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$959,000
4 Beds ⋅ 3 Baths
Beautifully updated and thoughtfully designed, this four-bedroom home offers exceptional indoor and outdoor living in the prestigious Annapolis waterfront community of Epping Forest. Where waterfront living and exceptional amenities combine to create an unparalleled lifestyle. This sought-after, water-privileged neighborhood features a new deep-water marina, wooded trails, a clubhouse overlooking the Severn River, tennis, pickleball and basketball courts, parks, and two sandy beaches perfect for swimming, relaxing, or launching your next adventure on the water. Inside, this beautifully designed home offers four spacious bedrooms, including a convenient main-level bedroom, ideal for guests, multigenerational living, or a private home office. The open, light-filled floor plan welcomes you with abundant natural light, effortless flow, and oak hardwood floors throughout, creating inviting spaces for both everyday living and entertaining. The chef’s kitchen is thoughtfully appointed with premium GE Café appliances, striking Blue-Eyed granite countertops, and abundant cabinetry, making meal preparation both functional and enjoyable. Just beyond, the inviting living room is anchored by a charming enclosed wood-burning fireplace, creating a warm and welcoming atmosphere throughout the seasons. The spacious dining area opens directly to the side patio, seamlessly extending indoor living and entertaining outdoors. Upstairs, the luxurious primary suite serves as a private retreat, featuring an expansive walk-in closet and a spa-inspired ensuite bath designed for relaxation. A charming Juliet balcony offers the perfect spot to enjoy a cool evening breeze or a quiet morning coffee. Two additional bedrooms and a well-appointed full bathroom provide comfortable accommodations for family and guests. The bright, finished lower level offers exceptional flexibility, with generous space for a recreation room, fitness area, media room, or home office. A large utility room with walk-out access to the rear patio adds both convenience and functionality. Outdoor living is equally impressive. The private patio provides an ideal setting for al fresco dining, morning coffee, or relaxing at the end of the day. Gather around the inviting fire pit on cool evenings, while the charming garden shed keeps outdoor essentials neatly organized. Beyond, a second secluded garden creates a peaceful retreat with plenty of room for family, friends, and pets to enjoy. The professionally landscaped and hardscaped grounds provide season-long color, beauty, and privacy, creating a tranquil outdoor oasis. Combining timeless style, thoughtful design, and the unmatched lifestyle of Epping Forest, this exceptional home offers a rare opportunity to experience the very best of Annapolis waterfront living. Epping Forest is a Special Tax District with an annual assessment of $2,003 and is governed by community Rules and Regulations.”

1724 Robinhood Rd, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$745,000
4 Beds ⋅ 3 Baths
There are homes that impress you. Then there are homes that make you imagine a completely different way of living. Imagine ending your workday with a walk to the beach to watch the sun set over the Chesapeake Bay. Weekend mornings begin with coffee on your deck surrounded by mature trees, afternoons are spent boating on the South River, swimming at the community pool, or exploring Quiet Waters Park, and evenings end with neighbors gathering for concerts, celebrations, and waterfront sunsets. This is the lifestyle that has made Hillsmere one of Annapolis' most cherished waterfront communities for generations—and it's waiting for you at 104 Groh Lane. Beautifully updated from top to bottom, this home offers the perfect balance of modern style and everyday comfort. Every room reflects a fresh, timeless aesthetic with thoughtful finishes, abundant natural light, and a warm, welcoming feel that allows you to simply move in and begin enjoying life from day one. The beautifully renovated kitchen is designed for those who love to cook. Whether you're preparing fresh Maryland crab cakes after a day on the water, perfecting your favorite family recipes, baking holiday desserts, or creating an elegant dinner for friends, this is a space where great meals become lasting memories. The adjoining dining and living areas flow effortlessly together, making entertaining feel natural while allowing everyone to stay connected long after dessert has been served. Step outside and discover one of this property's greatest assets—a lush, private, level backyard that's becoming increasingly difficult to find in Annapolis. This exceptional homesite offers endless possibilities, with room for the custom pool you've always envisioned, vibrant gardens, an outdoor kitchen, a fire pit, or simply a wide expanse of green lawn where children and pets can run freely. Host summer barbecues on the spacious deck, celebrate birthdays beneath the stars, enjoy quiet mornings listening to the birds, or spend peaceful evenings surrounded by the beauty of your own backyard sanctuary. The finished lower level provides the flexibility today's lifestyles demand, offering the perfect space for a recreation room, media lounge, fitness studio, home office, guest accommodations, or a combination of all four. Whether you're working from home, hosting overnight guests, or creating a place for everyone to spread out, this home easily adapts to the way you live. But what truly sets this property apart is what lies beyond your front door. Hillsmere is far more than a neighborhood—it's a true waterfront community where neighbors know one another and every season brings new opportunities to enjoy the outdoors. Residents have access to a private sandy beach overlooking the Chesapeake Bay, a private marina with boat slips and direct access to the South River, boat ramps, a community swimming pool, waterfront pavilions, playgrounds, volleyball courts, picnic areas, and an active calendar of events that creates a genuine sense of community. Quiet Waters Park, Hillsmere Elementary School, the library, shopping, restaurants, Eastport, Historic Downtown Annapolis, and City Dock are all just minutes away, giving you the perfect blend of convenience, recreation, and coastal charm. Finding a beautifully updated home is easy. Finding one on a lush, level lot in one of Annapolis' most beloved waterfront communities is not. 104 Groh Lane offers more than beautiful spaces and thoughtful updates. It offers morning walks to the water, evenings filled with laughter on the deck, lifelong friendships, unforgettable gatherings, and the simple joy of coming home to a place that feels exactly where you're meant to be.

104 Groh Ln, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,150,000
4 Beds ⋅ 2 Baths
Incredible opportunity to purchase two adjoining properties - one vacant commercial parcel and one residential property with an existing home. Situated on over half an acre combined in Annapolis, this unique offering has been owned by the same family for generations and presents endless possibilities for its next owner. The commercial parcel provides a blank slate for future development or investment, while the residential property features a 4-bedroom, 1.5-bath home with numerous updates, including a roof less than 10 years old and recently replaced HVAC system and hot water heater. Whether you're looking to develop, invest, or create your own vision, this is a rare opportunity you won't want to miss. Commercial Tax ID: 020600003497200 Residential Tax ID: 020600003498600

19 Old Solomons Island Rd, Annapolis

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033
$985,000
4 Beds ⋅ 3 Baths
111 Conduit Street is historic Annapolis living at its finest. Nestled in the heart of Historic Annapolis, this charming semi-detached residence seamlessly blends timeless character with modern convenience. Located just moments from Main Street, the City Dock, shops, restaurants, and waterfront attractions, this home offers the quintessential Annapolis lifestyle. Inside, original hardwood floors, classic architectural details, and three finished levels of living space create a warm and inviting atmosphere. The main level features spacious and distinct living and dining rooms, ideal for both everyday living and entertaining. An updated kitchen offers modern functionality while complementing the home's historic appeal. Step outside to enjoy a screened porch overlooking a private garden patio, providing a peaceful retreat rarely found in downtown Annapolis. The second level offers three bedrooms and a full bathroom, while the third floor is dedicated to a private primary suite featuring soaring ceilings, abundant natural light, and a separate room perfectly suited as a home office, dressing room, nursery, or sitting area. A rare opportunity to own a character-filled home in one of Annapolis' most sought-after historic locations, all within walking distance of Main Street, the Naval Academy, waterfront parks, dining, shopping, and entertainment.

111 Conduit St, Annapolis

Listing courtesy of Innovative Properties, Inc.. Contact:

$559,000
4 Beds ⋅ 3 Baths
Welcome to 1424 Regent Street, where modern style meets everyday comfort. This beautifully updated home offers exceptional curb appeal with a spacious driveway, a brand-new sprinkler system, and a fully fenced backyard featuring a large deck—perfect for entertaining, relaxing, or enjoying outdoor living. Step inside to discover a stunning custom-designed living room highlighted by a striking gold and white accent wall that creates a warm, sophisticated focal point. The adjoining dining area flows seamlessly into the show-stopping custom kitchen, complete with stylish cabinetry, gorgeous quartz countertops, and designer finishes that make cooking and gathering a true pleasure. The spacious primary suite features its own en-suite bathroom featuring custom designer finishes. An additional beautifully renovated full bathroom upstairs offers both style and convenience for family and guests. Throughout the home, you'll find thoughtfully designed custom bathrooms and quality updates that create a move-in-ready experience. The lower level offer additional entertaining space with a stone fireplace, as well as a bedroom and a full bathroom. With its modern upgrades, designer touches, functional layout, and inviting spaces, 1424 Regent Street is a home you'll be proud to call your own.

1424 Regent St, Annapolis

Listing courtesy of Allfirst Realty, Inc.. Contact: 4433201344
$694,999
4 Beds ⋅ 3 Baths
Stunning remodeled home in Hillsmere! Situated on a lovely street and a large flat lot, this breathtaking home has been fully remodeled and offers some of the nicest finishes in the community! Entering through a charming 3 season room, youll be greeted by brand new lvp flooring throughout the home, a spacious family room that opens into your brand new kitchen. Kitchen features include brand new cream shaker cabinets around the kitchen, a brand new shaker island featuring oak finish, quartz counters, and brand new SS appliances. Behind the kitchen is a charming addition with lots of natural light. The main level boast 2 bedrooms, 2 fully renovated and stunning full bathrooms, including an owners suite with 2 closets and a dual vanity. Downstairs youll find 2 more bedrooms, a fully remodeled full bathroom, and an extra and open family room. The home boasts lots of attic storage as well as generous closet space. Outside, youll notice a brand new patio, lovely landscaping, and a large firepit area. The community boasts beaches, pool, pavilion areas, and more. This is a must see and wont last long! Roof replaced in 2022 and HWH in 2025.

117 Pinecrest Dr, Annapolis

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

$845,000
4 Beds ⋅ 3 Baths
OPEN HOUSE FRIDAY 8/7/26 2-4PM Experience the best of Annapolis living in this beautifully updated 4-bedroom, 3-bath home located in a waterfront community. This move-in-ready home offers the perfect blend of modern updates, comfortable living, and an exceptional Chesapeake Bay lifestyle. The heart of the home has also been refreshed with updated kitchen countertops and appliances (2024/2025), making it ideal for everyday living and entertaining. Additional major improvements include a new HVAC system (2025), hot water heater (2025), water conditioning system (2025), and garage door (2025), providing peace of mind for years to come. Outside, the partially fenced backyard offers the perfect space to relax, entertain, or enjoy outdoor activities. All three full bathrooms have been completely renovated with designer tile, new flooring, and modern vanities. The thoughtfully updated interior showcases updated flooring throughout, featuring newly refinished hardwood floors on upper level, new fixtures, and along with a new staircase railing. The inviting fireplace has been refaced on the lower level, creating a stylish focal point in the living space. The home also offers a versatile den/office and a one-car garage. Enjoy Hillsmere’s community amenities including private sandy beaches on the South River, a private marina with boat slips and direct access to the South River, boat ramps, waterfront pavilions, a community swimming pool, playgrounds, volleyball courts, and picnic areas. Whether you're boating, kayaking, fishing, or simply taking in the waterfront scenery, this community offers an unmatched coastal lifestyle. Conveniently located just minutes from historic downtown Annapolis, Quiet Waters Park, shopping, and dining, this exceptional home combines extensive recent updates with one of the area's most desirable waterfront communities. Don't miss the opportunity to make this beautifully renovated home your own.

100 Oak Dr, Annapolis

Listing courtesy of Innovative Properties, Inc.. Contact:

$699,000
4 Beds ⋅ 5 Baths
Some homes ask you to spend your weekends maintaining them. This one gives your weekends back. Imagine finishing work on Friday, closing the garage door, and deciding whether the evening calls for dinner in Eastport, cocktails downtown, a concert at City Dock, or simply inviting friends over because your house was built for exactly that. The heart of the home is a kitchen that doesn't hide the cook from the party. It was designed for people who love to entertain—an oversized island where everyone naturally gathers, abundant workspace, gas cooking, and an open flow that keeps every conversation going. Whether it's wine and appetizers for six or Thanksgiving for twenty, this is the room where people linger long after dinner is over. When the weather is perfect—and in Annapolis that's often—the party simply moves outside. Open the doors and the stunning double-sided fireplace connects the elegant dining room with the private deck, creating one seamless indoor-outdoor living space that's equally suited for quiet evenings with a glass of wine or unforgettable gatherings under the stars. Unlike many townhomes, you'll never wonder where everyone is going to park. The spacious two-car garage, driveway parking for two additional vehicles, generous guest parking nearby, and electric vehicle charging station make everyday life remarkably easy. Need space? You have four finished levels that adapt as your life changes. The top-floor retreat with its own full bath can become a guest suite, executive office, fitness studio, media room, or the private escape everyone wishes they had. And then there's the lifestyle. Walk or bike into Eastport. Meet friends downtown without worrying about parking. Spend the afternoon on your boat instead of behind a lawn mower. Travel for weeks knowing your home will be exactly as you left it. This is the kind of low-maintenance, lock-and-leave lifestyle that's becoming harder and harder to find in Annapolis. You don't have to sacrifice space to simplify your life. Here, you get both. If you've been searching for a home that feels sophisticated without feeling complicated, that offers luxury without demanding constant maintenance, and that lets you enjoy everything Annapolis has to offer instead of spending your weekends taking care of a house, you've just found it.

103 Norma Aly, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$950,000
4 Beds ⋅ 4 Baths
Welcome to this exceptional 4-bedroom, 3.5-bath residence, beautifully renovated in 2017 in the highly sought-after, water-privileged community of Cape St. John. This outstanding home offers an ideal blend of luxury, comfort, and the coveted Chesapeake Bay lifestyle. Residents enjoy exclusive access to the South River, including a private beach, boat ramp, docks, pavilion, and playground. Whether spending the day on the water, gathering with neighbors, or taking in breathtaking sunsets along the shoreline, life here is defined by effortless waterfront living. Perfectly positioned on the corner of Cape St. John Road and Valley View Road, this well appointed home is designed for both refined entertaining and effortless everyday living. The professionally landscaped, fully fenced backyard creates a private outdoor retreat, highlighted by an elegant stone patio ideal for al fresco dining, evening cocktails, or relaxing around the fire pit under the stars. Inside, the open-concept living space is anchored by a dramatic six-foot fireplace, creating a sophisticated yet inviting atmosphere. The gourmet kitchen serves as the heart of the home, featuring a spacious quartz-topped island, soft-close cabinetry, and premium stainless steel appliances....perfect for casual gatherings and memorable celebrations alike. The main-level primary suite offers a luxurious private sanctuary, complete with a generous walk-in closet and spa-inspired en-suite bath. Upstairs three additional bedrooms and two-and-a-half baths provide ample space for family, guests, or dedicated office and flex spaces. The heated and air-conditioned garage adds exceptional versatility, ideal for a fitness studio, workshop, hobby space, or climate-controlled storage. Combining upscale finishes, thoughtfully designed living spaces, and access to one of Annapolis’ most desirable waterfront communities, this remarkable home offers a rare opportunity. to embrace the luxury lifestyle of Cape St. John! Located just minutes from Annapolis Town Center, restaurants, shopping and easy access to major highways Cape St John is the perfect location!

2978 Valley View Rd, Annapolis

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

$799,000
4 Beds ⋅ 3 Baths
Price improvement! Location, location, location. Don't miss out on this one, make it your next home. Located in desirable Hillsmere Shores! Looks can be deceiving, must see inside to appreciate the open, airy and light filled space. This home is located in the highly desirable Hillsmere Shores community, offering a private beach, community pool, marina, and multiple launch areas for boats, kayaks, canoes, and paddleboards — the perfect setting for anyone who loves life on the water. The home features four spacious bedrooms and three full baths, all set within an open, airy floor plan designed to capture natural light and create an inviting sense of space. A generously sized kitchen serves as the heart of the home, offering abundant prep areas, modern appliances, and effortless flow into the main living spaces. The living room is anchored by a refined propane fireplace, adding warmth and ambiance throughout the seasons. The lower-level functions as an extension of the home, complete with a private bedroom and full bath—ideal for guests or multigenerational living. A sprawling great room provides endless possibilities for entertaining or relaxation, while a dedicated laundry space and two additional flex rooms offer versatility for a home gym, office, studio, or hobby space. Bring your vision and ideas to make this space your own. Sitting on a generous lot, the property backs directly to Quiet Waters Park and includes a private path for easy access and all the park has to offer...hiking trails, a playground, dog park, outdoor summer concerts and several other fun events throughout the year. The fully fenced backyard is designed for entertaining, complete with a bar area and firepit for evenings outdoors. The detached garage/barn provides endless possibilities — workshop, studio, storage, or more. A massive, fully covered deck spans the back of the home, creating an ideal space for crab feasts, cookouts, or simply relaxing and enjoying the peaceful surroundings. This home is truly a must‑see. Looks can be deceiving — it is far more spacious than it appears from the outside, offering room to spread out and enjoy every part of the property and its incredible location.

278 Hillsmere Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,750,000
4 Beds ⋅ 5 Baths
Experience the best of Annapolis living in the sought-after, amenities-rich community of Fishing Creek Farm. Perfectly positioned to capture beautiful water views and surrounded by lush lawns and mature landscaping, this handsome brick-front Colonial offers a rare combination of timeless architecture, flexible living spaces, and an exceptional neighborhood lifestyle. A gracious foyer welcomes you into formal living and dining rooms designed for entertaining, with the current living room serving as a billiards room. At the heart of the home, the bright white kitchen features quartz countertops, abundant cabinetry, and a sunny breakfast nook that flows seamlessly into the impressive family room with soaring vaulted ceilings, a fireplace, and easy access to the patio and expansive backyard. Whether hosting summer gatherings or enjoying a quiet evening outdoors, the spacious front and rear yards provide room to relax, play, and take in the peaceful surroundings. Designed for both convenience and versatility, the main level includes a spacious primary suite, while a second upper-level primary suite enjoys sweeping water views and creates an ideal retreat for owners or guests. Two additional bedrooms share a well-appointed hall bath, providing ample space for family and friends. The partially finished lower level offers additional living space, generous storage, and easily accessible crawl spaces. Life in Fishing Creek Farm extends far beyond the property itself. Residents enjoy one of Annapolis' most coveted waterfront communities, complete with a community marina, swimming pool, sandy beach, tennis and pickleball courts, and year-round social activities. Located on the Annapolis Neck peninsula between the South River and the Chesapeake Bay, this special neighborhood offers a peaceful waterfront setting just minutes from downtown Annapolis, Eastport, and major commuting routes to Baltimore, BWI Airport, Fort Meade/NSA, Washington, D.C., and the Eastern Shore. A wonderful opportunity to enjoy the Chesapeake lifestyle in one of Annapolis' most desirable communities. Welcome Home!

3403 Hidden River View Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$1,025,000
4 Beds ⋅ 3 Baths
Don’t miss this rarely available 4-bedroom, 2.5-bath Colonial in the highly sought-after, water-privileged community of Amberley. Fresh paint and abundant natural light create a warm and inviting atmosphere throughout. The kitchen is filled with natural light and offers gray-toned cabinetry, recessed lighting, a sunny breakfast area, and peaceful tree-lined views. Perfect for both everyday living and entertaining, the spacious family room offers a cozy gas fireplace with a charming brick surround, custom built-ins, and direct access to the rear covered porch. Overlooking picturesque Whitehall Creek, this tranquil outdoor retreat provides the perfect setting to gather with friends or unwind while taking in the serene waterfront scenery at any time of day. Just beyond is a versatile formal dining area framed by lovely front lawn views. Whether hosting memorable dinners, creating a cozy sitting room, or using the space as a private home office, this room offers flexibility while enjoying a peaceful scenery. A nearby powder room and laundry room add convenience and functionality. Retreat upstairs to the spacious primary suite, where large windows adorned with plantation shutters fill the room with natural light. The walk-in closet is thoughtfully outfitted with a custom organization system, while the en-suite bath offers a tiled walk-in shower, creating a comfortable and private retreat at the end of the day. Three additional bedrooms, each with ample closet space, share a well-appointed hall bath with a tub/shower combo, completing the upper level. The unfinished lower level provides abundant storage space and shelving with the possibility for future expansion if finished. An attached two-car garage, complete with a built-in workshop, is ideal for hobbyists, DIY enthusiasts, or extra storage needs. An extended driveway offers ample off-street parking for 4+ cars. With nature as your backdrop, this spectacular 29,500 sq ft lot is an entertainer's dream. Create your own private oasis with breathtaking riverfront views and a meandering pathway leading to your private boat slip. Enjoy endless opportunities to relax or entertain outdoors, from cozy evenings around the firepit on the brick patio to peaceful mornings surrounded by mature trees that provide beauty, privacy, and a serene setting year-round. Amberley's exceptional amenities further enhance this waterfront lifestyle. Residents enjoy access to three community piers with 45 boat slips, kayak and dinghy racks, a kayak launch pier, and a boat ramp. In addition, more than 15 acres of preserved forest and open fields offer walking trails and scenic vistas, making this a truly special place to call home.

700 N Holly Dr, Annapolis

Listing courtesy of Keller Williams Capital Properties. Contact:

$6,995,000
4 Beds ⋅ 6 Baths
Set on a spectacular point of land where the South River meets the Chesapeake Bay, this extraordinary waterfront estate captures some of the most breathtaking views in Annapolis. With coveted southern exposure, the property is immersed in sunlight from dawn to dusk, creating an ever-changing backdrop of sparkling water, passing sailboats, and panoramic Chesapeake vistas. Completely reimagined in 2017 by renowned architect Cathy Purple Cherry, this residence was rebuilt and renovated to an exceptional standard, blending timeless coastal architecture with modern luxury and uncompromising construction quality. Spray-foam insulated walls and roof, steel reinforcement, double plywood construction, four-zone HVAC with humidifiers, gas backup heat, tankless propane water heaters, water treatment systems, generator backup, Sonos audio, and Lutron lighting create a home that is as efficient and functional as it is beautiful. Designed for both grand-scale entertaining and comfortable everyday living, the interior offers over-the-top craftsmanship and thoughtful details throughout. Maple hardwood flooring flows through elegant yet inviting spaces including a dramatic waterfront living room with a custom wet bar, an informal gathering room with built-in bookshelves, a private office with custom cabinetry, wet bar, balcony, and commanding views stretching down the Chesapeake Bay, and a state-of-the-art theater room complete with its own wet bar, refrigerator, and ice maker. The chef’s kitchen is a masterpiece featuring double Wolf ovens, Wolf cooktop, Sub-Zero refrigerator, three dishwashers, wine cooler, ice maker, built-in microwave, instant hot water, walk-in pantry with custom built-ins, and a sun-filled breakfast nook overlooking the water. The luxurious primary suite serves as a private waterfront retreat, highlighted by a stunning spa bath finished with Italian water-cut marble. Three additional bedrooms feature ensuite baths, while a full bath on the main level conveniently serves the pool and outdoor entertaining areas. Outdoor living rivals the finest resorts. Expansive Ipe decking surrounds a heated PebbleTec pool and spa, complemented by an outdoor kitchen, fire pit, integrated sound system, and extensive landscape lighting. The private pier is equipped with water, electric, approximately 4 feet of MLW, a 12,000-pound boat lift, an 8,500-pound boat lift, and a 1,500-pound personal watercraft lift, providing immediate access to the Chesapeake Bay and beyond. Offering 4 bedrooms, 5 full baths, 1 half bath, a dedicated office, and a deep four-car garage, this is a rare opportunity to own one of Annapolis’ premier waterfront properties in a setting where extraordinary architecture, unmatched craftsmanship, and world-class outdoor living come together on the shores of the Chesapeake.

3728 Ramsgate Dr, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$1,950,000
4 Beds ⋅ 3 Baths
Stunning offering in gated Epping Forest! This 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 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. Email for list of 925K spent on restoration since purchase including brand new private pier and brand new Kitchen and all 3 Full Baths. 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 with Non-Riparian Waterfront. Special financing via Pentagon Federal Credit Jumbo 7/6 ARM available to low as 5.50%.

1739 Vineyard Trl, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$2,950,000
4 Beds ⋅ 5 Baths
Perfectly positioned on one of the most coveted streets in Historic Annapolis, just steps from State Circle, the United States Naval Academy, City Dock, waterfront dining, boutiques, and yacht clubs, 238 King George Street offers a rare opportunity to own a completely reimagined luxury residence in the heart of Maryland’s capital city. Blending timeless historic charm with the modern conveniences today's discerning buyer expects, this exceptional home was extensively renovated and expanded in 2006–2007 and thoughtfully updated through 2025, including a new roof, HVAC systems, and water heater. Inside, four beautifully finished levels offer elegant living and entertaining spaces filled with natural light, custom millwork, rich hardwood flooring, high ceilings, and refined architectural details throughout. The gourmet kitchen opens seamlessly to inviting gathering spaces designed for both intimate evenings and large-scale entertaining, while the finished lower level with high ceilings and private walk-out entrance provides exceptional flexibility for guests, recreation, or a private office. The upper-level loft retreat offers additional living space ideal for guests, a studio, or a luxurious private sanctuary. Enjoy views of the iconic Naval Academy Chapel dome, a daily reminder of the unparalleled location and lifestyle this home affords. Rare off-street parking adds tremendous value and convenience, while the lock-and-leave nature of the property makes it ideal as a primary residence, weekend retreat, or executive pied-à-terre. Offered substantially furnished with only a few exclusions, this remarkable home provides the opportunity to move in and immediately begin enjoying the very best of Annapolis living. Luxury, history, walkability, and convenience converge at one of the city's most prestigious addresses.

238 King George St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,150,000
4 Beds ⋅ 4 Baths
Escape to your New Sanctuary on a 1.17 Acre Lot. Welcome to the Birch Model, one of our premier homes designed for those who desire the best in space, style, and comfort. This home offers everything you need for luxurious living. UP TO 5 Bedrooms: Perfect for large families or those who enjoy hosting guests, each bedroom is spacious and thoughtfully designed. UP TO 4.5 Bathrooms: Enjoy the convenience of four full bathrooms and a powder room, providing ample space and privacy for everyone. Extra Storage Space: Keep your home organized with plenty of storage throughout, including a dedicated storage room! Walk-In Pantry: A spacious pantry provides ample storage for all your kitchen essentials and more. Butler’s Bar: Entertain in style with a dedicated butler’s bar, perfect for serving drinks and hors d’oeuvres. Dedicated Office: An ideal space for working from home, studying, or managing household affairs. Open and Inviting Layout: The Birch Model features a seamless flow between the kitchen, dining, and living areas, perfect for both everyday living and entertaining. Luxurious Owner’s Suite: Retreat to your private haven, featuring a spacious bedroom, a spa-like en suite bathroom, and a large walk-in closet. Optional Upgrades and Customizations: Personalize your Birch Model with a variety of finishes, fixtures, and additional features to make it truly your own. The Birch Model offers unparalleled luxury and space, making it the perfect home for those who want it all. Discover what makes this home truly exceptional. Contact us today to schedule a tour and learn more about available customization options!

1353 Yorktown Rd, Annapolis

Listing courtesy of The Pinnacle Real Estate Co.. Contact:

$482,500
4 Beds ⋅ 2 Baths
Fully renovated rancher with all required permits in highly desired neighborhood. Completely updated kitchen with 42" cabinets, quartz countertop, separate island and stainless steel appliances. Main level hardwood floor. Fully finished basement with 4th bedroom and full bathroom, plus huge family room. New siding. New roof. New windows. New gas furnace. New central AC. New HWH. New sump pump. New deck. Private back yard. House located on quiet street, close to major routs and shopping.

105 Rosecrest Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$849,990
4 Beds ⋅ 3 Baths
Our Adams model with a 2' extenstion will be built at this beautiful location near Duvall Creek. Home is priced at the base house only - act fast to choose the options and additions to make this home your own. Photos are of the model with optional In-Law Suite. Contact Listing Agent to schedule appointment.

3268 Kitty Duvall Dr, Annapolis

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

$924,900
4 Beds ⋅ 3 Baths
Rarely does a home offer the perfect combination of over half an acre of privacy, neighborhood beach access, a heated and cooled 3-car garage, and the highly sought-after Broadneck school district—all just minutes from downtown Annapolis and the Chesapeake Bay. Arrive home by passing scenic, conservation-protected farmland before entering the desirable Pleasant Plains community. From the moment you step through the welcoming foyer, you'll appreciate the abundance of natural light and thoughtfully updated living spaces. The recently renovated kitchen flows seamlessly into the dining area, creating the ideal setting for everyday living and effortless entertaining. Just beyond the main living area, a spacious family room offers plenty of room to gather with friends and family, watch the big game, or simply unwind. Double sliding doors open to an expansive deck overlooking a fully fenced, 0.5+ acre backyard that blends open lawn with mature trees—perfect for summer barbecues, outdoor games, a swing set, pets, or peaceful evenings surrounded by nature. Upstairs, you'll find four generously sized bedrooms, two full bathrooms, and the convenience of a second-floor laundry room. The impressive primary suite features vaulted ceilings, a large walk-in closet, and a beautifully appointed en-suite bath complete with dual vanities, a soaking tub, and a separate walk-in shower. The lower level provides exceptional storage with two fully encapsulated crawl spaces equipped with a dehumidification system installed in 2020, ensuring clean, dry, and easily accessible storage year-round. Car enthusiasts, hobbyists, or anyone needing extra workspace will appreciate the heated and cooled, epoxy-finished three-car garage with abundant storage. Outside, the setting is just as special. A picturesque sod farm directly across the street creates a peaceful, open landscape, while the quiet neighborhood roads are ideal for walking, biking, and enjoying the outdoors. Just a short stroll away, residents enjoy neighborhood beach access where you can launch a kayak, watch sailboats drift by, or take in breathtaking Chesapeake Bay sunsets. This is a rare opportunity to enjoy privacy, modern updates, water access, and an unbeatable Annapolis location—all in one exceptional property. Recent Improvements Include: New roof (2020) Kitchen appliances (2020) Two encapsulated crawl spaces with dehumidification system (2020) Sidewalk and driveway leveling (2021) Ductless mini-split HVAC system (2022) Fresh interior paint (2026) Refinished hardwood floors (2026)

1469 Pleasant Lake Rd, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$1,100,000
4 Beds ⋅ 5 Baths
Stately brick traditional in sought-after Bowen Manor community. - Turn key,move- in ready just minutes from Historic Annapolis, major commuter routes, and marinas. Offering spacious, bright living throughout. Built with numerous custom upgrades and additions by the original owner, this beautifully maintained residence combines timeless elegance with thoughtful design and very low maintenance From the moment you open the handsome front doors, you'll appreciate the rich Brazilian cherry hardwood floors,elegant crown molding and timeless architectural details throughout this beautiful home. A private first-floor office with French doors and a sunny window provides the perfect space for working from home, reading or a quiet retreat. Designed for both comfortable living and entertaining, the chef's kitchen features gas cooking, center island, and generous gathering space flowing seamlessly into the inviting family room with a cozy gas fireplace. The luxurious primary suite offers a private sitting room, tray ceilings, and an generous walk- in closet. Four spacious bedrooms provide room for family and guests alike. Bedroom level laundry room. The walkout lower level is ideal fro expansive family room, second gas fireplace, and access to a wonderful brick patio area - perfectly suited for a future hot tub installation. Generous amounts of storage, the insulated under- deck drainage system helps keep the patio protected from rain. Additional highlights include all TVs convey, security system, and electric air filtration system. Perfectly located with convenient access to BWI Airport and just 15 minutes to the Beltway, this exceptional property offers comfort, convenience, and enduring quality. A warm and welcoming home you'll proudly call "Home Sweet Home"

216 Bowen Ct, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$10,850,000
4 Beds ⋅ 7 Baths
An extraordinary expression of waterfront luxury, this architecturally significant estate represents a rare convergence of world class design, craftsmanship, and lifestyle. Located within the prestigious enclave of Wimbledon Farms, surrounded by grand estates and moments from local vineyards and equestrian facilities, the residence was masterfully conceived by acclaimed architect Scarlett Breeding and flawlessly built by Pyramid Builders. A complete refit elevated the home to an uncompromising standard where timeless architecture and modern sophistication exist in perfect harmony. An enchanting winding crushed gravel driveway framed by Belgian block curbing sets the tone for the remarkable experience that awaits. Perfectly positioned with western exposure, the property captures breathtaking sunsets as golden light melts into the horizon across the river and the surrounding landscape. Professionally designed landscaping creates a lush resort like setting that enhances the home’s striking architectural presence. Inside, high lacquered woodwork, bespoke millwork, hidden passage doors, attention to detail, and coffered ceilings create an atmosphere of refined sophistication. Ultra luxe Chesneys fireplace surrounds anchor multiple living spaces with warmth and elegance, while expansive walls of glass frame sweeping water views and seamlessly connect the indoors with the surrounding waterfront setting. A richly appointed wood-clad office with custom built ins offers an executive retreat designed for both privacy and inspiration. At the heart of the residence, the extraordinary St. Charles kitchen rivals those found in internationally celebrated estates, featuring Premier custom cabinetry, a statement Le Cornue range and island, exquisite fixtures, and an artisan-crafted focal point range hood, all designed for elevated entertaining and effortless daily living. Outdoor living reaches resort caliber with an elevated spa and a spectacular four sided overflow vanishing edge pool, where the waterline sits flush with the pool edge, creating a seamless visual connection to the river beyond. Exotic Ipe hardwood decking surrounds the pool and expansive rear terrace, while pergolas and a screened porch provide beautifully designed spaces for entertaining and relaxation. A new private pier, private beach, and panoramic river and pond views complete this extraordinary waterfront lifestyle. The upper level offers four luxurious ensuite bedrooms, including a phenomenal primary suite with sweeping water views, barrel ceiling, a fireside sitting room, a boutique inspired dressing gallery, and a spa quality bath with a soaking tub overlooking the water. Integrated Control4 home automation delivers effortless comfort and convenience throughout. Tucked away on the coveted Annapolis Neck peninsula, Wimbledon Farms offers a rare blend of tranquility, exclusivity, and convenience. Just moments from Downtown Annapolis and major commuter routes, the setting feels worlds away, defined by peaceful surroundings and an unmistakable sense of retreat. Encompassing only 19 estate homesites, this intimate waterfront enclave is gracefully bordered by Harness Creek and the South River, creating a breathtaking backdrop for both sunrise and sunset vistas. Residents enjoy a warm yet private community atmosphere, highlighted by occasional neighborhood gatherings and an expansive marina on protected Harness Creek, a prized deep water haven known for its calm, sheltered waters and exceptional boating access. Welcome Home!

3344 Harness Creek Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$7,250,000
4 Beds ⋅ 4 Baths
Perfectly positioned along the waterfront in the prestigious Murray Hill neighborhood of Annapolis, this extraordinary estate represents a rare opportunity to own a fully reimagined luxury residence where privacy, walkability, boating lifestyle, and architectural sophistication converge in one of the East Coast’s most coveted waterfront settings. RenownedBohan Contracting has been extensively renovating the home since October 2025. The home has not been lived in since completion, offering an exceptionally rare “like-new” experience where every finish, appliance, system, and curated detail remains untouched. Set on an unusually expansive waterfront lot for downtown Annapolis standards, the property delivers a sense of scale and privacy that is nearly impossible to replicate within Murray Hill. Mature landscaping, multiple outdoor living spaces, Brazilian Ipe decking, and panoramic water views create a setting that feels worlds away while remaining just moments from the energy and charm of downtown Annapolis. Designed for the discerning buyer seeking a refined waterfront retreat, the residence effortlessly balances elevated entertaining with relaxed coastal living. Whether arriving by boat after a day on the Chesapeake Bay, hosting sunset gatherings overlooking Spa Creek, or enjoying peaceful mornings watching sailboats drift by, the home was designed around an experience. Inside, timeless design and modern luxury unfold at every turn. The fully reimagined chef’s kitchen rivals those found in premier custom estates, anchored by a complete JennAir Noir appliance suite including a 48-inch dual-fuel range with double ovens, professional refrigeration, dual integrated dishwashers, multiple beverage centers, built-in ice maker, and a butler's pantry designed as both a prep and entertaining space. Custom Schrock “Trademark” maple cabinetry, designer-selected Waterworks fixtures, Calacatta Miraggio Cielo quartz with dramatic waterfall detailing, and layered architectural lighting elevate the space into a true showpiece. Throughout the residence, every finish was intentionally selected to create warmth, sophistication, and understated luxury. Wide-plank white oak flooring, custom white oak ceiling beams, Restoration Hardware lighting, Baldwin hardware, integrated Sonos audio throughout the home, Lutron lighting controls, custom plaster fireplaces, upgraded insulation for sound attenuation, and CAT6 wiring provide the seamless blend of craftsmanship and modern infrastructure expected at this caliber of home. The primary suite serves as a private sanctuary, complete with custom built-ins, boutique-style California Closets systems, integrated laundry, and a bespoke fireplace designed to create an atmosphere reminiscent of a luxury waterfront hotel suite. Every secondary space continues the same level of thoughtful execution and design continuity rarely achieved in residential renovations. Outside, the waterfront experience becomes truly exceptional. A private pier with electric, boat lift, paver stone extended driveway, refinished gates, and oversized outdoor entertaining areas creates a lifestyle tailored for effortless luxury. The property’s unique positioning offers both protected water access and breathtaking views while maintaining an uncommon sense of seclusion in the heart of Annapolis. Located just minutes from Downtown Annapolis, the United States Naval Academy, award-winning restaurants, yacht clubs, boutique shopping, and private aviation access, this home is ideally suited for the executive or entrepreneur seeking an uncompromising second home or primary waterfront residence within easy reach of Washington D.C., Northern Virginia, Philadelphia, and New York. The ability to enjoy a true luxury waterfront lifestyle with boating access, walkability, privacy, and substantial land all within one of Annapolis’ most prestigious neighborhoods is extraordinarily rare.

11 S Acton Pl, Annapolis

Listing courtesy of Real Broker, LLC - Severna Park. Contact: 8445517325
$1,999,999
4 Beds ⋅ 4 Baths
Welcome to 146 Duke of Gloucester Street! As you approach the home, a welcoming front porch will greet you, offering a place to sit and take in all that Annapolis has to offer. Nestled in the heart of historic Annapolis, this beautifully appointed 4-bedroom, 3.5-bath residence seamlessly blends timeless charm with modern sophistication. Rich in character and thoughtfully updated throughout, this exceptional home offers an inviting open-concept main level designed for both comfortable living and effortless entertaining. Step inside to discover sun-filled living and dining spaces anchored by a stunning exposed brick fireplace that adds warmth and historic appeal. The modern kitchen is a true centerpiece, featuring stylish finishes, ample cabinetry, and a functional layout perfect for everyday living and hosting guests alike. The second level features three spacious bedrooms filled with natural light from oversized windows, generous closet space, and two beautifully appointed full bathrooms, creating comfortable accommodations for family and guests alike. Occupying the entire third floor, the expansive primary suite serves as a private retreat complete with a luxurious spa-inspired bath designed for relaxation and rejuvenation. Outside, enjoy a charming backyard—an ideal setting for outdoor dining, gardening, or simply unwinding in your own private oasis. Perfectly situated just moments from the waterfront, renowned restaurants, boutique shopping, and the rich history of downtown Annapolis, this home offers a rare opportunity to experience historic living with all the comforts of modern design.

146 Duke Of Gloucester St, Annapolis

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690
$1,350,000
4 Beds ⋅ 4 Baths
Nestled in the highly coveted Murray Hill neighborhood, one of Annapolis' most picturesque enclaves, this exceptional 1925 Craftsman masterpiece effortlessly blends historic charm with sophisticated modern luxury. Rich in architectural character and thoughtfully enhanced with extensive renovations, this remarkable residence offers an unparalleled lifestyle defined by elegance, convenience, and timeless appeal. From the moment you arrive, the home's undeniable curb appeal captivates with its fresh landscaping, newly renovated rear entry steps, and impeccable craftsmanship. Inside, refinished original hardwood floors, fresh designer paint, stylish new lighting, and beautifully curated updates create a seamless balance between historic integrity and contemporary comfort. Significant investments in the home's infrastructure, including a new HVAC system with a transferable 10-year warranty and upgraded electrical service, provide peace of mind while preserving the home's enduring character. Designed for both refined entertaining and comfortable everyday living, the main level showcases expansive gathering spaces filled with warmth and sophistication. Step into the four seasons room with new ceiling fans and surrounding windows. The original living room invites intimate conversation, while the formal dining room offers the perfect backdrop for memorable dinners and celebrations. At the heart of the home lies an impressive chef's kitchen within the thoughtfully designed addition: a true showpiece that combines luxury, functionality, and style. Featuring Brazilian cherry hardwood flooring and cabinet, granite counterops, stainless steel appliances, updated fixtures, generous prep space, an additional fireplace, and room for casual dining, this extraordinary culinary space was designed to inspire everything from morning coffee to elegant dinner parties. Throughout the home, exquisite architectural details including intricate millwork, original craftsmanship, and abundant natural light create an atmosphere that is both welcoming and refined. The luxurious primary serves as a private sanctuary, highlighted by a second fireplace that adds warmth and ambiance. Two expansive walk-in closets offer exceptional flexibility and can easily function as a private office, sitting room, dressing area, or personal retreat. The spa-inspired en-suite bath features dual vanities, a jetted soaking tub, and a spacious walk-in shower, creating a serene escape at the end of each day. Also plumbed for a wet bar and includes a separate closet for laundry. Three additional generously sized bedrooms provide ample accommodations for family and guests, while the home's three full bathrooms and one half bath have been thoughtfully appointed to blend comfort with elegance. The lower level offers exceptional versatility with a bonus room that can serve as an additional bedroom, fitness studio, home office, or recreation space, complemented by a conveniently located half bath. Additional unfinished basement space provides abundant storage or the opportunity for future customization. One of the home's most exciting opportunities lies within the expansive unfinished top level. Featuring soaring ceilings and substantial square footage, this remarkable space offers endless potential to create an additional bedroom suite, media room, executive office, artist's studio, or luxury recreation area while further enhancing the home's value and functionality. Outdoor living is equally impressive. The newly renovated detached two-car garage provides convenience and charm, while the beautifully maintained grounds create inviting spaces to relax and entertain. During the winter months, seasonal water views add yet another layer of distinction to this exceptional property. Just steps from your front door, stroll to the water taxi for your own nautical uber, restaurants, boutiques, galleries, and entertainment to experience all of what living in downtown Annapolis has to offer.

107 Monticello Ave, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$1,049,000
4 Beds ⋅ 4 Baths
PRICE IMPROVEMENT! Experience the best of Annapolis waterfront living with this beautifully updated home, complete with a private dock just off the South River and only minutes to the Chesapeake Bay. Bring your fishing rods, crab nets, kayaks, and boat; this is the waterfront lifestyle you've been waiting for. Inside, refinished hardwood floors and abundant natural light create a warm, inviting atmosphere. The updated kitchen features new GE stainless steel appliances and opens seamlessly to the cozy living room with a wood-burning fireplace and direct access to the spacious deck; perfect for outdoor dining while overlooking the tranquil backyard. A convenient main-level laundry/mudroom with a side entrance and ramp adds everyday functionality. The waterfront primary suite is a true retreat, offering a private balcony and an updated en-suite bath. Three additional bedrooms with brand-new carpet provide plenty of space for family, guests, or a home office. The fully finished walkout lower level offers exceptional flexibility with its own private entrance, full kitchen, spacious updated bathroom, and laundry hookup—ideal as an in-law suite, guest quarters, or entertaining space. Outside, enjoy 50 feet of waterfront, a private dock, kayak rack, and a generous 0.41-acre lot with room to relax, garden, or entertain. Conveniently located just minutes from Historic Annapolis, the U.S. Naval Academy, BWI Airport, and Washington, D.C., this home combines peaceful waterfront living with unbeatable accessibility. Don't miss this incredible opportunity to own your own piece of Annapolis waterfront at an improved price!

996 Headwater Rd, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$1,295,000
4 Beds ⋅ 4 Baths
House is framed and moving along quickly. Be in within 4 months. Perfectly situated just minutes from the heart of Downtown Annapolis, yet tucked away for privacy, this 4 br, 3.5 bath NEW CONSTRUCTION coastal inspired home with a 2 car garage by Whitehall Building & Company offers the best of both worlds—convenience and tranquility. With over 3,200 square feet of finely crafted living space across three levels, every detail has been thoughtfully designed to deliver both comfort and sophistication. Step inside and be greeted by soaring 10-foot ceilings, expansive wide-plank flooring, and an open-concept layout ideal for both everyday living and elegant entertaining. The chef’s kitchen is the centerpiece of the home, featuring a grand center island, quartz countertops with matching backsplash, premium stainless steel appliances, and abundant storage. Flowing seamlessly into the breakfast area and spacious family room, this home is designed for hosting unforgettable gatherings. Additional main-level highlights include a custom mudroom, walk-in pantry, and stylish powder room. The upper level is a true sanctuary, boasting a luxurious primary suite with a generous walk-in closet and spa-inspired bath complete with dual vanities, a frameless glass shower, and a freestanding soaking tub. Two additional bedrooms share a beautifully appointed guest bath, while a convenient second-floor laundry room adds ease to daily living. The lower level includes a spacious recreation room, full bath and 4th bedroom, perfect for overnight guests or extended family. All of this in an enviable location just minutes from the U.S. Naval Academy, fine dining, boutique shopping, waterfront attractions, and major commuter routes. Don’t miss the opportunity to be in your new luxury home of your dreams in the heart of Annapolis. Footers have been poured, framing is underway, and delivery of your new home is only 4 months away. 100% VA financing available.

13 Elliott Rd, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$3,250,000
4 Beds ⋅ 5 Baths
Welcome home. Perfectly positioned at the end of Market Street, this rare waterfront residence offers an exceptional blend of privacy, design and an impeccable lock and leave lifestyle. Located within an intimate six residence enclave, this fully reimagined contemporary brick townhome captures sweeping views of Spa Creek from every level, delivering a front row experience to Annapolis’ most iconic moments, from the Blue Angels to the holiday lighted boat parade. Completely rebuilt from the studs in the last few years with a refined nautical influence, the home spans four light filled levels, where thoughtful design and craftsmanship are evident throughout. Refinished hardwood floors run seamlessly from room to room, while custom steel stair elements made from sailboats, create a striking architectural focal point. An elevator services the main and upper levels, offering both convenience and ease of living. The main living level is both elegant and inviting, featuring a stunning half bathroom, spacious living room with a wood burning fireplace with a marble fireplace surround with custom surrounding built ins that look out to the water. The gourmet kitchen is designed for both everyday living and entertaining, offering high end appliances, a beverage refrigerator, and a dramatic marble waterfall countertop. Additional luxurious details include hidden hinges, walnut doors and tiles from Bali. Sightlines were intentionally designed to draw your eye straight through to the water the moment you enter. The upper level primary suite is a true retreat, offering panoramic water views and a spa inspired bath. An additional ensuite bedroom completes this level, along with a conveniently located second laundry area for effortless everyday living. The top floor provides two more generously sized bedrooms and a beautifully appointed full bath, ideal for guests. On the lower level, a fully equipped second kitchen, recreation space with gas fireplace, full bath with exquisite flooring, laundry, and storage create the perfect setting for extended stays or entertaining, with direct walk out access to the waterfront. Beyond the interiors, the lifestyle is equally compelling. A flagstone courtyard welcomes you home, while rare off street parking adds convenience for owners of this six townhome community. A deeded boat slip sits just steps from your door, offering immediate access to the water. Residents enjoy exclusive access to a heated gunite pool, beautifully maintained grounds, exterior maintenance including the roof, a floating dock and kayak storage, all within this private community. From here, it is a short stroll to the shops and restaurants of downtown Annapolis, or take a scenic water taxi ride and be picked up just steps away from your front door. This is a rare opportunity to experience turnkey waterfront living with effortless access to everything that makes Annapolis extraordinary.

5 Market Quay, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$3,750,000
4 Beds ⋅ 6 Baths
Ideally situated on the banks of Luce Creek with sweeping views down the Severn River, 1715 Porters Hill Road is a unique heritage property with over a century of history. Set on a 1.7 acre lot with 265 ft of waterfrontage, the property includes a large, hard-to-find boathouse that provides both charm and utility for all your waterfront adventures. The private pier has 7+ ft water depth and can accommodate a large vessel as well as an assortment of smaller boats. The tram makes access to the water effortless, and the entire property enjoys an exceptional privacy. Steeped in its storied past yet thoughtfully updated for modern living, this retreat captures the perfect balance of historic charm and casual elegance. The heart of the home is a sunlit great room with original log walls and quarried stone fireplace, a vaulted ceiling, and expansive windows which frame water views at every turn. An adjoining den, with separate entrance option, is a perfect place to relax. This could easily become another main level bedroom with ensuite bathroom. The kitchen is striking under its vaulted ceiling accented by exposed beams. The custom cabinetry, GE Monogram stainless steel appliances and generous island give the space so much functionality while maintaining the artisanal character. The kitchen opens to the dining area overlooking the water. The table is anchored by a craftsman-style light fixture, and the entire first and second floors have beautiful wood floors. Step outside and you’re embraced by nature: multiple porches and decks overlook lush, manicured grounds that lead down to the water’s edge. The main-level primary suite is a true sanctuary, designed for privacy and tranquility. The bedroom, with a vaulted ceiling, has a screened porch overlooking the water. Two expansive walk-in closets offer custom organization systems that would make a clothing connoisseur smile. The spa-like bathroom gets lots of natural light from the windows that frame the water, and the freestanding soaking tub is situated to enjoy this view. A dual-sink vanity, heated floors, generous walk-in shower with a built-in bench, and a spacious cosmetic area with dedicated seating make getting ready feel effortless and luxurious. A dedicated laundry area just off the hallway makes day-to-day living very easy. Part of the primary suite is a gracious office with gas fireplace and outdoor access. This is a totally flexible space: install a wall of bookshelves and you’d have a lovely library. Upstairs, there are two generously sized bedrooms. One has water views and a waterside balcony; the other overlooks the lush landscaping out front. There is a hall bathroom. A separate guest bedroom suite above the garage, complete with its own living area and luxe bathroom, is ideal for visiting friends and family who desire more privacy. The Historical Context: Originally built in the 1880s, this log house was one of three identical structures used as hunting lodges. The logs of this original structure were re-purposed in the renovation. The construction of the log walls is one of great craftmanship, including sizing each log to be approximately the same diameter as others. Lore has it that around the turn of the 20th century, the Naval academy wanted to acquire more land by the academy and traded this peninsula for land across from College Creek. The Naval Academy superintendent, Admiral David Porter, could be where the name Porter’s Hill derived from. In the 1920’s, the Whitehead family – three brothers known for running bootleg liquor to Baltimore and Washington during Prohibition — used the property as a place to entertain and stop on the way to Baltimore. In the 1940s, the brothers’ exploits caught up with them, and the State of Maryland confiscated the Porters Hill peninsula. Through a unique trade involving the Jones family’s gravel pit (now the site of the 895 Tunnel), this private waterfront enclave found its next chapter.

1715 Porters Hill Rd, Annapolis

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

$1,875,000
4 Beds ⋅ 5 Baths
An exceptional blend of timeless craftsmanship, thoughtful customization, and coastal elegance, 820 Bay Ridge Avenue offers over 4,000 square feet of beautifully finished luxury living across four levels in Eastport's coveted Sailor's Quay enclave. Unlike many homes in the community, this residence was thoughtfully customized with numerous builder upgrades and enhancements, creating a level of comfort, functionality, and long-term value that is immediately apparent. A charming white picket fence, manicured landscaping, and gracious brick front porch welcome you inside, where rich hardwood floors, soaring 9-foot ceilings, tray ceilings, detailed millwork, and plantation shutters throughout create an atmosphere of understated sophistication. The gourmet kitchen is both beautiful and functional, featuring honed granite countertops, premium appliances, abundant cabinetry, and a substantial center island that opens seamlessly to the inviting family room anchored by an upgraded gas fireplace. A formal dining room illuminated by a stunning chandelier provides an elegant setting for entertaining, while the adjoining sitting room or study offers the perfect space for reading, working from home, quiet conversation, or enjoying an evening bourbon. Outdoor living is equally impressive with a welcoming flower garden-facing front porch, a private English courtyard patio, and a second-floor terrace, both enhanced with ceiling fans for exceptional comfort, creating inviting spaces for morning coffee, outdoor dining, or relaxing at the end of the day. A dedicated natural gas line provides the convenience of connecting an outdoor grill or future fire pit. The professionally enhanced landscaping and more functional yard further elevate the outdoor experience. The luxurious primary suite serves as a private retreat with a custom walk-in closet, spa-inspired bath, and an expansive sitting room. A spacious junior suite with its own private bath provides outstanding accommodations for family or guests, while two additional vaulted-ceiling bedrooms share a beautifully appointed full bath on the upper level. The finished third-floor loft adds exceptional versatility for a home office, fitness room, guest retreat, or media space. The finished lower level offers a large family room and full bath, providing even more flexible living space. Designed with future accessibility in mind, the home also features a framed elevator shaft, allowing for a future elevator installation without altering the home's thoughtful design or flow. Additional electrical enhancements throughout the home reflect the careful planning and attention to detail invested during construction. Perfectly positioned just moments from Downtown Annapolis and the United States Naval Academy, this exceptional location offers a truly walkable lifestyle with easy access to waterfront dining, boutique shopping, marinas, parks, art galleries, and the vibrant coastal culture that defines Eastport. Whether strolling across the Spa Creek Drawbridge or taking the water taxi into downtown, every day feels connected to the waterfront lifestyle, while convenient access to Routes 50 and 97 provides an easy commute to Baltimore, Washington, D.C., and beyond. Combining timeless architecture, custom upgrades, sophisticated finishes, future elevator capability, exceptional outdoor living, and one of Annapolis' most desirable locations, 820 Bay Ridge Avenue presents a rare opportunity to own one of Sailor's Quay's finest residences.

820 Bay Ridge Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$775,000
4 Beds ⋅ 4 Baths
BEAUTIFULLY RENOVATED EASTPORT GEM with MODERN COASTAL FINISHES! Perfect for a Primary Residence, 2nd Home or Rental Investment! ABOUT THE HOME: 3 levels of luxury living featuring 4 Bedrooms and 3.5 Bathrooms. Open-concept main level with New Hickory hardwood floors and designer lighting throughout. THE GOURMET KITCHEN: Custom white Shaker cabinetry, modern black hardware, Quartz countertops, oversized center island, and premium stainless appliances with gas cooking. THE PRIMARY SUITE: A rare main-level primary retreat with walk-in closet and spa-like bath featuring custom tile work and glass-enclosed shower. THE FLEXIBLE LOWER LEVEL: Fully finished walk-up basement with a 4th bedroom/office, family room with wood accent wall, and a custom full bath—perfect for a guest or in-law suite. THE EXTERIOR: Iconic white picket fence in front, with cozy front porch, and a private rear yard with beautiful wood privacy fence is expanded by an additional 736 SF (included in sale). New Black Andersen 100 series windows, Hardie Plank siding, and new hardscaped paths. PARKING: Private driveway with 4 off-street parking spaces. LOCATION: Unbeatable walkability to Downtown Annapolis, Maritime activities, and local favorites. See Annapolis City site for details on the Eastport Choice Neighborhood Initiative! Enjoy all that Eastport has to Offer! Don't Let This One Get Away! Make your Appointment Today! Active Ring Camera on Property.

152 Jefferson St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com