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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

372

# of Listings

3

Avg # of Bedrooms

$476

Avg. $ / Sq.Ft.

$1,082,980

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

372 Properties Found. Page 17 of 25.

New on site 1 day ago

Welcome to your new home! This beautiful property offers 4 bedrooms and 2 and half bathrooms. There are 3 bedrooms and 2 baths on the top floor , on the main level there is 1 bedroom and a half bath. This room could be used as an additional entertainment area, gym, playroom or office. Kitchen is spacious w/ white cabinets and stainless appliances, there is room for table space. Recent updates: NEW Paint, NEW carpet in upper level bedrooms, NEW LVP Flooring (main floor bedroom) and NEW light fixtures were installed. Shiny hardwood floors on upper level 1 throughout. Gas fireplace in living room. The deck is spacious and great for entertaining - outdoor grill conveys. The yard is fully fenced , small patio in the back. Roof is approx 5 years old. Broadneck school district. Within walking distance to the new Broadneck walking/bike trail. (Seller prefered title co is Title Rite - offers reduced price on Owner's title insurance policy for the new buyer)

ANNAPOLIS

1412 ANNA MARIE COURT

4 Beds

2 Baths

2,340 Sq.Ft.

$495,000

MLS#: MDAA2116924

Location! Location! Resort living between two rivers in this lovely split level home! Twenty year homeowner never stopped improving the home, including recent architectural roof, HVAC with humidity control, home water filtration system, and a jumbo 75 gallon hot water heater. Oak patterned laminate floors throughout provide a warm & classy feel. The upper floor offers three bedrooms that are enhanced by a remodeled full bath. A galley kitchen is a chef’s delight, and leads to a custom rear door that takes you down to the patio and lush garden.

The fully finished lower level, considered “below grade”, has several large sunlit windows and opens to a spacious living room with French doors that open to a handsome stone deck for grilling, entertaining, or just relaxing with a book. Two additional large rooms with beds and closets share a full bath. The large rear yard has a stained wooden fence, beautiful greenery, and a generous 10’ x 20’ storage shed. Driveway for you boat or vehicles.

Nearby Safe Harbor Marina in Eastport offers premium resort amenities with a family atmosphere: boating, tennis, pickleball, swimming, and a poolside Cafe and Tiki bar. Also a few blocks walk from home is the Annapolis Athletic Club, offering an array of fitness classes, personal trainers, varied strength & cardio machines, massage, and locker rooms with lounge. Luxurious steam room & sauna, and showers with towel service end the ideal workout.

All of the day’s activities will enhance your appetite for deluxe dining at nearby seafood & steak restaurants. The Historic District, City Dock Market House, and United States Naval Academy are a mile walk or bike ride. Or head the other direction 1 &1/2 miles to Quiet Waters Park to enjoy the 340 acres of trails, paddle boarding/kayaking, picnic pavilions, or nationally renowned Dog Park along the South River. Annapolis has a vibrant arts community hosting exhibits at local galleries and cafes, as well as the Maryland Hall for the Creative Arts, which is home to the Annapolis Symphony Orchestra, ballet, and jazz/rock concerts. Your home is walking distance to the City treasure, Truxton Park, with an active tennis and pickleball community playing on remodeled and lighted courts. The park has a large swimming pool with adjacent children’s waterfalls and a covered pavilion.

Wooded walking/jogging trail leads to Spa Creek. Boater’s use a twin boat ramp that offers easy access to scenic Spa Creek, cruising past the historic Annapolis Yacht Club into the mouth of the glorious Severn River & Chesapeake Bay.

Conveniently located 23 miles from Baltimore International Airport & Amtrak, and 30 miles from the White House, world class travel, museums, and entertainment are at your doorstep!

Priced below condos with high monthly fees or townhomes with HOA…hurry it won’t last!

ANNAPOLIS

1022 TYLER AVENUE

5 Beds

2 Baths

1,854 Sq.Ft.

$494,900

MLS#: MDAA2100100

Welcome to 8 Ashford Ct. Close to everything Annapolis has to offer. This 2 Bedroom 1.5 Bath contemporary townhouse is ready to go. Packed with upgrades and spacious floor plan. The neighborhood of Hunt Meadow offers lots of amenities including pool, tennis court and walking paths.

ANNAPOLIS

8 ASHFORD COURT

2 Beds

1 Baths

1,248 Sq.Ft.

$485,000

MLS#: MDAA2115574

Lovely one BR condo with eastern view towards courtyard and pool. Luxurious downtown Annapolis living style. Just blocks to restaurants, entertainment and Annapolis City Dock, the heart of the city.
Condo fee includes several amenities and most utilities. Outdoor pool, Hot tub, Two outdoor gourmet kitchens for grilling, Lending Library, Party room, Fitness center, 24 hour live concierge/security person in lobby everyday. Outdoor Garden Patch area to grow vegetables, Dog park, Billiard Table area, TV/Media lounge.
Secure underground parking space included, Free shuttle service to downtown City Dock.
Luxury living in an ideal city location.

ANNAPOLIS

5 PARK PLACE 325

1 Beds

1 Baths

838 Sq.Ft.

$479,000

MLS#: MDAA2110342

Exceptional value in Annapolis. Discover the charm and comfort of the beautifully maintained rancher, offering over 2,300 sq ft of versatile living space on a generous 1/4 acre lot in a quiet, convenient neighborhood. This home features a large family room/dining room. Beneath the carpet in the living room and bedrooms, you'll find original hardwood floors just waiting to be revealed. The full, unfinished basement offers endless potential to create your dream space - a home gym, office, extra bedrooms, or media space. Attached garage with plenty of additional storage. Fenced back yard - great for pets or outdoor gatherings. Handicapped accessible making it ideal for all stages of life. A perfect blend of comfort, convenience, and potential. This well-maintained home presents an excellent opportunity for those seeking one-level living and offers great potential. Its neighborhood location is private, yet offers quick and easy access to Annapolis Town Center, restaurants, shopping and major commuter routes.

ANNAPOLIS

114 2ND STREET

3 Beds

2 Baths

1,600 Sq.Ft.

$475,000

MLS#: MDAA2104494

Price improvement! Live in the heart of desirable Eastport, as this inviting condo offers the best of Annapolis nautical living. 316 Burnside Street #304 , is just a short stroll from the serene waters of Spa Creek! This home offers an ideal retreat for those seeking both tranquility in the city of Annapolis! Updated kitchen offers rich cherry cabinetry, gleaming granite countertops, and stainless steel appliances. The kitchen is both functional and stylish. Modern, nautical ash and cherry wood floors flow seamlessly throughout, adding warmth and style to this comfortable space. Recent upgrades includes all new HVAC 2022 of 2 units, freshly painted, and recessed lighting. There is a tankless water heater inside of the unit. The Burnside Condominiums offers a unique blend of urban living and waterfront charm, featuring a rooftop pool and deck with panoramic views of Spa Creek, downtown Annapolis, and the U.S. Naval Academy. These amenities provide residents with a serene retreat to enjoy sunsets, watch events like the Blue Angels' flyovers, NAVY commissioning week, and parade of lights. Partake in kayaking, and paddle boarding with private dock space. and water taxis. Deep water boat slips available for a rental fee. Entertain your friends and watch the Annapolis fireworks from your deck without fighting the crowds. The Burnside Condominiums in Annapolis offers a unique blend of urban living and waterfront charm, featuring a rooftop pool and deck with panoramic views of Spa Creek, downtown Annapolis, and the U.S. Naval Academy. Take an easy stroll to some of the best waterside restaurants, yacht clubs, shopping, grocery store, and all the charm Annapolis has to offer! This is a secured building, with keyed entry, intercom system, and elevator access. There is laundry use on all condo levels and main floor storage unit for your condo space. Off street parking for residents on lot, and guest parking available. This a beautiful home and you will not want to miss a viewing! Move right in and enjoy Annapolis living at its best!

ANNAPOLIS

316 BURNSIDE STREET 304

1 Beds

1 Baths

526 Sq.Ft.

$475,000

MLS#: MDAA2114264

Welcome to 3290 Arundel on the Bay Road – a disco bungalow nestled in the water oriented neighborhood of Oyster Harbor. This delightful 2-bedroom home offers the ideal blend of character and efficiency, with thoughtful updates throughout. The renovated full bath (2020) adds a modern touch, while the open living spaces invite you to relax and unwind. Have peace of mind knowing the kitchen was remodeled in 2021, the roof was replaced in 2022 and the water heater was replaced in 2023. Step outside to your own private oasis – a fully fenced, serene yard that’s perfect for weekend BBQs, morning coffee, and gathering with friends. One of my favorite spots is the screened back porch. Whether you're looking for your first home, a weekend getaway, a precious Air-BnB, or a low-maintenance lifestyle in a vibrant water-access community, this gem is ready to welcome you home.

New to Oyster Harbor? We love our neighborhood, multiple places to launch a kayak or paddleboard, tot-lots and basketball quarts, a boat launch, a fishing pier, a great beach with pavilions and so much more all located within a10 minute drive or boat ride to downtown Annapolis!

ANNAPOLIS

3290 ARUNDEL ON THE BAY ROAD

2 Beds

1 Baths

1,138 Sq.Ft.

$475,000

MLS#: MDAA2114218

#MDAA2114876

ANNAPOLIS

586 WILD FLOWER GLADE

3 Beds

2 Baths

2,163 Sq.Ft.

$459,900

MLS#: MDAA2114876

Welcome to Heritage Harbour, the premier 55+ golf course community in Annapolis. Move right in to this renovated brick front, garage townhome offering over 2,000 sqft of finished living space with 2 bedrooms, 2 full and 1 half bathrooms and a bonus loft area! Entertain family or friends in the spacious layout with soaring, vaulted ceilings in the formal living room or outside on the patio in your fully fenced yard. Fresh neutral paint and gorgeous hardwood floors throughout the main level. The updated kitchen offers peninsula seating, white cabinetry and quartz countertops and is open to the family room and dining room beyond. Travel to the bedroom level with dual suites, each with a private en suite bathroom. The upper hallway offers a wonderful loft area with custom built in shelving overlooking the living room beyond. Heritage Harbour is a perfect senior community with activities for everyone! Golf, tennis, a private lake, clubhouse, games, classes and excursions & so much more.. Schedule your private tour today!

ANNAPOLIS

1022 BOOM COURT

2 Beds

2 Baths

2,092 Sq.Ft.

$459,000

MLS#: MDAA2109730

Location, location, location! This spacious three-level, 3-bedroom, 2.5-bath end-unit townhome is perfectly situated just minutes from downtown Annapolis, Eastport, major highways, shopping, grocery stores, and more!

Step inside to find beautiful hardwood floors and an open-concept main level that’s ideal for both everyday living and entertaining. The top floor features three comfortable bedrooms and two full baths, including a primary suite with a generous walk-in closet.

The versatile lower level offers the perfect space for a home office, playroom, additional family room or bedroom—whatever suits your lifestyle.

Outside, enjoy your own private retreat with a large deck and fully fenced backyard, ready for your personal touch. Plus, an attached garage adds convenience and extra storage.

Don’t miss this opportunity to own a well-located, move-in-ready home close to everything Annapolis has to offer!

ANNAPOLIS

935 FOREST HILLS AVENUE

3 Beds

2 Baths

2,126 Sq.Ft.

$450,000

MLS#: MDAA2112058

Welcome to 2932 Winters Chase Way, located in the sought-after Riva Trace community of Annapolis. This spacious townhome features 2 bedrooms, 2.5 bathrooms, a basement, a one-car garage, private deck, and a layout full of potential—offering a fantastic opportunity to make it your own with updates and personal touches.

The main level includes a kitchen with granite countertops, a pantry, and a cozy breakfast area. The open-concept living and dining spaces flow seamlessly to the deck—perfect for relaxing or entertaining. Upstairs, you'll find 2 generously sized bedrooms with their own en-suite bathrooms, while the finished basement offers potential additional living space, wine storage, and walk-out access. The exterior siding was repaired and painted in 2024.

Riva Trace is a beautifully maintained, amenity-rich community with walking trails, tennis and basketball courts, a playground, and water access on the South River. Enjoy the convenience of being just minutes to downtown Annapolis, the Annapolis Town Center, and major commuter routes to DC, Baltimore, and Fort Meade.

Offered as-is, this home presents an incredible opportunity to build equity in one of Annapolis’s most desirable neighborhoods.

ANNAPOLIS

2932 WINTERS CHASE WAY

2 Beds

2 Baths

1,424 Sq.Ft.

$450,000

MLS#: MDAA2116522

ASSUMABLE VA RATE! Welcome to this beautifully appointed 2-bedroom, 2.5 bath condo in the highly desirable community of Admiral Square, ideally situated just off Route 2 and Route 50—only a 5-minute drive to the heart of downtown Annapolis! This stunning residence features recently re-sealed hardwood floors, luxurious Quartz countertops, and an open-concept living space that’s perfect for entertaining. The spacious living room boasts soaring two-story ceilings, filling the home with natural light.
Upstairs, you'll find two spacious bedrooms, two full bathrooms, and a versatile loft—ideal for a home office or lounge. The primary suite includes a generous walk-in closet and a full bathroom with upgraded tile finishes. A convenient half bath is located downstairs, just off the kitchen.
Enjoy the ease of a rear-loading garage with a private driveway for added convenience.
Don’t miss your chance to own this modern, elegant home in a prime location—close to shopping, dining, just a blink away from historic Annapolis, and only a quick 40-minute drive to D.C!

ANNAPOLIS

543 LEFTWICH LANE

2 Beds

2 Baths

1,600 Sq.Ft.

$449,999

MLS#: MDAA2112834

#MDAA2113816

ANNAPOLIS

2007 BAY RIDGE AVENUE

4 Beds

1 Baths

1,189 Sq.Ft.

$449,000

MLS#: MDAA2113816

Welcome to this stunning 2BR/2BA Loft Condo in the highly desirable 55+ community of Four Seasons at St. Margarets! Bright and beautifully updated, this model unit features soaring vaulted ceilings, fresh paint throughout, new lighting fixtures and ceiling fans, and a refrigerator less than a year old. The gourmet kitchen boasts Corian countertops, top-tier cabinetry, and a cozy eat-in area. Enjoy the open layout with a spacious living room and a dramatic spiral staircase leading to a versatile loft—ideal for a home office, reading nook, or TV lounge.
The primary suite includes a large walk-in closet and an elegant en-suite bath with double sinks and a walk-in shower. The second full bath features a jetted Jacuzzi tub and a bidet toilet. You'll also appreciate the full-size washer and dryer, generous linen closet, and additional storage.
Located just steps from the elevator, this unit offers convenience and comfort. The meticulously maintained building and community provide resort-style amenities including a clubhouse, pool, fitness center, card and billiards rooms, and a party room with a full kitchen. All this, just minutes from downtown Annapolis and the Eastern Shore—come experience the lifestyle you deserve!

ANNAPOLIS

1507 BROADNECK PLACE 403

2 Beds

2 Baths

1,235 Sq.Ft.

$439,000

MLS#: MDAA2113954

Introducing a distinctive opportunity for visionary entrepreneurs and investors: a commercial/residential property brimming with potential, situated ideally for both business and pleasure. Formerly a boutique dress shop, this structure is primed for a creative transformation, making it a unique investment. The property houses two bedrooms/offices, two full bathrooms, and robust hardwood flooring throughout, presenting a promising canvas for renovation.

Strategically located, this property is in close proximity to essential amenities and community features. Public transportation is conveniently accessible with the Riva Road & Forest Drive bus station less than 700 meters away, enhancing the location's connectivity.

Additional features include a rear deck perfect for relaxation or casual gatherings, a useful rear shed for extra storage, and a generous off-street parking area that can accommodate up to 12 vehicles. Despite being sold as-is, with no repairs from the seller, the property's inherent potential and dual-use capability as both a residential and commercial space make it a lucrative deal.

Capitalize on the chance to customize this space into a thriving business venture or a mixed-use development that promises both rental income and renovation possibilities. Dive into this project and shape it into your vision of success! Property is being sold AS-IS, Seller will make no repairs. All offers must have $1000 deposit and proof of deposit. So much potential! Make this your today!!

ANNAPOLIS

40 OAK COURT

None Beds

None Baths

N/A

$434,900

MLS#: MDAA2112210

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