creating an effortless flow for everyday living and entertaining. An elegant dining room provides another inviting gathering space. The upper-level primary suite is a peaceful sanctuary featuring vaulted wood ceilings, expansive windows framing the water, a private balcony, and a beautifully renovated spa-inspired bath with a freestanding soaking tub and walk-in shower. Additional bedrooms offer comfortable accommodations for family and guests, while the lower-level recreation room with wet bar opens to a private patio. Outside, multiple decks and patios invite you to experience waterfront living from every perspective. Morning coffee overlooking the creek, afternoon gatherings surrounded by nature, and evenings watching the sunset become part of the everyday experience. A private tram provides convenient access to approximately 60 feet of shoreline and a 70-foot long deep-water pier with approximately 10 feet MLW, two boat slips, two boat lifts, two jet ski lifts and waterfront shed, an exceptional setting for boating enthusiasts. Extensive improvements to the home's interior, exterior, and landscaping complement its remarkable transformation. Offering four bedrooms, three full baths, a powder room, and 2 car garage, this extraordinary property captures the essence of waterfront living, where architectural beauty, thoughtful enhancements, and endless adventures on the water come together. Conveniently located in the coveted Broadview Estates community with easy access to Riva Road quickly leading to shopping, restaurants and commuter roads. Welcome Home!

379 Broadview Ln, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

$2,997,000

Rare Opportunity!!! A private retreat on nearly 5 acres of waterfront property minutes from downtown Annapolis! Singularly situated on the peninsula of Porter Point, the home enjoys panoramic views of the South River and Broad Creek from almost every room. This spacious sanctuary has four bedrooms, four full bathrooms, and multiple living spaces perfect for friends and family gatherings. A private office (possible fifth bedroom) is optimal for work-from-home while the covered flagstone patio and lounge with a wet bar are ideal for entertaining. Every bedroom accesses the wrap-around deck and the primary bedroom enjoys an almost 180 degree view of the water. The top floor is a loft with an unbeatable vista out to the Chesapeake Bay. This spacious interior is complemented by the expansive grounds which include a heated in-ground pool, putting green, and deep water pier with a private tidal beach. With an ideal location only ten minutes to downtown Annapolis, thirty minutes to BWI, and forty minutes to Baltimore or Washington, D.C. - this is seclusion without exclusion! Solar recently installed (late 2024), geothermal HVAC ( 2020), well-water, and generator.

Rare Opportunity!!! A private retreat on nearly 5 acres of waterfront property minutes from downtown Annapolis! Singularly situated on the peninsula of Porter Point, the home enjoys panoramic views of the South River and Broad Creek from almost every room. This spacious sanctuary has four bedrooms, four full bathrooms, and multiple living spaces perfect for friends and family gatherings. A private office (possible fifth bedroom) is optimal for work-from-home while the covered flagstone patio and lounge with a wet bar are ideal for entertaining. Every bedroom accesses the wrap-around deck and the primary bedroom enjoys an almost 180 degree view of the water. The top floor is a loft with an unbeatable vista out to the Chesapeake Bay. This spacious interior is complemented by the expansive grounds which include a heated in-ground pool, putting green, and deep water pier with a private tidal beach. With an ideal location only ten minutes to downtown Annapolis, thirty minutes to BWI, and forty minutes to Baltimore or Washington, D.C. - this is seclusion without exclusion! Solar recently installed (late 2024), geothermal HVAC ( 2020), well-water, and generator.

2929 Southaven Dr, Annapolis

Listing courtesy of Smart Realty, LLC. Contact:

$675,000

Nestled in the charming Cape St. Claire community, this delightful Colonial home offers a perfect blend of comfort and modern living. With 4 spacious bedrooms and 3.5 bathrooms, provides ample space for relaxation and entertaining. Step inside to discover a warm and inviting interior featuring beautiful hardwood flooring on main level. The heart of the home is the well-appointed kitchen, complete with stainless steel appliances, an eat-in area, and plenty of table space for casual dining. The formal dining room with wood burning fireplace, sets the stage for more elegant gatherings or space could easily be converted to another gathering space. Enjoy the luxury of a private bath ensuite in primary bedroom and take advantage of the walk-in closet for all your storage needs. Natural light floods the home through two bay and double-hung windows, enhancing the inviting atmosphere. Recessed lighting and wainscotting add a touch of sophistication. Lower level with family room and full bath offers an egress window access, The exterior of the home is equally appealing, featuring low-maintenance vinyl siding and thoughtful bump-outs that add character. The corner lot, spanning 0.26 acres, offers a level yard perfect for outdoor activities and gardening. An expansive deck off the kitchen with custom roll out awning is perfect for grilling, dining or simply relaxing. Enjoy serene views of the fenced rear yard and take advantage of the community's water access to the beautiful Magothy River, ideal for kayaking, swimming and fishing enthusiasts. Cape St. Claire is not just a neighborhood; it's a vibrant community with a wealth of amenities. Residents can enjoy access to a ball fields, basketball courts, and picnic areas. Kayak, paddle board or take a quick swim in the water accessed areas. The local beach and playgrounds provide endless opportunities for outdoor fun. Community pool available with membership at additional cost, With well-maintained common areas and a strong sense of community, this area is perfect for those seeking an active lifestyle. Public services are readily available, making daily life convenient and enjoyable. Local shopping nearby include grocery, coffee shop, hardware, restaurants as well as other shops & businesses, This home is more than just a property; it's a place where memories are made. Experience the warmth and charm of Cape St. Claire living, where comfort meets convenience.

Nestled in the charming Cape St. Claire community, this delightful Colonial home offers a perfect blend of comfort and modern living. With 4 spacious bedrooms and 3.5 bathrooms, provides ample space for relaxation and entertaining. Step inside to discover a warm and inviting interior featuring beautiful hardwood flooring on main level. The heart of the home is the well-appointed kitchen, complete with stainless steel appliances, an eat-in area, and plenty of table space for casual dining. The formal dining room with wood burning fireplace, sets the stage for more elegant gatherings or space could easily be converted to another gathering space. Enjoy the luxury of a private bath ensuite in primary bedroom and take advantage of the walk-in closet for all your storage needs. Natural light floods the home through two bay and double-hung windows, enhancing the inviting atmosphere. Recessed lighting and wainscotting add a touch of sophistication. Lower level with family room and full bath offers an egress window access, The exterior of the home is equally appealing, featuring low-maintenance vinyl siding and thoughtful bump-outs that add character. The corner lot, spanning 0.26 acres, offers a level yard perfect for outdoor activities and gardening. An expansive deck off the kitchen with custom roll out awning is perfect for grilling, dining or simply relaxing. Enjoy serene views of the fenced rear yard and take advantage of the community's water access to the beautiful Magothy River, ideal for kayaking, swimming and fishing enthusiasts. Cape St. Claire is not just a neighborhood; it's a vibrant community with a wealth of amenities. Residents can enjoy access to a ball fields, basketball courts, and picnic areas. Kayak, paddle board or take a quick swim in the water accessed areas. The local beach and playgrounds provide endless opportunities for outdoor fun. Community pool available with membership at additional cost, With well-maintained common areas and a strong sense of community, this area is perfect for those seeking an active lifestyle. Public services are readily available, making daily life convenient and enjoyable. Local shopping nearby include grocery, coffee shop, hardware, restaurants as well as other shops & businesses, This home is more than just a property; it's a place where memories are made. Experience the warmth and charm of Cape St. Claire living, where comfort meets convenience.

982 Mount Holly Dr, Annapolis

Listing courtesy of Synergy Realty. Contact:

$799,900

Nestled in the charming community of Cape St. Claire, this stunning transitional-style home offers a perfect blend of comfort and modern living. Built in 2008, this detached residence boasts 3,252 square feet of thoughtfully designed space, featuring four spacious bedrooms and two and a half bathrooms. The kitchen is a delightful space with a breakfast area, perfect for casual meals, while the combination dining/living area is perfect for entertaining. Enjoy the luxury of a soaking tub and a walk-in shower in the master bath, along with ample storage provided by walk-in closets throughout the home. Beautiful wood floors add warmth and elegance, enhancing the overall ambiance. The fully finished basement offers additional living space, perfect for a home theater, playroom, or office, catering to your lifestyle needs. An upper-floor laundry room adds convenience to your daily routine, making chores a breeze. Outside, the property features a lovely deck and extensive patio, ideal for barbecues or quiet evenings under the stars. The exterior is adorned with tasteful lighting, enhancing the home's curb appeal. With an oversized side-entry garage and a driveway that accommodates 2+ vehicles, parking is never a concern. Cape St. Claire is not just a neighborhood; it's a community that embraces a vibrant lifestyle. Residents enjoy access to a private beach, where swimming, canoeing, and kayaking are just steps away. The nearby bay offers opportunities for boating, making it a haven for water enthusiasts. The neighborhood fosters a sense of belonging, with friendly neighbors and a welcoming atmosphere. Public services are readily available, ensuring convenience and peace of mind for all residents. This home is not just a place to live; it's a sanctuary where memories are made, and a community where you can truly thrive. Experience the best of Cape St. Claire living in this beautiful residence, where comfort meets convenience in a picturesque setting.

Nestled in the charming community of Cape St. Claire, this stunning transitional-style home offers a perfect blend of comfort and modern living. Built in 2008, this detached residence boasts 3,252 square feet of thoughtfully designed space, featuring four spacious bedrooms and two and a half bathrooms. The kitchen is a delightful space with a breakfast area, perfect for casual meals, while the combination dining/living area is perfect for entertaining. Enjoy the luxury of a soaking tub and a walk-in shower in the master bath, along with ample storage provided by walk-in closets throughout the home. Beautiful wood floors add warmth and elegance, enhancing the overall ambiance. The fully finished basement offers additional living space, perfect for a home theater, playroom, or office, catering to your lifestyle needs. An upper-floor laundry room adds convenience to your daily routine, making chores a breeze. Outside, the property features a lovely deck and extensive patio, ideal for barbecues or quiet evenings under the stars. The exterior is adorned with tasteful lighting, enhancing the home's curb appeal. With an oversized side-entry garage and a driveway that accommodates 2+ vehicles, parking is never a concern. Cape St. Claire is not just a neighborhood; it's a community that embraces a vibrant lifestyle. Residents enjoy access to a private beach, where swimming, canoeing, and kayaking are just steps away. The nearby bay offers opportunities for boating, making it a haven for water enthusiasts. The neighborhood fosters a sense of belonging, with friendly neighbors and a welcoming atmosphere. Public services are readily available, ensuring convenience and peace of mind for all residents. This home is not just a place to live; it's a sanctuary where memories are made, and a community where you can truly thrive. Experience the best of Cape St. Claire living in this beautiful residence, where comfort meets convenience in a picturesque setting.

1184 Green Holly Dr, Annapolis

Listing courtesy of Samson Properties. Contact:

$1,225,000

Some homes offer a change of scenery. Others offer an entirely different perspective. Tucked away on 2.75 wooded acres bordering the Sherwood Forest Nature Preserve, 929 Sherwood Forest Road is a refreshing departure from the expected. Mature trees, natural beauty, and an exceptional sense of privacy create a setting that feels worlds away, yet remains just minutes from the heart of Annapolis. It's a rare balance of seclusion, convenience, and character. Inside, the home is every bit as compelling as its surroundings. Soaring vaulted ceilings, expansive windows, and a thoughtfully connected floor plan create an immediate sense of openness, with natural light and wooded views taking center stage. At the heart of the home, a beautifully designed kitchen makes a statement with a quartz waterfall island, a quartz backsplash, and a custom, handcrafted Italian induction range and oven. Envisioned for everyday living and effortless entertaining, the kitchen flows seamlessly into the main gathering spaces, including an inviting family room anchored by a wood-burning fireplace. Multiple decks extend the living experience outdoors. The upper level continues the home's inviting atmosphere, with the primary suite and additional bedrooms offering comfortable accommodations and flexibility for family or other evolving needs. The primary suite brings an entirely different level of comfort to everyday living. A beautifully renovated en-suite bath with dual vanities and an oversized shower creates a spa-like experience, while a spacious walk-in closet adds thoughtful functionality. The true standout is a private balcony overlooking the wooded landscape, where the natural surroundings become an extension of your own personal retreat. With more than 4,600 square feet of finished living space, there's room to entertain, create, unwind, and everything in between. The finished walkout lower level offers additional space for recreation and guests, while a detached custom studio presents an inspiring opportunity for a private office, creative retreat, or something entirely your own. An attached two-car garage adds everyday convenience without compromising the home's distinctive character. Beyond its architectural appeal, the property has benefited from substantial improvements, including a new roof (2020), a new front porch (2022), a new HVAC system (2025), and all-new electrical throughout. The septic system was also professionally pumped in 2025, further reflecting the care and attention invested in the home. 929 Sherwood Forest Road is more than a beautiful place to call home. It's an opportunity to experience Annapolis living from an entirely different perspective.

Some homes offer a change of scenery. Others offer an entirely different perspective. Tucked away on 2.75 wooded acres bordering the Sherwood Forest Nature Preserve, 929 Sherwood Forest Road is a refreshing departure from the expected. Mature trees, natural beauty, and an exceptional sense of privacy create a setting that feels worlds away, yet remains just minutes from the heart of Annapolis. It's a rare balance of seclusion, convenience, and character. Inside, the home is every bit as compelling as its surroundings. Soaring vaulted ceilings, expansive windows, and a thoughtfully connected floor plan create an immediate sense of openness, with natural light and wooded views taking center stage. At the heart of the home, a beautifully designed kitchen makes a statement with a quartz waterfall island, a quartz backsplash, and a custom, handcrafted Italian induction range and oven. Envisioned for everyday living and effortless entertaining, the kitchen flows seamlessly into the main gathering spaces, including an inviting family room anchored by a wood-burning fireplace. Multiple decks extend the living experience outdoors. The upper level continues the home's inviting atmosphere, with the primary suite and additional bedrooms offering comfortable accommodations and flexibility for family or other evolving needs. The primary suite brings an entirely different level of comfort to everyday living. A beautifully renovated en-suite bath with dual vanities and an oversized shower creates a spa-like experience, while a spacious walk-in closet adds thoughtful functionality. The true standout is a private balcony overlooking the wooded landscape, where the natural surroundings become an extension of your own personal retreat. With more than 4,600 square feet of finished living space, there's room to entertain, create, unwind, and everything in between. The finished walkout lower level offers additional space for recreation and guests, while a detached custom studio presents an inspiring opportunity for a private office, creative retreat, or something entirely your own. An attached two-car garage adds everyday convenience without compromising the home's distinctive character. Beyond its architectural appeal, the property has benefited from substantial improvements, including a new roof (2020), a new front porch (2022), a new HVAC system (2025), and all-new electrical throughout. The septic system was also professionally pumped in 2025, further reflecting the care and attention invested in the home. 929 Sherwood Forest Road is more than a beautiful place to call home. It's an opportunity to experience Annapolis living from an entirely different perspective.

929 Sherwood Forest Rd, Annapolis

Listing courtesy of Keller Williams Realty Centre. Contact:

$925,000

Located in the sought-after Saefern community, this distinctive home offers a rare combination of privacy, natural beauty, and access to an array of community amenities. Tucked away in a peaceful, wooded setting, the home is approached by a long, sloping driveway and surrounded by mature trees, creating a private retreat with a treehouse-like feel. Inside, the home's post-and-beam construction, soaring vaulted ceilings, exposed beams, and dramatic two-story brick fireplace create a warm and inviting atmosphere. Natural light fills the open living spaces, while multiple glass sliders connect the interior to the expansive ipe deck, providing an ideal setting for entertaining or simply enjoying the surrounding landscape. The kitchen features granite countertops, stainless steel appliances, 42-inch upper cabinets, double wall ovens, a separate cooktop, and a center island. The main level offers the convenience of a primary bedroom and bath, along with an open living and dining area anchored by an oversized wood-burning fireplace. Upstairs, a catwalk and loft overlook the main living space, adding architectural interest and offering beautiful views of the home's interior and wooded surroundings. The walk-out lower level expands the home's living space with 10-foot ceilings, an additional bedroom and full bathroom, a spacious 24 x 20 family room with a woodstove, and ample storage. A covered area beneath the deck provides additional sheltered outdoor space. Other features include an attached two-car garage and an irrigation system. Recent improvements include a new roof installed at the end of 2024, a new septic tank in 2025, and a new HVAC system installed in 2025, converting the home from oil heat to an electric heat pump system. Saefern offers an impressive selection of community amenities, including a marina, outdoor swimming pool, horse stables, scenic trails, dog park, fishing pond, and tennis and pickleball courts. Membership is optional, though highly recommended within the community, and provides access to these amenities. Boat slips at the marina are subject to availability, with options for vessels of varying sizes and water depths. Enjoy the feeling of a private retreat while remaining conveniently located near Annapolis Mall, downtown Annapolis, Anne Arundel Medical Center, and major commuter routes including Routes 50 and 97. With its distinctive architectural character, peaceful natural setting, recent system updates, and access to the Severn River and community amenities, this home offers a unique opportunity to enjoy Saefern living.

Located in the sought-after Saefern community, this distinctive home offers a rare combination of privacy, natural beauty, and access to an array of community amenities. Tucked away in a peaceful, wooded setting, the home is approached by a long, sloping driveway and surrounded by mature trees, creating a private retreat with a treehouse-like feel. Inside, the home's post-and-beam construction, soaring vaulted ceilings, exposed beams, and dramatic two-story brick fireplace create a warm and inviting atmosphere. Natural light fills the open living spaces, while multiple glass sliders connect the interior to the expansive ipe deck, providing an ideal setting for entertaining or simply enjoying the surrounding landscape. The kitchen features granite countertops, stainless steel appliances, 42-inch upper cabinets, double wall ovens, a separate cooktop, and a center island. The main level offers the convenience of a primary bedroom and bath, along with an open living and dining area anchored by an oversized wood-burning fireplace. Upstairs, a catwalk and loft overlook the main living space, adding architectural interest and offering beautiful views of the home's interior and wooded surroundings. The walk-out lower level expands the home's living space with 10-foot ceilings, an additional bedroom and full bathroom, a spacious 24 x 20 family room with a woodstove, and ample storage. A covered area beneath the deck provides additional sheltered outdoor space. Other features include an attached two-car garage and an irrigation system. Recent improvements include a new roof installed at the end of 2024, a new septic tank in 2025, and a new HVAC system installed in 2025, converting the home from oil heat to an electric heat pump system. Saefern offers an impressive selection of community amenities, including a marina, outdoor swimming pool, horse stables, scenic trails, dog park, fishing pond, and tennis and pickleball courts. Membership is optional, though highly recommended within the community, and provides access to these amenities. Boat slips at the marina are subject to availability, with options for vessels of varying sizes and water depths. Enjoy the feeling of a private retreat while remaining conveniently located near Annapolis Mall, downtown Annapolis, Anne Arundel Medical Center, and major commuter routes including Routes 50 and 97. With its distinctive architectural character, peaceful natural setting, recent system updates, and access to the Severn River and community amenities, this home offers a unique opportunity to enjoy Saefern living.

523a Epping Forest Rd, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$1,298,000

OPEN HOUSE - Sun 11/15, 12-2pm. Skip the renovations and settle right into this Eastport gem. From top to bottom, flawlessly turnkey in every detail, this home invites you to immediately embrace the coveted downtown lifestyle. Custom-built in 2021, this 3200 sq ft home perfectly blends modern luxuries with classic Eastport charm. Fine finishes, 9-foot ceilings, stunning millwork, and gorgeous white oak floors set the tone. The heart is the chef’s kitchen with a show-stopping center island and granite counters. The kitchen is open to the light-filled family room, flanked by a cozy gas fireplace and custom built-ins. A versatile 4th bedroom or office, full bath, and chic beverage center complete the main level. Upstairs features a convenient laundry room, three spacious bedrooms—including a vaulted primary suite—and two beautifully appointed bathrooms with modern tile and granite vanities. The fully finished lower level adds a large recreation area, another full bath and ample storage. For outdoor living, the amazing 300-square-foot screened porch will quickly become a favorite spot. Step off the porch and enjoy the crafted stone patio, firepit and a fully fenced, grassy backyard. Perfectly positioned, you are just moments from Eastport's celebrated restaurants, marinas, and waterfront parks, with an easy stroll across the Spa Creek Bridge to Historic Downtown Annapolis. This exceptional turn-key offering delivers the best of Eastport living in a flawless package. Check out the Interactive Floor Plan!

OPEN HOUSE - Sun 11/15, 12-2pm. Skip the renovations and settle right into this Eastport gem. From top to bottom, flawlessly turnkey in every detail, this home invites you to immediately embrace the coveted downtown lifestyle. Custom-built in 2021, this 3200 sq ft home perfectly blends modern luxuries with classic Eastport charm. Fine finishes, 9-foot ceilings, stunning millwork, and gorgeous white oak floors set the tone. The heart is the chef’s kitchen with a show-stopping center island and granite counters. The kitchen is open to the light-filled family room, flanked by a cozy gas fireplace and custom built-ins. A versatile 4th bedroom or office, full bath, and chic beverage center complete the main level. Upstairs features a convenient laundry room, three spacious bedrooms—including a vaulted primary suite—and two beautifully appointed bathrooms with modern tile and granite vanities. The fully finished lower level adds a large recreation area, another full bath and ample storage. For outdoor living, the amazing 300-square-foot screened porch will quickly become a favorite spot. Step off the porch and enjoy the crafted stone patio, firepit and a fully fenced, grassy backyard. Perfectly positioned, you are just moments from Eastport's celebrated restaurants, marinas, and waterfront parks, with an easy stroll across the Spa Creek Bridge to Historic Downtown Annapolis. This exceptional turn-key offering delivers the best of Eastport living in a flawless package. Check out the Interactive Floor Plan!

1010 Park Ave, Annapolis

Listing courtesy of Compass. Contact:

$749,999

Welcome home to this charming Waterview colonial in sought after Cape St Clarie community. Enjoy your morning coffee or an evening beverage on your expansive deck while taking in the views of the Little Magothy River. This home has so many wonderful features. The main level as you enter the home has a separate living area with a dining area right off that. The large gourmet kitchen will be the heart of the home with the sprawling open floor plan. Off the family room you step out to the spacious deck and enjoy the river views year-round. The upper level boasts 3 ample sized bedrooms, with the primary enjoying its own primary bath. If that wasn't enough, the lower level has another whole separate living area, with a kitchen, full bath, laundry, 2 bedrooms, a living room and its own separate entrance from the main level of the house. The exterior has a great, fenced yard for the family and the pets to enjoy, there is even an above ground pool for summertime enjoyment. The community has a beach, clubhouse and boat slips available for an additional fee. Don't miss out for a chance to own in this community!

Welcome home to this charming Waterview colonial in sought after Cape St Clarie community. Enjoy your morning coffee or an evening beverage on your expansive deck while taking in the views of the Little Magothy River. This home has so many wonderful features. The main level as you enter the home has a separate living area with a dining area right off that. The large gourmet kitchen will be the heart of the home with the sprawling open floor plan. Off the family room you step out to the spacious deck and enjoy the river views year-round. The upper level boasts 3 ample sized bedrooms, with the primary enjoying its own primary bath. If that wasn't enough, the lower level has another whole separate living area, with a kitchen, full bath, laundry, 2 bedrooms, a living room and its own separate entrance from the main level of the house. The exterior has a great, fenced yard for the family and the pets to enjoy, there is even an above ground pool for summertime enjoyment. The community has a beach, clubhouse and boat slips available for an additional fee. Don't miss out for a chance to own in this community!

962 Woodland Cir, Annapolis

Listing courtesy of Rosendale Realty. Contact:

$1,749,000

Stress melts away the moment you pull into the driveway. Set on 1.06 peaceful acres in sought-after Admiral Heights, this mid-century modern home offers expansive views of Weems Creek in both directions, with a resident bald eagle that has called the neighborhood home for more than a decade. The house was fully renovated to the studs in 2022, with new windows, doors, chef's kitchen, design-grade bathrooms, insulation and flooring throughout. Inside are 4 bedrooms and 3.5 baths across 2,382 square feet, with numerous windows designed to take in the water views and the quiet setting. Recent updates continue outside: the exterior was painted in 2025, and the front yard was fully redone and the upper roof replaced in 2026. The work is done, so you can move in and enjoy it. The property includes an approximately 0.2-acre subdivided buildable lot, which offers room for a second home, a guest house for extended household or relatives, or a future investment. This waterfront location is ready to finish, so bring your dock designer/builder and complete the picture. Admiral Heights is a popular water-privileged community with a voluntary improvement association, a neighborhood pool with membership options, several community-owned docks, and a local boat club. You’re minutes from downtown Annapolis and the Navy-Marine Corps Memorial Stadium, with easy access to Route 50 for commuting to DC, Baltimore and beyond. A rare chance to own a renovated, private retreat on Weems Creek, with space to grow.

Stress melts away the moment you pull into the driveway. Set on 1.06 peaceful acres in sought-after Admiral Heights, this mid-century modern home offers expansive views of Weems Creek in both directions, with a resident bald eagle that has called the neighborhood home for more than a decade. The house was fully renovated to the studs in 2022, with new windows, doors, chef's kitchen, design-grade bathrooms, insulation and flooring throughout. Inside are 4 bedrooms and 3.5 baths across 2,382 square feet, with numerous windows designed to take in the water views and the quiet setting. Recent updates continue outside: the exterior was painted in 2025, and the front yard was fully redone and the upper roof replaced in 2026. The work is done, so you can move in and enjoy it. The property includes an approximately 0.2-acre subdivided buildable lot, which offers room for a second home, a guest house for extended household or relatives, or a future investment. This waterfront location is ready to finish, so bring your dock designer/builder and complete the picture. Admiral Heights is a popular water-privileged community with a voluntary improvement association, a neighborhood pool with membership options, several community-owned docks, and a local boat club. You’re minutes from downtown Annapolis and the Navy-Marine Corps Memorial Stadium, with easy access to Route 50 for commuting to DC, Baltimore and beyond. A rare chance to own a renovated, private retreat on Weems Creek, with space to grow.

173 Williams Dr, Annapolis

Listing courtesy of Homecoin.com. Contact:

$1,795,000

Priced to Sell! This delightful and updated Eastport beauty embodies the true charm of Eastport! The classic style and curb appeal abound, and the updates are already done for you! Centrally located for easy access to shopping and restaurants in Eastport, as well as a quick trip to downtown Annapolis. Offering 4bedrooms (one on main level), 3.5 baths, a dedicated mudroom with a wet sink, a finished basement with storage, bar, and half bath. Hardwood flooring throughout. The original garage and car port are located on the rear alley. Sellers are offering completed architectural plans for an ADU - ready for submission. The front of the home (new sod) is the original bungalow with all of its charm, and a formal living room with an updated wood burning fireplace (2019). The fourth bedroom and full bath are on the main level. The upper level has a generously sized primary bedroom with a vaulted ceiling, multiple closets, and space for a desk, workout studio or expanded closets. The additional two bedrooms and bath on the upper level are generously sized and have hardwood flooring. Laundry is on the bedroom level. The main-level, hand-scraped white oak floors were re-sanded and given a matte finish in Oct 2026. Central to the rear addition in the gorgeous kitchen and great room with space for dining, two sitting rooms and a gas fireplace. The sizeable, fenced, backyard includes a large patio for entertaining, a detached finished game room/office that could be converted back to 2-car garage, and a car port and driveway with parking for 2-3 cars. Please note that the rear yard has an astro-turf product on it that was professionally installed for wear and proper drainage.

Priced to Sell! This delightful and updated Eastport beauty embodies the true charm of Eastport! The classic style and curb appeal abound, and the updates are already done for you! Centrally located for easy access to shopping and restaurants in Eastport, as well as a quick trip to downtown Annapolis. Offering 4bedrooms (one on main level), 3.5 baths, a dedicated mudroom with a wet sink, a finished basement with storage, bar, and half bath. Hardwood flooring throughout. The original garage and car port are located on the rear alley. Sellers are offering completed architectural plans for an ADU - ready for submission. The front of the home (new sod) is the original bungalow with all of its charm, and a formal living room with an updated wood burning fireplace (2019). The fourth bedroom and full bath are on the main level. The upper level has a generously sized primary bedroom with a vaulted ceiling, multiple closets, and space for a desk, workout studio or expanded closets. The additional two bedrooms and bath on the upper level are generously sized and have hardwood flooring. Laundry is on the bedroom level. The main-level, hand-scraped white oak floors were re-sanded and given a matte finish in Oct 2026. Central to the rear addition in the gorgeous kitchen and great room with space for dining, two sitting rooms and a gas fireplace. The sizeable, fenced, backyard includes a large patio for entertaining, a detached finished game room/office that could be converted back to 2-car garage, and a car port and driveway with parking for 2-3 cars. Please note that the rear yard has an astro-turf product on it that was professionally installed for wear and proper drainage.

830 Chester Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,475,000

Luxury New Construction | A Lifestyle of Walkability, Elegance & Annapolis Charm. Don’t miss this exceptional opportunity to own a stunning new-construction home in the highly desirable Homewood neighborhood of Annapolis! With permits in hand and construction about to begin, there is still time to personalize select finishes and make this beautiful home your own. Offering three finished levels of thoughtfully designed living space, this residence delivers more than luxury living, it offers a lifestyle centered around comfort, connection, and the best of Annapolis right outside your door. Inside, 9-foot ceilings on every level and a bright, open-concept floor plan create an inviting sense of space. The gourmet kitchen is designed to impress, featuring 42-inch custom cabinetry, quartz countertops with a coordinating backsplash, stainless steel appliances, and an oversized island that seamlessly connects the dining area and spacious family room. A cozy gas fireplace creates a warm and welcoming gathering space, while sliding glass doors open to a private deck, perfect for morning coffee, evening cocktails, or entertaining friends. A stylish powder room and convenient mudroom with laundry space complete the main level. Upstairs, the expansive primary suite offers a peaceful retreat, complete with a generous walk-in closet and spa-inspired bath featuring a double vanity, soaking tub, and glass-enclosed shower. Two additional bedrooms and a well-appointed full bath provide comfortable accommodations for family and guests. The finished lower level expands the possibilities with a spacious recreation room, fourth bedroom, and full bath, ideal for hosting overnight guests, accommodating extended family, or creating a flexible space for work and leisure. Set along a charming, tree-lined street, this home captures the character of Homewood while offering the style, comfort, and convenience of modern construction. Here, the lifestyle is just as special as the home itself. Enjoy a leisurely walk to downtown Annapolis for waterfront dining, boutique shopping, coffee with friends, and evenings spent exploring the city’s vibrant historic district. With inviting green spaces, a welcoming neighborhood atmosphere, and convenient access to major commuter routes, you can enjoy the perfect balance of urban convenience and residential charm. With its exceptional design, flexible living spaces, and coveted walkable location, this is more than a place to call home, it’s an opportunity to embrace the Annapolis lifestyle. And with construction just getting underway, you may still have the opportunity to add your own personal touch.

Luxury New Construction | A Lifestyle of Walkability, Elegance & Annapolis Charm. Don’t miss this exceptional opportunity to own a stunning new-construction home in the highly desirable Homewood neighborhood of Annapolis! With permits in hand and construction about to begin, there is still time to personalize select finishes and make this beautiful home your own. Offering three finished levels of thoughtfully designed living space, this residence delivers more than luxury living, it offers a lifestyle centered around comfort, connection, and the best of Annapolis right outside your door. Inside, 9-foot ceilings on every level and a bright, open-concept floor plan create an inviting sense of space. The gourmet kitchen is designed to impress, featuring 42-inch custom cabinetry, quartz countertops with a coordinating backsplash, stainless steel appliances, and an oversized island that seamlessly connects the dining area and spacious family room. A cozy gas fireplace creates a warm and welcoming gathering space, while sliding glass doors open to a private deck, perfect for morning coffee, evening cocktails, or entertaining friends. A stylish powder room and convenient mudroom with laundry space complete the main level. Upstairs, the expansive primary suite offers a peaceful retreat, complete with a generous walk-in closet and spa-inspired bath featuring a double vanity, soaking tub, and glass-enclosed shower. Two additional bedrooms and a well-appointed full bath provide comfortable accommodations for family and guests. The finished lower level expands the possibilities with a spacious recreation room, fourth bedroom, and full bath, ideal for hosting overnight guests, accommodating extended family, or creating a flexible space for work and leisure. Set along a charming, tree-lined street, this home captures the character of Homewood while offering the style, comfort, and convenience of modern construction. Here, the lifestyle is just as special as the home itself. Enjoy a leisurely walk to downtown Annapolis for waterfront dining, boutique shopping, coffee with friends, and evenings spent exploring the city’s vibrant historic district. With inviting green spaces, a welcoming neighborhood atmosphere, and convenient access to major commuter routes, you can enjoy the perfect balance of urban convenience and residential charm. With its exceptional design, flexible living spaces, and coveted walkable location, this is more than a place to call home, it’s an opportunity to embrace the Annapolis lifestyle. And with construction just getting underway, you may still have the opportunity to add your own personal touch.

1207 Mcguckian St, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$625,000

Beautifully Updated 5-Bedroom Home in The Landings of Annapolis! Welcome to 7 Landings Court, where spacious living, modern updates, and fantastic community amenities come together! This beautifully updated home offers 5 bedrooms, 3.5 bathrooms, and approximately 2,500 square feet of finished living space across three levels. Step inside to discover a thoughtfully designed floor plan featuring a convenient main-level bedroom, perfect for guests, a home office, or flexible living arrangements. The brand-new kitchen showcases all-new cabinetry and appliances, creating a fresh, inviting space for everyday living and entertaining. Upstairs, you’ll find three generously sized bedrooms and two full bathrooms, including a private primary suite. The finished lower level provides even more versatile living space, complete with a fifth bedroom, full bathroom, and plenty of room for recreation, entertaining, or relaxation. Enjoy outdoor living at its finest with a charming covered front porch, an expansive approximately 40-foot-wide rear deck, and a spacious, fully fenced backyard offering endless possibilities for entertaining, gardening, or simply unwinding. A two-car driveway provides convenient off-street parking. Located in the desirable Landings community, residents enjoy access to wonderful amenities, including a swimming pool, tennis courts, and pickleball courts, with an HOA fee of $140/Month. With five bedrooms, extensive updates, flexible living spaces, and outstanding community amenities, this Annapolis home offers an exceptional opportunity. Make sure to book your showing before its gone!

Beautifully Updated 5-Bedroom Home in The Landings of Annapolis! Welcome to 7 Landings Court, where spacious living, modern updates, and fantastic community amenities come together! This beautifully updated home offers 5 bedrooms, 3.5 bathrooms, and approximately 2,500 square feet of finished living space across three levels. Step inside to discover a thoughtfully designed floor plan featuring a convenient main-level bedroom, perfect for guests, a home office, or flexible living arrangements. The brand-new kitchen showcases all-new cabinetry and appliances, creating a fresh, inviting space for everyday living and entertaining. Upstairs, you’ll find three generously sized bedrooms and two full bathrooms, including a private primary suite. The finished lower level provides even more versatile living space, complete with a fifth bedroom, full bathroom, and plenty of room for recreation, entertaining, or relaxation. Enjoy outdoor living at its finest with a charming covered front porch, an expansive approximately 40-foot-wide rear deck, and a spacious, fully fenced backyard offering endless possibilities for entertaining, gardening, or simply unwinding. A two-car driveway provides convenient off-street parking. Located in the desirable Landings community, residents enjoy access to wonderful amenities, including a swimming pool, tennis courts, and pickleball courts, with an HOA fee of $140/Month. With five bedrooms, extensive updates, flexible living spaces, and outstanding community amenities, this Annapolis home offers an exceptional opportunity. Make sure to book your showing before its gone!

7 Landings Ct, Annapolis

Listing courtesy of Alberti Realty, LLC. Contact:

$1,395,000

Discover an exceptional blend of sophisticated design, resort-inspired living, and everyday convenience in this beautifully appointed Annapolis residence. Tucked along a quiet street yet remarkably close to everything that makes Annapolis so desirable, this distinctive home offers the perfect balance of privacy and accessibility. From the vibrant restaurants, boutiques, and waterfront attractions of Historic Downtown Annapolis to the charm of nearby neighborhoods and marinas, the very best of the Annapolis lifestyle is just moments away. Designed with both elegant entertaining and comfortable everyday living in mind, the home welcomes you with striking architectural details, beautifully curated finishes, and thoughtfully designed spaces throughout. The main level features gracious formal living and dining areas, complemented by a butler's pantry that makes hosting effortless. At the heart of the home, a beautifully appointed kitchen opens seamlessly to the casual dining area and inviting family room, where accordion glass doors overlook the backyard retreat with serene pool as the focal point The outdoor living experience is truly exceptional. A stunning private pool serves as the centerpiece of a beautifully designed backyard, framed by lush landscaping and mature greenery that create a wonderful sense of seclusion. An expansive covered patio with comfortable lounging and dining areas, ceiling fans, and a fully equipped outdoor kitchen provides the perfect setting for everything from leisurely summer afternoons to memorable evenings entertaining family and friends. The seamless connection between the interior living spaces and poolside retreat creates an atmosphere reminiscent of a private luxury resort. Upstairs, an open loft with a bar area provides an additional gathering space, ideal for relaxing or entertaining or can easily be transformed into an additional bedroom and bath. The luxurious primary suite offers a peaceful escape, complete with an expansive walk-in closet and beautifully appointed spa-inspired bath featuring a curbless walk-through shower. A private balcony overlooking the pool adds another inviting place to unwind. Two additional bedrooms share a well-appointed full bath, offering comfortable accommodations for family or guests. The finished lower level provides remarkable versatility, with a spacious living room, kitchenette, bedroom, and full bath creating an ideal arrangement for extended family, overnight guests, or multigenerational living. A dedicated wine cellar adds a sophisticated touch, while an additional bonus room, currently utilized as a conference room, offers endless possibilities as a private home theater, media lounge, or recreation space. With its elegant interiors, exceptional outdoor amenities, and peaceful setting just minutes from the energy and excitement of Annapolis, this remarkable residence offers an extraordinary opportunity to experience luxury living without compromising convenience. Welcome Home!

Discover an exceptional blend of sophisticated design, resort-inspired living, and everyday convenience in this beautifully appointed Annapolis residence. Tucked along a quiet street yet remarkably close to everything that makes Annapolis so desirable, this distinctive home offers the perfect balance of privacy and accessibility. From the vibrant restaurants, boutiques, and waterfront attractions of Historic Downtown Annapolis to the charm of nearby neighborhoods and marinas, the very best of the Annapolis lifestyle is just moments away. Designed with both elegant entertaining and comfortable everyday living in mind, the home welcomes you with striking architectural details, beautifully curated finishes, and thoughtfully designed spaces throughout. The main level features gracious formal living and dining areas, complemented by a butler's pantry that makes hosting effortless. At the heart of the home, a beautifully appointed kitchen opens seamlessly to the casual dining area and inviting family room, where accordion glass doors overlook the backyard retreat with serene pool as the focal point The outdoor living experience is truly exceptional. A stunning private pool serves as the centerpiece of a beautifully designed backyard, framed by lush landscaping and mature greenery that create a wonderful sense of seclusion. An expansive covered patio with comfortable lounging and dining areas, ceiling fans, and a fully equipped outdoor kitchen provides the perfect setting for everything from leisurely summer afternoons to memorable evenings entertaining family and friends. The seamless connection between the interior living spaces and poolside retreat creates an atmosphere reminiscent of a private luxury resort. Upstairs, an open loft with a bar area provides an additional gathering space, ideal for relaxing or entertaining or can easily be transformed into an additional bedroom and bath. The luxurious primary suite offers a peaceful escape, complete with an expansive walk-in closet and beautifully appointed spa-inspired bath featuring a curbless walk-through shower. A private balcony overlooking the pool adds another inviting place to unwind. Two additional bedrooms share a well-appointed full bath, offering comfortable accommodations for family or guests. The finished lower level provides remarkable versatility, with a spacious living room, kitchenette, bedroom, and full bath creating an ideal arrangement for extended family, overnight guests, or multigenerational living. A dedicated wine cellar adds a sophisticated touch, while an additional bonus room, currently utilized as a conference room, offers endless possibilities as a private home theater, media lounge, or recreation space. With its elegant interiors, exceptional outdoor amenities, and peaceful setting just minutes from the energy and excitement of Annapolis, this remarkable residence offers an extraordinary opportunity to experience luxury living without compromising convenience. Welcome Home!

204 S Villa Ave, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

$560,000

Also for Rent, Listing ID MDAA2150578. Welcome to 104 Vanguard, a bright and spacious 3 level townhome in the heart of Annapolis, nestled in the gated community of Village Greens. Enjoy shopping, dining and entertainment just steps from your front door. This beautifully maintained home is perfect for everyday living and entertaining alike. The entry level features a two car garage, a half bath, and flex space perfectly suited for a home office or recreation room. The main level includes a gourmet kitchen with granite countertops, stainless steel appliances, a large island with breakfast bar, and dining room that leads to a deck that is perfect for grilling, entertaining, or just relaxing. Rounding out this level is a family room that overlooks the community recreation area and an additional half bath. Upstairs are two generously-sized guest bedrooms, a guest bath, a laundry closet, and a sumptuous primary suite with spacious walk in closet and primary bath with dual vanities. Minutes from Eastport, Annapolis, the Naval Academy, and Quiet Waters Park, this home offers an unparalleled lifestyle with the added comfort of a gated community. Easy access to Rtes. 50 and 97 gives you plenty of commuting options to the Baltimore and DC areas. Come enjoy all that Annapolis has to offer. Your new lifestyle awaits! Welcome Home!

Also for Rent, Listing ID MDAA2150578. Welcome to 104 Vanguard, a bright and spacious 3 level townhome in the heart of Annapolis, nestled in the gated community of Village Greens. Enjoy shopping, dining and entertainment just steps from your front door. This beautifully maintained home is perfect for everyday living and entertaining alike. The entry level features a two car garage, a half bath, and flex space perfectly suited for a home office or recreation room. The main level includes a gourmet kitchen with granite countertops, stainless steel appliances, a large island with breakfast bar, and dining room that leads to a deck that is perfect for grilling, entertaining, or just relaxing. Rounding out this level is a family room that overlooks the community recreation area and an additional half bath. Upstairs are two generously-sized guest bedrooms, a guest bath, a laundry closet, and a sumptuous primary suite with spacious walk in closet and primary bath with dual vanities. Minutes from Eastport, Annapolis, the Naval Academy, and Quiet Waters Park, this home offers an unparalleled lifestyle with the added comfort of a gated community. Easy access to Rtes. 50 and 97 gives you plenty of commuting options to the Baltimore and DC areas. Come enjoy all that Annapolis has to offer. Your new lifestyle awaits! Welcome Home!

104 Vanguard Ln, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$950,000

Best Waterfront Value in Annapolis! Beautifully refreshed Waterfront colonial on a cul-de-sac, now offered with a substantial price improvement. Every inch shines with all-new interior and exterior paint, refinished hardwoods, and all-new carpeting. Main level kitchen has been upgraded with a new GE stainless steel appliance suite, combined with a family room that opens onto a deck with views of the creek, fire circle, playset area, and your own private pier with a boat slip. Main level mud room with laundry, built-in storage, and side entrance. Second level features a primary bedroom with a private balcony, upgraded fixtures in the primary and hall bathrooms, and three additional bedrooms. The fully-finished walkout lower level features granite counters, heated ceramic floors, a built-in electric fireplace, a second kitchen, and a spa bath with a second laundry room—perfect for guests or income potential. Enjoy maximum versatility and serenity minutes from Downtown Annapolis and the Naval Academy! Assumable first mortgage available at 3.25%.

Best Waterfront Value in Annapolis! Beautifully refreshed Waterfront colonial on a cul-de-sac, now offered with a substantial price improvement. Every inch shines with all-new interior and exterior paint, refinished hardwoods, and all-new carpeting. Main level kitchen has been upgraded with a new GE stainless steel appliance suite, combined with a family room that opens onto a deck with views of the creek, fire circle, playset area, and your own private pier with a boat slip. Main level mud room with laundry, built-in storage, and side entrance. Second level features a primary bedroom with a private balcony, upgraded fixtures in the primary and hall bathrooms, and three additional bedrooms. The fully-finished walkout lower level features granite counters, heated ceramic floors, a built-in electric fireplace, a second kitchen, and a spa bath with a second laundry room—perfect for guests or income potential. Enjoy maximum versatility and serenity minutes from Downtown Annapolis and the Naval Academy! Assumable first mortgage available at 3.25%.

996 Headwater Rd, Annapolis

Listing courtesy of Taylor Properties. Contact:

1954 Baltimore Annapolis Blvd, Annapolis

$1,150,000

Set on a beautiful one acre lot with a U shaped driveway, this expansive 4,500 square foot contemporary rancher offers seven bedrooms, three full baths, generous living spaces, and a layout filled with possibilities. Recently updated by its longtime owners in preparation for its next chapter, the home combines distinctive architectural details with extensive improvements throughout. Step inside to an impressive open floor plan where soaring vaulted ceilings with exposed wood beams immediately draw your eye. Hardwood floors extend through the main living areas, while a dramatic wall of floor to ceiling windows spans the rear of the home, filling the space with natural light and showcasing peaceful wooded views. A two sided fireplace creates a striking focal point between the living and dining areas, adding warmth and character to both spaces. The kitchen offers new appliances along with a separate eat in area and convenient half bath. The main level features four spacious bedrooms, all with ceilings over nine feet. The hall bath includes a soaking tub, while the primary suite offers its own private bath with a walk in shower and new vanity. Step outside from the primary bedroom onto a private balcony overlooking the wooded setting. The finished lower level provides an incredible amount of additional living and entertaining space. An exceptionally large recreation room continues the home's connection to the outdoors with another wall of windows spanning the rear. A bar area opens conveniently to the lower level patio, creating a great setup for entertaining indoors and out. Three additional bedrooms and a full hall bath provide tremendous flexibility for guests, extended family, hobbies, or additional work from home space. The lower level also includes a large cedar closet, additional storage, a laundry and utility room, and a separate bonus room that could serve as an office, gym, hobby room, or additional storage. Recent improvements include fresh interior paint throughout, refinished hardwood floors on the main level, new flooring throughout the lower level, new lighting, new appliances, a new front door and kitchen door, and a new air conditioning system. Located in Ferry Farms, a sought after water privileged community along the Severn River, the property offers the opportunity to enjoy the Annapolis waterfront lifestyle while still having the privacy and space of a full acre. Just across the Severn River from the U.S. Naval Academy and convenient to downtown Annapolis, the location offers a unique combination of water access, natural surroundings, and proximity to everything Annapolis has to offer. With more than 4,500 square feet of living space, seven bedrooms, multiple gathering areas, walls of windows, wooded views, and an acre of property, this is a truly unique home. Thoughtfully refreshed by owners who have loved and cared for it, the home is ready to welcome its next owner while still offering plenty of opportunity to personalize the space and make it your own.

7 Beds ⋅ 4 Baths

Set on a beautiful one acre lot with a U shaped driveway, this expansive 4,500 square foot contemporary rancher offers seven bedrooms, three full baths, generous living spaces, and a layout filled with possibilities. Recently updated by its longtime owners in preparation for its next chapter, the home combines distinctive architectural details with extensive improvements throughout. Step inside to an impressive open floor plan where soaring vaulted ceilings with exposed wood beams immediately draw your eye. Hardwood floors extend through the main living areas, while a dramatic wall of floor to ceiling windows spans the rear of the home, filling the space with natural light and showcasing peaceful wooded views. A two sided fireplace creates a striking focal point between the living and dining areas, adding warmth and character to both spaces. The kitchen offers new appliances along with a separate eat in area and convenient half bath. The main level features four spacious bedrooms, all with ceilings over nine feet. The hall bath includes a soaking tub, while the primary suite offers its own private bath with a walk in shower and new vanity. Step outside from the primary bedroom onto a private balcony overlooking the wooded setting. The finished lower level provides an incredible amount of additional living and entertaining space. An exceptionally large recreation room continues the home's connection to the outdoors with another wall of windows spanning the rear. A bar area opens conveniently to the lower level patio, creating a great setup for entertaining indoors and out. Three additional bedrooms and a full hall bath provide tremendous flexibility for guests, extended family, hobbies, or additional work from home space. The lower level also includes a large cedar closet, additional storage, a laundry and utility room, and a separate bonus room that could serve as an office, gym, hobby room, or additional storage. Recent improvements include fresh interior paint throughout, refinished hardwood floors on the main level, new flooring throughout the lower level, new lighting, new appliances, a new front door and kitchen door, and a new air conditioning system. Located in Ferry Farms, a sought after water privileged community along the Severn River, the property offers the opportunity to enjoy the Annapolis waterfront lifestyle while still having the privacy and space of a full acre. Just across the Severn River from the U.S. Naval Academy and convenient to downtown Annapolis, the location offers a unique combination of water access, natural surroundings, and proximity to everything Annapolis has to offer. With more than 4,500 square feet of living space, seven bedrooms, multiple gathering areas, walls of windows, wooded views, and an acre of property, this is a truly unique home. Thoughtfully refreshed by owners who have loved and cared for it, the home is ready to welcome its next owner while still offering plenty of opportunity to personalize the space and make it your own.

1954 Baltimore Annapolis Blvd, Annapolis

Listing courtesy of Cummings & Co. Realtors. Contact:

$570,000

Nestled in the prestigious gated community of Village Greens, this exquisite Colonial townhouse offers a harmonious blend of luxury and comfort. Built in 2016, this meticulously maintained residence spans 2,000 square feet, showcasing high-end finishes including a newly updated kitchen and thoughtful design throughout. Step inside to discover a warm and inviting atmosphere, where rich hardwood floors flow seamlessly through the main living areas. The spacious living room, anchored by a cozy fireplace for your indoor and outdoor enjoyment, invites relaxation and gatherings with loved ones. With three generously sized bedrooms, including a serene master suite with an ensuite bath, this home provides ample space for rest and rejuvenation. The two full and two half baths are beautifully appointed, offering both style and functionality. Enjoy the convenience of an attached finished rear-entry garage and driveway parking, ensuring easy access and ample space for guests. The low-maintenance outdoor area allows for leisurely afternoons spent soaking up the sun or enjoying a quiet evening under the stars. Experience the exclusive lifestyle that Village Greens has to offer, with its serene surroundings and proximity to local amenities. This stunning townhouse is not just a home; it's a sanctuary where luxury meets everyday living. Embrace the opportunity to make this exceptional property your own.

Nestled in the prestigious gated community of Village Greens, this exquisite Colonial townhouse offers a harmonious blend of luxury and comfort. Built in 2016, this meticulously maintained residence spans 2,000 square feet, showcasing high-end finishes including a newly updated kitchen and thoughtful design throughout. Step inside to discover a warm and inviting atmosphere, where rich hardwood floors flow seamlessly through the main living areas. The spacious living room, anchored by a cozy fireplace for your indoor and outdoor enjoyment, invites relaxation and gatherings with loved ones. With three generously sized bedrooms, including a serene master suite with an ensuite bath, this home provides ample space for rest and rejuvenation. The two full and two half baths are beautifully appointed, offering both style and functionality. Enjoy the convenience of an attached finished rear-entry garage and driveway parking, ensuring easy access and ample space for guests. The low-maintenance outdoor area allows for leisurely afternoons spent soaking up the sun or enjoying a quiet evening under the stars. Experience the exclusive lifestyle that Village Greens has to offer, with its serene surroundings and proximity to local amenities. This stunning townhouse is not just a home; it's a sanctuary where luxury meets everyday living. Embrace the opportunity to make this exceptional property your own.

1612 Belle Dr, Annapolis

Listing courtesy of O'Brien Realty ERA Powered. Contact:

$1,599,000

A Builder’s Personal Residence | A Signature Annapolis Home A rare opportunity to own the personal residence of a builder and an interior designer, whose expertise and craftsmanship are reflected throughout their exceptional Annapolis home. 3124 Starboard Drive represents their vision of quality, functionality, and enduring design—where no detail was overlooked and every improvement was thoughtfully executed. Known as one of the neighborhood’s exceptional residences, this home offers a level of craftsmanship and attention to detail that is difficult to replicate. From the quality of construction and materials to the thoughtful design choices, the property reflects the discerning standards of a professional who builds and renovates homes for a living. This extraordinary residential real estate transformation is the creation of Mac O’Brien, the owner of Great Eastern Contracting, and his wife Becca O’Brien from Intuitive Design. Together they joined forces and underwent a complete, down-to-the-studs renovation and expansion. They purchased this home in 2015 and over the course of time they turned a 2,000 square foot home into an over 3,700 square feet of luxurious, modern turnkey showpiece with no detail overlooked. This five-bedroom, four-bathroom residence, has an open and elegant floor plan flooded with natural light. The chef kitchen has a stunning 8.9’ x 6.9’ quartz Island countertop offering exceptional workspace and seating for five with striking oversized lantern-style pendant lamps. The Owner’s Suite Spa-inspired primary bath has a custom white double-vanity, luxurious marble countertops, polished brass fixtures, oversized mirrors, elegant glass pendant lighting and heated floors. The expansive walk-in shower is beautifully appointed in veined marble tile with a frameless glass enclosure, multiple shower fixtures and built-in niches, creating a sophisticated, resort-like retreat. The living and family rooms have gas fireplaces and built ins. In addition, the home features a recreation room, fully fenced backyard, a double garage converted into a conditioned and finished Golf simulator room, shed and golf-cart garage. Mechanical systems include a full-house back-up generator, dual zone HVAC systems, tankless water heater, RO water filtration in kitchen and below counter Scotsman Gourmet Ice Maker and water treatment with dual storage tanks, salinator, chlorinator, sediment filter and UV light. This residence was meticulously rebuilt in 2021 - walls, ceilings, floors, fixtures, electrical, and plumbing systems—all removed and replaced with high-end finishes and craftsmanship throughout. The result is a striking blend of contemporary comfort and timeless design. Located in the sought-after waterfront community of Anchorage, this distinctive residence combines sophisticated living with the relaxed character of an established Annapolis neighborhood, offering access to the community’s marina, pool, boat ramp and waterfront amenities.

A Builder’s Personal Residence | A Signature Annapolis Home A rare opportunity to own the personal residence of a builder and an interior designer, whose expertise and craftsmanship are reflected throughout their exceptional Annapolis home. 3124 Starboard Drive represents their vision of quality, functionality, and enduring design—where no detail was overlooked and every improvement was thoughtfully executed. Known as one of the neighborhood’s exceptional residences, this home offers a level of craftsmanship and attention to detail that is difficult to replicate. From the quality of construction and materials to the thoughtful design choices, the property reflects the discerning standards of a professional who builds and renovates homes for a living. This extraordinary residential real estate transformation is the creation of Mac O’Brien, the owner of Great Eastern Contracting, and his wife Becca O’Brien from Intuitive Design. Together they joined forces and underwent a complete, down-to-the-studs renovation and expansion. They purchased this home in 2015 and over the course of time they turned a 2,000 square foot home into an over 3,700 square feet of luxurious, modern turnkey showpiece with no detail overlooked. This five-bedroom, four-bathroom residence, has an open and elegant floor plan flooded with natural light. The chef kitchen has a stunning 8.9’ x 6.9’ quartz Island countertop offering exceptional workspace and seating for five with striking oversized lantern-style pendant lamps. The Owner’s Suite Spa-inspired primary bath has a custom white double-vanity, luxurious marble countertops, polished brass fixtures, oversized mirrors, elegant glass pendant lighting and heated floors. The expansive walk-in shower is beautifully appointed in veined marble tile with a frameless glass enclosure, multiple shower fixtures and built-in niches, creating a sophisticated, resort-like retreat. The living and family rooms have gas fireplaces and built ins. In addition, the home features a recreation room, fully fenced backyard, a double garage converted into a conditioned and finished Golf simulator room, shed and golf-cart garage. Mechanical systems include a full-house back-up generator, dual zone HVAC systems, tankless water heater, RO water filtration in kitchen and below counter Scotsman Gourmet Ice Maker and water treatment with dual storage tanks, salinator, chlorinator, sediment filter and UV light. This residence was meticulously rebuilt in 2021 - walls, ceilings, floors, fixtures, electrical, and plumbing systems—all removed and replaced with high-end finishes and craftsmanship throughout. The result is a striking blend of contemporary comfort and timeless design. Located in the sought-after waterfront community of Anchorage, this distinctive residence combines sophisticated living with the relaxed character of an established Annapolis neighborhood, offering access to the community’s marina, pool, boat ramp and waterfront amenities.

3124 Starboard Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$875,000

Back on the Market thou no fault to the seller! Welcome to 2801 Autumn Chase Circle, Beautifully appointed Annapolis home offering generous living space and timeless style, with an exceptional location ,just a short distance to downtown Annapolis and convenient commute to Washington DC and Baltimore. This home sits on a corner lot with an extensive paver patio and water fountain feature. The upper level features a large primary bedroom with hardwood floors and beautiful bath with heated floors ,soaking tub and dream shower, plus two walk in closets. Three additional bedrooms and one full bath complete the upper level. The light filled main level offers a formal living room and dining room an elegant space with board and batten trim, hardwood floors, plantation shutters perfect for entertaining. Just off the kitchen is the main level family room with hardwood floors and gas fireplace ideal for relaxing evenings at home. The finished lower level completes the home with a large additional family room and wet bar. All windows are covered with plantation shutters. This home is meticulously cared for and several major improvements offer added peace of mind, including a new roof in 2020, windows 2020 and new HVAC system in 2021

Back on the Market thou no fault to the seller! Welcome to 2801 Autumn Chase Circle, Beautifully appointed Annapolis home offering generous living space and timeless style, with an exceptional location ,just a short distance to downtown Annapolis and convenient commute to Washington DC and Baltimore. This home sits on a corner lot with an extensive paver patio and water fountain feature. The upper level features a large primary bedroom with hardwood floors and beautiful bath with heated floors ,soaking tub and dream shower, plus two walk in closets. Three additional bedrooms and one full bath complete the upper level. The light filled main level offers a formal living room and dining room an elegant space with board and batten trim, hardwood floors, plantation shutters perfect for entertaining. Just off the kitchen is the main level family room with hardwood floors and gas fireplace ideal for relaxing evenings at home. The finished lower level completes the home with a large additional family room and wet bar. All windows are covered with plantation shutters. This home is meticulously cared for and several major improvements offer added peace of mind, including a new roof in 2020, windows 2020 and new HVAC system in 2021

2801 Autumn Chase Cir, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$569,900

NEW PRICE!! Welcome home to this residence that lives like a spacious single-family home, just minutes from historic downtown Annapolis. Built by Pulte with an impressive selection of upgrades, this home features a large rear bump-out, 9-foot ceilings, upgraded flooring, custom built-ins, and abundant natural light. The location is impressive! Truxtun Park is just minutes away, with a pool, ball fields, playground, tennis and pickleball courts, a skate park, and free kayak, canoe, and boat launching. Pip Moyer Recreation Center is nearby too. Paddle into downtown Annapolis for lunch, or enjoy all that historic Annapolis has to offer. Open, airy, beautifully updated, and exceptionally spacious, this is a home that truly lives large. The main level showcases hardwood floors, custom millwork, and a cozy gas fireplace. Recent improvements include a refreshed kitchen with painted cabinetry, new hardware, stone countertops, newer appliances, a new garbage disposal (2025), and a new microwave with oven feature (2026). The main level also features updated light fixtures, a new bathroom faucet and mirror, a smart thermostat, and a Ring doorbell. The eat-in kitchen opens through large sliding doors to a deck overlooking a wooded view and semi-private green space. With its generous proportions and open layout, this home is ideal for everyday living and entertaining. Upstairs, you'll find a spacious primary suite with large banks of windows, two additional bedrooms, and a full bath. New carpet was installed on the stairs and throughout the upper level in 2025, along with updated hallway lighting. The primary bath features a new mirror, and custom blackout shades add privacy to all seven front-facing windows on both levels. The lower level provides exceptional flexibility, with heated wood floors, a large den, a spacious home office, a full bath, plenty of storage, and a flex room currently used as a fourth bedroom.

NEW PRICE!! Welcome home to this residence that lives like a spacious single-family home, just minutes from historic downtown Annapolis. Built by Pulte with an impressive selection of upgrades, this home features a large rear bump-out, 9-foot ceilings, upgraded flooring, custom built-ins, and abundant natural light. The location is impressive! Truxtun Park is just minutes away, with a pool, ball fields, playground, tennis and pickleball courts, a skate park, and free kayak, canoe, and boat launching. Pip Moyer Recreation Center is nearby too. Paddle into downtown Annapolis for lunch, or enjoy all that historic Annapolis has to offer. Open, airy, beautifully updated, and exceptionally spacious, this is a home that truly lives large. The main level showcases hardwood floors, custom millwork, and a cozy gas fireplace. Recent improvements include a refreshed kitchen with painted cabinetry, new hardware, stone countertops, newer appliances, a new garbage disposal (2025), and a new microwave with oven feature (2026). The main level also features updated light fixtures, a new bathroom faucet and mirror, a smart thermostat, and a Ring doorbell. The eat-in kitchen opens through large sliding doors to a deck overlooking a wooded view and semi-private green space. With its generous proportions and open layout, this home is ideal for everyday living and entertaining. Upstairs, you'll find a spacious primary suite with large banks of windows, two additional bedrooms, and a full bath. New carpet was installed on the stairs and throughout the upper level in 2025, along with updated hallway lighting. The primary bath features a new mirror, and custom blackout shades add privacy to all seven front-facing windows on both levels. The lower level provides exceptional flexibility, with heated wood floors, a large den, a spacious home office, a full bath, plenty of storage, and a flex room currently used as a fourth bedroom.

1152 August Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$2,995,000

A rare waterfront setting just off the Severn River, 1800 River Watch Lane is positioned on a private peninsula with more than 450 feet of shoreline along Luce Creek, offering exceptional privacy, sweeping water views and approximately 8 feet of protected deep water at the pier. From here, the Severn River is moments away and downtown Annapolis is an easy boat ride, an extraordinary setting for anyone who wants to make the Chesapeake Bay lifestyle part of everyday life. Approached by a long private drive and circular pea-stone courtyard, the extensively renovated residence sits high above the water, surrounded by mature trees and landscaping. Designed primarily on one level, the home takes full advantage of its elevated setting, with water views filling nearly every room and expansive outdoor living spaces overlooking the creek. At the center of the home, the dramatic living room pairs a wood-paneled cathedral ceiling with a floor-to-ceiling stone fireplace and an entire wall of glass facing the water. Doors open to a broad Ipe deck spanning the waterside of the home, creating a natural extension of the living space. Morning coffee overlooking the creek, dinner outside with friends or an evening in the hot tub all unfold against the backdrop of the water. The open layout continues into the dining and family areas, where cathedral ceilings, a gas fireplace and panoramic views create relaxed spaces equally suited to entertaining and everyday living. The adjoining chef's kitchen features marbled Silestone countertops, an extensive suite of Miele appliances, including double wall ovens, warming drawer and induction cooktop, along with a large walk-in pantry. The home's private spaces are equally thoughtful. A dedicated office with built-ins and an adjoining den or bedroom offer flexibility for working from home or accommodating guests. An architecturally distinctive, skylit hexagon hall leads to the bedroom wing and the waterside primary suite, a serene retreat with a gas fireplace, tray ceiling and oversized walk-in closet. The spa-inspired primary bath features a soaking tub positioned toward the view, large walk-in shower, double vanity and private sauna. Two additional bedrooms, including one ensuite, another full bath, separate laundry room and powder room complete the living spaces. Hardwood flooring, generous windows and clean contemporary finishes carry throughout the home, while a well-appointed mudroom connects to the oversized two-car garage. Outside is where the property becomes truly exceptional. The elevated homesite provides privacy and long views across Luce Creek, while a private funicular makes the trip from the house to the shoreline effortless. At the water, a substantial private pier with two boat lifts and approximately 8 feet MLW provides the kind of deep-water access that is increasingly difficult to find. The protected waters of Luce Creek offer an ideal home base for your boat, with the Severn River just beyond and the Chesapeake Bay easily accessible. Spend the morning on the water, cruise into downtown Annapolis for lunch or dinner, or simply enjoy the activity along the creek from the deck above. Despite its remarkably private setting, 1800 River Watch Lane remains convenient to downtown Annapolis as well as major routes to Baltimore, BWI, Washington, D.C. and the Eastern Shore. With its combination of substantial shoreline, protected deep water, immediate Severn River access, privacy and proximity to Annapolis, 1800 River Watch Lane offers a waterfront lifestyle that is increasingly hard to replicate.

A rare waterfront setting just off the Severn River, 1800 River Watch Lane is positioned on a private peninsula with more than 450 feet of shoreline along Luce Creek, offering exceptional privacy, sweeping water views and approximately 8 feet of protected deep water at the pier. From here, the Severn River is moments away and downtown Annapolis is an easy boat ride, an extraordinary setting for anyone who wants to make the Chesapeake Bay lifestyle part of everyday life. Approached by a long private drive and circular pea-stone courtyard, the extensively renovated residence sits high above the water, surrounded by mature trees and landscaping. Designed primarily on one level, the home takes full advantage of its elevated setting, with water views filling nearly every room and expansive outdoor living spaces overlooking the creek. At the center of the home, the dramatic living room pairs a wood-paneled cathedral ceiling with a floor-to-ceiling stone fireplace and an entire wall of glass facing the water. Doors open to a broad Ipe deck spanning the waterside of the home, creating a natural extension of the living space. Morning coffee overlooking the creek, dinner outside with friends or an evening in the hot tub all unfold against the backdrop of the water. The open layout continues into the dining and family areas, where cathedral ceilings, a gas fireplace and panoramic views create relaxed spaces equally suited to entertaining and everyday living. The adjoining chef's kitchen features marbled Silestone countertops, an extensive suite of Miele appliances, including double wall ovens, warming drawer and induction cooktop, along with a large walk-in pantry. The home's private spaces are equally thoughtful. A dedicated office with built-ins and an adjoining den or bedroom offer flexibility for working from home or accommodating guests. An architecturally distinctive, skylit hexagon hall leads to the bedroom wing and the waterside primary suite, a serene retreat with a gas fireplace, tray ceiling and oversized walk-in closet. The spa-inspired primary bath features a soaking tub positioned toward the view, large walk-in shower, double vanity and private sauna. Two additional bedrooms, including one ensuite, another full bath, separate laundry room and powder room complete the living spaces. Hardwood flooring, generous windows and clean contemporary finishes carry throughout the home, while a well-appointed mudroom connects to the oversized two-car garage. Outside is where the property becomes truly exceptional. The elevated homesite provides privacy and long views across Luce Creek, while a private funicular makes the trip from the house to the shoreline effortless. At the water, a substantial private pier with two boat lifts and approximately 8 feet MLW provides the kind of deep-water access that is increasingly difficult to find. The protected waters of Luce Creek offer an ideal home base for your boat, with the Severn River just beyond and the Chesapeake Bay easily accessible. Spend the morning on the water, cruise into downtown Annapolis for lunch or dinner, or simply enjoy the activity along the creek from the deck above. Despite its remarkably private setting, 1800 River Watch Lane remains convenient to downtown Annapolis as well as major routes to Baltimore, BWI, Washington, D.C. and the Eastern Shore. With its combination of substantial shoreline, protected deep water, immediate Severn River access, privacy and proximity to Annapolis, 1800 River Watch Lane offers a waterfront lifestyle that is increasingly hard to replicate.

1800 River Watch Ln, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

$929,000

Experience resort like living in the water-oriented community of Oyster Harbor! Why choose between elegance and Chesapeake living when you can have both?! This stunning property offers the perfect blend of style and comfort with the ease of access to a plethora of sought after water-oriented community amenities! The main level features a beautiful, open kitchen with walk-in pantry, stainless steel appliances, center island, and large eat-in space. The living room is truly the heart of the home featuring a cozy gas/propane fireplace- perfect for gathering for cozy evenings at home. The upper floor is home to all four bedrooms- two of which have attached bathrooms and walk-in closets- and the upper level laundry adds convenience to daily living. The attached garage, with space for two vehicles and additional storage, provides practicality without compromising on style with a large driveway making it easy for guest parking. One of the standout features of this property is the spacious deck and large backyard- indoor/ outdoor living at its finest! The community of Oyster Harbor offers an exclusive lifestyle for water enthusiasts, with opportunities for boating, fishing, and enjoying the natural beauty of the bay. Enjoy easy access to many community amenities including: a large beach with gazebo, two tot lots (one on the beach!), three community marinas, boat ramp, fishing pier, kayak storage, and more! This home is not just a residence; it's a gateway to a lifestyle of luxury and leisure. Experience the perfect blend of modern amenities and serene surroundings in this exceptional Oyster Harbor property.

Experience resort like living in the water-oriented community of Oyster Harbor! Why choose between elegance and Chesapeake living when you can have both?! This stunning property offers the perfect blend of style and comfort with the ease of access to a plethora of sought after water-oriented community amenities! The main level features a beautiful, open kitchen with walk-in pantry, stainless steel appliances, center island, and large eat-in space. The living room is truly the heart of the home featuring a cozy gas/propane fireplace- perfect for gathering for cozy evenings at home. The upper floor is home to all four bedrooms- two of which have attached bathrooms and walk-in closets- and the upper level laundry adds convenience to daily living. The attached garage, with space for two vehicles and additional storage, provides practicality without compromising on style with a large driveway making it easy for guest parking. One of the standout features of this property is the spacious deck and large backyard- indoor/ outdoor living at its finest! The community of Oyster Harbor offers an exclusive lifestyle for water enthusiasts, with opportunities for boating, fishing, and enjoying the natural beauty of the bay. Enjoy easy access to many community amenities including: a large beach with gazebo, two tot lots (one on the beach!), three community marinas, boat ramp, fishing pier, kayak storage, and more! This home is not just a residence; it's a gateway to a lifestyle of luxury and leisure. Experience the perfect blend of modern amenities and serene surroundings in this exceptional Oyster Harbor property.

1326 Harbor Rd, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$924,990

Huge Price Drop + $5,000 Closing Help! New Construction Colonial Ready by End of Year* New pictures coming soon!!! Schaefer Homes presents this stunning new Colonial in the prestigious Oyster Harbor community, with completion targeted for the end of 2026. Set on a sprawling 0.62-acre lot, it offers rare space and privacy, with plenty of room for a garden retreat, entertaining terrace, or open yard. The thoughtful floor plan includes 5 spacious bedrooms and 3.5 baths, plus a showstopping gourmet kitchen with upgraded design features and premium finishes. With its classic vinyl siding exterior and modern new-construction interior, this home blends timeless charm with the quality craftsmanship Schaefer Homes is known for. Oyster Harbor is a serene, exclusive community and one of the area’s most sought-after addresses. Don’t wait. Schedule your private appointment today! *Closing cost assistance terms and conditions apply.

Huge Price Drop + $5,000 Closing Help! New Construction Colonial Ready by End of Year* New pictures coming soon!!! Schaefer Homes presents this stunning new Colonial in the prestigious Oyster Harbor community, with completion targeted for the end of 2026. Set on a sprawling 0.62-acre lot, it offers rare space and privacy, with plenty of room for a garden retreat, entertaining terrace, or open yard. The thoughtful floor plan includes 5 spacious bedrooms and 3.5 baths, plus a showstopping gourmet kitchen with upgraded design features and premium finishes. With its classic vinyl siding exterior and modern new-construction interior, this home blends timeless charm with the quality craftsmanship Schaefer Homes is known for. Oyster Harbor is a serene, exclusive community and one of the area’s most sought-after addresses. Don’t wait. Schedule your private appointment today! *Closing cost assistance terms and conditions apply.

3268 Kitty Duvall Dr, Annapolis

Listing courtesy of Blackwell Real Estate, LLC. Contact:

$925,000

Welcome to 1422 Bay Head Road, a true Annapolis oasis offering flexible living space, thoughtful updates, and exceptional outdoor amenities. The upper level features four bedrooms, including a large primary suite with barn siding accents, a custom closet, and an ensuite bath with a large soaking tub and separate shower. Three additional bedrooms share a hall bathroom. The main level includes a living room, dining room, and kitchen with stainless steel appliances, granite countertops, and a center island. The family room features a fireplace and provides a comfortable space for everyday living and entertaining. The finished lower level adds even more versatility with a family room, custom bar, and a large storage room. Outside, enjoy professionally landscaped grounds, a large deck overlooking the built-in pool and spa, and convenient access to a full bathroom with shower. A generous yard with firepit creates an inviting setting for outdoor gatherings. The property also includes a greenhouse/chicken coop. The community offers nearby water access for kayaks and canoes and is close to parks and walking trails B&O bike trail, golf cart to Podickory Point Yacht & Beach Club. Conveniently located with easy access to Route 50, the Bay Bridge, and downtown Annapolis.

Welcome to 1422 Bay Head Road, a true Annapolis oasis offering flexible living space, thoughtful updates, and exceptional outdoor amenities. The upper level features four bedrooms, including a large primary suite with barn siding accents, a custom closet, and an ensuite bath with a large soaking tub and separate shower. Three additional bedrooms share a hall bathroom. The main level includes a living room, dining room, and kitchen with stainless steel appliances, granite countertops, and a center island. The family room features a fireplace and provides a comfortable space for everyday living and entertaining. The finished lower level adds even more versatility with a family room, custom bar, and a large storage room. Outside, enjoy professionally landscaped grounds, a large deck overlooking the built-in pool and spa, and convenient access to a full bathroom with shower. A generous yard with firepit creates an inviting setting for outdoor gatherings. The property also includes a greenhouse/chicken coop. The community offers nearby water access for kayaks and canoes and is close to parks and walking trails B&O bike trail, golf cart to Podickory Point Yacht & Beach Club. Conveniently located with easy access to Route 50, the Bay Bridge, and downtown Annapolis.

1422 Bay Head Rd, Annapolis

Listing courtesy of RE/MAX United Real Estate. Contact:

$1,300,000

A rare opportunity to own a fully metered triplex in the heart of Downtown Annapolis where historic charm, prime location, and remarkable versatility come together. Steeped in character and offering exceptional flexibility, this distinctive property presents an array of possibilities for both lifestyle and investment. With separately metered electricity, the property can be enjoyed as a multigenerational residence, with each family member having their own private space; an owner-occupied home with additional rental income from the remaining units; or a pure investment property with multiple income producing residences. For those envisioning something truly extraordinary, the entire building could be transformed back into a stunning single-family home. With original architecture and showcasing hardwood floors throughout, this property strikes the perfect balance between historic character and modern livability. The first floor features two bedrooms, each with an en-suite bath, kitchen, and living room, ideal for an owner-occupant or long-term tenant. The second floor offers one bedroom, a full bath, kitchen, living room, and access to a private balcony. The third floor impresses with two bedrooms, a full bath, kitchen, and living room, plus its own private balcony. An unfinished basement provides excellent storage space. A fenced backyard complete with a paver patio, provides an outdoor retreat ideal for relaxing or entertaining. Add to that the coveted off-street parking, a true rarity in Downtown Annapolis, and this property is as practical as it is beautiful. Whether you're an investor seeking immediate income potential, a buyer looking to offset your mortgage, or a multigenerational family wanting separate yet connected living spaces, this home checks every box. All of this just steps from the vibrant shops, restaurants, waterfront, and history that make Downtown Annapolis truly one of a kind.

A rare opportunity to own a fully metered triplex in the heart of Downtown Annapolis where historic charm, prime location, and remarkable versatility come together. Steeped in character and offering exceptional flexibility, this distinctive property presents an array of possibilities for both lifestyle and investment. With separately metered electricity, the property can be enjoyed as a multigenerational residence, with each family member having their own private space; an owner-occupied home with additional rental income from the remaining units; or a pure investment property with multiple income producing residences. For those envisioning something truly extraordinary, the entire building could be transformed back into a stunning single-family home. With original architecture and showcasing hardwood floors throughout, this property strikes the perfect balance between historic character and modern livability. The first floor features two bedrooms, each with an en-suite bath, kitchen, and living room, ideal for an owner-occupant or long-term tenant. The second floor offers one bedroom, a full bath, kitchen, living room, and access to a private balcony. The third floor impresses with two bedrooms, a full bath, kitchen, and living room, plus its own private balcony. An unfinished basement provides excellent storage space. A fenced backyard complete with a paver patio, provides an outdoor retreat ideal for relaxing or entertaining. Add to that the coveted off-street parking, a true rarity in Downtown Annapolis, and this property is as practical as it is beautiful. Whether you're an investor seeking immediate income potential, a buyer looking to offset your mortgage, or a multigenerational family wanting separate yet connected living spaces, this home checks every box. All of this just steps from the vibrant shops, restaurants, waterfront, and history that make Downtown Annapolis truly one of a kind.

135 Conduit St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

$789,900

Don't delay - grab your agent and schedule a tour today! Welcome to 2691 Claibourne Road, beautifully presented and ready to impress in the sought-after water-privileged community of Annapolis Roads. This spacious 4-bedroom, 3.5-bath Colonial offers a flexible floor plan, finished lower level, two-car garage and inviting indoor and outdoor spaces designed for everyday living and entertaining. Step inside to hardwood floors and light-filled living spaces that flow comfortably throughout the main level. The updated kitchen features granite countertops and opens to the home's gathering areas, while separate living and dining rooms provide plenty of room for entertaining. Just beyond, the screened-in porch overlooks the peaceful, wooded backyard and offers the perfect spot for morning coffee, outdoor dining or relaxing at the end of the day. Upstairs, the spacious primary suite features a vaulted ceiling, oversized walk-in closet and private bath with a sunken tub and separate shower. Three additional bedrooms and a full hall bath complete the upper level. Downstairs, the finished lower level adds even more flexibility with a family/rec room, full bath and generous storage—ideal for guests, a home office, workout space or additional living area. Additional features include a whole-house generator, newer heat pump, water-softening system, two-car garage and custom shed with electricity. Fresh landscaping and new mulch enhance the home's curb appeal, while the wooded backyard provides a private setting for relaxing and entertaining. Just a short walk down Claibourne Road, take in beautiful sights of Lake Heron—one more reminder of the special setting that surrounds this home. Annapolis Roads residents enjoy an exceptional water-privileged lifestyle with access to the community's private beach, boat ramp, piers, waterfront pavilion and picnic area, playground, fire pit, kayak storage, walking trails and neighborhood events. All of this is just minutes from Downtown Annapolis, shopping, dining and commuter routes. Beautifully staged, refreshed and ready for its next chapter—come experience 2691 Claibourne Road for yourself!

Don't delay - grab your agent and schedule a tour today! Welcome to 2691 Claibourne Road, beautifully presented and ready to impress in the sought-after water-privileged community of Annapolis Roads. This spacious 4-bedroom, 3.5-bath Colonial offers a flexible floor plan, finished lower level, two-car garage and inviting indoor and outdoor spaces designed for everyday living and entertaining. Step inside to hardwood floors and light-filled living spaces that flow comfortably throughout the main level. The updated kitchen features granite countertops and opens to the home's gathering areas, while separate living and dining rooms provide plenty of room for entertaining. Just beyond, the screened-in porch overlooks the peaceful, wooded backyard and offers the perfect spot for morning coffee, outdoor dining or relaxing at the end of the day. Upstairs, the spacious primary suite features a vaulted ceiling, oversized walk-in closet and private bath with a sunken tub and separate shower. Three additional bedrooms and a full hall bath complete the upper level. Downstairs, the finished lower level adds even more flexibility with a family/rec room, full bath and generous storage—ideal for guests, a home office, workout space or additional living area. Additional features include a whole-house generator, newer heat pump, water-softening system, two-car garage and custom shed with electricity. Fresh landscaping and new mulch enhance the home's curb appeal, while the wooded backyard provides a private setting for relaxing and entertaining. Just a short walk down Claibourne Road, take in beautiful sights of Lake Heron—one more reminder of the special setting that surrounds this home. Annapolis Roads residents enjoy an exceptional water-privileged lifestyle with access to the community's private beach, boat ramp, piers, waterfront pavilion and picnic area, playground, fire pit, kayak storage, walking trails and neighborhood events. All of this is just minutes from Downtown Annapolis, shopping, dining and commuter routes. Beautifully staged, refreshed and ready for its next chapter—come experience 2691 Claibourne Road for yourself!

2691 Claibourne Rd, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$1,875,000

***Owner financing available at 6%*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best.

***Owner financing available at 6%*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best.

400 Jefferson St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

$525,000

Price Reduction. Gorgeous 4 level townhome situated on a premium, landscaped lot with water views. Every level highlights the connection to nature and privacy in this well-maintained, thoughtfully designed home. The ground level features a one car garage with storage shelves and a spa-like ensuite bedroom that leads to a private screened porch and fenced backyard. Perfect for guests, this space evokes relaxation and privacy. The main level offers a spacious family room, a gourmet kitchen, and large dining area that leads to a deck with views of the backyard oasis. Options for entertaining here are endless, with comfortable spaces for all to enjoy. The bedroom level offers a unique primary bedroom suite with ample closet space, sitting room/second bedroom, and upgraded primary bath with a luxury shower, double vanity, and soaking tub. The water view is prominent on this level. The bonus loft level provides an additional bedroom or office/flex space and a full bath. The wooded walking trail that leads to the community pier is a short walk away, providing stunning views and water access. With hardwood flooring on each level this home shows exceptionally well and is just waiting for its next occupants. Welcome Home!