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$600,000

Imagine starting your morning with coffee in a sun-filled room, looking out over a peaceful backyard framed by trees. Later, you could launch a kayak, head to the community beach, take a walk through Quiet Waters Park, or be in downtown Annapolis in minutes. This is the lifestyle that makes Hillsmere Shores so special. Set near the Chesapeake Bay and the mouth of the South River, this updated 3-bedroom, 2.5-bath home blends comfort, character, and flexibility in one of Annapolis’s most loved waterfront communities. Inside, a thoughtful renovation created spaces that feel open, warm, and easy to enjoy. The expanded kitchen features a center island, eat-in area, custom tile backsplash, solid wood cabinetry, and plenty of room to gather. The primary suite was also expanded and now offers a sitting area, large walk-in closet, brand-new carpeting, and a beautifully renovated bath. But the room you may never want to leave is the four-season sunroom. Fresh paint, new luxury vinyl plank flooring, and views of the fenced backyard make it the perfect place to relax in every season.The finished lower level gives you even more room to spread out. Use it as a recreation room, office, gym, creative space, or potential fourth bedroom. A classic brick fireplace with an insert creates the perfect backdrop for cozy evenings, and a half bath adds extra convenience. Outside, the backyard offers privacy, trees, and room to enjoy the outdoors. And then there’s Hillsmere Shores itself: a private marina, boat ramps, kayak and canoe launch, community beach, swimming pool, playgrounds, picnic areas, and recreation spaces—all just minutes from downtown Annapolis, Key School, and Quiet Waters Park. This isn’t just Annapolis living. This is Chesapeake Bay living at its best.

3 Beds ⋅ 3 Baths

Imagine starting your morning with coffee in a sun-filled room, looking out over a peaceful backyard framed by trees. Later, you could launch a kayak, head to the community beach, take a walk through Quiet Waters Park, or be in downtown Annapolis in minutes. This is the lifestyle that makes Hillsmere Shores so special. Set near the Chesapeake Bay and the mouth of the South River, this updated 3-bedroom, 2.5-bath home blends comfort, character, and flexibility in one of Annapolis’s most loved waterfront communities. Inside, a thoughtful renovation created spaces that feel open, warm, and easy to enjoy. The expanded kitchen features a center island, eat-in area, custom tile backsplash, solid wood cabinetry, and plenty of room to gather. The primary suite was also expanded and now offers a sitting area, large walk-in closet, brand-new carpeting, and a beautifully renovated bath. But the room you may never want to leave is the four-season sunroom. Fresh paint, new luxury vinyl plank flooring, and views of the fenced backyard make it the perfect place to relax in every season.The finished lower level gives you even more room to spread out. Use it as a recreation room, office, gym, creative space, or potential fourth bedroom. A classic brick fireplace with an insert creates the perfect backdrop for cozy evenings, and a half bath adds extra convenience. Outside, the backyard offers privacy, trees, and room to enjoy the outdoors. And then there’s Hillsmere Shores itself: a private marina, boat ramps, kayak and canoe launch, community beach, swimming pool, playgrounds, picnic areas, and recreation spaces—all just minutes from downtown Annapolis, Key School, and Quiet Waters Park. This isn’t just Annapolis living. This is Chesapeake Bay living at its best.

416 Walnut Dr, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

$2,250,000

Welcome to one of Annapolis’ most sought-after water-access communities, where nearly $1 million in thoughtful improvements since 2022 have transformed this 3-bedroom, 3-bath home into a truly special offering. The home blends timeless character with extensive modern updates, including a beautifully renovated kitchen, luxurious primary bath, updated secondary bath, refinished flooring, custom millwork and library built-ins, upgraded lighting and electrical, and refreshed bedrooms. The sunroom has been enclosed to create additional year-round living space, while the family room features an inviting stove and updated mantel. Outside, the property is equally impressive. Extensive professional landscaping and hardscaping create a private, beautifully designed setting with a stone patio, firepit, landscape lighting, and multiple spaces for outdoor entertaining. A garage provides coveted off-street parking, with ample street parking available for guests. Living in Wardour is about much more than the home. Residents enjoy access to private community beaches, kayak storage, wooded trails and waterfront pathways—all just minutes from the heart of Annapolis. The neighborhood offers an exceptional combination of convenience and lifestyle, with a Blue Ribbon elementary school, coffee shop, ice cream shop, brewery, café, grocery store, upscale dining and numerous neighborhood restaurants close by. Downtown Annapolis and Navy-Marine Corps Memorial Stadium are both within walking distance, while nearby Route 50 provides easy access to Washington, D.C., Baltimore and the Eastern Shore. Extensively renovated, beautifully landscaped and ideally located, this is a rare opportunity to enjoy the best of the Annapolis lifestyle in one of its most desirable communities.

3 Beds ⋅ 3 Baths

Welcome to one of Annapolis’ most sought-after water-access communities, where nearly $1 million in thoughtful improvements since 2022 have transformed this 3-bedroom, 3-bath home into a truly special offering. The home blends timeless character with extensive modern updates, including a beautifully renovated kitchen, luxurious primary bath, updated secondary bath, refinished flooring, custom millwork and library built-ins, upgraded lighting and electrical, and refreshed bedrooms. The sunroom has been enclosed to create additional year-round living space, while the family room features an inviting stove and updated mantel. Outside, the property is equally impressive. Extensive professional landscaping and hardscaping create a private, beautifully designed setting with a stone patio, firepit, landscape lighting, and multiple spaces for outdoor entertaining. A garage provides coveted off-street parking, with ample street parking available for guests. Living in Wardour is about much more than the home. Residents enjoy access to private community beaches, kayak storage, wooded trails and waterfront pathways—all just minutes from the heart of Annapolis. The neighborhood offers an exceptional combination of convenience and lifestyle, with a Blue Ribbon elementary school, coffee shop, ice cream shop, brewery, café, grocery store, upscale dining and numerous neighborhood restaurants close by. Downtown Annapolis and Navy-Marine Corps Memorial Stadium are both within walking distance, while nearby Route 50 provides easy access to Washington, D.C., Baltimore and the Eastern Shore. Extensively renovated, beautifully landscaped and ideally located, this is a rare opportunity to enjoy the best of the Annapolis lifestyle in one of its most desirable communities.

102 Melvin Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$520,000

Tucked away down a tree-lined driveway on over half an acre, 1365 Moyer Road offers a rare combination of privacy, thoughtful updates, and convenient access to everything Annapolis has to offer. Located just off Arundel on the Bay Road, this beautifully renovated home is minutes from downtown Annapolis, Quiet Waters Park, local marinas, and the Chesapeake Bay. Inside, the home feels bright and refreshed with luxury vinyl plank flooring, fresh paint, and an updated kitchen featuring stylish cabinetry, countertops, and sink. The upper level includes three spacious bedrooms and two updated full baths, including a private primary suite with its own bath and direct access to the rear deck. The lower level provides additional living space with a fireplace, third full bath, and flexible bonus room ideal for a home office, gym, playroom, or guest space. Outside, enjoy a newer deck overlooking the fully fenced 0.65-acre backyard with plenty of room for entertaining, pets, recreation, or boat storage. Additional 2026 improvements include a new water pressure tank, serviced well, updated doors, and numerous updates throughout the home. Private, move-in ready, and ideally located near the water and downtown Annapolis, 1365 Moyer Road is ready for its next owner.

4 Beds ⋅ 3 Baths

Tucked away down a tree-lined driveway on over half an acre, 1365 Moyer Road offers a rare combination of privacy, thoughtful updates, and convenient access to everything Annapolis has to offer. Located just off Arundel on the Bay Road, this beautifully renovated home is minutes from downtown Annapolis, Quiet Waters Park, local marinas, and the Chesapeake Bay. Inside, the home feels bright and refreshed with luxury vinyl plank flooring, fresh paint, and an updated kitchen featuring stylish cabinetry, countertops, and sink. The upper level includes three spacious bedrooms and two updated full baths, including a private primary suite with its own bath and direct access to the rear deck. The lower level provides additional living space with a fireplace, third full bath, and flexible bonus room ideal for a home office, gym, playroom, or guest space. Outside, enjoy a newer deck overlooking the fully fenced 0.65-acre backyard with plenty of room for entertaining, pets, recreation, or boat storage. Additional 2026 improvements include a new water pressure tank, serviced well, updated doors, and numerous updates throughout the home. Private, move-in ready, and ideally located near the water and downtown Annapolis, 1365 Moyer Road is ready for its next owner.

1365 Moyer Rd, Annapolis

Listing courtesy of Cummings & Co. Realtors. Contact:

$1,025,000

Welcome to 98 Monticello Avenue, a charming Murray Hill residence that captures the character and ease of the Annapolis lifestyle. From the moment you step inside, a welcoming entryway sets the tone for a home filled with warmth, natural light and thoughtful spaces throughout. The main level offers a comfortable living room centered around a beautiful fireplace, creating an inviting place to gather and unwind. The adjacent kitchen is bright and beautifully appointed with hardwood flooring, a cooktop and a cozy breakfast nook. A convenient half bath completes the main level, while a spacious deck extends the living space outdoors and overlooks the fully fenced backyard- an ideal setting for morning coffee, entertaining, or enjoying time outdoors. Upstairs, three generously sized bedrooms share a full bath, offering comfortable accommodations for family and guests. Continue to the upper level to discover additional flexible space that can easily adapt to your lifestyle—whether used as a home office, playroom, creative space or additional storage. The lower level adds even more versatility with a full bathroom, laundry area and abundant storage, providing valuable functionality rarely found in a home of this character. Set in the highly desirable Murray Hill neighborhood, this water-oriented location offers easy access to Spa Creek and the waterfront lifestyle that makes Annapolis so special, while remaining just moments from downtown. Enjoy convenient access to the Naval Academy, local restaurants, shops, parks and the many experiences that define the Annapolis lifestyle. A home with timeless charm, flexible living spaces, outdoor living and an exceptional location, all within one of Annapolis' most beloved neighborhoods. PHOTO DISCLOSURE: Photo #1 has been AI-enhanced for marketing purposes. The fireplace flames were digitally added and are not intended to represent or warrant the condition, functionality, or operability of the fireplace.

3 Beds ⋅ 3 Baths

Welcome to 98 Monticello Avenue, a charming Murray Hill residence that captures the character and ease of the Annapolis lifestyle. From the moment you step inside, a welcoming entryway sets the tone for a home filled with warmth, natural light and thoughtful spaces throughout. The main level offers a comfortable living room centered around a beautiful fireplace, creating an inviting place to gather and unwind. The adjacent kitchen is bright and beautifully appointed with hardwood flooring, a cooktop and a cozy breakfast nook. A convenient half bath completes the main level, while a spacious deck extends the living space outdoors and overlooks the fully fenced backyard- an ideal setting for morning coffee, entertaining, or enjoying time outdoors. Upstairs, three generously sized bedrooms share a full bath, offering comfortable accommodations for family and guests. Continue to the upper level to discover additional flexible space that can easily adapt to your lifestyle—whether used as a home office, playroom, creative space or additional storage. The lower level adds even more versatility with a full bathroom, laundry area and abundant storage, providing valuable functionality rarely found in a home of this character. Set in the highly desirable Murray Hill neighborhood, this water-oriented location offers easy access to Spa Creek and the waterfront lifestyle that makes Annapolis so special, while remaining just moments from downtown. Enjoy convenient access to the Naval Academy, local restaurants, shops, parks and the many experiences that define the Annapolis lifestyle. A home with timeless charm, flexible living spaces, outdoor living and an exceptional location, all within one of Annapolis' most beloved neighborhoods. PHOTO DISCLOSURE: Photo #1 has been AI-enhanced for marketing purposes. The fireplace flames were digitally added and are not intended to represent or warrant the condition, functionality, or operability of the fireplace.

98 Monticello Ave, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

$1,295,000

Welcome to your future home in water-privileged Beacon Hill, where coastal living meets quality new construction. Set on a half-acre lot with a circular driveway, this to-be-built residence will be finished with durable Hardie Plank siding and architectural shingles for lasting beauty and low maintenance. The inviting design features a beautiful porch that wraps around to create a lovely seating area just outside the family room. Inside, 10-foot ceilings and luxury vinyl plank flooring create an airy, elegant main level with an open floor plan made for easy living and more formal entertaining if desired. The gourmet kitchen will inspire any home chef with quartz countertops, stainless steel appliances, and a generous pantry. A main-level bedroom offers flexibility for guests, multi-generational living, or single-level convenience. Upstairs, the primary suite is an oasis, complete with a gas fireplace, a luxurious bath, a walk-in closet, and private access to the veranda, the perfect spot for morning coffee or evening relaxation. Two additional bedrooms share a full bath, while an upstairs library provides a quiet space to read, work, or unwind. The laundry is conveniently located upstairs. A large shed adds valuable storage for kayaks, paddleboards, tools, and more. Don't miss the chance to tweak the options on the home you've been dreaming of in this exceptional waterside neighborhood! Beacon Hill has two access points for the Chesapeake Bay, and one is directly across from this property. It’s an easy commute into downtown Annapolis as well as to commute routes 50 and 97. Schools include Cape St. Claire elementary, Magothy River middle, and Broadneck high school.

4 Beds ⋅ 3 Baths

Welcome to your future home in water-privileged Beacon Hill, where coastal living meets quality new construction. Set on a half-acre lot with a circular driveway, this to-be-built residence will be finished with durable Hardie Plank siding and architectural shingles for lasting beauty and low maintenance. The inviting design features a beautiful porch that wraps around to create a lovely seating area just outside the family room. Inside, 10-foot ceilings and luxury vinyl plank flooring create an airy, elegant main level with an open floor plan made for easy living and more formal entertaining if desired. The gourmet kitchen will inspire any home chef with quartz countertops, stainless steel appliances, and a generous pantry. A main-level bedroom offers flexibility for guests, multi-generational living, or single-level convenience. Upstairs, the primary suite is an oasis, complete with a gas fireplace, a luxurious bath, a walk-in closet, and private access to the veranda, the perfect spot for morning coffee or evening relaxation. Two additional bedrooms share a full bath, while an upstairs library provides a quiet space to read, work, or unwind. The laundry is conveniently located upstairs. A large shed adds valuable storage for kayaks, paddleboards, tools, and more. Don't miss the chance to tweak the options on the home you've been dreaming of in this exceptional waterside neighborhood! Beacon Hill has two access points for the Chesapeake Bay, and one is directly across from this property. It’s an easy commute into downtown Annapolis as well as to commute routes 50 and 97. Schools include Cape St. Claire elementary, Magothy River middle, and Broadneck high school.

1546 Shipsview Rd, Annapolis

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

$1,650,000

Waterfront living with a private pier in Annapolis at an exceptional price in gated Epping Forest! Mid-century modern waterfront sanctuary rises above Saltworks Creek on a quiet protected cove all on a .34 Acre lot—where timeless design meets an ethereal, peaceful connection to the water and outside. Originally built in 1978, the almost 3600 sq. ft residence recently underwent a comprehensive renovation inside and out while honoring Mid-Century authenticity and maintaining an effortless flow and contemporary preference. From the street side, the home presents a timeless silhouette with a recent 70K Elevator with ramp that serves as a secondary entrance servicing 2 out of the 3 levels. Waterside, the home is the ultimate expression of blurring the line between nature and interior with floor to ceiling glass walls, 8' sliding glass doors and unobstructed water views from the deck. This home wasn't designed to look at the water but rather live with it. A massive stone central fireplace is the heart of the living area creating a cozy architectural retreat. Tasteful modernization but true to its mid-century roots, every element of the home has been considered preserving the architectural integrity while offering the comfort and convenience expected today. More than a home, this is a rare opportunity to own a piece of design history- reimagined for modern waterfront living. Current Owners invested 925K on restoration since purchase including elevator, brand new private pier, brand new Kitchen and all 3 Full Baths, selecting high end finishes throughout to create a setting for exceptional everyday living. Epping Forest is a Gated Waterfront Community on the Severn River with a community beach, waterfront clubhouse with restaurant and bar, tennis/pickleball and marina (new marina is currently under construction) Strong neighborhood connections where neighbors treat each other like family and fun happens weekly! Year around community events codify friendships, 4th of July Fireworks, Oyster & Bull Roast, Boat Club, Summer Volleyball League, community chapel, yoga & summer camps. Come experience the best Chesapeake Bay Maritime Annapolitan Lifestyle around! Epping Forest Inc is a special benefit tax district with bylaws and binding rules and regulations. Please see virtual house showcase listing from Zillow and read house bio in documents.

4 Beds ⋅ 3 Baths

Waterfront living with a private pier in Annapolis at an exceptional price in gated Epping Forest! Mid-century modern waterfront sanctuary rises above Saltworks Creek on a quiet protected cove all on a .34 Acre lot—where timeless design meets an ethereal, peaceful connection to the water and outside. Originally built in 1978, the almost 3600 sq. ft residence recently underwent a comprehensive renovation inside and out while honoring Mid-Century authenticity and maintaining an effortless flow and contemporary preference. From the street side, the home presents a timeless silhouette with a recent 70K Elevator with ramp that serves as a secondary entrance servicing 2 out of the 3 levels. Waterside, the home is the ultimate expression of blurring the line between nature and interior with floor to ceiling glass walls, 8' sliding glass doors and unobstructed water views from the deck. This home wasn't designed to look at the water but rather live with it. A massive stone central fireplace is the heart of the living area creating a cozy architectural retreat. Tasteful modernization but true to its mid-century roots, every element of the home has been considered preserving the architectural integrity while offering the comfort and convenience expected today. More than a home, this is a rare opportunity to own a piece of design history- reimagined for modern waterfront living. Current Owners invested 925K on restoration since purchase including elevator, brand new private pier, brand new Kitchen and all 3 Full Baths, selecting high end finishes throughout to create a setting for exceptional everyday living. Epping Forest is a Gated Waterfront Community on the Severn River with a community beach, waterfront clubhouse with restaurant and bar, tennis/pickleball and marina (new marina is currently under construction) Strong neighborhood connections where neighbors treat each other like family and fun happens weekly! Year around community events codify friendships, 4th of July Fireworks, Oyster & Bull Roast, Boat Club, Summer Volleyball League, community chapel, yoga & summer camps. Come experience the best Chesapeake Bay Maritime Annapolitan Lifestyle around! Epping Forest Inc is a special benefit tax district with bylaws and binding rules and regulations. Please see virtual house showcase listing from Zillow and read house bio in documents.

1739 Vineyard Trl, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$399,900

COMPLETELY RENOVATED & MOVE-IN READY IN CEDAR RIDGE! After 30 years of thoughtful ownership and meticulous care, this beautifully updated 3-bedroom, 2½-bath townhouse is ready for its next chapter. The pride of ownership is evident throughout, with updates made over the years and the home continually improved and maintained. The improvements begin with replacement windows installed in 2000 and continue to today with a beautifully updated kitchen featuring newer cabinetry, countertops, and appliances. All three bathrooms have been updated, and the HVAC system and hot water heater have both been replaced within the past four years. One of the home's standout features is the incredible amount of storage. The current owner made exceptional use of The Container Store's organizing systems throughout the home, maximizing virtually every inch of available space. Even the full-size stacked washer and dryer provide additional room and functionality. One bedroom is currently being used as a home office and features a Murphy bed that easily accommodates overnight guests. Step through the kitchen's sliding glass door and you'll discover a completely private, fenced rear yard with a beautiful patio—perfect for grilling, entertaining, or simply enjoying your own outdoor space. The kitchen's location directly off the patio makes indoor/outdoor entertaining easy. And then there's Cedar Ridge! Enjoy the convenience of an HOA that takes care of the exterior maintenance, including the roof and siding, helping provide greater predictability for homeowners. The community also offers a swimming pool and Tot Lot. Best of all, you're within walking distance of Eastport and downtown Annapolis, with its wonderful restaurants, shops, waterfront, and everything that makes the Annapolis lifestyle so special. This is a home that has been lovingly cared for, thoughtfully updated, and designed for comfortable living. Truly move-in ready—just unpack and enjoy! Schedule your private showing today. This one won't last long!

3 Beds ⋅ 3 Baths

COMPLETELY RENOVATED & MOVE-IN READY IN CEDAR RIDGE! After 30 years of thoughtful ownership and meticulous care, this beautifully updated 3-bedroom, 2½-bath townhouse is ready for its next chapter. The pride of ownership is evident throughout, with updates made over the years and the home continually improved and maintained. The improvements begin with replacement windows installed in 2000 and continue to today with a beautifully updated kitchen featuring newer cabinetry, countertops, and appliances. All three bathrooms have been updated, and the HVAC system and hot water heater have both been replaced within the past four years. One of the home's standout features is the incredible amount of storage. The current owner made exceptional use of The Container Store's organizing systems throughout the home, maximizing virtually every inch of available space. Even the full-size stacked washer and dryer provide additional room and functionality. One bedroom is currently being used as a home office and features a Murphy bed that easily accommodates overnight guests. Step through the kitchen's sliding glass door and you'll discover a completely private, fenced rear yard with a beautiful patio—perfect for grilling, entertaining, or simply enjoying your own outdoor space. The kitchen's location directly off the patio makes indoor/outdoor entertaining easy. And then there's Cedar Ridge! Enjoy the convenience of an HOA that takes care of the exterior maintenance, including the roof and siding, helping provide greater predictability for homeowners. The community also offers a swimming pool and Tot Lot. Best of all, you're within walking distance of Eastport and downtown Annapolis, with its wonderful restaurants, shops, waterfront, and everything that makes the Annapolis lifestyle so special. This is a home that has been lovingly cared for, thoughtfully updated, and designed for comfortable living. Truly move-in ready—just unpack and enjoy! Schedule your private showing today. This one won't last long!

1045 Cedar Ridge Ct, Annapolis

Listing courtesy of Academy Realty Inc.. Contact:

$399,000

Welcome to 71 Harbour Heights Drive, a well-appointed 3-bedroom, 2.5-bath home offering comfortable living in an incredibly convenient Annapolis location. The eat-in kitchen features granite countertops, a newer farmhouse-style sink, and refrigerator, stove, and microwave, with easy access to a private balcony—perfect for enjoying your morning coffee or a little fresh air. On cooler days, you can warm the kitchen with your gas fireplace. Upstairs, the spacious primary suite features a vaulted ceiling with ceiling fan, walk-in closet, and en suite bath with a double vanity. Two additional bedrooms, a full bath, and a conveniently located washer and dryer complete the bedroom level. Fantastic storage is available throughout the home, including a large coat closet at the entry and another large, deep closet on the main living level. In addition, a ground-level storage area provides plenty of room for bikes, paddle boards, trash cans, outdoor gear, and more—an especially useful bonus for an Annapolis lifestyle. Located just off Bestgate Road, this home is just minutes from Downtown Annapolis. The home also offers easy access to Trader Joe’s, Safeway, Annapolis Mall, shopping, dining, coffee shops, professional services, and major commuter routes. Sidewalks throughout the area add to the neighborhood’s walkability, putting everyday conveniences close at hand. A great opportunity to enjoy low-maintenance living with easy access to everything Annapolis has to offer.

3 Beds ⋅ 3 Baths

Welcome to 71 Harbour Heights Drive, a well-appointed 3-bedroom, 2.5-bath home offering comfortable living in an incredibly convenient Annapolis location. The eat-in kitchen features granite countertops, a newer farmhouse-style sink, and refrigerator, stove, and microwave, with easy access to a private balcony—perfect for enjoying your morning coffee or a little fresh air. On cooler days, you can warm the kitchen with your gas fireplace. Upstairs, the spacious primary suite features a vaulted ceiling with ceiling fan, walk-in closet, and en suite bath with a double vanity. Two additional bedrooms, a full bath, and a conveniently located washer and dryer complete the bedroom level. Fantastic storage is available throughout the home, including a large coat closet at the entry and another large, deep closet on the main living level. In addition, a ground-level storage area provides plenty of room for bikes, paddle boards, trash cans, outdoor gear, and more—an especially useful bonus for an Annapolis lifestyle. Located just off Bestgate Road, this home is just minutes from Downtown Annapolis. The home also offers easy access to Trader Joe’s, Safeway, Annapolis Mall, shopping, dining, coffee shops, professional services, and major commuter routes. Sidewalks throughout the area add to the neighborhood’s walkability, putting everyday conveniences close at hand. A great opportunity to enjoy low-maintenance living with easy access to everything Annapolis has to offer.

71 Harbour Hts Unit 71, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

$525,000

Pristine and move-in ready, 2 Silopanna Court offers just over 2000 square feet of flexible living space inside Annapolis city limits, minutes from Eastport and historic downtown. A well-planned addition expanded the home to include a spacious upstairs primary suite and a separate family room with an adjoining office area on the main level. The primary suite features a walk-in closet and a private bath, with sliding doors that open to its own balcony. Three additional generously sized bedrooms share a second full bath, keeping all four bedrooms together upstairs. A main-level powder room adds convenience for guests. A full wall of built-in shelving and cabinetry gives the living room character and ample storage. The kitchen features white cabinets and stainless steel appliances and opens to a dining area with sliding doors to the backyard patio. The family room provides space to spread out, while the adjoining office or sitting area accommodates working from home. Outside, the fenced backyard offers room to garden or play beneath mature trees. A broad paver patio extends the living space outdoors, with plenty of room for dining and gathering. A separate shed keeps tools and outdoor equipment neatly stored and out of sight. Just steps from the house, a wooded trail leads toward Spa Creek for waterside walks and opportunities to spot herons and turtles. Nearby waterfront parks include Amos Garrett, where a pier and water taxi pickup offer another way to enjoy Annapolis and reach Eastport or downtown. In the opposite direction, a footbridge connects to Truxtun Park and the city’s public pool. Maryland Hall is a short walk away, with West Street cafes and local restaurants close by. Historic downtown Annapolis offers shopping and live theater, along with waterfront dining and community events throughout the year. Welcome Home!

4 Beds ⋅ 3 Baths

Pristine and move-in ready, 2 Silopanna Court offers just over 2000 square feet of flexible living space inside Annapolis city limits, minutes from Eastport and historic downtown. A well-planned addition expanded the home to include a spacious upstairs primary suite and a separate family room with an adjoining office area on the main level. The primary suite features a walk-in closet and a private bath, with sliding doors that open to its own balcony. Three additional generously sized bedrooms share a second full bath, keeping all four bedrooms together upstairs. A main-level powder room adds convenience for guests. A full wall of built-in shelving and cabinetry gives the living room character and ample storage. The kitchen features white cabinets and stainless steel appliances and opens to a dining area with sliding doors to the backyard patio. The family room provides space to spread out, while the adjoining office or sitting area accommodates working from home. Outside, the fenced backyard offers room to garden or play beneath mature trees. A broad paver patio extends the living space outdoors, with plenty of room for dining and gathering. A separate shed keeps tools and outdoor equipment neatly stored and out of sight. Just steps from the house, a wooded trail leads toward Spa Creek for waterside walks and opportunities to spot herons and turtles. Nearby waterfront parks include Amos Garrett, where a pier and water taxi pickup offer another way to enjoy Annapolis and reach Eastport or downtown. In the opposite direction, a footbridge connects to Truxtun Park and the city’s public pool. Maryland Hall is a short walk away, with West Street cafes and local restaurants close by. Historic downtown Annapolis offers shopping and live theater, along with waterfront dining and community events throughout the year. Welcome Home!

2 Silopanna Ct, Annapolis

Listing courtesy of Compass. Contact:

$1,700,000

Experience the ultimate walkable lifestyle in the heart of Downtown Annapolis with this charming traditional home in the Historic District, where timeless character meets modern comfort. Built in 1900, this inviting residence captures the quintessential charm of Annapolis while offering thoughtful updates and the conveniences of contemporary living. Steps away from the welcoming front porch you'll find boutique shops, waterfront dining, historic landmarks, and the U.S. Naval Academy. Inside, original hardwood floors and classic architectural details create a warm and inviting atmosphere. The layout features three bedrooms, two full bathrooms, and a half bath. The main level offers comfortable living and entertaining spaces along with a welcoming kitchen, while a carefully renovated room addition provides valuable additional living space. The primary bathroom has been beautifully styled with a luxurious spa-like feel, creating a peaceful retreat at the end of the day. Outdoor living is equally inviting, with a private patio and lush turf yard overlooking Cumberland Court—an ideal setting for morning coffee, al fresco dining, summer gatherings, or simply enjoying the charm of downtown living. Surrounded by the history, culture, shops, restaurants, and waterfront that make the Historic District so special, this distinctive home offers an authentic Annapolis lifestyle, blending historic charm, modern comfort, exceptional walkability, and an unusually generous amount of private parking.

3 Beds ⋅ 3 Baths

Experience the ultimate walkable lifestyle in the heart of Downtown Annapolis with this charming traditional home in the Historic District, where timeless character meets modern comfort. Built in 1900, this inviting residence captures the quintessential charm of Annapolis while offering thoughtful updates and the conveniences of contemporary living. Steps away from the welcoming front porch you'll find boutique shops, waterfront dining, historic landmarks, and the U.S. Naval Academy. Inside, original hardwood floors and classic architectural details create a warm and inviting atmosphere. The layout features three bedrooms, two full bathrooms, and a half bath. The main level offers comfortable living and entertaining spaces along with a welcoming kitchen, while a carefully renovated room addition provides valuable additional living space. The primary bathroom has been beautifully styled with a luxurious spa-like feel, creating a peaceful retreat at the end of the day. Outdoor living is equally inviting, with a private patio and lush turf yard overlooking Cumberland Court—an ideal setting for morning coffee, al fresco dining, summer gatherings, or simply enjoying the charm of downtown living. Surrounded by the history, culture, shops, restaurants, and waterfront that make the Historic District so special, this distinctive home offers an authentic Annapolis lifestyle, blending historic charm, modern comfort, exceptional walkability, and an unusually generous amount of private parking.

219 King George St, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$560,000

Welcome to 1182 Bay Highlands Drive in Annapolis! This solid home offers a great opportunity for buyers looking to make a property their own in an established Annapolis community. The major systems have been replaced within the past few years, providing a strong foundation for future improvements. The home is ready for updating and TLC, including cosmetic improvements to the kitchen, baths, flooring, and finishes. With the major systems already addressed, buyers can focus on renovations and personal touches to bring out the home's full potential. The asking price is reflective of the home's current condition and the updates needed. Property is being sold strictly "AS IS." Seller will make no repairs. A great opportunity for buyers with vision who want to customize a solid home and build equity in Annapolis.

3 Beds ⋅ 3 Baths

Welcome to 1182 Bay Highlands Drive in Annapolis! This solid home offers a great opportunity for buyers looking to make a property their own in an established Annapolis community. The major systems have been replaced within the past few years, providing a strong foundation for future improvements. The home is ready for updating and TLC, including cosmetic improvements to the kitchen, baths, flooring, and finishes. With the major systems already addressed, buyers can focus on renovations and personal touches to bring out the home's full potential. The asking price is reflective of the home's current condition and the updates needed. Property is being sold strictly "AS IS." Seller will make no repairs. A great opportunity for buyers with vision who want to customize a solid home and build equity in Annapolis.

1182 Bay Highlands Dr, Annapolis

Listing courtesy of CENTURY 21 New Millennium. Contact:

$520,000

Beautifully appointed rancher in the sought-after Cape St. Claire community of Annapolis, just one block from the Magothy River and the Chesapeake Bay! Step inside to a spacious main level featuring gleaming hardwood floors and a bright, open living room centered around a tile-surround wood-burning fireplace with a reclaimed-style mantle and custom open shelving. The flowing layout leads seamlessly into the dining area, offering ample storage and direct access to a screened-in deck, perfect for indoor-outdoor living. The kitchen is thoughtfully designed with granite countertops, a classic subway tile backsplash, 36” cabinetry, and stainless steel appliances. The primary suite provides a comfortable retreat with crown molding, a generously sized closet with an organization system, and a private en-suite bath complete with a walk-in shower and updated vanity. Two additional bedrooms and a well-appointed hall bath complete the main level. The finished lower level expands your living space with plush carpeting, built-in shelving, a dedicated workshop, gym area, and a utility space featuring a convenient powder room, ideal for guests, a home office, or multigenerational living. Enjoy outdoor living in the fully fenced yard with a patio and secure storage, perfect for entertaining or relaxing. Conveniently located near major commuter routes, including US-50 and I-97, for easy access to Annapolis, Baltimore, and beyond.

3 Beds ⋅ 3 Baths

Beautifully appointed rancher in the sought-after Cape St. Claire community of Annapolis, just one block from the Magothy River and the Chesapeake Bay! Step inside to a spacious main level featuring gleaming hardwood floors and a bright, open living room centered around a tile-surround wood-burning fireplace with a reclaimed-style mantle and custom open shelving. The flowing layout leads seamlessly into the dining area, offering ample storage and direct access to a screened-in deck, perfect for indoor-outdoor living. The kitchen is thoughtfully designed with granite countertops, a classic subway tile backsplash, 36” cabinetry, and stainless steel appliances. The primary suite provides a comfortable retreat with crown molding, a generously sized closet with an organization system, and a private en-suite bath complete with a walk-in shower and updated vanity. Two additional bedrooms and a well-appointed hall bath complete the main level. The finished lower level expands your living space with plush carpeting, built-in shelving, a dedicated workshop, gym area, and a utility space featuring a convenient powder room, ideal for guests, a home office, or multigenerational living. Enjoy outdoor living in the fully fenced yard with a patio and secure storage, perfect for entertaining or relaxing. Conveniently located near major commuter routes, including US-50 and I-97, for easy access to Annapolis, Baltimore, and beyond.

1030 Mountain Top Dr, Annapolis

Listing courtesy of Northrop Realty. Contact:

$1,700,000

Come see this beautiful one-of-a-kind WATERFRONT property! Complete waterfront view from both levels of this home and every room. True master bedroom and large enough to fit a king-size bedroom suite and private bathroom. Covered patio to enjoy the view in every weather type! Large windows throughout the home brings in natural light while keeping the waterfront setting front and center. There are fireplaces on each level. Swim all year round with this heated indoor pool and hot tub. Dock rental slips are available for owners for a $500 fee for deep water (6ft) or lower water slips for $200 (3ft) with electricity. This property can have a personal pier added not to mention Just steps away from the community beach and docks. Arundel on the Bay also offers a community beach and an established waterfront neighborhood just minutes from everything Annapolis has to offer.

4 Beds ⋅ 3 Baths

Come see this beautiful one-of-a-kind WATERFRONT property! Complete waterfront view from both levels of this home and every room. True master bedroom and large enough to fit a king-size bedroom suite and private bathroom. Covered patio to enjoy the view in every weather type! Large windows throughout the home brings in natural light while keeping the waterfront setting front and center. There are fireplaces on each level. Swim all year round with this heated indoor pool and hot tub. Dock rental slips are available for owners for a $500 fee for deep water (6ft) or lower water slips for $200 (3ft) with electricity. This property can have a personal pier added not to mention Just steps away from the community beach and docks. Arundel on the Bay also offers a community beach and an established waterfront neighborhood just minutes from everything Annapolis has to offer.

1323 Magnolia Ave, Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

$895,000

Nestled within the serene embrace of nature, enjoy fabulous waterfront views of Hawkins Cove and Spa Creek from this stunning 2-bedroom, 2.5-bathroom penthouse condominium in the highly sought-after community of Shearwater in Eastport. With a contemporary coastal architectural style, this home is a perfect blend of sophistication and warmth. Step inside to discover an open floor plan that seamlessly integrates the living and dining areas, enhanced by a stunning spiral staircase that adds a touch of architectural flair. The living area is accentuated by cathedral ceilings. Natural light floods the space through skylights, creating an inviting atmosphere throughout. The flat was entirely upgraded by an interior design firm in 2024, featuring gleaming living room floors, new windows and a gourmet kitchen designed to elevate your culinary creations. This penthouse features an abundance of chic finishes including Spa-inspired luxury bathrooms. Of particular note is the upper level Master suite artfully designed and fashioned from what was a large open balcony. It features a private and cozy retreat with a luxurious ensuite bathroom. A home office has been thoughtfully designed with elegant built ins on the upper level. The main floor bedroom also offers ample space and privacy, making it ideal for guests. The exterior of the property is equally impressive, boasting a private balcony that overlooks the lush landscaping and the waterfront, providing a peaceful escape right from your terrace. This truly is a nature watchers’ paradise. In December, celebrate the famous Eastport Yacht Club annual Parade of Lights in style by your cozy wood-burning fireplace. In Spring/Summer enjoy the easy breeze with family and friends with your favorite libation. For water enthusiasts, the property offers direct access to Hawkins Cove and Spa Creek, complete with a private dock site and multiple slips for boating, fishing, and kayaking adventures. Surrounded by partly wooded areas and mature trees, the lot features a harmonious blend of nature and luxury, creating a serene environment for relaxation and recreation. It offers seamless access to the Chesapeake Bay and beyond. Your luxury lifestyle features the choice to relax poolside, play tennis/pickleball on the courts, or take a water taxi from the docks to enjoy the stunning array of restaurants, events, the arts and much more. Welcome home, your Annapolis dream has come true!

2 Beds ⋅ 3 Baths

Nestled within the serene embrace of nature, enjoy fabulous waterfront views of Hawkins Cove and Spa Creek from this stunning 2-bedroom, 2.5-bathroom penthouse condominium in the highly sought-after community of Shearwater in Eastport. With a contemporary coastal architectural style, this home is a perfect blend of sophistication and warmth. Step inside to discover an open floor plan that seamlessly integrates the living and dining areas, enhanced by a stunning spiral staircase that adds a touch of architectural flair. The living area is accentuated by cathedral ceilings. Natural light floods the space through skylights, creating an inviting atmosphere throughout. The flat was entirely upgraded by an interior design firm in 2024, featuring gleaming living room floors, new windows and a gourmet kitchen designed to elevate your culinary creations. This penthouse features an abundance of chic finishes including Spa-inspired luxury bathrooms. Of particular note is the upper level Master suite artfully designed and fashioned from what was a large open balcony. It features a private and cozy retreat with a luxurious ensuite bathroom. A home office has been thoughtfully designed with elegant built ins on the upper level. The main floor bedroom also offers ample space and privacy, making it ideal for guests. The exterior of the property is equally impressive, boasting a private balcony that overlooks the lush landscaping and the waterfront, providing a peaceful escape right from your terrace. This truly is a nature watchers’ paradise. In December, celebrate the famous Eastport Yacht Club annual Parade of Lights in style by your cozy wood-burning fireplace. In Spring/Summer enjoy the easy breeze with family and friends with your favorite libation. For water enthusiasts, the property offers direct access to Hawkins Cove and Spa Creek, complete with a private dock site and multiple slips for boating, fishing, and kayaking adventures. Surrounded by partly wooded areas and mature trees, the lot features a harmonious blend of nature and luxury, creating a serene environment for relaxation and recreation. It offers seamless access to the Chesapeake Bay and beyond. Your luxury lifestyle features the choice to relax poolside, play tennis/pickleball on the courts, or take a water taxi from the docks to enjoy the stunning array of restaurants, events, the arts and much more. Welcome home, your Annapolis dream has come true!

8 Spa Creek Lndg Unit A3, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

$879,000

Welcome Arundel on the Bay - a water oriented lifestyle community offering access to kayaking, paddle-boarding, beach and playground. All this with close proximity to shopping, restaurants, parks and downtown Annapolis. The quiet and calm neighborhood offers an island-like feeling. And this striking 3-story home is absolutely MOVE-IN READY! Gracious and plentiful windows leave you appreciating the timeless perennial gardens, majestic trees and peeks at Fishing Creek from multiple locations. As Fall arrives the "peeks" will become relaxing and lovely views! A bright and open floorplan features architectural lines and high ceilings which enhance the home's airy, gallery-like feel. Stunning wood floors offer warmth and continue the feeling of openness. We hope you like to cook and entertain - this Kitchen makes it not only possible but inviting and engaging. Extend your morning or evening and take a step out to the private back Deck tucked in to give you an intimate feeling with a lovely pergola and hanging lights. And it is only one of three Decks. The Primary Suite is magazine worthy - morning coffee on your Deck with lovely views or an evening toast to the day. Two more very spacious Bedrooms and updated Bath complete the 2nd Floor. And then the 3d Floor is worthy of the term "RETREAT". A wall of floor to ceiling windows with a side view of Fishing Creek and views of the trees and gardens below is icing on the cake! Amazing Community Features: Magnolia Avenue Beach, Newport Avenue Community Pier, Linden Avenue Recreational Pier, Redwood Avenue launching pier/boat ramp, and playgrounds.

3 Beds ⋅ 3 Baths

Welcome Arundel on the Bay - a water oriented lifestyle community offering access to kayaking, paddle-boarding, beach and playground. All this with close proximity to shopping, restaurants, parks and downtown Annapolis. The quiet and calm neighborhood offers an island-like feeling. And this striking 3-story home is absolutely MOVE-IN READY! Gracious and plentiful windows leave you appreciating the timeless perennial gardens, majestic trees and peeks at Fishing Creek from multiple locations. As Fall arrives the "peeks" will become relaxing and lovely views! A bright and open floorplan features architectural lines and high ceilings which enhance the home's airy, gallery-like feel. Stunning wood floors offer warmth and continue the feeling of openness. We hope you like to cook and entertain - this Kitchen makes it not only possible but inviting and engaging. Extend your morning or evening and take a step out to the private back Deck tucked in to give you an intimate feeling with a lovely pergola and hanging lights. And it is only one of three Decks. The Primary Suite is magazine worthy - morning coffee on your Deck with lovely views or an evening toast to the day. Two more very spacious Bedrooms and updated Bath complete the 2nd Floor. And then the 3d Floor is worthy of the term "RETREAT". A wall of floor to ceiling windows with a side view of Fishing Creek and views of the trees and gardens below is icing on the cake! Amazing Community Features: Magnolia Avenue Beach, Newport Avenue Community Pier, Linden Avenue Recreational Pier, Redwood Avenue launching pier/boat ramp, and playgrounds.

3401 Saratoga Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$974,990

Construction is underway — and something truly special is taking shape! Schaefer Homes is proud to present this stunning newly constructed Colonial in the prestigious Oyster Harbor community, with a target completion date of November 2026. From the moment construction began, every detail has been thoughtfully considered to deliver a home that is as beautiful as it is livable. Set on a sprawling 0.62-acre lot, this exceptional residence offers the kind of space and privacy that is increasingly rare — plenty of room to create the outdoor oasis you've always envisioned, whether that's a garden retreat, entertaining terrace, or simply wide open space to enjoy the beauty of your surroundings. Inside, the elegant Colonial layout unfolds beautifully across a thoughtfully designed floor plan featuring 4 spacious bedrooms and 2.5 elegantly appointed bathrooms. The showstopping gourmet kitchen is the heart of the home, outfitted with upgraded design features and premium finishes that will inspire everything from weeknight dinners to unforgettable gatherings with family and friends. From its classic vinyl siding exterior to its sophisticated interior appointments, this home strikes the perfect balance between timeless architectural charm and the fresh, modern feel of new construction. Every finish, every detail, and every design choice reflects the quality and craftsmanship that Schaefer Homes is known for throughout Maryland. Oyster Harbor is more than a community — it's a lifestyle. Serene, exclusive, and truly one of a kind, this is the kind of neighborhood where neighbors become friends and every day feels like a retreat. This is your opportunity to plant roots in one of the area's most sought-after addresses. Don't wait — opportunities like this don't come around often. Schedule your private appointment today and take the first step toward making this dream home yours!

4 Beds ⋅ 3 Baths

Construction is underway — and something truly special is taking shape! Schaefer Homes is proud to present this stunning newly constructed Colonial in the prestigious Oyster Harbor community, with a target completion date of November 2026. From the moment construction began, every detail has been thoughtfully considered to deliver a home that is as beautiful as it is livable. Set on a sprawling 0.62-acre lot, this exceptional residence offers the kind of space and privacy that is increasingly rare — plenty of room to create the outdoor oasis you've always envisioned, whether that's a garden retreat, entertaining terrace, or simply wide open space to enjoy the beauty of your surroundings. Inside, the elegant Colonial layout unfolds beautifully across a thoughtfully designed floor plan featuring 4 spacious bedrooms and 2.5 elegantly appointed bathrooms. The showstopping gourmet kitchen is the heart of the home, outfitted with upgraded design features and premium finishes that will inspire everything from weeknight dinners to unforgettable gatherings with family and friends. From its classic vinyl siding exterior to its sophisticated interior appointments, this home strikes the perfect balance between timeless architectural charm and the fresh, modern feel of new construction. Every finish, every detail, and every design choice reflects the quality and craftsmanship that Schaefer Homes is known for throughout Maryland. Oyster Harbor is more than a community — it's a lifestyle. Serene, exclusive, and truly one of a kind, this is the kind of neighborhood where neighbors become friends and every day feels like a retreat. This is your opportunity to plant roots in one of the area's most sought-after addresses. Don't wait — opportunities like this don't come around often. Schedule your private appointment today and take the first step toward making this dream home yours!

3268 Kitty Duvall Dr, Annapolis

Listing courtesy of Blackwell Real Estate, LLC. Contact:

$850,000

Welcome to 327 Beach Drive, where thoughtful design, quality craftsmanship, and the relaxed Annapolis lifestyle come together in the heart of Hillsmere Shores a waterfront community. Completely transformed with a warm, modern aesthetic, this 4-bedroom, 3-bath home offers approximately 2,450 square feet of beautifully finished living space. From the moment you arrive, the crisp white board-and-batten exterior and inviting curb appeal set the tone. Inside, brand-new natural birch flooring, solid wood interior doors, crown molding, recessed lighting, and carefully selected finishes create a bright, cohesive feel throughout the main level. The open living spaces are designed for both everyday living and entertaining, highlighted by a custom shiplap fireplace that adds warmth and character. The kitchen flows naturally into the surrounding living and dining areas, creating an easy gathering space at the center of the home. A fully permitted addition created a stunning primary suite that feels like a private retreat, complete with a spacious bedroom, walk-in closet, and beautifully finished luxury bath. The additional main-level bedrooms are complemented by a custom-designed hall bathroom with timeless finishes and attention to detail. The finished lower level adds even more flexibility with a fourth bedroom, full bath, home office, additional living space, laundry, and storage—ideal for guests, working from home, or creating a separate recreation area. Outside, the large, level .41-acre lot is fully fenced and offers exceptional space for entertaining, pets, play, or gardening. A low-maintenance Trex patio extends the living space outdoors and provides the perfect setting for summer dinners, grilling, and relaxing with friends. Located in sought-after Hillsmere Shores with access to the community’s waterfront lifestyle and amenities of marinas, beach and pool, 327 Beach Drive offers the rare combination of a beautifully renovated home, generous outdoor space, flexible living areas, and an Annapolis location that makes it easy to enjoy everything the area has to offer. This isn’t simply an updated home—it has been thoughtfully redesigned for the way you want to live.

4 Beds ⋅ 3 Baths

Welcome to 327 Beach Drive, where thoughtful design, quality craftsmanship, and the relaxed Annapolis lifestyle come together in the heart of Hillsmere Shores a waterfront community. Completely transformed with a warm, modern aesthetic, this 4-bedroom, 3-bath home offers approximately 2,450 square feet of beautifully finished living space. From the moment you arrive, the crisp white board-and-batten exterior and inviting curb appeal set the tone. Inside, brand-new natural birch flooring, solid wood interior doors, crown molding, recessed lighting, and carefully selected finishes create a bright, cohesive feel throughout the main level. The open living spaces are designed for both everyday living and entertaining, highlighted by a custom shiplap fireplace that adds warmth and character. The kitchen flows naturally into the surrounding living and dining areas, creating an easy gathering space at the center of the home. A fully permitted addition created a stunning primary suite that feels like a private retreat, complete with a spacious bedroom, walk-in closet, and beautifully finished luxury bath. The additional main-level bedrooms are complemented by a custom-designed hall bathroom with timeless finishes and attention to detail. The finished lower level adds even more flexibility with a fourth bedroom, full bath, home office, additional living space, laundry, and storage—ideal for guests, working from home, or creating a separate recreation area. Outside, the large, level .41-acre lot is fully fenced and offers exceptional space for entertaining, pets, play, or gardening. A low-maintenance Trex patio extends the living space outdoors and provides the perfect setting for summer dinners, grilling, and relaxing with friends. Located in sought-after Hillsmere Shores with access to the community’s waterfront lifestyle and amenities of marinas, beach and pool, 327 Beach Drive offers the rare combination of a beautifully renovated home, generous outdoor space, flexible living areas, and an Annapolis location that makes it easy to enjoy everything the area has to offer. This isn’t simply an updated home—it has been thoughtfully redesigned for the way you want to live.

327 Beach Dr, Annapolis

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

$1,250,000

Welcome to 313 Fourth St, one of only three townhomes at The Tecumseh and a rare opportunity in one of Eastport’s most distinctive waterfront communities. Completed in 1968 on the site of a former boatyard, The Tecumseh was Annapolis’s earliest condominium communities, designed around the boating lifestyle that continues to define Eastport today. Set directly on Spa Creek, the community offers a 72-slip private marina, waterfront swimming pool and deck, and gated private parking. Located at the corner of Fourth St and Severn Ave, this three-story, approximately 2,700-square-foot residence offers three bedrooms, two-and-a-half baths, expansive third-floor bonus space, charming Eastport street appeal, and a private rear courtyard. The main level is filled with character, featuring charming arched details, a newly renovated powder room, spacious kitchen with breakfast nook, dining area, walk-in butler’s pantry, and custom built-in bookshelves surrounding a gas fireplace. A generous living area opens through sliding glass doors to a private courtyard with a paved patio—perfect for dining al fresco and entertaining. Upstairs, the second floor features a spacious primary suite with an ensuite bath and two closets, plus two additional bedrooms that share a full bath. The third floor surprises with vaulted ceilings, a large finished bonus room, additional unfinished space, and a laundry area—offering tremendous flexibility for a home office, gym, playroom, studio, or additional living space. Just beyond your back door is direct access to The Tecumseh’s waterfront amenities, including its marina and waterfront swimming pool. For the boater, ownership also includes a 40-foot boat slip entitlement. What truly sets this property apart is the lifestyle. Step outside and you’re moments from Spa Creek and just steps from Eastport’s Restaurant Row, while downtown Annapolis is easily accessible across the bridge. Rarely available, 313 Fourth St offers the opportunity to become part of a waterfront community cherished for its history, location, boating lifestyle, and enduring connection to Annapolis’s maritime heritage. The Tecumseh Condominium has a 15-day first right of refusal.

3 Beds ⋅ 3 Baths

Welcome to 313 Fourth St, one of only three townhomes at The Tecumseh and a rare opportunity in one of Eastport’s most distinctive waterfront communities. Completed in 1968 on the site of a former boatyard, The Tecumseh was Annapolis’s earliest condominium communities, designed around the boating lifestyle that continues to define Eastport today. Set directly on Spa Creek, the community offers a 72-slip private marina, waterfront swimming pool and deck, and gated private parking. Located at the corner of Fourth St and Severn Ave, this three-story, approximately 2,700-square-foot residence offers three bedrooms, two-and-a-half baths, expansive third-floor bonus space, charming Eastport street appeal, and a private rear courtyard. The main level is filled with character, featuring charming arched details, a newly renovated powder room, spacious kitchen with breakfast nook, dining area, walk-in butler’s pantry, and custom built-in bookshelves surrounding a gas fireplace. A generous living area opens through sliding glass doors to a private courtyard with a paved patio—perfect for dining al fresco and entertaining. Upstairs, the second floor features a spacious primary suite with an ensuite bath and two closets, plus two additional bedrooms that share a full bath. The third floor surprises with vaulted ceilings, a large finished bonus room, additional unfinished space, and a laundry area—offering tremendous flexibility for a home office, gym, playroom, studio, or additional living space. Just beyond your back door is direct access to The Tecumseh’s waterfront amenities, including its marina and waterfront swimming pool. For the boater, ownership also includes a 40-foot boat slip entitlement. What truly sets this property apart is the lifestyle. Step outside and you’re moments from Spa Creek and just steps from Eastport’s Restaurant Row, while downtown Annapolis is easily accessible across the bridge. Rarely available, 313 Fourth St offers the opportunity to become part of a waterfront community cherished for its history, location, boating lifestyle, and enduring connection to Annapolis’s maritime heritage. The Tecumseh Condominium has a 15-day first right of refusal.

313 Fourth St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$995,000

A long private lane beneath a canopy of mature trees leads to a distinctive mid-century modern retreat that feels worlds away, yet is just minutes from the restaurants, shopping, and everyday conveniences of Annapolis. Tucked into the woods in the sought-after Downs on the Severn, this four-season sanctuary offers the best of both worlds, the privacy and escape of a secluded setting paired with the community and resort-style amenities of one of the area’s most desirable water-privileged neighborhoods. Each season brings a different backdrop. Spring arrives with an explosion of color throughout the surrounding landscape, summer fills the property with lush greenery, fall transforms the tree canopy, and winter reveals the quiet architectural beauty of the home and its wooded setting. The result is a property that feels deeply connected to nature throughout the year. The natural setting is truly part of the experience here. A stream winds through the landscape to a beaver pond, becoming increasingly visible as the leaves begin to fall and adding another beautiful dimension to the views. Wildlife is a regular part of daily life, with deer, wild turkeys, birds, ducks on the pond, and more making frequent appearances. Summer evenings bring the sounds of bullfrogs, while owls can often be heard among the trees. For anyone who appreciates nature and wildlife, the property offers an ever-changing view and soundtrack throughout the seasons. Inside, the home blends contemporary style with the warmth and character of its mid-century roots. Vaulted wood ceilings, exposed beams, brick accents, expansive windows, and multiple skylights create a vintage-meets-modern aesthetic while filling the interiors with natural light. The open floor plan feels relaxed and inviting, with a dramatic brick fireplace anchoring the main gathering spaces. The gourmet kitchen flows easily into the living and dining areas, while walls of glass frame the trees beyond and reinforce the home's connection to its surroundings. Outdoor living is equally inviting. An expansive rear deck stretches across the back of the home, creating a private perch among the trees for morning coffee, outdoor dining, entertaining, or simply taking in the peaceful setting. Below, the walkout lower level opens to a spacious patio and offers additional light-filled living space with a family room, two bedrooms, and a full bath. Large windows continue the connection to nature on both levels. The property also offers a two-car garage that can accommodate most standard sedans, along with a detached two-car carport providing additional covered parking. Recent improvements include a new refrigerator (2026), arborist inspection and tree trimming (September 2026), resurfaced asphalt driveway with one-year warranty (September 2026), new wood floors in the primary bedroom (September 2026), upgraded exterior outlets (2026), septic system service (2026), flue and chimney service and cleaning (2026), new washing machine (2025), exterior painting and repairs (2025), rear deck reinforcement and staining (2024), interior painting throughout (2023), and more. Beyond the privacy of home, Downs on the Severn offers a wonderful sense of community with a deep-water marina, a clubhouse, swimming pool, and tennis/pickleball courts. This special property offers the character of a true Annapolis neighborhood with the feeling of a secluded retreat, an architectural sanctuary in the woods with waterfront recreation and the conveniences of town just minutes away. Welcome Home!

3 Beds ⋅ 3 Baths

A long private lane beneath a canopy of mature trees leads to a distinctive mid-century modern retreat that feels worlds away, yet is just minutes from the restaurants, shopping, and everyday conveniences of Annapolis. Tucked into the woods in the sought-after Downs on the Severn, this four-season sanctuary offers the best of both worlds, the privacy and escape of a secluded setting paired with the community and resort-style amenities of one of the area’s most desirable water-privileged neighborhoods. Each season brings a different backdrop. Spring arrives with an explosion of color throughout the surrounding landscape, summer fills the property with lush greenery, fall transforms the tree canopy, and winter reveals the quiet architectural beauty of the home and its wooded setting. The result is a property that feels deeply connected to nature throughout the year. The natural setting is truly part of the experience here. A stream winds through the landscape to a beaver pond, becoming increasingly visible as the leaves begin to fall and adding another beautiful dimension to the views. Wildlife is a regular part of daily life, with deer, wild turkeys, birds, ducks on the pond, and more making frequent appearances. Summer evenings bring the sounds of bullfrogs, while owls can often be heard among the trees. For anyone who appreciates nature and wildlife, the property offers an ever-changing view and soundtrack throughout the seasons. Inside, the home blends contemporary style with the warmth and character of its mid-century roots. Vaulted wood ceilings, exposed beams, brick accents, expansive windows, and multiple skylights create a vintage-meets-modern aesthetic while filling the interiors with natural light. The open floor plan feels relaxed and inviting, with a dramatic brick fireplace anchoring the main gathering spaces. The gourmet kitchen flows easily into the living and dining areas, while walls of glass frame the trees beyond and reinforce the home's connection to its surroundings. Outdoor living is equally inviting. An expansive rear deck stretches across the back of the home, creating a private perch among the trees for morning coffee, outdoor dining, entertaining, or simply taking in the peaceful setting. Below, the walkout lower level opens to a spacious patio and offers additional light-filled living space with a family room, two bedrooms, and a full bath. Large windows continue the connection to nature on both levels. The property also offers a two-car garage that can accommodate most standard sedans, along with a detached two-car carport providing additional covered parking. Recent improvements include a new refrigerator (2026), arborist inspection and tree trimming (September 2026), resurfaced asphalt driveway with one-year warranty (September 2026), new wood floors in the primary bedroom (September 2026), upgraded exterior outlets (2026), septic system service (2026), flue and chimney service and cleaning (2026), new washing machine (2025), exterior painting and repairs (2025), rear deck reinforcement and staining (2024), interior painting throughout (2023), and more. Beyond the privacy of home, Downs on the Severn offers a wonderful sense of community with a deep-water marina, a clubhouse, swimming pool, and tennis/pickleball courts. This special property offers the character of a true Annapolis neighborhood with the feeling of a secluded retreat, an architectural sanctuary in the woods with waterfront recreation and the conveniences of town just minutes away. Welcome Home!

1707 Trinity Pl, Annapolis

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

$1,675,000

Ideally situated on the corner of Prince George & College Ave(across from St Johns College), this distinguished residence is tucked in the heart of Historic Downtown Annapolis. This exceptional home offers the charm of an Historic home built circa 1800's with modern conveniences. Soaring ceilings and windows create sun-drenched rooms with beautiful views of the grounds at St. Johns College. This home was built for entertaining. It has amazing flow to entertain your guests for a dinner party. Take a short walk to outdoor dining on West Street during "Dinner Under the Stars" or host friends for all the amazing Downtown events like Midnight Madness. This home is in the heart of it all! The electrical and plumbing was updated in 1990, new hot water heater in 2024, 2 heat pumps in 2025 and new Shake Shingle roof in 2026. There are 4 bedrooms and 2 full baths on the second floor with a bonus room on the third floor great for guests or office. All this just 1.5 blocks from the Naval Academy and steps to the shops and amazing restaurants Annapolis has to offer! There is driveway with private parking for 2 cars and plenty of street parking for guests. Walk to City Dock for morning coffee and watch the boats pass by or sit in the morning room and enjoy your coffee looking over the grounds of St. Johns. This is an amazing house in an amazing location with all that Annapolis has to offer.

5 Beds ⋅ 3 Baths

Ideally situated on the corner of Prince George & College Ave(across from St Johns College), this distinguished residence is tucked in the heart of Historic Downtown Annapolis. This exceptional home offers the charm of an Historic home built circa 1800's with modern conveniences. Soaring ceilings and windows create sun-drenched rooms with beautiful views of the grounds at St. Johns College. This home was built for entertaining. It has amazing flow to entertain your guests for a dinner party. Take a short walk to outdoor dining on West Street during "Dinner Under the Stars" or host friends for all the amazing Downtown events like Midnight Madness. This home is in the heart of it all! The electrical and plumbing was updated in 1990, new hot water heater in 2024, 2 heat pumps in 2025 and new Shake Shingle roof in 2026. There are 4 bedrooms and 2 full baths on the second floor with a bonus room on the third floor great for guests or office. All this just 1.5 blocks from the Naval Academy and steps to the shops and amazing restaurants Annapolis has to offer! There is driveway with private parking for 2 cars and plenty of street parking for guests. Walk to City Dock for morning coffee and watch the boats pass by or sit in the morning room and enjoy your coffee looking over the grounds of St. Johns. This is an amazing house in an amazing location with all that Annapolis has to offer.

250 Prince George St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$335,000

Nestled in the charming and convenient Annapolis Overlook community, this inviting townhouse offers a perfect blend of comfort and investment potential. This traditional-style townhome boasts 1,694 square feet of thoughtfully designed living space, making it an ideal choice for both homeowners and savvy investors looking to capitalize on a desirable rental market. Step inside to discover a warm, welcoming interior with an open floor plan that seamlessly connects the kitchen and dining areas. Brand-new luxury vinyl plank flooring highlights the combined living, kitchen, and dining spaces, making it perfect for entertaining with a touch of modern elegance. The kitchen also offers ample table space, making it a cozy spot for casual meals. The home features three spacious bedrooms, including a primary suite that encompasses the entire third floor, with a luxurious walk-in closet and an en-suite bathroom. Additional highlights include a laundry room, a second-floor bathroom, updated lighting, ceiling fans for added comfort, and plush carpeting that enhances the inviting atmosphere throughout. The stainless steel refrigerator and gas range, washer, dryer, carpet, and heat pump have all been updated within the past 5 years. The home has a brand-new storm door and bay window at the front of the house). Homeowners and investors will appreciate the low-maintenance lifestyle this property offers, with an association fee that includes lawn maintenance and snow removal. The community amenities include outdoor common grounds, a refreshing pool, and a fitness center. Parking is hassle-free with two parking permits included -one parking place is assigned and located directly in front of the townhome. An additional car can be parked (with permit), in the "Permit Required" spaces. The community's prime location (close proximity to Quiet Waters Park, Downtown Annapolis, the US Naval Academy, and shopping) ensures easy access to local amenities and attractions. Whether you're looking to buy or invest, this Annapolis Overlook property is a fantastic opportunity. With its blend of modern features, community amenities, and strategic location, it stands ready to deliver both comfort and value for years to come. Don't miss your chance to purchase this delightful home!

3 Beds ⋅ 3 Baths

Nestled in the charming and convenient Annapolis Overlook community, this inviting townhouse offers a perfect blend of comfort and investment potential. This traditional-style townhome boasts 1,694 square feet of thoughtfully designed living space, making it an ideal choice for both homeowners and savvy investors looking to capitalize on a desirable rental market. Step inside to discover a warm, welcoming interior with an open floor plan that seamlessly connects the kitchen and dining areas. Brand-new luxury vinyl plank flooring highlights the combined living, kitchen, and dining spaces, making it perfect for entertaining with a touch of modern elegance. The kitchen also offers ample table space, making it a cozy spot for casual meals. The home features three spacious bedrooms, including a primary suite that encompasses the entire third floor, with a luxurious walk-in closet and an en-suite bathroom. Additional highlights include a laundry room, a second-floor bathroom, updated lighting, ceiling fans for added comfort, and plush carpeting that enhances the inviting atmosphere throughout. The stainless steel refrigerator and gas range, washer, dryer, carpet, and heat pump have all been updated within the past 5 years. The home has a brand-new storm door and bay window at the front of the house). Homeowners and investors will appreciate the low-maintenance lifestyle this property offers, with an association fee that includes lawn maintenance and snow removal. The community amenities include outdoor common grounds, a refreshing pool, and a fitness center. Parking is hassle-free with two parking permits included -one parking place is assigned and located directly in front of the townhome. An additional car can be parked (with permit), in the "Permit Required" spaces. The community's prime location (close proximity to Quiet Waters Park, Downtown Annapolis, the US Naval Academy, and shopping) ensures easy access to local amenities and attractions. Whether you're looking to buy or invest, this Annapolis Overlook property is a fantastic opportunity. With its blend of modern features, community amenities, and strategic location, it stands ready to deliver both comfort and value for years to come. Don't miss your chance to purchase this delightful home!

40 Ironstone Ct Unit B, Annapolis

Listing courtesy of RE/MAX One. Contact:

$755,000

Nestled in the sought-after community of Hunt Meadow, and on a quiet cul-de-sac, this perfectly-kept colonial home offers the right blend of comfort and privacy. Featuring 4 bedrooms and 2.5 baths, a family room with a cozy fireplace, raised hearth and framed in brick. Vaulted ceilings, and custom oak hardwood floors. The kitchen features stainless steel appliances, granite counter tops and modern plank flooring. The entire second level and stairs feature all NEW carpeting. The primary bedroom has a spacious en-suite bath. Two additional bedrooms and an additional full bath are on this level. The finished basement offers additional space for recreation with a Movie Room featuring a large TV screen, movie projector and stereo system that all conveys with the property. A walk-in cedar-lined storage closet, a laundry room with front-load washer and dryer, and a fourth bedroom. The exterior features a brand NEW deck, and fire pit - ideal for enjoying the quiet outdoors. The back yard is private, partly wooded, and has trails leading from it for exploration. The garage is equipped with shelves and a workbench for projects. Residents enjoy access to community amenities such as the large outdoor pool, tennis courts, and scenic jog/walk paths that connect to Quiet Waters Park. The neighborhood is well-maintained, with sidewalks for leisurely strolls. Lots of community spirit here with swim meets, 5k runs, food trucks, holiday celebrations and other get-togethers. Hunt Meadow is just minutes from downtown Annapolis and convenient to Rts. 97 and 50

4 Beds ⋅ 3 Baths

Nestled in the sought-after community of Hunt Meadow, and on a quiet cul-de-sac, this perfectly-kept colonial home offers the right blend of comfort and privacy. Featuring 4 bedrooms and 2.5 baths, a family room with a cozy fireplace, raised hearth and framed in brick. Vaulted ceilings, and custom oak hardwood floors. The kitchen features stainless steel appliances, granite counter tops and modern plank flooring. The entire second level and stairs feature all NEW carpeting. The primary bedroom has a spacious en-suite bath. Two additional bedrooms and an additional full bath are on this level. The finished basement offers additional space for recreation with a Movie Room featuring a large TV screen, movie projector and stereo system that all conveys with the property. A walk-in cedar-lined storage closet, a laundry room with front-load washer and dryer, and a fourth bedroom. The exterior features a brand NEW deck, and fire pit - ideal for enjoying the quiet outdoors. The back yard is private, partly wooded, and has trails leading from it for exploration. The garage is equipped with shelves and a workbench for projects. Residents enjoy access to community amenities such as the large outdoor pool, tennis courts, and scenic jog/walk paths that connect to Quiet Waters Park. The neighborhood is well-maintained, with sidewalks for leisurely strolls. Lots of community spirit here with swim meets, 5k runs, food trucks, holiday celebrations and other get-togethers. Hunt Meadow is just minutes from downtown Annapolis and convenient to Rts. 97 and 50

303 Riding Ridge Rd, Annapolis

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

$449,000

Back On The Market Through No Fault Of The Seller!! A wonderful second opportunity for buyers who missed it the first time!! Beautifully updated and move-in ready in an ideal Annapolis location! HVAC, ROOF, & HOT WATER HEATER ALL REPLACED APPROX. 2021. This inviting home has been thoughtfully refreshed with updated kitchen finishes, new flooring, fresh interior paint and beautifully updated bathrooms, creating a bright, fresh feel throughout. The main level offers a comfortable, functional layout with generous living and entertaining spaces and a beautifully updated kitchen at the heart of the home. Upstairs, spacious bedrooms and refreshed bathrooms continue the clean, updated feel. Enjoy additional living space and flexibility throughout the home, along with outdoor space perfect for relaxing or entertaining. Ideally located in Annapolis just minutes from Quiet Waters Park, downtown Annapolis, Eastport, shopping, dining and major commuter routes. With so many of the important updates already completed, this home offers an incredible opportunity to move right in and enjoy everything the Annapolis lifestyle has to offer!

3 Beds ⋅ 3 Baths

Back On The Market Through No Fault Of The Seller!! A wonderful second opportunity for buyers who missed it the first time!! Beautifully updated and move-in ready in an ideal Annapolis location! HVAC, ROOF, & HOT WATER HEATER ALL REPLACED APPROX. 2021. This inviting home has been thoughtfully refreshed with updated kitchen finishes, new flooring, fresh interior paint and beautifully updated bathrooms, creating a bright, fresh feel throughout. The main level offers a comfortable, functional layout with generous living and entertaining spaces and a beautifully updated kitchen at the heart of the home. Upstairs, spacious bedrooms and refreshed bathrooms continue the clean, updated feel. Enjoy additional living space and flexibility throughout the home, along with outdoor space perfect for relaxing or entertaining. Ideally located in Annapolis just minutes from Quiet Waters Park, downtown Annapolis, Eastport, shopping, dining and major commuter routes. With so many of the important updates already completed, this home offers an incredible opportunity to move right in and enjoy everything the Annapolis lifestyle has to offer!

150 Quiet Waters Pl, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$995,000

Experience the best of downtown Annapolis living from this exceptional corner residence in highly sought-after Acton’s Landing. This 2 bedroom, with an extra den unit, offers nearly 2,000 square feet of beautifully designed living space. This extraordinary condominium combines the ease of maintenance-free living with a rare feature that truly sets it apart: its own exterior entrance. Step directly outside and begin enjoying the restaurants, shops, waterfront, events, and unmistakable charm of downtown Annapolis without ever having to walk through the building. The private exterior entrance also provides exceptional convenience for guests, particularly after concierge hours, allowing them to arrive directly at your door. Inside, the spacious, open-concept floor plan has been freshly painted and features brand-new carpeting, abundant natural light, and a wall of windows overlooking the outdoor patio area. The gourmet kitchen is designed for both everyday living and entertaining, with granite countertops, stainless steel appliances—including gas cooktop and a new refrigerator —and a generous island/breakfast bar that opens seamlessly to the main living area. The thoughtfully designed layout provides excellent separation between the two expansive bedroom suites. The primary suite features two closets, including a walk-in, along with a spacious private bath complete with a separate soaking tub. On the opposite side of the residence, the second bedroom offers its own en-suite bath, creating an ideal private retreat for overnight guests. A separate den/office provides valuable additional living space and offers the flexibility to serve as a home office, library, media room, or occasional guest space. A conveniently located powder room makes entertaining especially easy. Adding to the exceptional convenience are two garage parking spaces located just steps from the residence, along with an owned private storage unit—valuable amenities for downtown Annapolis living. Acton’s Landing further enhances the lifestyle with a fitness center, library, recreation/community room, beautifully landscaped courtyard, and concierge service. And when you are ready to venture out, downtown Annapolis is right outside your door. Few residences offer this combination of nearly 2,000 square feet, two garage parking spaces, private storage, luxury amenities, and the rare convenience of a direct entrance/exit with its own outdoor, covered patio—all within walking distance of everything that makes Annapolis such an extraordinary place to live. This is more than simply a downtown condo; it is an opportunity to enjoy the Annapolis lifestyle with the space, comfort, convenience, and accessibility of a true luxury residence.

2 Beds ⋅ 3 Baths

Experience the best of downtown Annapolis living from this exceptional corner residence in highly sought-after Acton’s Landing. This 2 bedroom, with an extra den unit, offers nearly 2,000 square feet of beautifully designed living space. This extraordinary condominium combines the ease of maintenance-free living with a rare feature that truly sets it apart: its own exterior entrance. Step directly outside and begin enjoying the restaurants, shops, waterfront, events, and unmistakable charm of downtown Annapolis without ever having to walk through the building. The private exterior entrance also provides exceptional convenience for guests, particularly after concierge hours, allowing them to arrive directly at your door. Inside, the spacious, open-concept floor plan has been freshly painted and features brand-new carpeting, abundant natural light, and a wall of windows overlooking the outdoor patio area. The gourmet kitchen is designed for both everyday living and entertaining, with granite countertops, stainless steel appliances—including gas cooktop and a new refrigerator —and a generous island/breakfast bar that opens seamlessly to the main living area. The thoughtfully designed layout provides excellent separation between the two expansive bedroom suites. The primary suite features two closets, including a walk-in, along with a spacious private bath complete with a separate soaking tub. On the opposite side of the residence, the second bedroom offers its own en-suite bath, creating an ideal private retreat for overnight guests. A separate den/office provides valuable additional living space and offers the flexibility to serve as a home office, library, media room, or occasional guest space. A conveniently located powder room makes entertaining especially easy. Adding to the exceptional convenience are two garage parking spaces located just steps from the residence, along with an owned private storage unit—valuable amenities for downtown Annapolis living. Acton’s Landing further enhances the lifestyle with a fitness center, library, recreation/community room, beautifully landscaped courtyard, and concierge service. And when you are ready to venture out, downtown Annapolis is right outside your door. Few residences offer this combination of nearly 2,000 square feet, two garage parking spaces, private storage, luxury amenities, and the rare convenience of a direct entrance/exit with its own outdoor, covered patio—all within walking distance of everything that makes Annapolis such an extraordinary place to live. This is more than simply a downtown condo; it is an opportunity to enjoy the Annapolis lifestyle with the space, comfort, convenience, and accessibility of a true luxury residence.

66 Franklin St Unit 102, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$610,000

Welcome to this beautifully updated ranch-style home in Hillsmere Estates... where modern comfort meets serene living. Located on a spacious corner lot with ample driveway parking, this warm and charming retreat boasts four bedrooms and three full bathrooms and is designed to accommodate all your lifestyle needs. The open well-appointed kitchen is ready for your culinary adventures boasting plenty of sleek counter space along with an abundance of cabinets. Gather around the roomy kitchen island or the bright and cheerful dining area for your social events or comforting traditional meals. Cozy up to the newly updated fireplace in the living room that creates the perfect ambiance for quiet evenings or festive gatherings. Hardwood flooring on the main floor adds to the appeal of this home. The inviting sunroom is ready when you need extra space for game time adventures or a moment to lean back with your feet up to revel in your comfy quiet world. The fully finished basement offers plenty of room for your bedroom/office along with a family room for entertainment and the added convenience of a full bathroom. It also features a kitchenette space that can easily be converted to a full kitchen with a laundry area to create an accommodating in-law suite. Not only are there endless options in the basement living areas, this generous space includes plentiful storage room for your handy tools and treasured keepsakes. Stepping out to the back yard, the WOW feature continues as you gaze out to the fully fenced and expansive 0.32-acre flat lot where your options are limitless. A picturesque atmosphere where you can be the host of a special occasion or unwind in your private outdoor oasis. As nature smiles in this abundant space, a large shed has been gently nestled in allowing you to organize some well-deserved lounging furniture, gardening implements as well as your entertaining games and toys for all your pleasures. As you venture out from the sanctuary of your lovely home, the amenities for the Hillsmere Shores community are ready to be enjoyed. Feel the charm as you walk down Hillsmere Drive beneath a canopy of historic cypress trees. Treat yourself with exclusive access to a private marina on the South River, a sandy beach, waterfront pavilions, a community pool, and multiple playgrounds. Potential adventures abound in a community where you are within easy walking distance to Quiet Waters Park sharing its nature trails, dog beach and playgrounds. For water enthusiasts, you are only 2 miles from the South River, providing easy access for boating, fishing and kayaking. Multiple slips are available by lease making your aquatic adventures just a stone's throw away. Embrace the lifestyle you've always wanted in a community that offers both tranquility and recreational opportunities and is conveniently located near schools, a library along with dining and shopping experiences. This is more than just a house... it is your home and community where you can create lasting memories. Don't miss your chance to make this home your own!

4 Beds ⋅ 3 Baths

Welcome to this beautifully updated ranch-style home in Hillsmere Estates... where modern comfort meets serene living. Located on a spacious corner lot with ample driveway parking, this warm and charming retreat boasts four bedrooms and three full bathrooms and is designed to accommodate all your lifestyle needs. The open well-appointed kitchen is ready for your culinary adventures boasting plenty of sleek counter space along with an abundance of cabinets. Gather around the roomy kitchen island or the bright and cheerful dining area for your social events or comforting traditional meals. Cozy up to the newly updated fireplace in the living room that creates the perfect ambiance for quiet evenings or festive gatherings. Hardwood flooring on the main floor adds to the appeal of this home. The inviting sunroom is ready when you need extra space for game time adventures or a moment to lean back with your feet up to revel in your comfy quiet world. The fully finished basement offers plenty of room for your bedroom/office along with a family room for entertainment and the added convenience of a full bathroom. It also features a kitchenette space that can easily be converted to a full kitchen with a laundry area to create an accommodating in-law suite. Not only are there endless options in the basement living areas, this generous space includes plentiful storage room for your handy tools and treasured keepsakes. Stepping out to the back yard, the WOW feature continues as you gaze out to the fully fenced and expansive 0.32-acre flat lot where your options are limitless. A picturesque atmosphere where you can be the host of a special occasion or unwind in your private outdoor oasis. As nature smiles in this abundant space, a large shed has been gently nestled in allowing you to organize some well-deserved lounging furniture, gardening implements as well as your entertaining games and toys for all your pleasures. As you venture out from the sanctuary of your lovely home, the amenities for the Hillsmere Shores community are ready to be enjoyed. Feel the charm as you walk down Hillsmere Drive beneath a canopy of historic cypress trees. Treat yourself with exclusive access to a private marina on the South River, a sandy beach, waterfront pavilions, a community pool, and multiple playgrounds. Potential adventures abound in a community where you are within easy walking distance to Quiet Waters Park sharing its nature trails, dog beach and playgrounds. For water enthusiasts, you are only 2 miles from the South River, providing easy access for boating, fishing and kayaking. Multiple slips are available by lease making your aquatic adventures just a stone's throw away. Embrace the lifestyle you've always wanted in a community that offers both tranquility and recreational opportunities and is conveniently located near schools, a library along with dining and shopping experiences. This is more than just a house... it is your home and community where you can create lasting memories. Don't miss your chance to make this home your own!

301 Cedar Ln, Annapolis

Listing courtesy of ExecuHome Realty. Contact:

$2,795,000

Live authentically. The Chesapeake Bay is the view, the backdrop and the reason to linger. From the covered bluestone porch, the horizon opens across the Bay with uninterrupted sky and water. Morning coffee, an afternoon breeze through open doors, evenings around the fire—the water sets the pace. Extensively renovated inside and out since 2019, this charming craftsman styled gem in the sought-after Bay Ridge Community offers easy one-floor living and a natural connection to the outdoors. Windows and skylights, French doors and Phantom screens invite the sunshine and bay breeze inside. New Café Elite appliances, induction cooktop, and laundry. Freshly painted, craftsman style trim, molding and shiplap accents. Open floor plan with wide plank hickory flooring. Set on a generous .31 are lot, the flat, manicured backyard leaves plenty of room for games, children and pets. Low-maintenance Ipe deck and rear entry porch made for entertaining. Ample storage for water toys, paddle boards and bikes. Outdoor shower adding another practical touch to life by the water. Oversized parking pad for guests. Detached 2 car garage/studio, heated and cooled, skylight and separate personnel door offers flex space for home gym, office or guests. Functional updates include architectural shingle roofs, Pella windows, Hardie siding, hurricane French doors, blown attic insulation and generator hook- up. Then there is Bay Ridge itself—a walkable waterfront community with the quiet, unhurried character of a New England shore town. Tree lined streets, community beaches, deep water marina, pool and clubhouse are part of the fabric, while effortless biking connects the neighborhood to shoreline points along the South and Severn Rivers. A coveted pool bond conveys. Eastport, with its waterfront restaurants, marinas and distinctly maritime character, is close by, as are the Annapolis Maritime Museum & Park and Quiet Waters Park, with miles of trails and waterfront access. Historic downtown Annapolis, City Dock and the U.S. Naval Academy bring dining, shopping, sailing, history and the traditions of one of the country's most distinctive institutions at your doorstep. Zippy routes south to Washington, DC and Northern Virginia, north toward Baltimore, and across the Chesapeake Bay Bridge to Maryland’s Eastern Shore. BWI Airport and the Amtrak/MARC station are under 35 minutes away. Chesapeake Bay cottage lifestyle with the water in front of you, a community around you and the region within easy reach. Cultivate your existence. The art of uniting human and home.

3 Beds ⋅ 3 Baths

Live authentically. The Chesapeake Bay is the view, the backdrop and the reason to linger. From the covered bluestone porch, the horizon opens across the Bay with uninterrupted sky and water. Morning coffee, an afternoon breeze through open doors, evenings around the fire—the water sets the pace. Extensively renovated inside and out since 2019, this charming craftsman styled gem in the sought-after Bay Ridge Community offers easy one-floor living and a natural connection to the outdoors. Windows and skylights, French doors and Phantom screens invite the sunshine and bay breeze inside. New Café Elite appliances, induction cooktop, and laundry. Freshly painted, craftsman style trim, molding and shiplap accents. Open floor plan with wide plank hickory flooring. Set on a generous .31 are lot, the flat, manicured backyard leaves plenty of room for games, children and pets. Low-maintenance Ipe deck and rear entry porch made for entertaining. Ample storage for water toys, paddle boards and bikes. Outdoor shower adding another practical touch to life by the water. Oversized parking pad for guests. Detached 2 car garage/studio, heated and cooled, skylight and separate personnel door offers flex space for home gym, office or guests. Functional updates include architectural shingle roofs, Pella windows, Hardie siding, hurricane French doors, blown attic insulation and generator hook- up. Then there is Bay Ridge itself—a walkable waterfront community with the quiet, unhurried character of a New England shore town. Tree lined streets, community beaches, deep water marina, pool and clubhouse are part of the fabric, while effortless biking connects the neighborhood to shoreline points along the South and Severn Rivers. A coveted pool bond conveys. Eastport, with its waterfront restaurants, marinas and distinctly maritime character, is close by, as are the Annapolis Maritime Museum & Park and Quiet Waters Park, with miles of trails and waterfront access. Historic downtown Annapolis, City Dock and the U.S. Naval Academy bring dining, shopping, sailing, history and the traditions of one of the country's most distinctive institutions at your doorstep. Zippy routes south to Washington, DC and Northern Virginia, north toward Baltimore, and across the Chesapeake Bay Bridge to Maryland’s Eastern Shore. BWI Airport and the Amtrak/MARC station are under 35 minutes away. Chesapeake Bay cottage lifestyle with the water in front of you, a community around you and the region within easy reach. Cultivate your existence. The art of uniting human and home.

113 Bay Dr, Annapolis

Listing courtesy of Krauss Real Property Brokerage. Contact:

$750,000

Welcome to 580 Pinedale Dr, a spacious 4-bedroom, 2.5-bath home set on a beautiful 1.8-acre lot in Annapolis. Offering a comfortable blend of character, functionality, and privacy, this home provides plenty of space for everyday living and entertaining. The impressive lofted living room is filled with natural light and features skylights that create an open, airy atmosphere. The inviting family room offers a propane fireplace, providing a cozy gathering space for relaxing evenings. The spacious kitchen offers plenty of cabinet and counter space, providing a functional and inviting setting for preparing meals and gathering with family and friends. A convenient half bath completes the main level. The spacious primary bedroom features its own ensuite bathroom and private laundry, creating a comfortable retreat with added convenience. Three additional bedrooms provide flexibility for family, guests, a home office, or hobby space. Outside, the expansive 1.8-acre property offers room to enjoy the outdoors and plenty of privacy, while the attached 2-car garage provides ample parking and storage. With its generous lot, versatile floor plan, lofted living space, and sought-after Annapolis location, 580 Pinedale Dr offers an opportunity to enjoy both space and convenience.

4 Beds ⋅ 3 Baths

Welcome to 580 Pinedale Dr, a spacious 4-bedroom, 2.5-bath home set on a beautiful 1.8-acre lot in Annapolis. Offering a comfortable blend of character, functionality, and privacy, this home provides plenty of space for everyday living and entertaining. The impressive lofted living room is filled with natural light and features skylights that create an open, airy atmosphere. The inviting family room offers a propane fireplace, providing a cozy gathering space for relaxing evenings. The spacious kitchen offers plenty of cabinet and counter space, providing a functional and inviting setting for preparing meals and gathering with family and friends. A convenient half bath completes the main level. The spacious primary bedroom features its own ensuite bathroom and private laundry, creating a comfortable retreat with added convenience. Three additional bedrooms provide flexibility for family, guests, a home office, or hobby space. Outside, the expansive 1.8-acre property offers room to enjoy the outdoors and plenty of privacy, while the attached 2-car garage provides ample parking and storage. With its generous lot, versatile floor plan, lofted living space, and sought-after Annapolis location, 580 Pinedale Dr offers an opportunity to enjoy both space and convenience.

580 Pinedale Dr, Annapolis

Listing courtesy of Cummings & Co. Realtors. Contact:

$1,595,000

Rarely does a home of this historical significance become available in the heart of Historic Annapolis. Believed to date to the late 17th century, the extraordinary residence is among the city's oldest surviving homes, seamlessly blending centuries of architectural heritage with sophisticated modern living. Perched at the water end of Market St overlooking Spa Creek, this home is instantly recognizable by its iconic red standing-seam roof and timeless presence. Rich in character, the interior showcases exposed original beams, soaring ceilings, abundant natural light, and thoughtfully designed living spaces that honor the home's remarkable past while embracing contemporary comfort. A nationally recognized renovation in 1977 by Gate One Builders, transformed the residence into a one of a kind masterpiece, preserving its historic integrity while creating an open, light filled floor plan unlike any other in Annapolis. The beautifully appointed Kitchen, inviting living and dining areas, combination gas and wood burning fireplaces and a tranquil large Sunroom addition all flow effortlessly to a private walled courtyard, an intimate outdoor retreat ideal for entertaining or quiet relaxation. Features 2 ensuite Bedrooms and a spacious open loft easilty adapted into a private 3rd BR, home office or gym while still preserving the home's architectural flow. Water Views of Spa Creek, exceptional craftsmanship, and architectural details at every turn make this home as captivating as it is livable. Adding to its rarity are amenities seldom found with the Historic District, including two covered off street parking spaces and an unparalleled waterfront setting just moments from City Dock, the USNA, fine dining, boutiques, galleries and yacht club. Whether enjoyed as a full time residence or an exceptional Annapolis retreat, 100 Market Street represents a once in a generation opportunity to own an irreplaceable piece of the city's history, where more than three centuries of heritage meet the very best of coastal luxury living.

2 Beds ⋅ 3 Baths

Rarely does a home of this historical significance become available in the heart of Historic Annapolis. Believed to date to the late 17th century, the extraordinary residence is among the city's oldest surviving homes, seamlessly blending centuries of architectural heritage with sophisticated modern living. Perched at the water end of Market St overlooking Spa Creek, this home is instantly recognizable by its iconic red standing-seam roof and timeless presence. Rich in character, the interior showcases exposed original beams, soaring ceilings, abundant natural light, and thoughtfully designed living spaces that honor the home's remarkable past while embracing contemporary comfort. A nationally recognized renovation in 1977 by Gate One Builders, transformed the residence into a one of a kind masterpiece, preserving its historic integrity while creating an open, light filled floor plan unlike any other in Annapolis. The beautifully appointed Kitchen, inviting living and dining areas, combination gas and wood burning fireplaces and a tranquil large Sunroom addition all flow effortlessly to a private walled courtyard, an intimate outdoor retreat ideal for entertaining or quiet relaxation. Features 2 ensuite Bedrooms and a spacious open loft easilty adapted into a private 3rd BR, home office or gym while still preserving the home's architectural flow. Water Views of Spa Creek, exceptional craftsmanship, and architectural details at every turn make this home as captivating as it is livable. Adding to its rarity are amenities seldom found with the Historic District, including two covered off street parking spaces and an unparalleled waterfront setting just moments from City Dock, the USNA, fine dining, boutiques, galleries and yacht club. Whether enjoyed as a full time residence or an exceptional Annapolis retreat, 100 Market Street represents a once in a generation opportunity to own an irreplaceable piece of the city's history, where more than three centuries of heritage meet the very best of coastal luxury living.

100 Market St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$750,000

RARE OPPORTUNITY! TWO HOMES ON ONE LOT IN EASTPORT! This versatile property offers an exceptional combination of character, functionality, and flexibility with a renovated 2-bedroom, 1.5-bath main home PLUS a separate 1-bedroom, 1-bath guest house. The main residence features gleaming hardwood floors, a cozy fireplace, and a spacious kitchen with abundant counter space, a large peninsula, and stainless-steel appliances. The inviting layout provides comfortable living spaces while retaining the charm and character buyers love. The detached guest house is a standout feature, offering a private bedroom, full bath, living room, washer/dryer, and separate utilities. Ideal for guests, extended family, a private home office, or other flexible living arrangements. Enjoy the outdoors in the pleasant, tree-lined backyard, enclosed by a privacy fence. A 1+ car garage and shed provide plenty of room for parking, storage, hobbies, and outdoor equipment. Located conveniently to the restaurants, shops, waterfront, and attractions of Eastport and Downtown Annapolis, this property puts you close to everything while offering the flexibility of two separate living spaces. Notable recent improvements include: New roof and skylights (2023) New driveway (2022) Guest house electrical wiring (2022) New dishwasher (2024) Two homes. One lot. Endless possibilities. A unique opportunity in a highly desirable Annapolis location!

3 Beds ⋅ 3 Baths

RARE OPPORTUNITY! TWO HOMES ON ONE LOT IN EASTPORT! This versatile property offers an exceptional combination of character, functionality, and flexibility with a renovated 2-bedroom, 1.5-bath main home PLUS a separate 1-bedroom, 1-bath guest house. The main residence features gleaming hardwood floors, a cozy fireplace, and a spacious kitchen with abundant counter space, a large peninsula, and stainless-steel appliances. The inviting layout provides comfortable living spaces while retaining the charm and character buyers love. The detached guest house is a standout feature, offering a private bedroom, full bath, living room, washer/dryer, and separate utilities. Ideal for guests, extended family, a private home office, or other flexible living arrangements. Enjoy the outdoors in the pleasant, tree-lined backyard, enclosed by a privacy fence. A 1+ car garage and shed provide plenty of room for parking, storage, hobbies, and outdoor equipment. Located conveniently to the restaurants, shops, waterfront, and attractions of Eastport and Downtown Annapolis, this property puts you close to everything while offering the flexibility of two separate living spaces. Notable recent improvements include: New roof and skylights (2023) New driveway (2022) Guest house electrical wiring (2022) New dishwasher (2024) Two homes. One lot. Endless possibilities. A unique opportunity in a highly desirable Annapolis location!

906 Jackson St, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$879,990

Ameri-Star Homes is proud to offer this exceptional opportunity to build a brand-new Craftsman-style home on a beautiful 9,225-square-foot corner homesite in the sought-after waterfront community of Cape St. Claire in Annapolis. For A Limited Time - Builder is offering $25,000 towards Financing, Closing Costs or Options, with the use of the builder’s approved lender and title company! The exciting Bancroft model offers approximately 2,411 square feet of above-grade living space and is thoughtfully appointed with the quality features and finishes today’s homebuyers desire. Enjoy a spacious 12’ x 16’ sunroom, 9-foot ceilings on the main level, engineered hardwood flooring throughout the entire first floor, granite or quartz kitchen countertops, and upgraded cabinetry with soft-close doors and drawers. Additional included features include ceramic tile in the bathrooms and laundry room, stainless steel kitchen appliances, a washer and dryer package, upgraded Craftsman-style moldings, Craftsman newel posts with oak handrails and black iron pickets, stone exterior accents, architectural roof shingles, a Wi-Fi-enabled garage door opener, a sodded lawn, a generous landscaping package, and so much more. Best of all, these exceptional features are included as standard! There is also plenty of opportunity to expand your living space with available options, including a finished recreation room, additional basement bedroom, and full bathroom, all available at an additional cost. Come home and enjoy the incredible lifestyle and amenities offered in this water-privileged community. Cape St. Claire offers three community beaches, community docks, a fishing and crabbing pier, picnic areas, boat launches, playgrounds, baseball fields, basketball courts, marinas, boat ramp and slips, a community clubhouse, and an outdoor pool available with membership. Conveniently located with easy access to Annapolis, Baltimore, and Washington, D.C., this is a rare opportunity to enjoy new construction in the desirable Cape St. Claire community. A home you will be proud to come home to! Photos and images shown may be representative of the builder’s work, craftsmanship, and quality and may include optional features not included in the base price. Prices, terms, conditions, features, and availability are subject to change without prior written notice.

4 Beds ⋅ 3 Baths

Ameri-Star Homes is proud to offer this exceptional opportunity to build a brand-new Craftsman-style home on a beautiful 9,225-square-foot corner homesite in the sought-after waterfront community of Cape St. Claire in Annapolis. For A Limited Time - Builder is offering $25,000 towards Financing, Closing Costs or Options, with the use of the builder’s approved lender and title company! The exciting Bancroft model offers approximately 2,411 square feet of above-grade living space and is thoughtfully appointed with the quality features and finishes today’s homebuyers desire. Enjoy a spacious 12’ x 16’ sunroom, 9-foot ceilings on the main level, engineered hardwood flooring throughout the entire first floor, granite or quartz kitchen countertops, and upgraded cabinetry with soft-close doors and drawers. Additional included features include ceramic tile in the bathrooms and laundry room, stainless steel kitchen appliances, a washer and dryer package, upgraded Craftsman-style moldings, Craftsman newel posts with oak handrails and black iron pickets, stone exterior accents, architectural roof shingles, a Wi-Fi-enabled garage door opener, a sodded lawn, a generous landscaping package, and so much more. Best of all, these exceptional features are included as standard! There is also plenty of opportunity to expand your living space with available options, including a finished recreation room, additional basement bedroom, and full bathroom, all available at an additional cost. Come home and enjoy the incredible lifestyle and amenities offered in this water-privileged community. Cape St. Claire offers three community beaches, community docks, a fishing and crabbing pier, picnic areas, boat launches, playgrounds, baseball fields, basketball courts, marinas, boat ramp and slips, a community clubhouse, and an outdoor pool available with membership. Conveniently located with easy access to Annapolis, Baltimore, and Washington, D.C., this is a rare opportunity to enjoy new construction in the desirable Cape St. Claire community. A home you will be proud to come home to! Photos and images shown may be representative of the builder’s work, craftsmanship, and quality and may include optional features not included in the base price. Prices, terms, conditions, features, and availability are subject to change without prior written notice.

1049 Sun Valley Dr, Annapolis

Listing courtesy of Douglas Realty LLC. Contact: