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$1,750,000
4 Beds ⋅ 3 Baths
Set back off the road on a quiet cul-de-sac in the coveted Saefern community, this contemporary home offers peaceful water views, a private wooded setting, and endless potential to make it your own. Whether you're looking to move right in and enjoy the home as it is or reimagine the space into your dream retreat, this property presents an incredible opportunity in one of Annapolis' most sought-after waterfront communities. Designed to embrace its natural surroundings, the home is filled with light and features soaring ceilings, warm wood architectural details, and expansive windows that bring the outdoors in. The dramatic living room is anchored by a striking brick fireplace and flows into the dining area and kitchen, creating an inviting space for gathering. Three sets of sliding glass doors open to the expansive balcony, seamlessly blending indoor and outdoor living while framing peaceful water and woodland views. Just beyond, the enclosed porch with vaulted ceilings provides a year-round place to relax while taking in the peaceful water and woodland views. The thoughtfully designed main level offers two bedrooms, including a spacious primary suite with a private sitting area and ensuite bath, along with a second bedroom that is served by a full hall bath, ideal for guests, family, or a home office. The walkout lower level expands the living space with a generous family room featuring a second fireplace, a built-in bar area, and access to the adjoining sunroom and patio, creating the perfect setting for entertaining. Two additional bedrooms are located on this level, including one with a private ensuite bath and private patio. An additional bedroom offers flexible accommodations for guests or multigenerational living. Life in Saefern is about much more than the home itself. Membership in the renowned Saefern Saddle & Yacht Club (SSYC) includes a boat slip, marina, swimming pool, tennis and pickleball courts, horse stables, dog park, playground, and an active community lifestyle. Just minutes from Historic Annapolis, the U.S. Naval Academy, shopping, dining, and convenient commuter routes to Washington, D.C. and Baltimore, this is a rare opportunity to invest in a home with outstanding bones, water views, and the chance to create something truly special. Welcome Home!

500 Sara Dr, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$600,000
3 Beds ⋅ 2 Baths
Discover the opportunity to create your dream home in one of Annapolis’ most desirable waterfront communities. Nestled on nearly half an acre, this charming property offers privacy, mature surroundings, and endless potential just minutes from Historic Downtown Annapolis, the U.S. Naval Academy, shopping, dining, and commuter routes. With approximately 1,872 square feet of living space, 3 bedrooms, two full bathrooms, this home provides a solid foundation for renovation, expansion, or personalization to suit your lifestyle. Whether you’re searching for a primary residence, a weekend retreat, or an investment opportunity, this property offers the rare combination of a generous homesite and an exceptional location. Enjoy the peaceful setting of Luce Creek while remaining close to marinas, parks, waterfront recreation, and all that Annapolis has to offer. Opportunities like this don’t come along often—bring your vision and make this property your own. Established neighborhood in Annapolis. Minutes to downtown, shopping, restaurants, and waterfront attractions Excellent opportunity to renovate or customize

1871 Luce Creek Dr, Annapolis

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$559,000
4 Beds ⋅ 4 Baths
Welcome to 79 Windwhisper Lane, a refreshed contemporary home featuring vaulted ceilings, fresh neutral paint, new carpeting, hardwood floors, and a bright kitchen with marble-look tile and stainless-steel appliances. The family room includes a fireplace and opens to a spacious rear deck overlooking a tree-lined yard. A finished lower level adds flexible living space, a bedroom, and a full bath, while the attached one-car garage, newer roof, and central air provide added convenience.

79 Windwhisper Ln, Annapolis

Listing courtesy of Sell Your Home Services. Contact: 8882193009
$475,000
4 Beds ⋅ 2 Baths
Welcome to 1099 Linden Tree Drive, an incredible opportunity to own a four-bedroom, two-full-bath colonial in the desirable waterfront community of Cape St. Claire! Offering approximately 1,880 finished square feet, this home provides a functional layout with plenty of room for everyday living, working from home and entertaining. Several important updates have already been completed, including a newer roof, well pump, hot water heater, windows, heat pump, gutters, gutter guards and attic insulation. These improvements provide added value while still allowing the next owner the opportunity to personalize the home and make it their own. Outside, enjoy a spacious deck overlooking the fully fenced backyard—perfect for pets, play, gardening or summer gatherings. Cape St. Claire residents enjoy access to multiple community beaches, parks and marinas, while nearby parks offer trails, athletic fields, playgrounds, picnic areas and additional outdoor recreation. Conveniently located near shopping, schools, Route 50, the Chesapeake Bay Bridge, Downtown Annapolis and Maryland’s Eastern Shore, this home offers a wonderful combination of community amenities, outdoor recreation and commuter convenience. Bring your vision and make this Cape St. Claire home your own!

1099 Linden Tree Dr, Annapolis

Listing courtesy of Samson Properties. Contact: 4439757555
$595,000
4 Beds ⋅ 3 Baths
Nestled in the charming Cape St. Claire community, this exquisite split foyer home offers a perfect blend of comfort and luxury. With 2,168 square feet of thoughtfully designed living space, this residence features four spacious bedrooms including a massive owners suite and three full bathrooms, ensuring ample room for relaxation and entertaining. Step inside to discover a warm and inviting atmosphere, highlighted by an open floorplan that seamlessly connects the kitchen and dining areas. The kitchen, complete with electric appliances and generous table space, is perfect for culinary enthusiasts. Enjoy cozy evenings by the fireplace, where natural light pours in. The fully finished basement offers endless possibilities, whether you envision a home gym, office, or additional living space. Outside, sits on the perfect corner lot, providing a unique outdoor experience. Just a short stroll away, indulge in the community's exceptional amenities, including access to the beautiful Chesapeake Bay and Magothy River. Imagine sipping your morning coffee on the porch while taking in serene water views, or spending weekends at the nearby beach and boat dock. This property is not just a home; it's a lifestyle, offering a perfect blend of tranquility and recreation. Experience the best of waterfront living in this exclusive community, where every day feels like a vacation.

994 Hillendale Dr, Annapolis

Listing courtesy of LPT Realty, LLC. Contact: 8773662213
$649,900
4 Beds ⋅ 3 Baths
Experience the perfect blend of modern luxury and waterfront living at 1412 Ellis Road in the highly sought-after, water-privileged community of Oyster Harbor. This beautifully renovated home offers exceptional style, flexible living spaces, and outstanding indoor and outdoor entertaining—all just minutes from downtown Annapolis. The main residence features 3 spacious bedrooms and 2 full bathrooms, thoughtfully updated with today's finishes and designed for comfortable everyday living. The gourmet kitchen is the heart of the home, showcasing sleek cabinetry, premium appliances, and generous prep space, making it ideal for everything from casual family meals to hosting friends. A standout feature of this property is the detached studio suite, complete with its own kitchen, full bathroom, and washer and dryer. Perfect as a guest house, private home office, creative studio, or space for extended family. Does someone need a place to stay when visiting the Naval Academy. $$ This would work. The inviting living area offers a warm, welcoming atmosphere year-round. During the cooler months, relax in the cozy interior spaces, and when the weather warms up, step outside to enjoy two expansive rear decks that seamlessly extend your living space outdoors. Whether you're grilling, dining under the stars, or simply unwinding with family and friends, these outdoor spaces were designed to be enjoyed in every season Beyond the home, Oyster Harbor provides an exceptional Chesapeake Bay lifestyle with community amenities that include a private beach, boat ramp, fishing pier, kayak launch, playground, and picnic area. Here, you'll enjoy the charm of waterfront living while remaining just minutes from Historic Annapolis, shopping, restaurants, and major commuter routes.

1412 Ellis Rd, Annapolis

Listing courtesy of Compass. Contact: (443) 873-3585
$3,395,000
4 Beds ⋅ 4 Baths
Once-in-a-Lifetime Opportunity to Build Your Dream Waterfront Home in Bay Ridge. Don't miss your chance to own the last remaining waterfront lot and be in your new home by next boating season in the prestigious and highly sought-after Bay Ridge community. This is a rare opportunity to work with the builder to design and build your dream home on a premium lot offering 57 feet of serene waterfront on protected Lake Ogleton. Also listed as just a lot without a house package. Enjoy breathtaking, unobstructed views and the peaceful lifestyle that only true waterfront living can offer. Whether you're envisioning a luxurious modern retreat or a timeless coastal home, this lot is the perfect canvas. Contact the listing agent for insight and inspiration on potential home designs tailored to this exceptional property. Bay Ridge is renowned for its rich history, vibrant community, and unmatched amenities, including a bayfront community pool and newly renovated clubhouse, sandy beaches and scenic waterfront , a large community marina, basketball and pickleball courts, a children's playground, and year-round community events. Located just minutes from downtown Annapolis and Eastport, Bay Ridge offers the charm of a tight-knit neighborhood with the convenience of city access. Experience the perfect blend of tranquility and community in one of the most desirable waterfront enclaves on the Chesapeake Bay. This is more than just a lot—it's the beginning of your dream lifestyle and opportunity to customize the perfect paradise.

48A E Lake Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$600,000
3 Beds ⋅ 2 Baths
Welcome home to this beautifully renovated split-level in a sought-after community! Featuring a bright, open floor plan with quality finishes throughout, this move-in ready home offers wood floors, an updated kitchen, and fully renovated baths. The three-bedroom layout provides comfortable living spaces designed for today's lifestyle. Nestled on a private, wooded 0.40-acre lot backing to Annapolis Waterworks Park, you'll enjoy peaceful views and direct access to nature right in your backyard. An oversized one-car garage offers ample room for a workshop, hobbies, and extra storage, while the encapsulated crawl space provides even more storage options. New septic tank. New roof and heat pump installed in 2024. Residents appreciate the community elementary school and voluntary association. The location is truly exceptional—just minutes from downtown Annapolis, the medical center, shopping, restaurants, and local pubs. Commuters will love the quick access to major routes, making travel throughout the region a breeze. This turnkey home combines charm, convenience, and value in one fantastic package. Don't miss your chance to make it yours!

622 Wayward Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$874,900
3 Beds ⋅ 3 Baths
Experience the best of the Annapolis maritime lifestyle in this beautifully renovated coastal-inspired home, ideally located in the sought-after Hillsmere Shores community one block from the marina, private beach, waterfront playground/parks, community pool, and boat ramp. Thoughtfully redesigned with high-end finishes throughout, this turnkey home offers the perfect blend of style, flexibility, and everyday comfort. The bright, open main level is designed for gathering, featuring a beautifully updated white kitchen with quartz countertops, stainless appliances, custom backsplash, generous workspace, and seamless flow into a dining and seating area accented by shiplap details and French doors opening to an expansive entertaining deck overlooking the oversized, fully fenced backyard. The spacious primary suite includes a sitting area, custom California Closets walk-in, and a bathroom with 4' vanity, an extra large Smart Mirror/Medicine Cabinet and marble shower. The walkout lower level offers exceptional flexibility with a large room currently enjoyed as a family room but could easily serve as a fourth bedroom, complete with fireplace, closet, full egress, and direct access to a private covered deck with hot tub. Two additional bedrooms, both with California Closet systems, a beautifully renovated full bath with double vanity, extended tub and an updated laundry room complete this level. A bonus feature of this house is the separate, flex space adjacent to the garage with its own beautifully renovated powder room, mini-split HVAC, large deck, with endless possibilities as a home office, fitness studio, media room, teen hangout, creative workspace, or guest overflow. Outside, the oversized fenced-in back yard provides rare privacy and room to play, entertain, or garden, complemented by multiple outdoor living areas and a detached shed/workshop with power and air conditioning. The large two car garage features Flow Wall storage system, epoxy floor coating, and an EV charging plug as well as direct access to the rear yard. Extensive renovations throughout include the kitchen, baths, roof, siding, windows, HVAC, flooring, lighting, garage, landscaping, and countless custom details, creating a truly move-in-ready home. Enjoy one of Annapolis' most beloved waterfront communities with a voluntary HOA, private beach on the South River, marina, community pool, playgrounds, and year-round neighborhood events—all just minutes from Downtown Annapolis.

117 Sunset Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,080,000
6 Beds ⋅ 5 Baths
Prepare to be absolutely wowed. Nestled in one of Annapolis's most sought-after communities, this stunning six-bedroom, four-and-a-half-bathroom Colonial has been completely and thoughtfully renovated from top to bottom, delivering a rare combination of timeless elegance, modern luxury and exceptional space across three beautifully finished levels. Step inside and immediately feel the difference. Rich hardwood floors flow throughout the entire main level, complemented by exquisite custom moldings and wainscoting that speak to the level of craftsmanship and attention to detail found at every turn. The main level offers an effortless and inviting flow designed for both everyday living and grand entertaining: a private home office, a gracious dining area, two distinct living spaces and a cozy gas fireplace. And then there's the kitchen. The ultimate chef's kitchen. Anchored by a breathtaking commercial-grade 48-inch GE Monogram gas range- GE's highest tier of luxury appliances- and boasting five ovens, this is a space that serious home cooks and entertainers dream about. No detail was overlooked, no compromise was made. This kitchen doesn't just function beautifully- it commands the room. Step outside to the beautiful deck, perfectly positioned for morning coffee, al fresco dining, or evening unwinding after a night of entertaining. Upstairs, the custom moldings and wainscoting continue, lending a sense of refined consistency and elegance throughout. Retreat to a truly spectacular primary bedroom sanctuary- a spacious, serene haven with its own additional living space, offering the kind of personal escape that makes coming home the best part of every day. Three additional bedrooms complete the upper level, including a private en suite and a generous full bathroom for guests or family. The lower level delivers even more, with two additional bedrooms and expansive recreational space that adapts beautifully to your needs- a home gym, media room, playroom, or guest retreat. The two-car garage adds everyday convenience and storage, while outside, the pergola brings it all together- a stunning, dedicated entertaining space that elevates outdoor living to match the luxury found within. Located just minutes from historic downtown Annapolis, premier dining, marinas, and major commuter routes to DC and Baltimore, 214 Bowen Court isn't just a home- it's a lifestyle.

214 Bowen Ct, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$730,000
3 Beds ⋅ 2 Baths
Open House on 9/13 has been cancelled. Please contact listing agent for showings directly. **NEW PRICE — a fresh opportunity to call Hillsmere Shores home!** Just two blocks from the community’s private beach and playground on the South River, this updated 3-bedroom, 2-bath home puts one of Hillsmere’s best amenities practically at your doorstep. Watch the sunrise at the water, afternoons at the beach, and evenings watching sailboats and ships pass along the Chesapeake Bay are all part of the lifestyle here. Inside, the split-level design offers more space and flexibility than you might expect, with multiple living areas to spread out and make your own. The main living room features a cozy pellet fireplace insert, while a spacious family room and additional finished lower-level room provide plenty of options for a home office, gym, playroom, hobby space, or guests. Hardwood flooring extends throughout two levels, complemented by luxury vinyl plank flooring on the remaining two. The updated kitchen features quartz countertops and stainless steel appliances, and both full baths have beautifully renovated showers. A convenient mudroom/laundry room connects directly to the attached one-car garage, while just off the kitchen, a paver patio creates an easy spot for grilling, dining, and entertaining outdoors. And then there’s Hillsmere! Residents enjoy a private beach, marina, community pool, boat ramps, playgrounds, and year-round neighborhood events—all just minutes from downtown Annapolis. **With its new price, flexible living space, garage, updates, and location just two blocks from the South River, this home deserves another look!**

110 Lake View Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$1,250,000
3 Beds ⋅ 3 Baths
Nestled in the heart of Eastport, this thoughtfully designed 3-bedroom, 2.5-bath home offers the perfect combination of comfortable living, modern updates, and one of Annapolis' most sought-after walkable locations. Complete with a rare detached two-car garage, this is an exceptional opportunity to enjoy the Eastport lifestyle in an established neighborhood that continues to attract significant investment and enduring demand. The main level features hardwood flooring throughout, a spacious living room, separate dining room, and an inviting family room with a wood-burning fireplace that opens directly to the kitchen—creating an ideal space for everyday living and entertaining. The kitchen is equipped with stainless steel appliances, a gas cooktop, and a separate main-level laundry/mudroom for added convenience. A spacious three-season porch extends the living space and creates a wonderful transition to the beautifully landscaped backyard, complete with a flagstone patio, attractive stone retaining wall, and detached two-car garage—ideal for relaxing or entertaining. Upstairs, the spacious primary suite offers a walk-in closet and private bath, along with two additional bedrooms and a full bathroom. The unfinished lower level provides abundant storage, a dedicated workshop area, and exterior access to the rear yard. Recent improvements include a new HVAC system (2024), newer garage doors, and a low-maintenance composite front porch. Step outside and enjoy everything that makes Eastport one of the most desirable waterfront communities in the region. Walk or bike to neighborhood restaurants, coffee shops, marinas, the Annapolis Athletic Club, Spa Creek, multiple yacht clubs, and Historic Downtown Annapolis via the Eastport Bridge. Hop aboard the Water Taxi, spend afternoons on the waterfront, or simply enjoy the vibrant coastal lifestyle that surrounds you. Opportunities to purchase in established Eastport neighborhoods continue to become more limited as significant investment and redevelopment enhance the surrounding area. Whether you're looking for a wonderful place to call home or a long-term investment in one of Annapolis' most coveted communities, 1105 Boucher Avenue offers both lifestyle and lasting value.

1105 Boucher Ave, Annapolis

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

$1,295,000
3 Beds ⋅ 3 Baths
A rare opportunity to own over 2 private acres in one of Annapolis’ most desirable waterfront communities. Complete with a private tennis court and backing to a sprawling horse farm, this exceptional property offers the perfect blend of privacy, recreation, and the Chesapeake lifestyle. Nestled in the sought-after Whitehall Beach neighborhood, residents enjoy community water access, a fishing pier, and the relaxed coastal lifestyle this special enclave is known for. Lovingly maintained by the same owners for many years, this custom home has been exceptionally cared for and thoughtfully preserved. Offering the best of both worlds, it combines tranquil country living with the convenience of being just minutes from downtown Annapolis, waterfront dining, marinas, Route 50, and the highly regarded Broadneck school district. Inside, you’ll find a warm and inviting floor plan with high ceilings, abundant natural light, and timeless custom built-ins that create an inviting main living area. The spacious unfinished lower level provides endless possibilities for future living space, a home gym, workshop, or additional storage. The expansive grounds offer plenty of room to entertain, garden, or simply enjoy your own private retreat, with potential space for a future pool or additional outdoor amenities, subject to buyer verification and all applicable approvals - making this an exceptional offering where privacy, community, and the Chesapeake lifestyle come together. Schedule your private tour today!

718 Whitehall Beach Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$2,099,000
5 Beds ⋅ 3 Baths
Originally built in 2005 and renovated with high end materials, this exceptional Craftsman-style home offers over 3,500 square feet of beautifully finished living space and has been meticulously maintained and thoughtfully updated throughout. The open-concept floor plan offers the perfect balance of comfortable everyday living and effortless entertaining, featuring abundant natural light, crown molding, recessed lighting, and seamless flow between the main living spaces. At the heart of the home is the newly renovated kitchen, complete with a large island with Quartz countertops and seating for up to eight, custom wood-paneled refrigerator and freezer, Signature custom cabinetry, and premium Wolf and Monogram appliances. The adjoining family room features custom built-in bookcases, a Montigo gas fireplace, Sonance in-wall speaker system, and direct access to the screened porch, creating an inviting space for gathering year-round. Additional highlights include a custom wet bar, a main-level bedroom and full bath, and a finished lower level offering flexible space for recreation, guests, or a home office. Outside, the fully fenced, level backyard is a private retreat with mature trees, a spacious patio with a Caldera hot tub, and a built-in outdoor fireplace making it perfect for entertaining in every season. Ideally located in the heart of West Annapolis, this home is just a few blocks from local restaurants, shops, and the community boat ramp. With easy access to Route 50, commuting is simple and convenient. As an added benefit, owners receive approximately $12,000 in rental income during Commissioning week, providing an excellent opportunity to offset ownership costs. Offering timeless style, premium updates, and thoughtful design, this home is a rare opportunity in one of Annapolis' most desirable neighborhoods.

8 Shiley St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,750,000
4 Beds ⋅ 4 Baths
Nestled in the heart of Eastport, this stunning Craftsman-style home offers the perfect blend of timeless charm and modern luxury. This was a complete remodel in 2012! Boasting 4 bedrooms and 4 full baths, this thoughtfully designed residence features an open floor plan accented by beautiful bamboo flooring adding warmth and style throughout. The gourmet kitchen is the centerpiece of the home, complete with a striking marble center island, black granite countertops, stainless steel appliances, a pantry, and an expansive dining area that seamlessly flows into the inviting living room. The main-level primary suite is a true retreat with a spa-inspired bath featuring a soaking tub, walk-in shower, and generous walk-in closet. Upstairs, you'll find two large bedrooms, that share a full bath and an additional bedroom with its own private full bath, and a versatile sun-drenched sitting area with a dramatic vaulted ceiling. The walk-out lower level includes a full bath and versatile space to suit your lifestyle. Outside, a private rear deck perfect for relaxing or entertaining and charming stone walkways and welcoming front porch add historic like charm. A private driveway is for convenient off-street parking, and a storage shed is perfect to house all of your outdoor needs. Ideally located within walking distance of historic downtown Annapolis, you'll enjoy easy access to waterfront dining, boutique shopping, historic landmarks, entertainment, and all the vibrant attractions this sought-after area has to offer. The Eastport lifestyle truly one of a kind!

219 Lockwood Ct, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 224-4999
$1,150,000
3 Beds ⋅ 2 Baths
Welcome to 783 Sonne Drive, where life on the Chesapeake takes center stage. Perfectly positioned on an elevated waterfront lot just under 1 acre in the sought-after Bon Haven community, this exceptional South River residence offers breathtaking water views and the rare opportunity to embrace the very best of the Chesapeake lifestyle. Designed to maximize its spectacular setting, the home seamlessly blends indoor and outdoor living. Expansive windows fill the interior with natural light, while the wraparound deck creates the perfect backdrop for morning coffee, sunset entertaining, or simply taking in the river's peaceful rhythm. Every day here feels like a vacation. Offering three bedrooms and two full baths, the home presents endless possibilities. Maintain its timeless, traditional character or reimagine the layout with a more open, modern design to suit today's lifestyle. An oversized two-car attached garage provides ample space for parking, storage, and all of your waterfront gear. Step outside to your own private waterfront pier, where boating, kayaking, paddleboarding, fishing, and waterfront entertaining become part of everyday life. With easy access to the Chesapeake Bay, waterfront dining, and historic downtown Annapolis, 783 Sonne Drive offers an exceptional combination of privacy, recreation, and convenience in a very desirable waterfront community.

783 Sonne Dr, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$1,500,000
5 Beds ⋅ 4 Baths
Sunsets, Water Views & Effortless Coastal Living in Hillsmere Perfectly positioned on one of the quietest streets in Hillsmere, this exceptional residence offers breathtaking water views of Lake Hillsmere in the foreground and the South River beyond—without the expense of waterfront taxes. Designed to embrace its spectacular setting, the home is oriented to the west, delivering unforgettable sunsets from two expansive waterfront-facing decks and covered balconies. Set on a generously sized lot with ample setbacks, the property provides privacy, space, and a rare sense of tranquility. Best of all, the home is outside the floodplain, so flood insurance is not required, and an elevation certificate is available. Inside, over three finished levels, you'll find thoughtfully updated living spaces featuring hardwood floors, 9-foot ceilings, abundant natural light, and multiple indoor and outdoor areas designed for gathering and entertaining. The beautifully updated kitchen features granite countertops, stainless steel appliances, island seating, a pantry with built-in shelving, and sliding doors that open to the deck and water views beyond. The main-level primary suite is a true retreat, complete with private deck access, a custom walk-in closet by California Closets, and a renovated spa-inspired bath with a soaking tub, double vanity, and glass-enclosed shower. Additional bedrooms and flexible living spaces provide endless options for guests, recreation, a home office, or multigenerational living. The lower level offers a welcoming mudroom entry, family room with fireplace and wood stove insert, full bath, dedicated office or optional sixth bedroom, laundry room, and abundant storage. Outdoor living is equally impressive, featuring IPE decking, a rear deck, three-season room overlooking the backyard, kayak and paddleboard racks, two sheds, and a private driveway leading to the oversized two-car garage with additional storage. Meticulously maintained and exceptionally efficient, the home includes newer HVAC systems, a whole-house Generac generator, Cat 8 Ethernet throughout, closed-cell spray foam insulation, LED lighting, energy-efficient windows, and remarkably low utility costs for its size. Just three blocks away, enjoy the community beach for swimming, relaxing, or launching kayaks and paddleboards. Residents of Hillsmere enjoy an unparalleled waterfront lifestyle with a private marina, boat ramps, community pool, parks, playgrounds, waterfront pavilions, and direct access to the 340-acre Quiet Waters Park. This is a rare opportunity to enjoy panoramic water views, extraordinary sunsets, and an exceptional lifestyle—without waterfront taxes or flood insurance requirements.

621 Harbor Dr, Annapolis

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

$2,250,000
5 Beds ⋅ 7 Baths
Welcome to this exceptional custom-built estate set on 3.1 acres in Wyatts Hill community. Offering three finished levels of thoughtfully designed living space, this five-bedroom, seven-bathroom home combines timeless architecture, modern updates, and resort-inspired outdoor living. A grand two-story foyer welcomes you with a sweeping curved staircase and soaring ceilings. The main level is designed for both everyday living and entertaining, featuring a formal dining room, private office, dramatic two-story family room with a fireplace, and a sunroom connected by French doors that fills the home with natural light. The gourmet kitchen serves as the heart of the home with an oversized center island, custom cabinetry, granite countertops, a spacious breakfast area, and a butler’s pantry, creating an ideal space for gatherings large and small. The main level also features a spacious primary suite with an en-suite bath, providing flexibility for a variety of living arrangements. An additional office, laundry room, and powder room complete the main level. Upstairs, a second primary suite offers a private retreat with a sitting area and en-suite bath. Three additional bedrooms each feature their own private en-suite bathrooms, providing comfort and privacy throughout the upper level. The walkout lower level expands the home’s living and entertaining space with a large recreation room, second kitchen, half bath, and abundant storage. Completed in 2023, the backyard was transformed into an exceptional outdoor living space featuring a heated saltwater pool, expansive patio, outdoor fireplace, and a fully equipped outdoor kitchen designed for entertaining and enjoying an outdoor lifestyle. Recent improvements include a new roof (2025), two new HVAC systems (2022), new wood front and garage doors, a Tesla EV charger, and a lawn irrigation system. Located in the desirable Wyatts Hill community with no HOA, this home offers convenient access to Historic Annapolis, BWI Airport, Fort Meade, Baltimore, Washington, D.C., and major commuter routes including I-97 and Route 50.

1614 Annesley Ct, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$455,000
3 Beds ⋅ 2 Baths
Rare opportunity to buy into a premiun Annapolis neighborhood at a fraction of the cost and remodel /design your perfect coastal dream home in the highly coveted, water-privileged community of Annapolis Roads! Nestled on a private .40-acre lot on a quiet cul-de-sac, this charming rancher offers main level living, a spacious layout , wood-burning fireplace and access to an expansive upper level deck. The lower level features a walkout basement and two additional bedrooms and bath- great for privacy! Living in Annapolis Roads means embracing a vibrant resort lifestyle offering sandy beaches with sweeping views of the Chesapeake Bay , a waterfront pavillion, playground and firepit, community dock and boat ramp, walking trails in Ogleton Woods and Fusco althetic park and numerous community events - all within walking distance to your home! There is no HOA- it is a special tax district with taxes included in the property tax. Minutes from downtown Annapolis, shopping and restaurants and major commuting routes, this home is awaiting it's transformation!

1110 Jenniper Ln, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$499,900
6 Beds ⋅ 2 Baths
Welcome Home! This spacious 6-bedroom Split Foyer in the highly sought-after Cape St. Claire community offers Chesapeake Bay views from a prime location directly across the street from the water. With 3 bedrooms on the main level and 3 additional bedrooms on the lower level, this home provides exceptional flexibility for multi-generational living, guests, home offices, or growing households. The main level features a bright living room that flows into the dining area, kitchen, and a generously sized family/sunroom, creating an ideal space for both everyday living and entertaining. Two full bathrooms, abundant storage, and a functional layout offer comfort and convenience throughout. The lower level includes three additional bedrooms, a laundry room, storage room, and a large workshop with rear exterior access, perfect for hobbies, a home business, fitness space, or extra storage. Enjoy the unmatched amenities of Cape St. Claire, including community beaches, a fishing and crabbing pier, boat ramp, marina, playgrounds, and more. Conveniently located near shopping, dining, and everyday necessities, and just minutes from Downtown Annapolis. Commuters will appreciate the easy access to Route 50, I-97, Washington, D.C., Baltimore, and Fort Meade. A rare opportunity to enjoy Bay views, outstanding community amenities, and a fantastic location while creating the home of your dreams!

1247 River Bay Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4107407100
$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:

$699,990
4 Beds ⋅ 3 Baths
Some neighborhoods give you an address. Hillsmere gives you a way of life. At 104 Groh Lane, you’ll find a beautifully updated four-bedroom, three-bath home with approximately 2,300 square feet of finished living space, an exceptionally versatile floor plan, and a wonderful level, fenced backyard—all within one of Annapolis’ most beloved waterfront communities. Three bedrooms and two full baths are conveniently located on the main level, including the primary suite, while light-filled living and dining spaces, a fireplace, and a beautifully renovated kitchen create a warm and inviting setting for everyday living and entertaining. The finished walk-out lower level adds nearly 1,000 square feet of additional living space with a fourth bedroom, full bath, recreation area, and laundry, offering wonderful flexibility for guests, a home office, fitness space, or additional living area. Outside, a spacious deck overlooks the expansive backyard framed by mature trees—a private setting for summer dinners, gardening, children at play, and four-legged family members. But what makes this home particularly special is everything waiting just beyond the front door. Hillsmere is the kind of neighborhood where children ride their bikes down tree-lined streets, neighbors walk their dogs and stop to talk, and families head to the beach together on summer evenings. It’s Fourth of July bike parades ending at the water, Halloween parades, ice cream socials, beach gatherings, live music, the annual oyster roast, and Santa making his way through the neighborhood during the holidays. Residents enjoy a sandy community beach overlooking the Chesapeake Bay, marina and boat ramps, waterfront pavilions, playgrounds, and community pool, while the trails, dog park, and natural beauty of Quiet Waters Park are practically next door. Eastport, Historic Annapolis, City Dock, restaurants, shopping, and the waterfront are only minutes away. Beautifully updated and wonderfully livable, 104 Groh Lane offers something increasingly difficult to find: a home you’ll love in a neighborhood that still feels like a community.

104 Groh Ln, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$579,500
4 Beds ⋅ 2 Baths
Listing is under contract contingent on buyer obtaining contract on their current home, however, there is a 72 hr kick out clause in case a more favorable offer is received. $22k credit at closing which the buyer may use towards closing costs or for needed deck repairs. Nestled in the charming community of Cape St. Claire, this delightful raised ranch home offers a perfect blend of comfort and convenience, making it an ideal retreat for those seeking a vibrant neighborhood lifestyle. With 4 spacious bedrooms and 2 full bathrooms, this residence boasts a generous 2,327 square feet of living space, perfect for gatherings or quiet evenings at home. The main floor laundry adds to the ease of living, ensuring that daily tasks are a breeze. Step outside onto the expansive screened in porch where you can enjoy morning coffee or evening cocktails while taking in the serene surroundings. Cape St. Claire is renowned for its community spirit and access to the beautiful Magothy River. Residents can enjoy a community pool, perfect for those hot summer days, and the nearby parks offer ample opportunities for outdoor activities, picnics, and leisurely strolls. The neighborhood is designed for an active lifestyle, with walking trails and green spaces that encourage exploration and connection with nature. The community is also well-served by public services, making daily life convenient and stress-free. Living in Cape St. Claire means embracing a lifestyle enriched by water features and community amenities. Whether you're kayaking on the river, enjoying a swim at the community pool, or simply relaxing in your backyard, this home offers a unique opportunity to create lasting memories in a welcoming environment. With its prime location, spacious layout, and community-focused amenities, this property is more than just a house; it's a place to call home. Experience the warmth and charm of Cape St. Claire, where every day feels like a getaway. The home is wired for a generator, however, a generator is not included. Existing VA loan may be assumable for qualified buyers subject to lender approval. Contact listing agent for current interest rate, loan balance, assumption requirements and timeline.

1045 Skyview Dr, Annapolis

Listing courtesy of Samson Properties. Contact: 4439757555
$1,295,000
3 Beds ⋅ 3 Baths
Welcome to this impeccably maintained and extensively updated ranch-style residence, offering an exceptional blend of luxury, comfort, and resort-inspired living just minutes from historic Annapolis. From the moment you arrive, the quality craftsmanship and meticulous attention to detail are evident throughout. At the heart of the home is a beautifully appointed gourmet kitchen featuring premium Wolf appliances, abundant custom cabinetry, quartz countertops, a beverage and wine refrigerator, and generous space for both everyday living and entertaining. Two double-sided gas fireplaces—one shared by the living room and the other featured in the primary suite—offer both warmth and architectural elegance, adding a distinctive touch to this exceptional home. Recent renovations have enhanced the home's appeal, highlighted by a spectacular oversized primary suite designed as a private retreat. The suite features a spacious walk-in closet and a spa-inspired ensuite bath complete with heated floors, instant hot water, and integrated Bluetooth speakers/exhaust fan. The fully finished lower level offers remarkable flexibility with luxury vinyl plank flooring, a custom wet bar with a full-size refrigerator/freezer with ice maker, a full bath, and a private exterior entrance—ideal for entertaining, hosting guests, multigenerational living, or a home-based business. Outdoor living is equally impressive. The fully fenced backyard is surrounded by mature landscaping, creating a private setting that rivals a boutique resort. Enjoy the heated in-ground pool, newly replastered in 2024, relax in the 15-foot swim spa, or entertain with ease at the custom-built tiki bar and outdoor kitchen. Thoughtfully designed, the tiki bar features a built-in grill, refrigerator, stainless steel storage, accent lighting, television, and bar seating. A stamped concrete pool deck and expansive composite deck with cable railings provide multiple spaces for gathering, dining, and unwinding. Adding even greater versatility is the detached pool house, complete with electricity and air conditioning. Whether used as a home office, fitness studio, creative workspace, or private retreat, this space offers endless possibilities. Additional highlights include a brand-new stamped concrete driveway with parking for up to five vehicles. Combining sophisticated interior finishes with extraordinary outdoor amenities, this turnkey property delivers a lifestyle rarely found in such a convenient Annapolis location.

1501 Ritchie St, Annapolis

Listing courtesy of Samson Properties. Contact: 7033493900
$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
$4,600,000
5 Beds ⋅ 4 Baths
An extraordinary opportunity to own one of Annapolis’ most distinctive waterfront properties, offering some of the finest views on Spa Creek and the rare privilege of owning your own private marina in your backyard with dockside parking. Perfectly positioned to capture breathtaking panoramic vistas, this elegant Nantucket-inspired residence is filled with natural light, featuring walls of glass that showcase the ever-changing waterfront from nearly every room. Multiple balconies and an expansive waterside terrace invite effortless indoor-outdoor living, creating exceptional spaces for entertaining or simply enjoying the beauty of life on the water. A dockside workshop is a great opportunity to work and enjoy waterfront living. The thoughtfully designed floor plan includes spacious living areas, a versatile 1800 square feet (approximate) lower level with an in-law suite or private guest accommodations, and endless opportunities to personalize the home to suit your lifestyle. This home even has a koi pond in the front yard. Whether you’re an avid yachtsman, seeking a multigenerational waterfront retreat, or searching for a truly one-of-a-kind Annapolis property, this exceptional offering combines luxury, privacy, and an unmatched boating lifestyle in one remarkable setting.

140 Spa Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$715,000
3 Beds ⋅ 3 Baths
** This stunning 3-bedroom, 3-full-bath detached home in Heritage Harbor is a true GEM!** Main Level laminated wood flooring throughout the living room- dinning room and Kitchen. The Kitchen features Elegant gold-and-white granite countertops. A cozy matching granite table that seats three. Brand new white cabinets adorned with gold knobs and pull handles. Complete with modern stainless steel appliances, offering a Z line brand hood above a new 4-burner stove. The Interior home has been freshly painted and re-carpeted, giving it a modern feel. On the main level The Master bathroom is a standout feature: Gold-and-white granite sinks. Spacious shower area. Well-designed closet spaces with flooring that matches the elegant theme. Two walk-in closets for ample storage. The 2nd bedroom has plenty of natural light and plenty of room. The 3rd quest room is located on the second level with a loft looking onto the newly renovated large closed-in sunroom and below a lovely family room...The "Florida "Sunroom equally has new flooring with plenty of sliding glass doors, offering natural light, with a separate heating & air conditioning system, looking out to plenty of greenery- perfect for relaxation. This home is not only beautifully designed with many upgrades for comfort and style, but also a must-see. If you’re considering moving or looking for a beautiful home in a desirable neighborhood. This property won’t last long in today’s market.

708 Sydney Ter, Annapolis

Listing courtesy of Taylor Properties. Contact:

$549,900
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
$1,350,000
3 Beds ⋅ 3 Baths
Welcome to a waterfront retreat where timeless coastal living meets modern luxury. Perfectly positioned on approximately one private acre along the tranquil waters of Mill Creek with direct access to the Chesapeake Bay, this custom-built home offers the exceptional lifestyle that Annapolis is known for. Designed to capture breathtaking water views from nearly every room, this beautifully appointed 3 bedroom, 2.5 bath Chalet features an open, light-filled floor plan with soaring ceilings, rich hardwood flooring, a cozy fireplace, and expansive windows that bring the outdoors in. The gourmet kitchen flows seamlessly into the living and dining spaces, creating an inviting atmosphere for entertaining or relaxing while enjoying picturesque waterfront vistas. The fully equipped kitchen boasts modern stainless steel appliances and ample space for entertaining. Wake up each morning in the serene primary suite overlooking the water, which features a large walk-in closet and a whirlpool soaking tub. Then, step outside to experience your own private waterfront oasis. The expansive deck is ideal for hosting family and friends, enjoying morning coffee, or taking in spectacular sunsets over Mill Creek. This property includes docking for two boats and deep-water access, perfect for boating, crabbing, and fishing. Conveniently located just five minutes from the U.S. Naval Academy, West Annapolis, and historic downtown Annapolis, this home provides easy access to shopping, dining, and entertainment. Washington, D.C and Baltimore are each only 30 minutes away. Local highlights include Cantler's Riverside Restaurant, a renowned spot for seafood and steamed crabs right on the water, as well as the charming shops and cafes along Main Street and in nearby West Annapolis. Outdoor lovers will appreciate the close proximity to Sandy Point State Park, as well as nearby golf courses and trails for year-round recreation. Whether you’re searching for a primary residence or legacy waterfront property to enjoy for generations, this extraordinary home offers a rare opportunity to own one of Annapolis’ most desirable waterfront settings. Schedule your private tour today and discover the Chesapeake lifestyle you’ve been dreaming of.

2203 Mulberry Hill Rd, Annapolis

Listing courtesy of Keller Williams Preferred Properties. Contact:

$694,999
4 Beds ⋅ 3 Baths
Stunning 2400 sq ft 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: