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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

211

# of Listings

3

Avg # of Bedrooms

$517

Avg. $ / Sq.Ft.

$1,092,234

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

211 Properties Found. Page 6 of 15.

Modern accents meet classic Georgian design in a downtown Annapolis private enclave of customized homes. Monthly neighborhood get togethers, progressive dinners, holiday celebrations and lovingly curated green spaces for outdoor living. Self managed HOA includes yard care and snow removal for lock and leave convenience.

If you’re looking for rolling acres with grass to cut weeds to pull beds to mulch and snow to shovel this is not the home for you. If you desire almost 4000 sq feet with a small carbon footprint energy efficient with Georgian timeless beauty turn key lock and leave where weekends are your own then this is the one for you. Add a close knit community of only 30 homes with holiday and social gatherings to attend (or not) walking biking distance to Historic Annapolis and Eastport and short DC Baltimore commute.
Two ensuites, office space, flex space and huge storage rooms. Private outdoor paved patio and 2 car garage with additional 2 driveway spaces along with extra guest parking, rare for in town Annapolis living.
Hardwoods on upper and lower levels with carpeted bonus room in fully finished basement offering its own full bath. Brick front and Hardiplank siding.

Gym, hiking trails, sports and pickle ball courts, and boat/ kayak/paddle launch across the street.

Urban vibe with suburban feel, premier coastal living, Restaurants shopping and conveniences within biking and walking distance.

Summer nights at Dining Under the Stars on West Street. Morning walks to the historic waterfront of City Dock
Kayaking on Spa Creek just across the street. Happy hours in Downtown Annapolis. Water taxi or bike ride to Eastport for dinner. Navy game days coming soon!

With nearby marinas for boating, waterfront parks, and recreation centers within walking distance everything you need to live and love Annapolis.

Primrose Hill is coastal living among an exceptional collection of homes where every day feels like a retreat in your luxury primary residence or weekend sanctuary. Beautiful private neighborhood areas for dog walking. Residents enjoy picnics and relaxing outdoors in amazing community areas.

Iconic Craftmark design with model upgrades throughout create a luxury home with all the modern touches for easy living. Newly built to age gracefully with modern accents set against classic design.

Finished Lower level with family room, full bathroom, office, storage and additional room for wellness space, spa, music room or other flexible lifestyle area.

ANNAPOLIS

52 PRIMROSE HILL LANE

5 Beds

4 Baths

3,978 Sq.Ft.

$924,900

MLS#: MDAA2138534

Experience the best of Annapolis living in this beautifully cared-for Kingsport home, offering a perfect blend of comfort, style, and thoughtful upgrades. Built by Basheer & Edgemoore, this 4 bedroom, 4.5 bath residence welcomes you with a bright two-story foyer and an inviting layout designed for both everyday living and effortless entertaining.
Hardwood floors, plantation shutters. recessed lighting, and detailed trim work enhance the main level. The formal dining room is ideal for gatherings, while the spacious eat-in kitchen features a center island with cooktop, double wall ovens, granite countertops, pantry and stainless steel appliances. The kitchen opens directly into the impressive two-story family room, complete with a gas fireplace and a dramatic wall of windows that fill the room with natural light.
A private office, powder room, laundry with utility sink and built-ins and access to the upgraded 2-car garage complete the main level.
Upstairs, the generous primary suite offers two walk-in closets with built-ins, a sitting room and a spa-like bath with soaking tub and separate shower. A second bedroom includes an en-suite bath, while the other two bedrooms share a Jack-and-Jill bathroom.
The lower level includes a full bath, recreation room, abundance storage and an egress window - ideal for adding a fifth bedroom. Plenty of space for gym equipment, workshop and still have plenty of storage space.
The backyard is fenced in and has private patio area with lovely landscaping. No need for a grasscutter in the back.
Kingsport amenities include walking/biking trails, water access with kayak dock, two playgrounds and a community pool with hot tub. Nice public areas for sitting, picnics and dog walking . Convenient to downtown Annapolis, Naval Academy, shopping, dining , marinas and major commuter routes.

ANNAPOLIS

706 DRAKE WAY

4 Beds

4 Baths

4,571 Sq.Ft.

$905,000

MLS#: MDAA2139344

GREAT OPPORTUNITY! Huge building offers two levels with office on main level and office on upper level, both units are vacant and ready to run your business as you rent the other unit out or combine both. Close to Annapolis Mall, Route 50 and much more!

ANNAPOLIS

2563 FOREST DRIVE

None Beds

None Baths

20,173 Sq.Ft.

$899,999

MLS#: MDAA2135848

New Construction in Cape St. Claire. Home construction will start in March. 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 a previous 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. Home is scheduled to be completed by August/September of 2026.

ANNAPOLIS

1217 HAMPTON ROAD

4 Beds

2 Baths

2,700 Sq.Ft.

$896,000

MLS#: MDAA2130056

At last, the one you've been waiting for. A beautiful home in a waterfront community. Move right in and start enjoying the Annapolis lifestyle. Anchorage is an amenity filled waterfront community in which the yearly HOA fee includes the use of a boat slip, community pool and more.
This characterful 5 bedroom 2 1/2 bath home has approximately 2,354SF of living space and has been renovated within the last 4 years. Upgrades that include HVAC, tankless hot water heater, well pump, sewer line, roof, downspouts, gutters, soffit and windows make this home a low maintenance joy. A bespoke new sunroom addition off of the kitchen includes a wood burning stove. Simply delightful!
The sparkling kitchen with a new double oven and stainless appliances has an easy flow with classically beautiful cabinetry and quartz counters. Wood floors continue through the living room and down the hall to 3 bedrooms which include the primary with ensuite bath and an additional half bath.
Downstairs there are 2 bedrooms, a full bath, laundry room, storage room and family room with a fully lined fireplace and wood stove. Garage access is through this room. In the 2 car garage you'll find 2 EV chargers. The harmonious floor plan guides you from room to room with ease.
Sitting on nearly 1/2 acre, the outdoor space won't disappoint. Entertaining is a breeze here, enjoy the spacious deck which is adjacent to the sunroom and overlooks the level, lightly treed and fenced backyard. Landscaping which has matured with the years adds to the natural charm of the property.
Two storage sheds provide plenty of storage with one facing the driveway for easy bike storage access.
The community waterfront on Lake Ogleton includes 49 deep water slips in the marina, community pool, kayak storage, boat ramp and basketball court. The Chesapeake Bay is a quick motor away and historic downtown Annapolis is minutes by car underscoring the desirability of this home's locale.
Filled with amenities and coupled with location, Anchorage is a community that truly has it all.

ANNAPOLIS

1106 MAINSAIL DRIVE

5 Beds

2 Baths

2,059 Sq.Ft.

$895,000

MLS#: MDAA2139090

RECENTLY CONSTRUCTED 4 BEDROOM, 2.5 BATH COLONIAL LOCATED IN THE HIGHLY DESIRED WATER-PRIVILEGED COMMUNITY OF CAPE ST. CLAIRE. WELCOMING COVERED FRONT PORCH. MAIN LEVEL FEATURES CROWN MOLDING, HARDWOOD FLOORS THROUGHOUT, AND A CONVENIENT HALF BATH. BEAUTIFUL WHITE KITCHEN WITH WOLF CABINETRY, QUARTZ COUNTERTOPS, WORKING ISLAND, PANTRY, STAINLESS STEEL APPLIANCES, AND EAT-IN TABLE SPACE. SEPARATE DINING ROOM FOR FORMAL GATHERINGS. FAMILY ROOM OFF THE KITCHEN OFFERS OPEN CONCEPT LIVING WITH A COZY GAS FIREPLACE. THE 2ND FLOOR IS ACCESSED BY A CUSTOM STAIRCASE WITH OAK HANDRAILS AND WROUGHT IRON SPINDLES. SPACIOUS AND TRANQUIL PRIMARY SUITE FEATURES A CUSTOM TRAY CEILING, EN-SUITE BATH WITH SOAKING TUB, SEPARATE GLASS SHOWER, DUAL VANITY, AND 2 WALK-IN CLOSETS. 3 ADDITIONAL GENEROUSLY SIZED BEDROOMS AND A FULL BATH COMPLETE THE UPPER LEVEL. CONVENIENT AND SPACIOUS LAUNDRY ROOM ALSO LOCATED ON THE UPPER LEVEL. THE UNFINISHED LOWER LEVEL IS A BLANK CANVAS WITH PLUMBING ROUGH-IN FOR AN ADDITIONAL BATHROOM AND SPACE FOR A FUTURE BEDROOM AND/OR RECREATION ROOM. WALK OUT TO THE REAR YARD FEATURING A CUSTOM PATIO AND LANDSCAPING THAT IS IDEAL FOR ENTERTAINING. 2-ZONE HVAC AND 9 FT. CEILINGS THROUGHOUT. CONVENIENTLY LOCATED NEAR GOLFING, RECREATION, THE CHESAPEAKE BAY BRIDGE, AND DOWNTOWN ANNAPOLIS.

ANNAPOLIS

1176 GREEN HOLLY DRIVE

4 Beds

2 Baths

2,594 Sq.Ft.

$889,000

MLS#: MDAA2138386

Significant Price Improvement!! A rare opportunity! Priced to sell, won't last long. Welcome to this beautifully maintained 5 bed, 4.5 bath, colonial home situated on almost a half of acre and only 2 blocks to the Chesapeake Bay where you can hear the sounds of the ships passing by in your backyard! Located in the very desirable and relaxed Oyster Harbor Community. This move-in ready home features: over 3,100 finished sqft, 2 primary suites with private full baths which makes it perfect for multi-generational living. The main level is filled with natural light, cathedral ceilings, and an open layout. The main level primary suite offers a spacious bedroom with costume shutters, a walk-in closet with extra room for storage, and a oversized walk-in shower with floor to ceiling tile, multiple shower heads, and a bench. The upper level features the second primary suite with a full bath, 2 additional bedrooms and another full bath. The huge lower level has multiple rooms including a large rec room that can fit a pool table, games and a bar area, plus a family room or theatre room, a 5th bedroom, and a full bath! There is even space for a kitchenette! The lower level has outside access which would make it perfect for an in-law suite. The backyard is fully fenced in and perfect for summertime entertaining! When spring hits you will be surrounded by green trees; the lot next to the home is a preserved lot. This home is nestled between Oyster Creek, Fishing Creek, and the Chesapeake Bay. Oyster Harbor offers the best of Coastal Maryland living—just minutes from historic downtown Annapolis, top-rated restaurants, shopping, and commuter routes. Quiet Waters Park is only minutes away with walking trails, dog park and beach, concerts, ice skating, and so much more! Walking distance to Thomas Pointe Park. The Coast Guard is just down the street. This home is MOVE-IN READY AND A MUST-SEE!

ANNAPOLIS

3280 ARUNDEL ON THE BAY ROAD

5 Beds

4 Baths

3,144 Sq.Ft.

$850,000

MLS#: MDAA2138708

Set on 2.48 private acres with potential subdivision opportunity, this beautiful log home offers the perfect mix of character, space, and thoughtful updates. Surrounded by mature trees and landscaping, the property provides peaceful treetop views and seasonal water views during the winter months. The two-story living room features a striking wood-burning fireplace and opens to the dining area and updated kitchen with granite countertops, breakfast bar seating, ample cabinet space, and all major appliances. The layout is ideal for both everyday living and entertaining. Three spacious bedrooms are located on the main level, all with hardwood floors. The primary suite includes a walk-in closet, ceiling fan, spa-style bath with soaking tub and separate shower, and private access to the rear deck. Upstairs, a bright loft with oversized skylights and a full bath offers flexible space for a home office, family room, or additional living area. The finished basement adds even more usable space with a large recreation room, fourth bedroom, laundry area, and plenty of storage. Enjoy outdoor living on the rear deck overlooking wooded privacy, plus a welcoming front paver walkway and deck. The driveway offers ample parking, and community beach access is just a short walk away. Conveniently located near major commuter routes and downtown Annapolis, this home combines privacy with easy access to shopping, dining, and everyday amenities.

ANNAPOLIS

2977 SOUTHAVEN DRIVE

4 Beds

4 Baths

1,936 Sq.Ft.

$849,900

MLS#: MDAA2138068

New on site 3 days ago

Set on a beautifully landscaped 0.34-acre corner lot in sought-after Winchester-on-the-Severn, this thoughtfully renovated residence offers a seamless blend of style, comfort, and everyday livability. A fully fenced backyard creates a private outdoor retreat, complete with a deck, patio, garden, playground, and storage shed, perfectly designed for both entertaining and relaxed daily living.

Inside, an open and airy floor plan is anchored by a vaulted ceiling and a striking brick fireplace, creating a warm yet elevated main living space. The living room, dining area, and renovated kitchen flow effortlessly together, with direct access to the deck for easy indoor-outdoor living.

The upper level features three bedrooms, including a spacious primary suite with a beautifully appointed ensuite bath, while two additional bedrooms share a well-designed hall bath. The lower level offers a comfortable family room with walkout access to the patio, along with two additional rooms ideal for guest bedrooms, offices, or flex space, complemented by a full bath. Just beyond, an additional lower level expands the home’s versatility with a dedicated laundry room, playroom, gym area, and generous storage space.

Located just minutes from Route 50 and downtown Annapolis, Winchester-on-the-Severn is a vibrant, amenity-rich waterfront community offering residents access to a private beach on the Severn River, marina, boat ramp, multiple piers, beach pavilion, playground, dog beach, and the Chase Creek Swim Club. The nearby B&A Trail adds even more opportunity for outdoor recreation. Positioned within the Blue Ribbon Broadneck School District and convenient to Baltimore, BWI, Ft. Meade/NSA, and Washington, DC, this home presents an exceptional opportunity to enjoy a coveted neighborhood lifestyle in a beautifully updated setting. Welcome Home!

ANNAPOLIS

1519 WINCHESTER ROAD

5 Beds

3 Baths

2,375 Sq.Ft.

$849,000

MLS#: MDAA2139874

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.

ANNAPOLIS

92 CLIFFORD BOULEVARD

4 Beds

2 Baths

2,252 Sq.Ft.

$835,000

MLS#: MDAA2139188

#MDAA2137260

ANNAPOLIS

76 OLD MILL BOTTOM ROAD N 205

3 Beds

3 Baths

1,729 Sq.Ft.

$825,665

MLS#: MDAA2137260

YES, YOU CAN HAVE IT ALL.

Completely remodeled from top to bottom in one of the most sought-after neighborhoods around—this one checks ALL the boxes.

The kitchen, the great room… this is the hub. The heart of the home. And the best part? You’re not dreaming about what it could be—the work is already done. Big island, open flow—everyone ends up here. Whether you’re cooking, hanging out, or just catching up at the end of the day, it’s easy, comfortable, and it works. And it flows right out to the deck—so your living space doesn’t stop at the back door.

And then… the yard. Over 1/3 acre of flat, usable space—which in Hillsmere is a big deal.
This isn’t a “look at it from the window” yard. This is a run around, roam around, throw a ball, set up a fire pit, bring all the toys (for kids and adults) kind of yard. The kind you actually use. There is plenty of storage space to store all those toys in your extra deep one car garage which is an added bonus.

Back inside—everything’s been done.
Hardwood floors throughout the upper level, freshly painted, and ready for you. Kitchen, baths, finishes—clean, updated, and done right. No projects. No guesswork. Just move in and start living.

Upstairs offers three bedrooms and 1.5 baths.
Downstairs? A private primary suite with a full bath, plus additional living space that flexes however you need it—guests, office, gym, or all three.

And then there’s the lifestyle that makes Hillsmere what it is…
Just a few blocks in any direction takes you to the best of Hillsmere—the beach, marina, boat launch, pool, playground, pavilion… and right across from Key School.

Your Morning walks by the water, spontaneous sunset plans, weekends that don’t need planning—YES, YOU CAN HAVE IT ALL.

ANNAPOLIS

101 HUSE DRIVE

4 Beds

2 Baths

2,016 Sq.Ft.

$800,000

MLS#: MDAA2140304

Experience upscale urban living in this stunning 3rd-floor Everest model at Grandview, ideally located on the retail boulevard side of Annapolis Town Center. This residence offers a true city feel with unbeatable walkability to premier shopping and dining.
The open-concept living and dining area features bamboo flooring, a dramatic tray ceiling, and floor-to-ceiling glass doors leading to a private balcony filled with natural light. Elegant French doors open to a versatile bonus room, ideal as a home office or third bedroom.
The kitchen is designed for both entertaining and everyday living, showcasing stone and granite countertops, a professional-grade double oven, and a peninsula breakfast bar. A spacious laundry room and additional storage cage add convenience.
Two luxury bedroom suites each feature custom closet organizers. The primary suite includes a spa-inspired bath with a soaking tub and walk-in shower, while the second suite offers a double-sink vanity and walk-in shower—perfect for guests or flexible living.
Enjoy resort-style amenities including concierge services, fitness center, and a rooftop pool with social lounges, plus two assigned garage parking spaces. Walk to Whole Foods, Target, and top restaurants like True Food Kitchen and Cooper’s Hawk. Minutes from Historic Downtown Annapolis, Anne Arundel Medical Center, Annapolis Mall, with easy access to Route 50 and I-97.
A must-see for those seeking a luxury, maintenance-free lifestyle.

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 309

2 Beds

2 Baths

1,681 Sq.Ft.

$770,000

MLS#: MDAA2135756

#MDAA2137876

ANNAPOLIS

2771 GINGERVIEW LANE

3 Beds

3 Baths

3,208 Sq.Ft.

$767,000

MLS#: MDAA2137876

Welcome to an exceptional living experience at Chesapeake Harbour, where this well maintained 3 bedroom, 3 full bath condo offers not just a home but a lifestyle. Perfectly situated in a premium location, this residence boasts breathtaking views of the Bay Bridge and the sparkling waters of the Bay, providing a serene backdrop to your daily life. Step into a well-designed space that seamlessly blends comfort and elegance. Each room is thoughtfully crafted to maximize both style and functionality, ensuring a home that meets all your needs. The spacious living areas are perfect for entertaining, while the large windows invite natural light and those stunning views into your home. Living in this gated community means enjoying a host of exclusive amenities. Spend your days relaxing by the marina, where boating enthusiasts will feel right at home. Looking for something more active? Enjoy playing pickleball or tennis on the tennis courts or take your kayak out and watch the sun rise over the bay. With the vibrant community spirit and secure environment, you can enjoy peace of mind while indulging in the luxurious offerings of Chesapeake Harbour. Despite its tranquil setting, this condo is just a short distance from the lively heart of Downtown Annapolis. Explore a variety of excellent restaurants and boutiques, making every outing an adventure. Whether you're seeking relaxation or excitement, this home offers the perfect balance, making it an ideal choice for those who want the best of both worlds.

ANNAPOLIS

2018 QUAY VILLAGE COURT 201

3 Beds

3 Baths

1,645 Sq.Ft.

$750,000

MLS#: MDAA2132738

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