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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

288

# of Listings

3

Avg # of Bedrooms

$447

Avg. $ / Sq.Ft.

$1,027,069

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

288 Properties Found. Page 11 of 20.

Nestled in the picturesque, waterfront community of Annapolis Roads, this freshly painted four-bedroom, two-and-a-half bath home offers a perfect blend of comfort and coastal charm. With spacious living areas and inviting interiors, this property is designed for relaxed living and entertaining. Enjoy the family room with fireplace and a bright sunroom that opens to a deck, perfect for indoor-outdoor living. Updates include Roof (2016), HVAC (2021), Washer/Dryer (2018). The large backyard offers plenty of room to play and entertain, while residents can also take advantage of community waterfront amenities including a private beach on the Chesapeake Bay, a pavilion, playground, dock, and kayak/canoe storage. Conveniently located between Baltimore and Washington, DC.

ANNAPOLIS

1008 HARBOR DRIVE

4 Beds

2 Baths

1,956 Sq.Ft.

$545,000

MLS#: MDAA2121000

Welcome to this beautifully maintained and updated end-unit townhouse in the ideally situated Baystone community of Annapolis. Offering over 2,070 square feet of living space, this home combines timeless style, thoughtful upgrades, and a private setting backing to trees.

Move up to the light-filled, open-concept main level showcasing Brazilian cherry floors, 9-ft ceilings, and an inviting gas fireplace for year-round comfort. The modern kitchen features granite countertops, stainless steel appliances, and opens directly to a large, low-maintenance Ipe deck—ideal for entertaining or enjoying peaceful views.

On the upper level, the primary suite offers dual walk-in closets and a fully renovated bath with elegant finishes. The second upstairs bath has also been completely renovated with beautiful marble tile for a luxurious, cohesive feel. The upper level includes three spacious bedrooms.

The lower level offers a flexible family or recreation room with access to the patio and garden. Just outside the lower-level walkout, a working water-feature pond adds a tranquil touch to the patio space. This home’s location is both peaceful and convenient—just steps from pedestrian paths along College Parkway, Broadneck Park, and Bay Hills Shopping Center. Recent improvements include a new roof in 2023, new carpeting on the upper level in July 2025, and a full interior repaint, also completed in July 2025.

With a private-feeling end-unit position, fresh modern updates, sunlit interiors, and a perfect blend of indoor and outdoor spaces, 642 Baystone Court is move-in ready and offers the best of Annapolis living in one of the area’s most sought-after school districts.

ANNAPOLIS

642 BAYSTONE COURT

3 Beds

3 Baths

2,072 Sq.Ft.

$536,000

MLS#: MDAA2123616

Excellent opportunity to own a centrally located commercial property in the heart of Annapolis. This two-story building, built in 1976, offers 2,024 square feet of space above grade on a 1,344 square foot lot. Includes two off-street parking spaces located at the rear of the building.

Previously used as a barbershop on the main level with a residential unit above, the property is now zoned BR – Business Revitalization. This flexible zoning supports a wide range of commercial uses including retail, professional office, club or lodge, vocational or art/music/dance school, fitness studio, religious facility, laboratory, museum, or art gallery.

Prime location directly across from the Whitmore Parking Garage and within walking distance to downtown Annapolis, government buildings, shops, restaurants, and more. Ideal for entrepreneurs and business owners seeking visibility and convenience in a vibrant, community-focused area.

Don’t miss this unique opportunity to establish your presence in one of Annapolis’s most active commercial corridors.

ANNAPOLIS

42 CLAY STREET

None Beds

None Baths

2,024 Sq.Ft.

$535,000

MLS#: MDAA2120418

#MDAA2114734

ANNAPOLIS

2828 BERTH COURT

2 Beds

2 Baths

1,434 Sq.Ft.

$529,900

MLS#: MDAA2114734

This charming 3-bedroom, 1.5-bathroom split-level home is tucked away on a quiet dead-end street, offering both privacy and convenience with easy access to major highways such as Route 50 and Route 97, as well as quick access to downtown. Recent updates over the past few years include a new roof, windows, and siding, along with a new HVAC system, updated bathroom and closets, new flooring on the ground level, fresh interior paint, and a newly paved driveway. Enjoy outdoor living with a generously sized screened-in porch that overlooks a patio and spacious fenced-in yard with no rear neighbors. The ground level also features a versatile bonus room with direct access, located just off the family room, offering plenty of space to fit your lifestyle needs. Additional highlights include a basement-level laundry area with a washer and dryer less than a year old, ample storage space, and a convenient half bath. This home has so much to offer and is ready to welcome its new owners. A must-see!

ANNAPOLIS

1954 FAIRFAX ROAD

3 Beds

1 Baths

2,258 Sq.Ft.

$525,000

MLS#: MDAA2122838

This approximately 2,500 square foot townhome features two/three bedrooms and three and a half bathrooms. The home offers an ELEVATOR for convenient access to main and upper levels.

The open-concept design of the main living area creates a bright and airy atmosphere. The kitchen is equipped with modern appliances and ample counter space and boasts an eating area . The upper level primary bedroom suite boasts a spacious layout and ensuite bathroom. The loft on this level offers flexible space for any of your needs.
The additional bedrooms provide comfortable accommodations for guests or household members. The three and a half bathrooms throughout the home ensure privacy and convenience. Walk out from the lower level family room and den to the patio through sliding doors.
Situated in a well-maintained, water privileged community, this property offers a desirable lifestyle with access to shared amenities including water front/beach picnic area and kayak rack,tennis and basketball courts, playground,wooded walking trails, all within easy walking or driving distance to shopping and dining along the Riva Road corridor.

ANNAPOLIS

124 CRANES CROOK LANE

2 Beds

3 Baths

2,556 Sq.Ft.

$524,500

MLS#: MDAA2119942

Building One Nearly Sold Out! Bright, spacious unit showcasing gorgeous design upgrades throughout. Start an exciting new chapter in this amenity-rich 55+ community conveniently located mere minutes to downtown Annapolis, retail shopping, waterfront dining and Bay Bridge. Reserved parking space included. Turnkey luxury, private balcony... Tour this stunning new home today!

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 207

2 Beds

2 Baths

1,318 Sq.Ft.

$523,655

MLS#: MDAA2095514

Welcome to this Wonderful home very close to Annapolis & the properties to be in a private area but close proximity to be in the City of Annapolis! Located in close proximity to restaurants , shopping, and entertainmemt . You will enjoy summer evenings dining - out in the over large deck out back! The Home offers an open floor plan that leads you to entertaining with a spacious living room, Dining Room & Remodeled Kitchen with Granite counter tops and New stainless steel Appliances. The dining & Living room boasts beautiful refinished hardwood flooring and Open to a Kitchen . The primary bedroom offers private Full remodeled bath with access to shower In addition to 2 others great size bedrooms and a Full renovated bathroom! Relax in the finished basement that offers large rec room, Additional bedroom/office/playroom and full renovated 3rd bath! You will love this home! Ready for your buyer to move-in!!

ANNAPOLIS

1971 DOMINOE ROAD

4 Beds

3 Baths

2,163 Sq.Ft.

$519,900

MLS#: MDAA2101268

Move-In Ready! This beautifully updated home features an updated kitchen with modern appliances, a fully renovated bathroom, new washer & dryer, new hot water heater, new HVAC system, refinished hardwood floors, and a new roof. Additional highlights include a wood-burning fireplace, a spacious screened-in rear porch, and a one-car garage that is currently in the process of being converted back into a functional garage. The entire house will also be fully repainted prior to settlement. Located within walking distance to Truxton Park and Annapolis public transit, this home offers convenience, comfort, and charm.

ANNAPOLIS

9 EDELMAR DRIVE

4 Beds

2 Baths

936 Sq.Ft.

$519,900

MLS#: MDAA2108848

HUGE PRICE REDUCTION!!! SELLER MOTIVATED — BRING YOUR OFFER! Rare opportunity for flexible living in the heart of Annapolis. This beautifully updated home features 5 bedrooms, 2 full bathrooms, and TWO complete living spaces — ideal for multigenerational living, rental income, or house hacking!

The main level offers 3 bedrooms, a full bath, kitchen, and laundry. The finished lower level includes 2 additional bedrooms, a second full kitchen, full bath, and a private laundry area — perfect for extended family, guests, or rental potential.

Enjoy peace of mind with a new roof, HVAC, windows, plumbing, appliances, and more — all updated within the last 3 years. Situated on a spacious 0.57 acre lot with a large porch, oversized shed/workshop, and ample parking.

Minutes from the Naval Academy, local beaches, parks, and Anne Arundel County schools. This is the space and setup you’ve been waiting for. Showings are easy — schedule yours today!

ANNAPOLIS

187 BROWNS WOODS ROAD

5 Beds

2 Baths

2,128 Sq.Ft.

$515,000

MLS#: MDAA2120152

New Phase at Element at Mill Creek! Building B, The Banyan, is already half-sold! Featuring lounge areas, party room, 2-story clubroom, upper & lower terraces, and more! Start your exciting new chapter in this amenity-rich 55+ community located minutes to downtown Annapolis, shopping, waterfront dining and Bay Bridge. Spacious home with large private balcony boasts desirable southern exposure and showcases stylish design upgrades throughout. Includes true chefs kitchen, huge owners closet, reserved parking. Low condo fee. Tour this stunning home and this building's incredible amenities today!

ANNAPOLIS

76 OLD MILL BOTTOM ROAD N 308

1 Beds

2 Baths

1,076 Sq.Ft.

$511,300

MLS#: MDAA2115854

Lovely home in Annapolis close to everything you need. 4bd, 1.5ba Raised Rancher with a large 2.5 Bay garage and plenty of parking in the driveway. The main level has LVT flooring with 3bd/1 Full bath, a sun filled living room and a kitchen which features 42" Oak cabinets, corian countertops and newer appliances as well as access to a private backyard deck with a new sun awning. The lower level boasts a private bedroom with ceiling fan, large family room with new LVT flooring, wood stove with glass viewing window to better enjoy a warm fire , a utility room/half bath with Samsung Over/Under Washer/Dryer, utility shower, refrigerator & mechanicals. The garage is a full 2.5 bays with automatic door entry, plenty of room for storage and/or a work bench as well as entries to the backyard, driveway and the lower level interior. The spacious yard has freshly mulched & well maintained gardens with lots of perennials and a thriving banana tree.
The home is within walking distance to Pip Moyer Rec Center, the Chesapeake Children's Museum and a short walk across a bridge to Truxtun Park Pool, Skate board park, Tennis & Pickleball courts and a public boat ramp for boating enthusiasts. Nearby as well, is Maryland Hall for theater & concerts, West Street with restaurants & shopping as well as Dining under the stars in season. You are no more than 10 minutes to Downtown Annapolis, Annapolis Town Center, Anne Arundel Medical Center as well as Aris Allen Blvd which takes you to Rte 50 and any direction you'd like to go.

ANNAPOLIS

102 BOXWOOD ROAD

4 Beds

1 Baths

1,728 Sq.Ft.

$510,000

MLS#: MDAA2119372

Welcome to easy living in a vibrant 55+ community! This charming end-unit home offers both comfort and convenience with 1,514 square feet of thoughtfully designed single-level living. Featuring 2 spacious bedrooms and 2 full bathrooms, this house blends style with simplicity—just the way life should be.

Step through the inviting entryway into a bright, open-concept layout perfect for both relaxing and entertaining. The living and dining areas flow beautifully, filled with light from generously sized windows. The kitchen offers ample counter space, plenty of cabinetry, and the perfect spot for morning coffee—no barista required.

Retreat to the peaceful primary bedroom, complete with an en suite bathroom and roomy closet space. The second bedroom is ideal for guests, a home office, or crafting space—the only limit is your imagination.

As an end unit, this home offers added privacy and bonus natural light that makes every room feel just a little cheerier. And because it’s in an age-qualified community, you'll find friendly neighbors and amenities geared toward relaxing and enjoying your days.

Whether you’re downsizing or just ready for fewer stairs and more time for hobbies, this home checks all the right boxes. Practical, peaceful, and perfectly sized—what more could you ask for, besides maybe someone else doing the yard work? Well, that might be included too.

Don't miss the chance to enjoy easy days and cozy nights in your new home. Schedule a tour and see it for yourself—you might just fall in love.

ANNAPOLIS

2600 COMPASS DRIVE

2 Beds

2 Baths

1,514 Sq.Ft.

$509,000

MLS#: MDAA2120576

ONLINE REAL ESTATE AUCTION!! Online Bidding Opens - Monday, September 1, 2025. Online Bidding Closes - Wednesday, September 3, 2025 at 11:00 AM. List price is opening bid only. 199 Prince George Street is situated in the Downtown Annapolis Historic District, one block east of State Circle, and one block northwest of the City Dock. The home is within a short walk of Maryland State government offices, the State House, legislative houses, the US Naval Academy, restaurants, hotels, shops, historic sites and Annapolis Harbor. Prince George Street is a picturesque one-way street, lined with detached homes and townhomes often exceeding 100 years of age.

ANNAPOLIS

199 PRINCE GEORGE STREET

3 Beds

3 Baths

2,134 Sq.Ft.

$500,000

MLS#: MDAA2122376

Enjoy a fantastic lifestyle in this beautiful and pristine 2BR/2BA condo in the very desirable and vibrant 55+ community of Four Seasons at St Margarets! Enter the very well-kept secure building and access your second floor home by stairs or elevator ...OR use your garage door remote and enter the building through your private, over-sized garage. The dramatic open floor plan is ideal with kitchen island overlooking the huge living room with gorgeous hardwood floors and plantation shutters. The living room leads to a large, private balcony. The primary bedroom is massive with a large bay window and an over-sized walk-in closet. The attached bathroom has a walk-in shower and separate soaking tub. The second bedroom has a bay window, two double closets and is served by a hall bath. A large laundry room and multiple closets complete this side of the condo. Nothing to do but move in and enjoy the incredible amenities - stunning community center has several beautifully furnished party areas to entertain your guests and meet with neighbors. There is a kitchen, bar, billiards room, library, fitness center and inviting outdoor pool with many tables and chairs to enjoy the beautiful weather and wooded surroundings. The location is ideal - tucked away, but very close to shopping, public library, hiking and bike trail, and easy access to downtown Annapolis! Smoking Restricted Community

ANNAPOLIS

1509 FERAL DAE LANE 204

2 Beds

2 Baths

1,442 Sq.Ft.

$500,000

MLS#: MDAA2114444

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