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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

277

# of Listings

3

Avg # of Bedrooms

$506

Avg. $ / Sq.Ft.

$1,381,680

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

277 Properties Found. Page 17 of 19.

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 2 days ago

Exceptional Rivergate loft-style condominium offering the perfect blend of modern updates and urban convenience. This stunning two-bedroom, two-full-bath residence showcases soaring vaulted ceilings, an open-concept design, and sophisticated finishes throughout. The 2026 remodeled gourmet kitchen is highlighted by quartz countertops, stainless steel appliances, and stylish LVT flooring extending through the kitchen, dining, and living areas. The dramatic loft overlooks the main living space and provides ideal flexibility for a private office, media room, or additional lounge area. Both expansive bedroom suites feature walk-in closets and adjoining full baths, including a beautifully remodeled primary bath retreat. Step outside to the oversized balcony—perfect for outdoor entertaining or quiet evenings. A/C 2020 and newer Thompson Creek Windows. Ideally situated minutes from Downtown Annapolis, the U.S. Naval Academy, major commuter routes including 50 and 97, dining, shopping, and waterfront destinations.

ANNAPOLIS

2003 WARNERS TERRACE N 324

2 Beds

2 Baths

1,072 Sq.Ft.

$389,000

MLS#: MDAA2144518

New on site 4 days ago

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 and guest parking. Open floor plan with multiple windows plus sliding doors to private balcony provide desired light throughout. Upgraded features include Tuscan terra cotta-style tile flooring, stainless appliances, Space-saving "all-in-one" washer-dryer combination, gas heat, ceiling fans. Home has been lightly used and shows beautifully. 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 lifestyle.

ANNAPOLIS

936 BAY RIDGE AVENUE 201

2 Beds

2 Baths

1,175 Sq.Ft.

$388,000

MLS#: MDAA2148540

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

New on site 3 days ago

#MDAA2149226

ANNAPOLIS

1008 CEDAR RIDGE COURT

3 Beds

2 Baths

1,320 Sq.Ft.

$369,900

MLS#: MDAA2149226

Welcome Home to 1356 Hazel Nut Ct! A beautifully updated 2-bedroom, 1.5-bath townhome nestled in the Walnut Ridge community. Ideally located with easy access to Route 50, nearby parks, scenic walking trails, and a shopping center with restaurants, groceries, and everyday conveniences just a short walk away. Step inside to an inviting open floor plan featuring new LVP flooring (2022), recessed lighting, and spacious living and dining areas filled with natural light. The fully renovated kitchen offers modern finishes, ample cabinet space, and updated appliances. A stylish half bath completes the main level. Sliding glass doors, replaced in 2022, lead to the deck and backyard. Perfect for entertaining, relaxing, or enjoying the outdoors. Upstairs, you’ll find two generously sized bedrooms and a beautifully renovated full bathroom (2022). Additional updates include a new washer and dryer (2022), exterior paint (2025), and newer roof and HVAC systems for added peace of mind. A move-in ready home in a convenient commuter location. Mortgage savings may be available for buyers of this listing.

ANNAPOLIS

1356 HAZEL NUT COURT

2 Beds

1 Baths

1,296 Sq.Ft.

$360,000

MLS#: MDAA2146708

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

New on site 3 days ago

Welcome to a beautifully maintained home with so many amazing features! This 2 bedroom 2 bathroom 3rd floor top level unit with over 1,080 sq ft offers a spacious, open concept layout. If you are looking for a move-in-ready property that you can be proud of, then search no further! When you walk in the front door, you will first notice the open-concept living area. The living area has so much room for entertaining. A beautiful fireplace that accents the entire space. The kitchen is beautiful with a modern style, including beautiful cabinets, countertops and matching appliances. It flows into a nice extra space for an office or eat in kitchen. This open concept has a rear porch area and a peaceful wooded scenery to enjoy nature and the outdoors. Nature is offered all around this property and many ways to enjoy it. Either walking on the wooded paths, enjoying the playgrounds, working out in the fitness center or relaxing by the pool.

Both bedrooms are a good size with quality closet space and space for large furniture. The main entrance to the building has an intercom system directly to each unit for gaining access. As part of the condominium fees, it covers for common area maintenance, exterior building maintenance, lawn maintenance, snow removal, trash services, water/sewer bill and more. To top it off and ensure you move in worry-free, the home has a new gas hot water heater (2026) and a washer/dryer in the unit. This home will have you beyond excited and stress-free! Do not miss your chance to own this unique property! You will have peace of mind knowing your new home was meticulously maintained and cared for. Not to mention move-in-ready! The location is ideal for commuting, as well as being in proximity to local shops, restaurants and walking distance to many amenities! It's time for you to call it HOME!

ANNAPOLIS

501 MATHIAS HAMMOND WAY 301

2 Beds

2 Baths

1,081 Sq.Ft.

$349,900

MLS#: MDAA2149028

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

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