Quick Annapolis MD MLS Search

Browse All Annapolis MD Single Family Properties for Sale

16 Maryland Ave, Annapolis
$3,449,000
6 Beds ⋅ 5 Baths
A truly exceptional historic residence is now available in the heart of downtown Annapolis. Welcome to 16 Maryland Avenue, a distinguished circa-1830 Greek Revival home masterfully restored in collaboration with the renowned Hammond-Wilson Architects. Perfectly positioned just steps from State Circle and the United States Naval Academy, this iconic three-story brick property seamlessly blends timeless architectural beauty with sophisticated modern livability. The main property features 4,474 square feet of refined above-grade living space, complemented by a fully legal, licensed lower-level apartment that offers immense versatility for multi-generational living or premium rental income. In total, the property features six bedrooms, 4.5 bathrooms, and beautifully curated living spaces defined by rich period details, soaring ceilings, and remarkable craftsmanship. Six fully rebuilt, functional wood-burning fireplaces (three equipped with gas starters) serve as stunning architectural focal points throughout the home. Equally captivating are the enchanting outdoor spaces. Here, manicured grounds, lush landscaping, vibrant flower beds, and a serene koi pond create a private garden retreat rarely found downtown. Set on a prime 7,324-square-foot lot along one of the city’s most coveted historic streets, the property offers tranquility just moments from the waterfront and bustling downtown scene. Zoned as a two-family residence, this remarkable property represents a rare, premium investment or a luxurious private estate. Residents will enjoy an unmatched lifestyle, surrounded by boutique shopping, acclaimed waterfront dining, art galleries, historic landmarks, and the unmistakable charm of Annapolis Harbor. Elegant, iconic, and rich with history, 16 Maryland Avenue represents downtown Annapolis living at its absolute finest.

16 Maryland Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

1132 Bay Ridge Rd, Annapolis
$650,000
3 Beds ⋅ 3 Baths
SELLER IS OFFERING $10,000 toward a new fence or buyer closing costs, providing added flexibility and value for the next homeowner. This exceptional Annapolis home truly has it all. Beautifully maintained, move-in ready home on a private lane. Updated with features that include a new roof, skylight, gutters, heat pump, hot water heater, carpet, sliding glass door, basement outdoor steps, fresh paint and more. The spacious kitchen’s vaulted ceiling has a skylight with a remote-controlled shade, beautiful quartz countertops, tile backsplash, breakfast bar, stainless steel appliances and opens to the family room with a wood-burning fireplace. The expansive screened porch is perfect for morning coffee, relaxing and entertaining. Elegant wood style flooring enhances the main living areas including a separate dining room and a large living room. Bathrooms have been tastefully updated. The unfinished basement with DryLok painted walls offers excellent potential for future living space. Well insulated, water softener system owned, very spacious garage with a large driveway. Water privileges at end of Lake Ogleton. Just a few minutes’ walk to Peninsula Park to enjoy Pickleball, Tennis, Trails, Picnic areas, Playground, Baseball, Basketball and a multi-purpose field. Ideally located just minutes from Historic Downtown Annapolis, dining, shopping, marinas, medical, the U.S. Naval Academy, schools and major commuter routes to Washington DC, Baltimore, Fort Meade and the Eastern Shore. SCHEDULE your showing today!

1132 Bay Ridge Rd, Annapolis

Listing courtesy of Blackwell Real Estate, LLC. Contact:

1470 Log Inn Rd, Annapolis
$535,000
3 Beds ⋅ 2 Baths
Beautifully updated and filled with thoughtful improvements, this Cape Cod in Annapolis combines model-like interiors, a recently finished lower level, and inviting outdoor living just minutes from the Chesapeake Bay. Blooming perennial landscaping and a covered front porch create a warm welcome, while inside, a deceptively spacious open concept floor plan showcases hardwood flooring, recessed lighting, and a soft neutral palette that carries throughout the home. The living room is bright and airy, highlighted by a partial vaulted ceiling accented with skylights that fill the space with natural light. Just beyond, the renovated kitchen blends style and function with stainless steel appliances, a tile backsplash, abundant cabinetry, roll-out shelving, and a swing-out pantry designed for effortless organization. A dedicated dining area with a modern light fixture completes the main living space with a polished touch. The main level includes a spacious bedroom with a walk-in closet featuring a built-in organization system. Also on this level is a beautifully renovated full bath complete with a double sink vanity, stylish finishes, and a tiled tub and shower surround. Nearby, the laundry room provides storage shelving and convenient access to the backyard. Upstairs, two generously sized bedrooms share an updated full bath with a tiled shower enclosed by frameless glass. One of the upper level bedrooms is enhanced by a charming shiplap accent wall and a cozy window seat, adding character and a tucked-away place to relax. The recently finished lower level expands the living space with a comfortable family room featuring durable wood-look tile flooring, a versatile bonus room, and a sizable storage area. Outdoor spaces are equally inviting, with a deck and patio overlooking the spacious backyard, creating room to entertain, relax, or enjoy the surrounding greenery. A storage shed with a garage door adds functionality, while major updates including the roof and water heater offer additional peace of mind. This location places you moments from some of Annapolis’ most scenic waterfront recreation, including Sandy Point State Park with its sandy beach, marina, fishing and crabbing access, and sweeping Chesapeake Bay Bridge views. Jonas Green Park, Quiet Waters Park, and Thomas Point Park are also nearby, offering trails, kayaking, waterfront overlooks, and endless opportunities to enjoy the natural beauty of the Annapolis area. Hop on the Broadneck Peninsula Trail across the street and head to Sandy Point Park or connect to the B&A Trail.

1470 Log Inn Rd, Annapolis

Listing courtesy of Northrop Realty. Contact:

158 Prince George St, Annapolis
$1,375,000
3 Beds ⋅ 3 Baths
BACK ON THE MARKET - RARE OPPORTUNITY TO OWN A REMARKABLE PIECE OF ANNAPOLIS HISTORY! The Patrick Creagh House c. 1740 (also known as 160 Prince George Street) is an architecturally significant residence with a gambrel roof structure and features header and English bond brick walls. This property has been thoughtfully adapted for modern living while preserving its timeless character and craftsmanship. Ideally located in the heart of Annapolis just one block from the US Naval Academy Gate 1, City Dock, Main Street and the Maryland State House, this exceptional home offers the best of historic charm and downtown convenience. A welcoming center hall introduces spacious living and dining rooms designed for both elegant entertaining and comfortable everyday living. The private patio and garden create a serene outdoor extension of the home’s living spaces. Upstairs, the home features a primary suite with full bath, two additional bedrooms, a second full bath, and convenient laundry. The lower level provides ideal space for a wine cellar, storage, or additional utility needs. The property’s kitchen, baths and wiring have been updated and the home is move-in ready! This distinguished 18th-century property has been extensively researched and documented and is listed on the NATIONAL REGISTER OF HISTORIC PLACES for its architectural importance and contribution to local history. Patrick Creagh was a man of many skills and was considered an important person in the community. He is mostly known for building the Old Treasury c. 1737 on the Maryland State House Grounds, the oldest public building in the state that was fully restored and opened to the public this year. ***NOTE: FURNISHINGS REMOVED AND INTERIOR WALLS HAVE BEEN PAINTED. Some photos have been virtually staged/AI generated to illustrate the property's design potential only. ***

158 Prince George St, Annapolis

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

202 Wardour Dr, Annapolis
$1,549,000
5 Beds ⋅ 2 Baths
Welcome to 202 Wardour Drive! This classic 1940 Dutch Colonial offers timeless character, generous living space, and an unbeatable Annapolis location. Situated on a quarter acre lot with large front yard, the south facing location ensures sunny days ahead! Located in the elegant Wardour community which reflects the naturalistic style of its designer, Frederick Law Olmstead, Jr, with its mature trees, meandering roads and preserved open spaces that foster community connection. Inside, the home features five bedrooms, two bathrooms, gorgeous oak floors (recently refinished in 2026), fireplace, bright sun-porch and large 12x 32 back deck. The south-facing orientation fills the home with natural light, creating a bright and cheerful atmosphere throughout. Recent improvements include freshly painted interior and exterior spaces, a newer roof approximately four years old, new porch benches, and a beautifully installed brick paver sidewalk that enhances the home’s curb appeal. A long driveway and rear detached garage provide ample parking and storage. Residents benefit from access to seven community beach areas and a shaded walking trail traversing the neighborhood, that provide a tranquil retreat for adults and a natural wonderland to explore. Conveniently located within walking distance of the local elementary school, Navy Stadium, Annapolis Street shopping and dining, Historic Downtown Annapolis and offers easy access to Rt. 50 for commuters. With classic architecture, spacious interiors, abundant natural light, and an exceptional in-town location close to everything Annapolis has to offer, this is a rare opportunity to own in one of the area’s most beloved neighborhoods. Schedule your private tour today!

202 Wardour Dr, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

11 S Acton Pl, Annapolis
$5,999,999
4 Beds ⋅ 4 Baths
Perfectly positioned on the waterfront in Annapolis’ coveted Murray Hill neighborhood, 11 S Acton Place offers a rare combination of privacy, boating access, substantial outdoor space, and walkability to downtown Annapolis. The home has undergone an extensive renovation encompassing the interiors, systems, and outdoor living spaces. Never lived in since completion, it offers the rare opportunity to enjoy a newly reimagined waterfront home with fresh finishes, appliances, and modern infrastructure throughout. Set on an exceptionally generous waterfront property for Murray Hill, the home offers a sense of space and privacy rarely found this close to downtown. Mature landscaping, expansive outdoor living areas, Brazilian Ipe decking, and panoramic water views take full advantage of the setting. A private pier with electric and boat lift provides direct access to the water, while an extended paver driveway and refinished gates enhance both the arrival and functionality of the property. Inside, wide-plank white oak flooring, custom white oak ceiling beams, Restoration Hardware lighting, Baldwin hardware, and custom plaster fireplaces create a cohesive interior. The reimagined chef’s kitchen features a complete JennAir Noir appliance suite with a 48-inch dual-fuel range and double ovens, professional refrigeration, two integrated dishwashers, multiple beverage centers, and a built-in ice maker. Custom Schrock “Trademark” maple cabinetry, Waterworks fixtures, Calacatta Miraggio Cielo quartz with waterfall detailing, and layered architectural lighting complete the space. An adjoining butler’s pantry provides additional prep, storage, and entertaining space. The primary suite features custom built-ins, California Closets systems, integrated laundry, and a bespoke fireplace. Secondary bedrooms and living spaces continue the same attention to materials and detail throughout the home. Integrated Sonos audio, Lutron lighting controls, upgraded sound-attenuating insulation, and CAT6 wiring provide modern technology and infrastructure throughout. Outdoors, generous entertaining spaces and Ipe decking provide multiple areas for dining and gathering overlooking the water. From quiet mornings along Spa Creek to evenings entertaining outdoors or returning home by boat after a day on the Chesapeake Bay, the property captures the waterfront lifestyle that makes Annapolis so distinctive. Located minutes from downtown Annapolis, the United States Naval Academy, restaurants, yacht clubs, and boutique shopping, 11 S Acton Place is equally suited as a primary residence or waterfront retreat. Its combination of substantial land, private boating access, extensive renovation, and proximity to downtown presents a rare opportunity in one of Annapolis’ most established waterfront neighborhoods.

11 S Acton Pl, Annapolis

Listing courtesy of Real Broker, LLC - Severna Park. Contact:

146 Duke Of Gloucester St, Annapolis
$1,950,000
4 Beds ⋅ 4 Baths
Price improvement!!! 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:

2035 Maidstone Farm Rd, Annapolis
$8,750,000
5 Beds ⋅ 7 Baths
Commanding extraordinary panoramic Chesapeake Bay views from its south-facing setting, this exceptional waterfront estate offers 210 feet of shoreline on 3.10 private acres in the exclusive Maidstone Farm community. Designed to embrace its remarkable waterfront setting, the residence captures sweeping, unobstructed views from nearly every principal room, with magnificent sunrises, vibrant sunsets, and ever-changing Bay vistas creating a stunning backdrop for everyday living. Enjoy mornings overlooking the water, afternoons boating from your private pier, and evenings entertaining along the shoreline. The protected waters of Burley Creek feature a private pier with 6–7 feet MLW, a 34' x 15' platform, and a 10,000 lb lift, providing effortless access to the Chesapeake Bay. The shoreline offers the perfect launch point for kayaks and paddleboards, while the expansive level lawn creates an exceptional setting for outdoor entertaining and waterfront gatherings. Designed by ABS Architects and custom built in 2019, this exceptional residence blends timeless coastal architecture with sophisticated craftsmanship and modern amenities. The thoughtfully designed floor plan features expansive living spaces filled with natural light, five ensuite bedrooms, 6 full and 1 half baths, four fireplaces including two propane, extensive custom built-ins, and seamless indoor-outdoor living with covered porches and waterside verandas. Architectural details include coffered ceilings, extensive crown molding, 10-foot ceilings on the main level, 9-foot ceilings on the upper and lower levels, 8-foot solid wood doors, 8-inch baseboards, designer lighting, and provisions for a future elevator. The gourmet kitchen is designed for both everyday living and entertaining, featuring two oversized islands, Eucalyptus cabinetry, a La Cornue range, two Sub-Zero refrigerators, Sub-Zero refrigerator drawers, premium hardware, and mitered-edge countertops. The waterfront primary suite offers a private retreat with a barrel vaulted ceiling, sitting area, oversized walk-in closet, and sweeping Bay views. Additional ensuite bedrooms feature custom tile work and refined finishes. A four-car garage with a private flex space above includes a full bath and exercise room, ideal for guests, office, studio, or additional living space. The unfinished 3,664-square-foot lower level provides endless possibilities for future expansion. Additional highlights include a heated saltwater pool overlooking the water, circular driveway, six-zone HVAC, spray foam insulation, 400-amp electrical service, Kohler propane whole-house generator with 2,000-gallon tank, security system, and Control4 audio and lighting automation. Minutes from downtown Annapolis, City Dock, waterfront dining, shopping, and cultural attractions, this extraordinary Chesapeake Bay estate offers a rare opportunity to enjoy a private waterfront lifestyle defined by boating, entertaining, relaxation, and the beauty of the Bay.

2035 Maidstone Farm Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

192 Duke Of Gloucester, Annapolis
$1,950,000
6 Beds ⋅ 4 Baths
Welcome to the Thomas Hyde House – a rare opportunity to own a piece of Annapolis history in the heart of downtown. Built in 1769, this impeccably restored Federal- style property blends 18th-century charm with modern luxury. Perfectly situated on sought- after Duke of Gloucester Street, this vibrant and colorful home offers stunning views of the Maryland State House and extremely rare off-street parking for 6+ vehicles. Originally configured as office space, the residence has been reimagined into six spacious bedrooms and four full baths across two beautifully fully remodeled levels, with the potential for third floor updating plus a large basement with ample storage and updating space. The first floor offers true single level living with a primary suite and second bedroom, while the second level features four additional bedrooms and a convenient laundry area. No detail has been overlooked – from new appliances, countertops, and cabinetry to frameless glass showers, ceramics, extensive trim and molding, recessed lighting, fresh interior and exterior paint, new plumbing/electric and sprinkler system, updated flooring, freshly painted standing seam roof/front dormers and more. The result is a turnkey home where historic character meets modern sophistication & luxury. The property is offered with negotiable furnishings, electronics and art, The Thomas Hyde House is as versatile as it is fun and captivating. Just steps from downtown Annapolis shopping, dining, yacht clubs, local marinas & major commuter routes. Whether as a primary residence, investment property, or distinctive downtown retreat. schedule your showing today.

192 Duke Of Gloucester, Annapolis

Listing courtesy of Samson Properties. Contact:

5 Franklin St, Annapolis
$12,500,000
5 Beds ⋅ 7 Baths
A rare opportunity on Spa Creek, this fully reimagined Murray Hill residence offers an extraordinary waterfront lifestyle just moments from downtown Annapolis. Completed in late 2023 after a full ground-up rebuild, the home spans 5,900+ sq. ft. of impeccably crafted living space, where natural materials, refined architectural details, and top-tier systems create a seamless blend of comfort and sophistication. Set on just under a half acre of level waterfront, the property showcases one of the most complete private pier systems in the area: a heavily built main pier, two floating docks, and three boat lifts (16,000lb, 8,000lb, and 2,500lb), plus lighting, water, 30/50-amp shore power, Tide Slide moorings, and 6' MLW at the 70' T-head. A charming boathouse and waterside deck capture the magic of Spa Creek from morning to sunset. Outdoor living is exceptional. A stunning 40' x 20' PebbleTec saltwater pool—rebuilt in 2024—anchors a series of Ipe decks and natural stone patios and decks designed for effortless entertaining. The outdoor kitchen with piped natural gas grill, refrigerator, and sink extends gatherings well into the warm months, while covered and uncovered spaces offer year-round enjoyment. The exterior speaks to enduring quality with Carderock stone foundations, mahogany trim and ceilings, Loewen windows, Canadian cedar siding, copper gutters and flashings, and custom mahogany entry doors. A detached heated and cooled two-car garage includes a beautifully finished upper level with kitchenette, laundry, living/sleeping area, and private bath—ideal for guests or an au pair. Inside, the home is defined by warm natural luxury featuring a stunning barrel vaulted mahogany ceiling with cove lighting. Additional curated details include: mahogany doors, black bronze hardware, 5" Cumaru flooring, custom cabinetry, and extensive millwork throughout. The chef’s kitchen features Sub-Zero and Wolf appliances with granite and soapstone surfaces. The main level Primary suite with inspiring view of pool and waterfront provides convenience and options for aging in place. The lower-level recreation spaces provide a relaxed retreat with a private bedroom suite, family room, wet bar, gym and full laundry room. An abundance of thoughtful design is presented throughout the home with multiple wet bars, radiant heated tile floors in five bathrooms and the main-level bar, and four separate laundry areas. Less than half a mile from Church Circle, this residence delivers the rare ability to live on the water while enjoying the full walk-everywhere lifestyle of historic Annapolis. This is Spa Creek living at its finest: sophisticated, effortless, and undeniably special. Welcome Home!

5 Franklin St, Annapolis

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

8 Spa View Cir, Annapolis
$9,998,000
5 Beds ⋅ 6 Baths
NEW PRICE — $9,998,000. A rare opportunity to acquire an extraordinary Annapolis waterfront estate, now thoughtfully repositioned for today’s discerning buyer. Set along 168' of Spa Creek waterfront, this approximately 6,000 SF residence is privately positioned within an exclusive enclave of just three homes. The private deep-water dock offers approximately 8' MLW and accommodates a 60–70' sailboat or yacht with wide beam. Cruise to City Dock and downtown restaurants in minutes, or enjoy panoramic water and unobstructed Annapolis skyline views from home, including front-row views of the Blue Angels, fireworks and annual boat parade. The heated saltwater pool, expansive Ipe deck and beautifully landscaped grounds create exceptional waterfront entertaining. Meticulously maintained and extensively renovated by Pyramid Builders, the architecturally distinctive residence features a dramatic marble foyer, floor-to-ceiling windows, solid wood doors, rich stained black oak flooring and two striking gas fireplaces. The sophisticated white kitchen features Sub-Zero refrigeration, a eight-burner Viking cooktop, high-gloss Premier cabinetry and Neolith porcelain countertops, complemented by designer lighting and a striking floating staircase. A private speakeasy with a custom marble-topped bar creates an intimate setting for cocktails and entertaining. The residence offers 4–5 bedrooms and 5 full and 1 half baths, including a first-floor bedroom suite. A two-car garage, generous parking and private pier complete this exceptional Murray Hill waterfront offering. Enjoy deep-water boating, resort-style outdoor living, sophisticated entertaining and downtown Annapolis—all from one extraordinary private setting.

8 Spa View Cir, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

83 Market St, Annapolis
$2,295,000
5 Beds ⋅ 4 Baths
This exceptional Historic District home combines the charm of a classic Annapolis address with a substantial 2026 renovation in all the right places. A stunning new kitchen, custom wet bar, expanded pantry area, completely reimagined third floor, new full bath, and New HVAC system bring modern function and style to this timeless home. Water access is at the end of the block, Acton's Cove waterfront park is around the corner, and City Dock, Main Street, restaurants, shops, and the Naval Academy are all within easy walking distance. Easy parking on quiet Market Street. The new kitchen features custom cabinetry, Taj Mahal quartzite countertops, ceramic tile backsplash, unlacquered brass hardware, designer lighting, and a full suite of GE Monogram appliances. The expanded pantry area offers plenty of storage, a separate freezer, and ice maker, while the custom wet bar includes reeded glass cabinetry, brass detailing, a dedicated sink, and generous storage for entertaining. A full-width screened porch spans the front of the home, while 10-foot ceilings, original architectural details, and multiple gathering spaces create warmth and character throughout. The main level includes a paneled office, formal living and dining rooms, and a casual family room that opens to the eat-in kitchen and rear patio with gazebo. Seasonal water views can be enjoyed from several rooms. Upstairs, the primary suite offers winter water views, dual organized closets, and an updated bath. A 2nd bedroom with hall bath and laundry room are located on this level. The 3rd floor has been completely reimagined to create 3 additional rooms with built-in storage and a beautiful new full bath featuring classic finishes, custom millwork, and quartz countertops. A rare opportunity to enjoy the character of Historic Annapolis with the benefits of a major recent renovation, all tucked on a quiet street in the heart of the Historic District. Water access is just steps away, downtown Annapolis is an easy walk, and everyday convenience is rarely this effortless.

83 Market St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

1603 Winchester Rd, Annapolis
$2,500,000
6 Beds ⋅ 7 Baths
READY TO BUILD NOW!! Introducing an exceptional opportunity to build your dream home with a local custom home builder on a rare 2.19-acre homesite in the highly sought-after water-privileged community of Winchester on the Severn—a neighborhood where everyday living feels like a vacation. This thoughtfully designed custom home will offer over 6,700 square feet of finished living space, featuring 6 bedrooms, 6 full baths, and 1 half bath, along with a 3-car garage, blending timeless craftsmanship with modern luxury and functionality. The main level is designed with both comfort and entertainment in mind, showcasing an open-concept floor plan anchored by a gourmet kitchen featuring high-end appliances, an expansive workspace, and seamless flow into gathering spaces. A beautifully appointed butler’s pantry includes a built-in ice maker and is complemented by a walk-in pantry, demonstrating the careful attention to detail found throughout the home. A rare main-level bedroom with en suite bath, along with a dedicated private office, provides exceptional flexibility for guests, multi-generational living, or work-from-home convenience. Upstairs, you’ll find four generously sized bedrooms, each offering its own walk-in closet and own en suite bathroom —a rare and highly desirable feature. The primary suite serves as a luxurious retreat, complete with separate his-and-hers walk-in closets and a spa-inspired bathroom featuring a soaking tub and oversized walk-in shower. The finished lower level is designed for entertainment and relaxation, featuring a spacious recreation room, a dedicated theater room, and an optional bar area with its own pantry and possible wine storage room. An additional en suite bedroom on this level makes the space ideal for extended guests, in-laws, or a live-in nanny. Set on an exceptionally rare 2.19-acre homesite, the property offers endless possibilities for outdoor living, including space approved for a future pool, pickleball court, or custom outdoor entertainment retreat of your choice —creating the ultimate private backyard oasis. Life in Winchester on the Severn offers an unmatched lifestyle. Simply hop on your golf cart and head to one of the finest community beaches on the Severn River, where residents enjoy a playground, pavilion, sandy beach, swimming pier, kayak and paddleboard storage and launch, boat ramp, and breathtaking sunsets over the water. This is an extremely rare opportunity to create a custom residence in one of the area’s most desirable water-privileged communities—where luxury, space, and lifestyle come together seamlessly.

1603 Winchester Rd, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

1200 Bay Ave, Annapolis
$669,000
5 Beds ⋅ 2 Baths
Nestled in a serene setting, this exquisite Colonial-style residence offers a harmonious blend of elegance and comfort, perfect for those seeking a luxurious lifestyle. Potenial five bedroom, Built in 2001, this detached home spans an impressive 2,399 square feet, providing ample space for both relaxation and entertainment. As you step inside, you are greeted by a warm and inviting atmosphere that flows seamlessly throughout the home. The thoughtfully designed layout features five spacious bedrooms, ensuring that everyone has their own private retreat. The two full bathrooms are tastefully appointed, showcasing high-end finishes that elevate everyday living into a spa-like experience. The heart of the home is undoubtedly the expansive living area, where natural light pours in through large windows, creating a bright and airy ambiance. This space is perfect for hosting gatherings or enjoying quiet evenings with loved ones. The open-concept design allows for effortless transitions between the living room, dining area, and kitchen, making it ideal for entertaining. The kitchen is a chef's dream, equipped with modern appliances and ample counter space, making meal preparation a delight. Whether you're hosting a dinner party or enjoying a casual breakfast, this culinary haven is sure to inspire your inner gourmet. Step outside to discover a private outdoor oasis, perfect for savoring morning coffee or unwinding after a long day. The meticulously maintained grounds offer a tranquil escape, while the driveway provides convenient parking for you and your guests. This home is not just a residence; it's a lifestyle. Enjoy the peace of mind that comes with living in a well-established neighborhood, where community and comfort are paramount. With no association fees or restrictive amenities, you have the freedom to personalize your space and create the home of your dreams. Experience the perfect balance of luxury and warmth in this stunning Colonial home. Whether you're looking to entertain, relax, or simply enjoy the finer things in life, this property is a true sanctuary that invites you to create lasting memories. Don't miss the opportunity to make this exceptional residence your own.

1200 Bay Ave, Annapolis

Listing courtesy of Powerhouse Realty, LLC.. Contact:

220 West St, Annapolis
$824,899
3 Beds ⋅ 2 Baths
Welcome to 220 West Street in Annapolis, Maryland. A rare, fully gut-renovated detached property located in the heart of the Downtown Arts District at a row home's price, offering exceptional flexibility with mixed-use zoning that allows for both residential and commercial use. Completed in 2024, this property has been completely transformed from top to bottom. Every major system and finish has been replaced, delivering a true turnkey opportunity for buyers seeking lifestyle, investment potential, or business use in one of the most walkable and desirable areas in Annapolis. Unlike the majority of Downtown Annapolis properties, this is a fully detached home, not a rowhome or townhouse, providing enhanced privacy, natural light, and a more versatile footprint. The extensive renovation includes a brand new roof, all new electrical and plumbing systems, a new high-efficiency mini-split HVAC system, redesigned floor plan, new flooring throughout, updated lighting, and fully rebuilt kitchen and bathrooms. The outdoor spaces have been completely upgraded with a new deck, new brick patio pavers, new fencing, and ambient lighting that creates a warm and inviting atmosphere for evening entertaining. Inside, the home features a bright two-story entry foyer and a professionally curated interior design that blends modern comfort with intentional functionality. With three bedrooms and two full bathrooms, the layout is flexible enough to support full-time living, guest accommodations, workspace needs, or commercial adaptation. The main-level primary suite opens directly to a private brick patio, while the second bedroom features access to a rear deck overlooking the fully fenced yard. These indoor-outdoor connections are rarely found in Downtown Annapolis and significantly enhance livability. The kitchen has been completely reimagined with new cabinetry, countertops, and appliances, designed to support both daily living and entertaining. The open dining area comfortably accommodates gatherings, reinforcing the home’s versatility. Adding even more value, this property is being sold fully furnished. Every piece has been professionally selected, allowing the next owner to move in immediately, operate as a short-term rental, or transition into a commercial or mixed-use setup with minimal effort. Historically, this property has served multiple purposes, including a furniture store, office space, and duplex residence, highlighting the true flexibility and long-term value of its mixed-use zoning designation. Step outside into a fully fenced private yard featuring a brick patio, outdoor dining area, lounge seating, and ambient lighting, creating a unique urban retreat just steps from the energy of Downtown Annapolis. Located just moments from restaurants, shops, nightlife, City Dock, the Maryland State House, and the U.S. Naval Academy, this property offers unmatched walkability and access. With convenient proximity to Baltimore, Washington D.C., and BWI Airport, it is equally appealing for commuters, investors, and second-home buyers. This is more than a home. It is a rare, fully renovated, detached mixed-use opportunity in Downtown Annapolis where lifestyle, flexibility, and long-term value align.

220 West St, Annapolis

Listing courtesy of Keller Williams Realty Centre. Contact:

92 Clifford Blvd, Annapolis
$715,000
4 Beds ⋅ 3 Baths
Amazing home at an amazing price point! Welcome home to this beautifully maintained transitional Craftsman in sought-after Clifford Estates, NO HOA! From the moment you arrive, you’re greeted by a spacious Trex front porch, the perfect place to sip your morning coffee, unwind after a long day, and wave to neighbors passing by. Step inside to discover an inviting, light filled interior featuring Brazilian cherry hardwood flooring, neutral tones, and a traditional, flowing layout designed for both everyday living and entertaining. The bright and airy living room offers abundant natural light, while the chef’s kitchen truly shines with granite countertops, updated backsplash, stainless steel appliances, a large island with additional storage, ample cabinetry, a pantry, and space for a breakfast table. A formal dining room provides the perfect setting for holiday gatherings or casual dinners, and a convenient main level powder room completes the space. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite featuring extra windows, a large walk-in closet, and an ensuite bath with dual vanities. An additional full hallway bath and bonus storage area add even more functionality. The lower level offers incredible flexibility currently set up as a home gym, it’s ready for your vision. Finish it for additional living space, create guest quarters, or simply enjoy the storage. A cozy pellet stove adds warmth and charm as an additional heat source. Situated on a large corner lot, this home provides plenty of room to spread out. The rear Trex deck creates an ideal outdoor living space for entertaining or relaxing. With a detached garage, storage shed, attached three car garage, and a two car driveway, parking and storage are effortless. Additional highlights include a new roof (2025) for peace of mind. Enjoy a prime location just minutes from shopping, dining, and entertainment, including Annapolis Mall and the Maryland Renaissance Festival, with easy access to USNA, Fort Meade, Baltimore, Washington, DC, and BWI Airport. This is the one you’ve been waiting for, schedule your private tour today.

92 Clifford Blvd, Annapolis

Listing courtesy of Compass. Contact:

349 Sherwood Trl, Annapolis
$2,395,000
3 Beds ⋅ 5 Baths
Perched above the Severn River in the gated waterfront community of Epping Forest, this exceptional property captures sweeping water views and effortless indoor/outdoor living just minutes from downtown Annapolis. Thoughtfully designed with an open floor plan and walls of windows, the home is filled with natural light, high ceilings, custom millwork and seamless sightlines to the Severn river from nearly every vantage point. Expansive ipe decks with sleek cable railing extend the living space outdoors, creating the perfect setting for sunset entertaining or quiet mornings overlooking the water. The primary suite is a true retreat, complete with a private balcony overlooking the Severn; an idyllic perch for enjoying elevated river views and summer breezes. On the lower level, a covered flagstone patio offers an additional outdoor haven, ideal for relaxed evenings, gathering with friends or stepping directly out toward the waterfront. Inside, beautifully appointed gathering spaces flow easily from the gourmet kitchen to the dining and living areas, offering both comfortable everyday living and gracious entertaining. Three spacious bedrooms, three full baths and two half baths are thoughtfully distributed across four finished levels, providing flexibility for guests, work from home needs or additional recreation space. The private pier with deep water and two lifts, including a dedicated jet ski lift, invites endless days on the Severn, with quick access to Annapolis waterways and beyond. Ideally positioned close to Epping Forest’s renowned amenities, residents enjoy a clubhouse with waterside dining, marina, sandy beach, boat ramp, tennis courts, walking trails and a vibrant calendar of social events. An additional 0.115-acre parcel on Sherwood Trail (Tax ID: 224010114205) conveys with the sale and offers convenient supplemental parking, providing easy access for the many guests who will be sure to come visit. A rare opportunity to embrace panoramic river views, exceptional community amenities and the quintessential Annapolitan waterfront lifestyle. Epping Forest is a Special Tax District ($3,059.47 annually) with binding Rules and Regulations. Welcome Home!

349 Sherwood Trl, Annapolis

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

1 Shipwright Hbr, Annapolis
$5,675,000
3 Beds ⋅ 4 Baths
Stately French Villa on Spa Creek in downtown Annapolis! This jewel box of a home was designed and built by a renowned local architect as the culmination of an award-winning career. Offered completely turn-key, this exceptional residence conveys fully furnished and thoughtfully appointed—including furniture, fully equipped kitchen, linens, etc —allowing you to arrive with nothing more than a suitcase and begin enjoying the Annapolis waterfront lifestyle from day one. The unrivaled architectural detail, exquisitely curated finishes, and sweeping views across Spa Creek elevate this residence into a class of its own. Privately positioned at the end of a quiet street within one of downtown’s most coveted waterfront enclaves, this 3-bedroom, 3.5-bath retreat is equally suited as an elegant weekend escape or a full-time residence. Dramatic Palladian windows bathe the interiors in natural light while perfectly framing the ever-changing harbor views. At the heart of the home, the gourmet kitchen—appointed with custom cabinetry, premium appliances, and a striking designer hood—flows seamlessly into both the formal living room and inviting family room, each enhanced by a gas fireplace and captivating water vistas. A main-level secondary primary suite offers comfort and flexibility for guests of all generations. Upstairs, the extraordinary waterside primary suite features vaulted ceilings, walls of glass, a gas fireplace, spa-inspired bath with soaking tub, and a custom dressing room with center island. A private balcony provides the ideal perch for sunrise coffee or sunset reflections overlooking Spa Creek, Annapolis Harbor, and Eastport. Designed for effortless waterfront living, two deep-water piers with approximately 9 feet of MLW accommodate substantial vessels, with immediate access to the Severn River, the Chesapeake Bay, and beyond. Walkable to the shops, restaurants, and charm of downtown, this rare offering delivers convenience, privacy, elegance, and ease in one remarkable package. Welcome Home!

1 Shipwright Hbr, Annapolis

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

769 Robinhood Rd, Annapolis
$1,250,000
3 Beds ⋅ 2 Baths
769 Robinhood Road is one of the most desirable Waterfront properties in Sherwood Forest. Uniquely situated on a point you will enjoy river breezes from your living room and front porch while experiencing stunning views of the Severn River Bridges into Annapolis and down the Idle toward the Sherwood Forest Marina. On a clear day you can see the Eastern Shore! Watch as sail boats, wind surfers and yachts cruise by your front porch. Another unique benefit of 769 is that, unlike many of the Sherwood properties, it has ample parking for 5+ cars. This 1 level, 3 bedroom, 2 bathroom home, has been in the same family since 1940. Included in the listing documents are a home inspection report, already developed building plans, and information about a brand new septic in the works. Home is being sold AS IS. Take advantage of the varied Club amenities while you savor one of the best views in all of Sherwood Forest. **Sherwood Forest is a gated Community of 341 homes, situated on the Severn River. It's peninsula shape and sweeping elevations create gorgeous vistas of the surrounding creeks, river and the Severn River Bridge. **Walk along the 2 mile waterfront road and take in bridges framing the mouth of the Chesapeake Bay. **Bike or hike the 5 miles of outer Forest trails. Most residents prefer their Golf Carts for easily navigating the scenic hills. **Established in 1915, the Community is anchored by a grand nostalgic Clubhouse which overlooks the Community Pool - and houses a Dance Hall, Duckpin Bowling Alley, a Stage for Community Productions, a Grand Stone Fireplace, Library, and a Nature Lab for educating the children about Chesapeake life. Members enjoy many events at the Clubhouse including Community Dances, Anniversary Celebrations, and Cultural Arts Presentations. The Clubhouse is available to members to rent for Weddings or Private Events. ** The Sherwood Forest Market serves ready-made meals and stocks staples for your cottage kitchen. ** Sherwood is known for the Children's Summer camp where your children learn numerous activities including Sailing, Swimming and Archery. **Other outstanding amenities are a 9-Hole Golf Course, Tennis Courts, Pickleball Courts, Basketball Court, Badminton, Softball field and a Lacrosse/Soccer field. ** For the Chesapeake lovers, Sherwood has a Marina, a , Small Piers and a Main Pier where river swim meets are held. **Make memories with events like the 3rd of July Fireworks, 4th of July Parade and and Annual "not be be missed" Corn Roast. There are tennis, golf and pickleball tournaments for adults and children alike. *With a purchase of a home, Sherwood Forest requires a one-time $20,000 club membership fee.

769 Robinhood Rd, Annapolis

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

Start Your Search

Annapolis Single Family Real Estate

Our website features the best real estate search for single family properties available in Annapolis and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

How much is your home worth?

Get instant property value now!