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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
276
# of Listings
3
Avg # of Bedrooms
$515
Avg. $ / Sq.Ft.
$1,434,627
Med. List Price

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127 Properties Found. Page 2 of 9.

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.
#MDAA2140068

ANNAPOLIS

220 WEST STREET

3 Beds

2 Baths

1,540 Sq.Ft.

$899,900

MLS#: MDAA2140068

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 SUNDAY 11/31 11AM-1PM. 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

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.

$899,000

MLS#: MDAA2135402

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

Some addresses just make life better. This one is tucked back in Beechwood on the Burley — a sought-after water-privileged community in St. Margarets, with private access to Burley Creek for kayaking, canoeing, and boating, plus a community pier, dock slips, and picnic area steps from your door. Downtown Annapolis is less than 2 miles away, yet the setting feels genuinely private, sheltered under a canopy of mature trees on a generous 0.7-acre lot. The house itself offers a rare combination: five bedrooms a, an open kitchen-to-family-room layout, a potential main-level bedroom and full bath ideal for guests or multigenerational living, a kitchen island, and built-in Bose surround sound with TV that conveys. A dedicated main-floor den gives you the flexibility to work from home without sacrificing living space. The two-car attached garage with four additional driveway spaces means there is always room for boats, bikes, kayaks, and company. 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 restaurants, shopping, and marinas by both boat and car. Whether you are upsizing into a home that finally fits the whole family, seeking a place to launch a kayak on a Tuesday morning before work, or looking for a Chesapeake Bay-area property that gives you space without sacrificing proximity to Annapolis, this home delivers on all counts. Come see it before summer is in full swing!
#MDAA2144280

ANNAPOLIS

1848 CHERRY ROAD

6 Beds

3 Baths

3,150 Sq.Ft.

$895,000

MLS#: MDAA2144280

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.

$889,000

MLS#: MDAA2143576

New on site today
Phenomenal Downtown property was the winner of Historic Annapolis Founation's Renovation award! Overflowing with charm and personality, this wonderful home radiates good vibes from so many good times enjoyed here! Enter the welcoming hallway with the elegant staircase. and step into the living room with the double-sized gas fireplace and fun curved wall. Through the arched doorway, find the perfectly sized dining room where the coffered ceiling and gas fireplace enhance the ambiance. The dining is open to the sunny, well-planned kitchen with two skylights, gas cooking, a large island, and great storage. The main level is completed with a powder room. Through the glass door from the kitchen, step onto the gorgeous, tranquil terrace where guests and family will unwind and stay a while. The 2nd level has two bedrooms and a full bath and the top level is the 3rd bedroom. The lower level houses the laundry and there is plenty of great storage! Lots of great updates, including new roofs! Premier location just blocks to everything fun Annapolis has to offer!
#MDAA2148978

ANNAPOLIS

22 COLLEGE AVENUE

3 Beds

1 Baths

1,510 Sq.Ft.

$876,000

MLS#: MDAA2148978

Charming water-privileged split-foyer residence in the desirable Beale Manor community, offering 3,145 finished square feet of thoughtfully designed living space. Recent updates include a roof replacement, a newer water heater, fresh interior paint, and beautifully refinished flooring throughout the main level, enhancing both style and peace of mind. // The traditional layout begins with a formal living room featuring large picture windows that draw in abundant natural light and flows seamlessly into the formal dining room, creating an inviting setting for gatherings. The updated eat-in kitchen is both stylish and functional, showcasing crisp white cabinetry with sleek bar pulls, a peninsula breakfast bar, black appliances including double ovens, a built-in workstation, and a bright breakfast area with sliding door access to the screened porch. Just off the kitchen, the welcoming family room is highlighted by a white-washed brick fireplace and filled with natural light, while a convenient powder room and laundry area complete the main level. // The upper level features four generously sized bedrooms, including a spacious owner’s suite with a comfortable sitting area, dual closets—one a walk-in with a custom organization system—and a private ensuite bath with a soaking tub and separate shower. A centrally located full bathroom with an extended vanity serves the additional bedrooms. The walk-out finished lower level provides exceptional versatility, offering a large recreation space, a full bathroom, a bar area with a rough-in for a sink, and a fifth bedroom ideal for a home office, gym, or guest space. // Outdoor living is equally appealing, with a screened porch overlooking the backyard, an open-air deck that steps down to a patio, and a spacious, flat, fully fenced yard backing to trees for added privacy. // Residents of Beale Manor enjoy a wealth of community amenities, including a scenic waterfront pool, a basketball court, and a whimsical pollinator garden, fostering a vibrant, connected lifestyle.
#MDAA2134882

ANNAPOLIS

3135 ANCHORAGE DRIVE

5 Beds

3 Baths

3,145 Sq.Ft.

$875,000

MLS#: MDAA2134882

Welcome to Kingsport—where timeless elegance meets waterfront living. Nestled within this coveted, water-privileged community, this exceptional 5-bedroom, 4.5-bath residence offers a seamless blend of sophistication, comfort, and everyday luxury. A grand entry welcomes you with rich hardwoods and graceful architectural details, leading to a formal oval dining room, refined living room, and a private main-level office—perfect for today’s lifestyle. The heart of the home is a beautifully appointed gourmet kitchen, featuring a custom center island with cooktop, dual wall ovens, gleaming granite countertops, and extensive cabinetry. The space flows effortlessly into a dramatic family room, highlighted by soaring vaulted ceilings, plantation shutters, and a warm gas fireplace. Upstairs, the primary suite is a true retreat, offering a spa-inspired bath and dual walk-in closets. An elegant en-suite bedroom and two additional bedrooms with a shared bath complete the upper level, offering both comfort and privacy. The fully finished lower level is designed for entertaining and relaxation, featuring a spacious recreation room with a wet bar, a private guest suite, a playroom, and abundant storage. Outdoors, a fully fenced backyard invites quiet moments and gatherings alike, with a paver patio, raised garden beds, and serene wooded views backing to scenic walking paths. Residents of Kingsport enjoy an exceptional lifestyle with resort-style amenities including a community pool, playgrounds, hiking and biking trails, kayak launch and storage, and a picturesque pier on Crab Creek—ideal for sunset views, fishing, or peaceful afternoons by the water. Perfectly positioned just minutes from downtown Annapolis and convenient to major commuter routes, this home offers the rare opportunity to live beautifully in one of the area’s most desirable communities.
#MDAA2143706

ANNAPOLIS

730 CRISFIELD WAY

5 Beds

4 Baths

3,586 Sq.Ft.

$865,000

MLS#: MDAA2143706

Our Adams model with a 2' extenstion will be built at this beautiful location near Duvall Creek. Home is priced at the base house only - act fast to choose the options and additions to make this home your own. Photos are of the model with optional In-Law Suite. Contact Listing Agent to schedule appointment.
#MDAA2147542

ANNAPOLIS

3268 KITTY DUVALL DRIVE

4 Beds

2 Baths

2,474 Sq.Ft.

$849,990

MLS#: MDAA2147542

New on site 1 day ago
Welcome to 1848 Carriage Road, a timeless gem that is beautifully situated in the highly sought-after Lindamoor community. Just a short stroll from the community beach and only a few streets from both neighborhood docks, this home offers the perfect blend of water accessibility, convenience, and undeniable charm. Step inside to discover a warm and inviting main level filled with large windows and natural light. The spacious living room flows seamlessly into the dining area and kitchen, creating an ideal layout. Designed for easy living, the home functions like a rancher, with three generous sized, sun-filled bedrooms, two bathrooms and everything you need on the main level. The kitchen opens onto a deck overlooking a spacious, wooded backyard — perfect for gardening, entertaining, pets, or play. The fully finished walk-out lower level significantly expands the living space and offers exceptional flexibility. With direct access from the garage and a large sliding door to the backyard, this level features a spacious family room, a separate sitting area perfect for a media room or home office, a large fourth bedroom, and a full bathroom. Abundant storage and versatile spaces provide endless possibilities for guests, fitness, recreation, or work-from-home needs. Ideally located just minutes from historic downtown Annapolis, you'll enjoy easy access to waterfront restaurants, boutique shopping, marinas, and year-round cultural events, along with convenient commuting routes to both Washington, D.C. and Baltimore. Offered at an attractive price and ready for its next owners, this is a rare opportunity to enjoy the lifestyle and amenities that make Lindamoor one of Annapolis’ desirable waterfront communities. Don't miss your chance to make this charming property your new home.
#MDAA2148380

ANNAPOLIS

1848 CARRIAGE DRIVE

4 Beds

3 Baths

2,622 Sq.Ft.

$849,000

MLS#: MDAA2148380

New on site 2 days ago
Located in the sought-after water-oriented community of Cape St. John, this stunning colonial offers exclusive access to a community boat ramp and sandy beach on the South River. Thoughtfully updated with top-of-the-line appliances and finishes, this home is designed for both everyday comfort and elegant entertaining. The gourmet kitchen is a true showpiece, perfect for hosting gatherings of any size. Forno gas burning stove, with a overhead vent. Chef's dream. Loads of counter space with 48in cabinets installed. Upstairs, you’ll find three spacious bedrooms, all with great size closets and two full bathrooms, while the main level features a bright, open living area with abundant natural light and a cozy gas-burning fireplace. Step outside to a Trex deck overlooking the elevated backyard, complete with a paver-layered patio ideal for outdoor dining and relaxation. A custom-built shed provides extra storage, and a county-approved permit for a pool offers exciting future potential. Outside basement access. Optional HOA. Enjoy the best of waterfront living in a vibrant, amenity-rich neighborhood—all just minutes from Annapolis and major commuter routes.
#MDAA2144896

ANNAPOLIS

164 WOODSIDE TRAIL

3 Beds

2 Baths

1,768 Sq.Ft.

$849,000

MLS#: MDAA2144896

NEW PRICE, UPDATED SQUARE FOOTAGE + NEW PHOTOS ADDED — INCREDIBLE OPPORTUNITY! Boasting 1,549 sq. ft. of finished historic charm, this 1905 Homewood treasure sits on a rare, oversized 0.26-acre lot—offering space and flexibility nearly impossible to find this close to City Dock. While the main house charms with high ceilings, refinished hardwoods, and a light-filled 3-seasons wrap-around porch, the true crown jewel is the backyard oasis. Surrounded by stunning, mature trees, the sprawling lawn features an existing 1-car garage ripe for transformation. Bring your vision to easily rebuild this structure into a premier Accessory Dwelling Unit (ADU), income-producing apartment, or a private home office oasis. Walk to the Navy Stadium, local cafes, and the Poplar Trail. With room to grow, update, and build equity, this is a rare Annapolis footprint waiting for your personal touch! Note on Square Footage: Finished square footage has been updated to 1,549 sq. ft. based on recent agent measurements. Public tax records currently reflect inaccurate historical data (1,442 sq. ft.) and do not fully capture the complete finished living area.
#MDAA2144864

ANNAPOLIS

21 WOODLAWN AVENUE

3 Beds

2 Baths

1,549 Sq.Ft.

$849,000

MLS#: MDAA2144864

Pure Privacy on this wooded paradise here in Annapolis. Situated on a private, 1.42 acre lot, you're going to love the sun-filled family room and adjacent sunroom. The kitchen has been remodeled with gorgeous, wooded cabinetry, granite counters and high-end appliances. There is a formal living and dining room for all of your functions. The basement has been waterproofed and is walk-out level and ready to be finished. There are three bedrooms upstairs with an open office/loft area. Explore nature or just enjoy the hummingbirds from the back deck and porch. Close to everything, but feels miles away!
#MDAA2143460

ANNAPOLIS

1812 CROSSPOINTE DRIVE

3 Beds

2 Baths

2,792 Sq.Ft.

$845,000

MLS#: MDAA2143460

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