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Annapolis

One of the most popular communities provided by Maryland Sandbox

Annapolis

About Annapolis

Nestled on the shores of the Chesapeake Bay, Annapolis, Maryland, is a charming and historic community that seamlessly blends waterfront beauty with rich maritime heritage. As the state capital and home to the United States Naval Academy, Annapolis boasts a vibrant downtown area filled with unique shops, gourmet restaurants, and stunning colonial architecture. Residents and visitors alike can enjoy picturesque strolls along the scenic harbor, where sailboats and yachts bob in the water. With its engaging cultural scene, including art galleries, theaters, and annual festivals, Annapolis offers a lively atmosphere for all ages. The community takes pride in its top-rated schools, making it an ideal place for families. Outdoor enthusiasts can explore numerous parks, nature trails, and waterfront activities, while history buffs can immerse themselves in the city's storied past at landmarks such as the Maryland State House. Whether you're seeking a lively urban environment or a peaceful retreat by the bay, Annapolis is a vibrant community that truly has something for everyone.
One of the most popular communities provided by Maryland Sandbox
274
# of Listings
3
Avg # of Bedrooms
$510
Avg. $ / Sq.Ft.
$1,357,507
Med. List Price

Browse Annapolis Real Estate Listings

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274 Properties Found. Page 8 of 19.

Just across the street from the water in Southaven, this Annapolis home offers the kind of space and flexibility that’s increasingly hard to find. Recently updated, the main level includes a renovated kitchen with quartz countertops, dual ovens, gas cooking, stainless steel appliances, and modern cabinetry. The main level also features a living room with built-in speakers, a dining room, an optional sitting room, a half bath, garage access, and a coat closet at the front entry. Upstairs are four well-sized bedrooms, two thoughtfully updated full baths designed with a clean, timeless aesthetic, and a laundry room. The walkout lower level remains unfinished and offers excellent storage, along with a bathroom rough-in for those who may wish to explore future expansion. Exterior updates include a newer roof and a recently paved driveway. The attached two-car garage supports everyday needs, while the detached three-car garage offers access to an unfinished upper-level space that provides additional room to tailor to personal needs. A back deck extends off the main level, with a second deck accessible from the unfinished space above the three-car garage. Community water access is located across the street. The Southaven community also offers a community pier and a kayak/paddleboard launch area. Set on a generous lot with ample storage and water access, 2942 Southaven Drive combines usability with the relaxed coastal character that makes this part of Annapolis so appealing.
#MDAA2131620

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

2,142 Sq.Ft.

$949,900

MLS#: MDAA2131620

Welcome to 909 White Marlin Way, an elegant brick-front Colonial ideally positioned on a quiet cul-de-sac in the highly sought-after Chesapeake Preserve community on the Broadneck Peninsula. Built in 1999 and set on a beautifully sized .49-acre lot within the desirable Broadneck School District, this meticulously maintained home offers over 4,200 square feet of finished living space, thoughtfully designed for both everyday living and effortless entertaining. Inside, you’ll find 5 bedrooms and 3.5 baths, complemented by a spacious, well-appointed layout. The main level showcases hardwood flooring, a private office with custom built-ins and crown molding, and a warm, inviting family room anchored by a wood-burning brick fireplace with a decorative mantel. The kitchen seamlessly blends function and style, featuring white cabinetry, granite countertops, a contrasting cherry island, stainless steel appliances, a walk-in pantry, and a built-in desk flowing naturally into the heart of the home. Upstairs, the expansive primary suite offers a true retreat, complete with a tray ceiling, two walk-in closets, and a well-appointed en-suite bath with a jetted tub. Brand new carpet (2026) throughout the upper level and stairs adds a fresh, modern touch. The finished lower level provides exceptional flexibility to suit a variety of lifestyles, offering a full bath, wet bar, and versatile spaces ideal for a home theater, gym, or potential sixth bedroom, along with abundant storage and a convenient walk-up exit to the backyard. Outdoor living is equally impressive. A large screened-in porch opens to a beautifully designed paver patio with firepit, perfect for relaxing evenings or hosting gatherings, surrounded by extensive hardscaping and a spacious, usable yard. Additional highlights include a two-car side-load garage, low HOA fees, and numerous updates: new patio and firepit (2024), screened-in porch was rescreened (2025), new carpet (2026), washer and dryer (2024), window screens (2021), large-capacity water heater (2020), and updated kitchen chandelier (2026). Ideally located just minutes from downtown Annapolis, top-rated restaurants, shopping, and major commuter routes to Baltimore, Washington, D.C., and the Eastern Shore. Enjoy convenient access to the new Broadneck walking trail, just a short distance from your front door. This is the perfect blend of space, style, and location, offering the lifestyle today’s buyers are looking for. Contact me to book your tour today.
#MDAA2140786

ANNAPOLIS

909 WHITE MARLIN WAY

5 Beds

3 Baths

4,170 Sq.Ft.

$949,900

MLS#: MDAA2140786

Prime West Annapolis Opportunity | B-1 Zoning | 13 Annapolis Street. Positioned in the heart of high-demand West Annapolis, 13 Annapolis Street presents an exceptionally rare opportunity to acquire a property with B-1 zoning flexibility in one of Annapolis’ most dynamic commercial districts. This is the kind of location where vision, creativity, and smart planning can translate into long-term value. B-1 zoning opens the door to a variety of potential uses such as boutique retail, professional offices, wellness studios, salons, galleries, cafés, creative workspaces, or thoughtfully designed mixed-use concepts (buyer to verify specific uses with the City). Whether you’re an entrepreneur looking to establish a flagship presence, a business owner seeking visibility, or an investor with a redevelopment vision, this property offers the versatility to bring those plans to life. Adding to its appeal is a feature rarely found in West Annapolis: a private driveway with abundant off-street parking, a significant advantage for clients, customers, or tenants and a true differentiator in this walkable corridor. Surrounded by beloved local restaurants, shops, and everyday conveniences, the property benefits from strong foot traffic, excellent visibility, and the vibrant energy that defines West Annapolis. Opportunities with this combination of location, zoning, and parking simply do not come along often.
#MDAA2135402

ANNAPOLIS

13 ANNAPOLIS STREET

None Beds

None Baths

2,240 Sq.Ft.

$925,000

MLS#: MDAA2135402

Major price reduction, exceptional value for over 3,292 finished sq ft tucked among the trees in the gated waterfront community of Epping Forest. This spacious three-level home features vaulted tongue-and-groove wood plank ceilings, light-filled interiors, and peaceful wooded views. So many options for furniture placement and usable space. The kitchen is designed for both everyday living and entertaining, featuring an expanded center island, abundant cabinetry, built-in shelving, and a wood-burning stove for added warmth. It opens to a flexible family room and flows into an expansive dining and living area with soaring vaulted ceilings, skylights, and a pellet stove set against a dramatic brick hearth. Upstairs, the primary suite offers a private retreat with an en-suite bath and access to an adjoining bedroom, ideal for an office or second bedroom. The lower level features a great room, two additional bedrooms, a full bath, workshop space, and walk-out access to a shaded deck. Epping Forest offers a unique waterfront lifestyle on the Severn River, with a private beach, a marina with boat slips, a clubhouse with a restaurant, tennis, pickleball, a playground, and year-round community events. Ideally located just 20 minutes to BWI, 30 minutes to Washington, D.C., and Baltimore, and minutes to downtown Annapolis.
#MDAA2137250

ANNAPOLIS

349 EPPING WAY

4 Beds

2 Baths

3,292 Sq.Ft.

$925,000

MLS#: MDAA2137250

Welcome to 220 West Street in Annapolis, Maryland. A rare, fully gut-renovated detached property located in the heart of the Downtown Arts District, 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.
#MDAA2140068

ANNAPOLIS

220 WEST STREET

3 Beds

2 Baths

1,540 Sq.Ft.

$924,900

MLS#: MDAA2140068

New on site today
Upscale Ryland Manor home in St. Margaret’s Landing showcasing an inspired open floor plan, thoughtful updates, and flexible living spaces throughout. Featuring 5 bedrooms and 3.5 baths, this beautifully maintained home has been freshly prepared for market with brand new paint throughout, new carpet, and a stunning renovated primary suite bath. SPECIAL FINANCING INCENTIVE AVAILABLE — QUALIFIED BUYERS MAY ACCESS A 6.125% FIXED RATE WITH A 1-YEAR BUYDOWN PROGRAM TO 5.125%! The main level offers formal living and dining rooms that flow seamlessly into the rear great room with fireplace ambiance, casual dining area, and an updated kitchen complete with butler’s pantry and mudroom. Sliders lead to the backyard patio, creating the perfect setup for entertaining and everyday living. The finished lower level offers exceptional versatility with a home theater, bar area, additional bedroom and full bath — ideal for recreation, guests, or potential in-law quarters. The vaulted primary suite serves as a private retreat with a luxurious updated bath and generous closet space. Additional highlights include a 2-car garage, multi-vehicle parking, and a prime location within St. Margaret’s Landing just minutes from Downtown Annapolis, the Chesapeake Bay, USNA, shopping, dining, and commuter routes. Special financing incentive available for qualified buyers that may help create lower monthly payments during the first year of ownership. Contact listing agent for details.
#MDAA2144004

ANNAPOLIS

707 BUOY COURT

5 Beds

3 Baths

3,729 Sq.Ft.

$924,900

MLS#: MDAA2144004

Tucked away on a private cul-de-sac in one of Annapolis's most coveted enclaves, this exceptional residence offers the refined living the Chesapeake Bay region is celebrated for. From the moment you arrive, beautifully manicured landscaping and an elegant facade set the tone for what awaits inside. Hardwood floors flow throughout the main level, anchoring an open floor plan where formal and informal living spaces are thoughtfully balanced. A gracious formal living room with a fireplace provides an elegant setting for entertaining, while the informal living room, anchored by a second fireplace, offers the kind of relaxed comfort that makes a house feel like a home. The heart of it all is a stunning two-story great room off the kitchen, where soaring ceilings soar overhead and natural light pours in from every angle; a breathtaking space that never loses its ability to impress. The chef-inspired eat-in kitchen is equally spectacular, appointed with a large center island, Corian countertops, gas cooktop, and dual wall ovens. Whether hosting an intimate dinner party or a festive gathering, this kitchen performs flawlessly. Recessed lighting throughout the main level lends a polished, gallery-like ambiance at every turn. The coveted first-floor primary suite is a true sanctuary, offering a generous walk-in closet and the ease of single-level living at its finest. First-floor laundry adds an everyday luxury that discerning buyers will immediately appreciate. Upstairs, two spacious bedrooms share a well-appointed full bath, while a versatile loft overlooks the living spaces below, equally suited as a private home office, library, or lounge. The finished lower level is nothing short of spectacular. Custom built-in bookcases, a third fireplace, a full bath, and a wet bar make this space ideal for entertaining, relaxing, or hosting overnight guests in style. A whole-home generator ensures uninterrupted comfort in every season. Outside, a paver patio and deck extend your living and entertaining space into the serene, landscaped backyard; the perfect backdrop for al fresco dining, morning coffee, or simply savoring the beauty of an Annapolis evening. A two-car garage completes this picture of thoughtful convenience. This is Annapolis living at its finest; where classic elegance, modern comfort, and Chesapeake Bay charm converge into something truly special.
#MDAA2143576

ANNAPOLIS

1604 TRAWLER LANE

3 Beds

3 Baths

4,295 Sq.Ft.

$915,000

MLS#: MDAA2143576

New on site 2 days ago
Brand new to the market in enchanting Epping Forest—one of Annapolis’ most sought-after gated, waterfront communities. Perched among the higher elevations, this home offers a seasonal winter water view from the expansive deck and is ideally positioned on one of the quietest streets in the neighborhood. Enjoy the best of Epping Forest with affordable living, a vibrant, water-centric community known for its unmatched lifestyle and amenities. Originally built in 1931, with the current structure rebuilt in 1994, this home has been fully renovated in 2026 and is truly move-in ready with new stainless-steel appliances, brand new bathrooms and freshly paint throughout. A rare main-level bedroom with an adjacent brand-new walk-in shower provides exceptional convenience for aging relatives. Recently refinished hardwood flooring extends throughout the home, including the staircase and upper level. Upstairs, both bedrooms feature cathedral ceilings and share a newly renovated full bath, while the secondary bedroom offers excellent potential for a walk-in closet, yoga room or flex space. A dramatic, light-filled staircase leads to the lower-level recreation space, complete with a built-in workspace, bookshelves, wine rack, and wet bar—ideal for entertaining or working from home. A third full bath with a jetted tub enhances the space, along with access to a private screened porch and yard, creating a comfortable and versatile guest or retreat area. Epping Forest is a Gated Waterfront Community on the Severn River with a community beach, waterfront clubhouse with restaurant and bar, tennis/pickleball and marina (new marina is currently under construction) Strong neighborhood connections where neighbors treat each other like family and fun happens weekly! Year around community events codify friendships, 4th of July Fireworks, Oyster & Bull Roast, Boat Club, Summer Volleyball League, community chapel, yoga & summer camps. Come experience the best Chesapeake Bay Maritime Annapolitan Lifestyle around! Epping Forest Inc. is a special benefit tax district with bylaws and binding rules and regulations
#MDAA2139650

ANNAPOLIS

1714 BROADLEE TRAIL

3 Beds

3 Baths

1,920 Sq.Ft.

$900,000

MLS#: MDAA2139650

GREAT OPPORTUNITY! Huge building offers two levels with office on main level (currently rented @$4500 a month and office on upper level is vacant and ready for you to run your business as the other is rented or just have them both rented. Close to Annapolis Mall, Route 50 and much more!
#MDAA2135848

ANNAPOLIS

2563 FOREST DRIVE

None Beds

None Baths

20,173 Sq.Ft.

$899,999

MLS#: MDAA2135848

Welcome home to 2906 Boyds Cove Drive, a stunning stone-front Colonial nestled in the highly sought-after, upscale enclave of Boyds Ridge. This home offers over 3,800 square feet of elegant above-grade living space, perfectly blending sophisticated design with everyday comfort. Step inside to an open flowing layout with gleaming hardwood floors, crown molding, and classic chair railings. The gourmet eat-in kitchen features granite countertops, cherry cabinetry, a gas cooktop, and a center island, flowing seamlessly into a breakfast nook and sunken family room anchored by a stone-front, wood burning fireplace, perfect for gathering with family and friends. A formal dining room rounds out the first floor, which also boasts an additional living room and library upon entrance to the house. Upstairs, the luxurious primary suite serves as a true private retreat. It boasts soaring cathedral ceilings, a gas fireplace, and expansive his-and-hers walk-in closets. The en-suite spa bath features a relaxing soaking tub and double vanities. Three additional generously sized bedrooms complete the upper level. The full walkout basement offers expansive unfinished space—a blank canvas ready to be transformed into a home theater, gym, or in-law suite. It already includes rough-in plumbing for a potential full bathroom, adding even more flexibility. Outside, enjoy a spacious rear deck overlooking a private lot, all tucked away on a quiet cul-de-sac. Located just minutes from Historic Downtown Annapolis, the Parole town center, and major commuter routes, this home offers the ultimate combination of luxury, space, and convenience. Don't miss your opportunity to own in Boyds Cove!
#MDAA2143826

ANNAPOLIS

2906 BOYDS COVE DRIVE

4 Beds

3 Baths

3,770 Sq.Ft.

$899,900

MLS#: MDAA2143826

Open House Friday , 5/15 4:30-6:30PM & Saturday 5/16 12-2PM. Please join us!Adorable bungalow coming soon in sought-after West Annapolis! Super fun, walkable location—catch Navy Midshipmen football games or stroll to Chessie’s Wharf, Positano’s, Bean Rush Cafe , Always Ice Cream Company & more! Just a short distance to Downtown Annapolis for waterfront dining, shopping, and historic charm. Easy one-level living with a great fenced-in yard and a large detached garage. Professional interior photos coming soon—stay tuned!
#MDAA2136076

ANNAPOLIS

607 MELVIN AVENUE

2 Beds

2 Baths

1,102 Sq.Ft.

$899,000

MLS#: MDAA2136076

New on site 3 days ago
LOCK AND LEAVE CAREFREE LIFESTYLE IN A WATERFRONT GATED COMMUNITY! DESIGNER SHOWCASE including a custom painted entry that draws you in the moment you open the door. Owner worked with a reputable interior designer to select all finishes to include designer light fixtures, gorgeous real hardwood floors, custom designed bathrooms, and so many interesting trim details. Transitional timeless design with a coastal twist. ONE OF A KIND and RARE GEM! END UNIT. Not one detail has been overlooked! And a beautiful gated waterfront and water-privileged community. BE PREPARED to be wowed when you open the front door with a top of the line renovation over $350,000. NOTICE ALL OF THE BEAUTIFUL ARCHED DOORWAYS! Bosch 3-ton with 96% gas HVAC, and Navien tankless hot water heater. All the vents were professionally cleaned after renovation. This is an opportunity that doesn't come along too often to move right into a turn-key TOTALLY RENOVATED & AND REDESIGNED BY AMAZING LOCAL DESIGNER AND CONTRACTOR!! gorgeously designed home in the exclusive community of Chesapeake Harbour. No expense has been spared to make this custom first-class from floor to ceiling. Totally redesigned and totally renovated with all permits. Custom window treatments throughout and designer light fixtures. Custom gourmet kitchen with quartz counters, stainless steel appliances, an abundance of drawer storage, perfect bar/pass through and much more! Three bedrooms and three full bathrooms. Each space offers light and invites you to relax and be happy you don't have to redo anything. Two-car garage with storage room and storage installed in ceiling of garage. Two gas fireplaces. Beautiful custom shiplap in living room and master bedroom. Multiple decks and from the top deck off master, owner loves to relax and watch the boats and bay bridge. His and her custom closets. Roofs, gutters and all trim painted in the last two weeks. Marvin windows will be installed prior to settlement in guest room and one in office.... And talk about the community, Community beach and pier and two pools, one heated and one waterfront looking out at the Bay. Tennis and pickleball courts for your fun and exercise. Don't worry about getting your steps in with all the waterfront walking paths, If you don't feel like cooking, walk on over to The Beacon with dockside seating . This is a gated community with 24/7 security and guard gate. You can have it all with the best of coastal living in this vibrant and secure community. The pictures really don't do it justice. This is the one you've been waiting for! A MUST SEE!
#MDAA2145640

ANNAPOLIS

7015 CHESAPEAKE HARBOUR DRIVE 23B

3 Beds

3 Baths

2,041 Sq.Ft.

$899,000

MLS#: MDAA2145640

Step into the charm and character of Annapolis living at 21 Woodlawn Ave — a beautifully updated 1905 home in the Germantown-Homewood community, blending timeless architecture with thoughtful modern improvements, all in one of the city’s most walkable locations. This 3-bedroom, 2-bath home is filled with warmth and original character, featuring high ceilings, hardwood floors, natural light, and a stunning wrap-around three-seasons porch that acts like an extension of the living space. The renovated kitchen offers brand-new cabinetry, appliances, and finishes while maintaining the home’s historic charm. Additional recent updates include all new interior and exterior paint, newly refinished hardwood floors on the second level, bathroom upgrades, and the addition of a functional mudroom at the rear entrance. Beyond the home itself, the property offers something truly rare in downtown Annapolis — an exceptionally spacious backyard with incredible flexibility and future potential. Whether you envision expanding outdoor living space, creating gardens, building an in-law suite or private office above/within the existing garage footprint, or exploring the possibility of subdivision (buyer to verify), the opportunities here add meaningful long-term value. Bonus features include a walk-up unfinished attic with potential to create additional finished living space, an unfinished basement with laundry area and exterior access, and off-street parking that is increasingly hard to find this close to town. Enjoy the lifestyle that comes with this location — just moments from downtown Annapolis, City Dock, Navy-Marine Corps Memorial Stadium, Naval Academy events, Maryland Hall, restaurants, coffee shops, the library, and the Poplar Trail bike path. A rare opportunity to own a piece of Annapolis history with space, flexibility, and future potential close to the heart of the city.
#MDAA2144864

ANNAPOLIS

21 WOODLAWN AVENUE

3 Beds

2 Baths

1,442 Sq.Ft.

$899,000

MLS#: MDAA2144864

New Construction in Cape St. Claire. Home construction has now started. Delivery date will be end of August or beginning of September. Days on the market began when lot was purchased. Please look at the documents section of the listing to see all standard features included with this home and all floor plans and site plan. Pictures shown in this listing are of the home now framed and a previous completed home built at 1216 Ramblewood Drive Annapolis, Md. also located in Cape St. Claire during the construction of that home. This same floor plan will be constructed on this site. Please contact listing agent with any questions.
#MDAA2130056

ANNAPOLIS

1217 HAMPTON ROAD

4 Beds

2 Baths

2,700 Sq.Ft.

$896,000

MLS#: MDAA2130056

AVAILABLE TO TOUR FRIDAY, MAY 15 — CALL NOW TO SCHEDULE YOUR PRIVATE SHOWING OR VISIT THE OPEN HOUSE THIS SATURDAY! Just in time to enjoy summer in the fabulous water-privileged community of Beechwood on the Burley. Ideally located approximately 2 miles from Downtown Annapolis, yet tucked within a quiet, tree-lined setting that feels worlds away. This spacious home offers wonderful living spaces inside and out! Versatile main level den can easily be transformed into main level bedroom suite complete with attached full bath. Meticulously maintained with numerous updates including a new roof (2025), garage doors + operating system (2025), hot water heater, whole-house generator, and more. Launch your boat from the private community ramp with quick access to Burley Creek and the Severn River, enjoy the community pier and waterfront playground, and experience the Annapolis lifestyle at its finest — with easy access to Downtown Annapolis, City Dock, restaurants, shopping, and marinas by both boat and car. Don’t miss the opportunity to enjoy privacy, Blue Ribbon schools, and water-oriented living in one of Annapolis’ most desirable neighborhoods. Easy access to major commuting routes make this one a 10++
#MDAA2144280

ANNAPOLIS

1848 CHERRY ROAD

6 Beds

3 Baths

3,150 Sq.Ft.

$895,000

MLS#: MDAA2144280

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