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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

Browse Annapolis Real Estate Listings

$250,000 - $500,000

47 Properties Found. Page 2 of 4.

FRESHLY PAINTED AND NEW CARPET THROUGHTOUT. WALKOUT BASEMENT.
THANK YOU FOR SHOWING

ANNAPOLIS

1531 HICKORY WOOD DRIVE

3 Beds

2 Baths

916 Sq.Ft.

$439,900

MLS#: MDAA2140770

.
Extremely attractive 4 bedroom 3.5 bath townhouse. Located near major roads and amenities in Annapolis.
The kitchen has all stainless steel appliances and quartz counter top. The entire house has been repainted and and also the deck . The deck can be accessed from the living room... The master bedroom has a private bathroom and is a good size... There is a powder room on the main level and the entry from the garage is conveniently located on this level also.... There is space in the back for a nice cookout gathering also...The home has laminate flooring and is very well maintained. This is a great property for any buyer.........

ANNAPOLIS

126 BRIGHTWATER DRIVE, ANNAPOLIS, MD 21401

4 Beds

3 Baths

1,780 Sq.Ft.

$419,990

MLS#: MDAA2144288

#MDAA2142548

ANNAPOLIS

1019 PRESIDENT STREET

3 Beds

2 Baths

1,350 Sq.Ft.

$400,000

MLS#: MDAA2142548

Nestled in the heart of Annapolis, this 3-bedroom, 1-bath home offers a fantastic opportunity for investors or buyers looking to add their personal touch. The property features a solid layout with great bones and includes an unfinished ±800 sq ft addition—providing ample space to expand and customize to your needs. With a little vision and renovation, this home has tremendous potential to shine. Whether you're looking to create your dream home or your next investment project, the possibilities here are endless. Conveniently located near local amenities, shopping, dining, and major commuter routes. Don’t miss this chance to unlock the value and make it your own!

ANNAPOLIS

3 CYPRESS ROAD

3 Beds

1 Baths

1,206 Sq.Ft.

$399,999

MLS#: MDAA2140302

Prepare to fall in love with this totally renovated gem! A complete and tasteful remodel has just been completed for the lucky new owners. Stunning LPV flooring, a beautiful gourmet kitchen with granite counters and new Stainless Steel Appliances, a fully remodeled bath and great details like new contemporary closet doors await the new owners.. The exterior has been refreshed for great curb appeal with the same attention to detail as the interior from new house numbers to planted window boxes to a charming new mailbox and freshly painted retaining wall. Walk into the warm and welcoming sunroom which leads to the open floor plan living room and dining room. The expansive rear deck and huge fenced yard are perfect for outdoor activities and entertaining. The unfinished lower level provides storage and room for future expansion. Add the off street parking and you have everything you need at a great price!

ANNAPOLIS

1226 TYLER AVENUE

3 Beds

1 Baths

1,056 Sq.Ft.

$399,000

MLS#: MDAA2147246

Owner is offering $ 5,000.00 for helping buyer with closings costs!!
Great location! Sweet, cozy, and lovely semi-detached home. 3 bedroom, 1 1/2 baths and semi finished basement. The house is ready for your personal touch! NEW ROOF 2023. Close to Truxtun Park and easy access to downtown Annapolis and US 50 /97 HWY. GREAT OPPORTUNITY! Bring your best offer.

ANNAPOLIS

108 CONLEY DRIVE

3 Beds

1 Baths

1,880 Sq.Ft.

$395,000

MLS#: MDAA2133422

Welcome to 2004 Quay Village Ct #T1, located in the sought-after waterfront community of Chesapeake Harbour in Annapolis. This well-maintained 1-bedroom, 1.5-bath condominium offers comfortable, low-maintenance living with abundant natural light, spacious living areas, and two covered patios that seamlessly extend the living space outdoors.
Residents enjoy access to an exceptional collection of resort-style amenities, including a private marina, kayak facilities, sandy beach access along the Chesapeake Bay, outdoor waterfront pools, tennis and pickleball courts, walking paths, picnic areas, and beautifully maintained common grounds. Trident Marina, located at the heart of the community, offers boat slips for lease accommodating yachts from approximately 30 to 120 feet, making it an ideal home base for boating enthusiasts.
One of the community's most cherished traditions is gathering at the beach and waterfront common areas to watch the Wednesday Night Sailing Races, a long-standing Annapolis tradition featuring some of the region’s top sailors. Residents also enjoy front-row views of the annual Blue Angels Air Show, with spectacular aerial performances often visible directly from the community's waterfront vantage points.
Additional conveniences include an on-site restaurant and pub, assigned parking, and gated entry with 24-hour security.
The condominium association fee includes common area maintenance, exterior building maintenance, lawn care, pool and recreation facility access, security gate services, snow removal, and trash collection.
Ideally situated near downtown Annapolis, major commuting routes, shopping, dining, and waterfront attractions, this property offers a unique opportunity to experience the best of Chesapeake Harbour’s waterfront lifestyle, combining boating, recreation, community events, and stunning Chesapeake Bay views in one exceptional setting.
IMPORTANT TAX CORRECTION: the assessed value listed in SDAT is incorrect. Call co-listing agent with any questions.

ANNAPOLIS

2004 QUAY VILLAGE COURT T1

1 Beds

1 Baths

1,100 Sq.Ft.

$395,000

MLS#: MDAA2145666

Welcome to 198 Clay Street in the heart of Annapolis! This charming row home offers water views of College Creek and a short stroll to downtown and West Annapolis, where shops, dining, entertainment, and the U.S. Naval Academy are right at your doorstep. The location also provides easy commuter access to Routes 50 and 97 for Washington, D.C., Baltimore, and BWI Airport. Thoughtfully updated in the past year, the home features new flooring and paint throughout, all new kitchen appliances, countertops, and sink, new siding, four mini-split units, and all new upstairs windows. Walls were opened between the kitchen, dining, and laundry areas to create a more open flow, and a new upper-deck door leads to an expanded rooftop deck with water views. Additional highlights include exposed brick and beamed ceilings, a fenced rear yard, private access to College Creek, and rare rear parking. With a proven rental history including $21,500 earned on Airbnb in 2024, this home is ideal as a primary residence or investment opportunity.
As of 5/28/26 a new EPDM rubber roof/membrane with additional sealant and chimney closure have been installed.

ANNAPOLIS

198 CLAY STREET

2 Beds

1 Baths

902 Sq.Ft.

$389,000

MLS#: MDAA2139810

New on site today

Grand opportunity in Eastport's Conte Gardens with ELEVATOR! Spacious and meticulously cared-for 2BR, 2BA condominium in the heart of Eastport with assigned parking. Located across the street from Eastport Shopping Center featuring restaurants, coffee shop, catering/carryout, drugstore, athletic club and more.
Walk to everything that DTA has to offer and enjoy being a part of the Annapolis life as we head into Summer fun.

ANNAPOLIS

936 BAY RIDGE AVENUE 201

2 Beds

2 Baths

1,175 Sq.Ft.

$388,000

MLS#: MDAA2148540

New on site 1 day ago

Welcome to this meticulously updated interior townhome, fully renovated in 2022 and thoughtfully maintained since. With modern upgrades and a neutral, move‑in‑ready palette, this home is the perfect canvas for its next owner.
Step inside to find new luxury flooring, fresh neutral paint, and stylish lighting throughout. The kitchen impresses with new cabinetry, modern appliances, and clean lines designed for cooking and entertaining. Both the full and half baths have been completely renovated with contemporary finishes.
Major updates include a new roof, gutters, windows, and siding—providing peace of mind and lasting curb appeal.
This home combines modern comfort with timeless style, ready for you to move in and make it your own.

ANNAPOLIS

1410 FOXWOOD COURT

3 Beds

1 Baths

1,280 Sq.Ft.

$380,000

MLS#: MDAA2148170

#MDAA2147286

ANNAPOLIS

1808 LINCOLN DRIVE

3 Beds

1 Baths

1,008 Sq.Ft.

$375,000

MLS#: MDAA2147286

#MDAA2146586

ANNAPOLIS

15 COPLEY COURT

2 Beds

1 Baths

1,704 Sq.Ft.

$374,900

MLS#: MDAA2146586

Step into this beautifully maintained top-floor 3-bedroom, 2-bath condo in the desirable Scott’s Crossing Condominiums, offering over 1,320 square feet and a prime location just minutes from the vibrant charm of downtown Annapolis. As you enter, you're welcomed by fresh paint throughout (2026), a foyer with a convenient coat closet, and elegant column accents that open into a bright and airy main living space. The kitchen features warm wood cabinetry, granite countertops, a tiled backsplash, and stainless steel appliances, along with a cozy breakfast nook framed by a bay window overlooking peaceful wooded views. Entertain with ease or unwind at the end of the day in the well-appointed living and dining areas, complete with hardwood floors, 9+ ft ceilings, a cozy gas fireplace, and access to a private patio that offers a serene setting to relax and take in the views. The primary suite is a true retreat, showcasing a vaulted ceiling with a lighted fan and a charming bay window, perfect for a reading nook or sitting area with a tranquil backdrop. Two spacious closets and an ensuite bath with a dual sink vanity and tub/shower combo complete the space. Two secondary bedrooms, each with ample closet space, are thoughtfully positioned for added privacy and versatility, whether used as guest rooms or an in-home office, and share a full bath with a large walk-in shower. A dedicated laundry room with additional storage and a full-sized washer and dryer adds everyday convenience. Recent updates include a newer HVAC (2021), water heater (2022), and plush new carpet (2026). Parking is a breeze in the off-street parking lot. Beyond the community, enjoy the nearby Bestgate Park, Trader Joe’s and Annapolis Mall, plus easy access to major highways for a quick commute to Baltimore, DC, and more. Don’t miss this rare find!

ANNAPOLIS

2161 SCOTTS CROSSING COURT 302

3 Beds

2 Baths

1,328 Sq.Ft.

$364,900

MLS#: MDAA2140698

This colonial home, built in 1950, blends classic appeal with modern comfort. Spanning 1,584 square feet, this detached residence features four spacious bedrooms and two full bathrooms, making it an ideal retreat for those seeking both space and style. Venture inside to discover a warm and inviting interior adorned with carpet and hardwood floors. The eat-in kitchen, designed for both functionality and social gatherings, offers ample table space, perfect for casual dining or entertaining. The bathrooms feature a convenient tub-shower combination, providing a relaxing oasis after a long day. The unfinished full basement presents a blank canvas for customization, whether you envision a home gym, workshop, or additional storage. Outside, the property features a well-maintained front and rear yard, ideal for outdoor activities or serene relaxation. Parking is a breeze with off-street options or a driveway. This home is conveniently located with easy access to local dining, market and shopping. So, don't miss this opportunity to make his home your own

ANNAPOLIS

7 CARVER STREET

4 Beds

2 Baths

1,584 Sq.Ft.

$350,000

MLS#: MDAA2144184

Beautifully maintained 3-level townhome in the desirable Annapolis Overlook community in Annapolis! This spacious home offers approximately 1,680 sq ft with 3 bedrooms, 2.5 baths, and a functional layout designed for comfortable living. The main level features a bright living area, separate dining space, and an updated kitchen with ample cabinet storage and room for entertaining.

Upstairs you’ll find generously sized bedrooms including a primary suite with private bath and great closet space.

Enjoy low-maintenance living in a well-established community conveniently located near downtown Annapolis, the Naval Academy, shopping, restaurants, and major commuter routes. The 21403 area is known for its coastal lifestyle, outdoor recreation, and close proximity to the Chesapeake Bay.

Perfect for first-time buyers, investors, or anyone looking for easy living in a prime Annapolis location!

ANNAPOLIS

40 IRONSTONE COURT J

3 Beds

2 Baths

1,680 Sq.Ft.

$345,000

MLS#: MDAA2140034

1 2 3 4

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