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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

388

# of Listings

3

Avg # of Bedrooms

$475

Avg. $ / Sq.Ft.

$1,078,329

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

388 Properties Found. Page 21 of 26.

New on site today

Note: The Offer Deadline has been set to Monday, 5 PM! Welcome to this well-maintained 3-bedroom, 2.5-bath home nestled in one of Annapolis’s most desirable neighborhoods! With a fully finished basement that includes a third full bathroom and two generously sized dens—perfect for use as additional bedrooms, guest rooms, or home offices—this home offers impressive flexibility for growing families or savvy investors.

Inside, the layout is both functional and inviting, featuring spacious, sun-filled living areas and a thoughtfully updated interior. The kitchen has been tastefully renovated with modern finishes, ideal for cooking and entertaining. Upstairs bathrooms have also been updated, blending style and comfort for everyday living.

Downstairs, the basement expands your options with a private living space that’s perfect for extended family, a rental opportunity, or a cozy entertainment zone.

Step outside and enjoy the convenience of living just minutes from shopping, dining, parks, and top-rated schools, with easy access to major commuter routes connecting you to D.C., Baltimore, and beyond. Whether you’re looking for your forever home or a smart investment, this property offers exceptional value in a prime location.

Don’t miss your chance to own this gem in Annapolis—schedule your private tour today!

ANNAPOLIS

704 GREAT BAY AVENUE

3 Beds

2 Baths

1,246 Sq.Ft.

$335,000

MLS#: MDAA2116836

#MDAA2107838

ANNAPOLIS

60 SANDSTONE COURT G G

3 Beds

2 Baths

1,119 Sq.Ft.

$319,900

MLS#: MDAA2107838

Want to live in the City of Annapolis and walk to work? Here's your chance! Hang your hat in this cozy place. Own this home without the added expense of HOA/Condo fees. It is ideally located within walking distance to the Navy Stadium for all your tailgating and football fun, Maryland Hall for the Arts, and the city's vibrant restaurants and pubs. Enjoy easy access to the Annapolis Free Downtown Shuttle, with a pickup just a short stroll away. Once a neighborhood grocery store, this unique home has been thoughtfully converted into a two-level residence, offering two bedrooms, one full bath, a full kitchen, and laundry. The main-level bedroom and bath provide excellent accessibility, while the upper-level bedroom is accessible via a spiral staircase. Roof, central air and heat were recently updated, and while there’s room for personal touches, the home needs some TLC to be ready to welcome you to the heart of Annapolis living!

ANNAPOLIS

67 SPA ROAD

1 Beds

1 Baths

1,053 Sq.Ft.

$315,000

MLS#: MDAA2112532

Welcome to this beautifully appointed and well maintained 3-bedroom, 2-bath home, offering the perfect blend of comfort and convenience! Featuring a spacious and open layout, this home boasts a modern kitchen with granite countertops, stainless steel appliances, and ample cabinet space. The kitchen also offers a wine cooler. The living area is perfect for relaxing or entertaining, while the generously sized bedrooms provide a cozy retreat. The unit has laminate floors, newer carpet, updated lighting and an updated bathroom.

ANNAPOLIS

10 SANDSTONE COURT H

3 Beds

2 Baths

1,198 Sq.Ft.

$313,900

MLS#: MDAA2110670

Experience effortless accessibility and modern comfort in this beautifully maintained lower-level 2-bedroom, 2-bath home. The spacious open layout invites relaxation and entertaining, featuring a newly upgraded kitchen with sleek granite countertops, stainless steel appliances, and ample cabinetry. The bright and airy living area creates a welcoming atmosphere, while the generously sized bedrooms offer a cozy retreat. The enclosed back porch is a charming breezeway leading to a peaceful back patio with serene forest views—an ideal spot for unwinding. The main bath has been tastefully updated with stylish finishes, adding a touch of luxury. Recent enhancements include Closet Maker custom closets in the hallway and guest bedroom, top-down bottom-up window shades throughout, new ceiling fans in both bedrooms, two new low-flush toilets, two new sliding glass doors, and a new MaxAir HVAC system installed in 2022.
Beyond the home itself, enjoy a vibrant community with fantastic amenities, including a pool, fitness center, and clubhouse—all conveniently located just minutes from downtown Annapolis, the Chesapeake Bay, and major commuter routes. This move-in-ready gem won’t last long—schedule your showing today!

ANNAPOLIS

30 HEARTHSTONE COURT C C

2 Beds

2 Baths

1,217 Sq.Ft.

$299,000

MLS#: MDAA2116192

New on site 3 days ago

**Gas Heat Included in Condo Fee! ** Don't miss the opportunity to purchase this stunning penthouse
located in one of the most sought-after locations in Eastport/Annapolis. Enjoy your morning coffee on your own private balcony surrounded by trees and sunlight. This updated condo shows pride of ownership with fresh custom paint throughout, professionally cleaned, steam cleaned carpets, recessed lighting, granite countertops in the kitchen, ceramic tile in kitchen/baths, **lower-level private storage**. Community offers inground pool, club house, fitness center, reserved parking, all walking distance to Truxton Park which features a boat ramp, tennis courts, picnic areas, and a 5-minute water taxi to Downtown Annapolis! Call today to arrange your private showing today!

ANNAPOLIS

1117 PRIMROSE COURT 304

2 Beds

2 Baths

1,015 Sq.Ft.

$295,000

MLS#: MDAA2117092

RARELY available floorplan with second story loft! 1 BR and 1FB but loft could be additional bedroom or home office space. 1,133 sq. ft. making this floorplan the largest available in the building. W/D are in the unit. Updated kitchen has stainless steel appliances and granite counters. Patio space offers room for enjoying the outdoors from the upper level of the condo building. Dues include trash removal, pool/tennis court access. Condos are FHA Approved - Lender to confirm.

ANNAPOLIS

1231 GEMINI DRIVE L

1 Beds

1 Baths

1,133 Sq.Ft.

$290,000

MLS#: MDAA2104306

RARELY available floorplan with second story loft! 1 BR and 1FB but loft could be additional bedroom or home office space. 1,133 sq. ft. making this floorplan the largest available in the building. W/D are in the unit. Updated kitchen has stainless steel appliances and granite counters. Bath tub and shower have been recently tiled/resurfaced. Patio space offers room for enjoying the outdoors from the upper level of the condo building. Dues include trash removal, pool/tennis court access. Condos are FHA Approved - Lender to confirm.

ANNAPOLIS

1231 GEMINI DRIVE L

1 Beds

1 Baths

1,133 Sq.Ft.

$290,000

MLS#: MDAA2115238

Experience the best of both nature and city living in this spacious top-floor unit at Annapolis Overlook. With nearly 1,400 sq ft, this 2-bedroom, 2-bathroom home offers high ceilings, generous living space, a cozy fireplace, and a balcony overlooking a wooded setting—yet it's just minutes from Downtown Annapolis! You'll enjoy easy access to restaurants, shopping, and entertainment, as well as close proximity to the U.S. Naval Academy and local schools. Quick access to Route 50 and the Bay Bridge makes commuting a breeze.

Recent upgrades include a new HVAC unit installed in Fall 2023 and new energy-efficient patio doors, installed in 2023 and new toilets. The home also features updated vanities, mirrors, and fresh paint throughout. Don’t miss this opportunity for a top-floor unit in an incredibly convenient location! Secured front door access and assigned parking spaces complete the package.

ANNAPOLIS

40 HEARTHSTONE COURT K K

2 Beds

2 Baths

1,376 Sq.Ft.

$284,900

MLS#: MDAA2116574

#MDAA2096604

ANNAPOLIS

7101 BAY FRONT DRIVE 400

1 Beds

1 Baths

1,000 Sq.Ft.

$275,000

MLS#: MDAA2096604

#MDAA2110104

ANNAPOLIS

7101 BAY FRONT DRIVE 400

1 Beds

1 Baths

1,000 Sq.Ft.

$275,000

MLS#: MDAA2110104

#MDAA2116362

ANNAPOLIS

7101 BAY FRONT DRIVE 400

1 Beds

1 Baths

1,000 Sq.Ft.

$275,000

MLS#: MDAA2116362

Updated 3 Bedroom/2 Bathroom Condo in Sought-After Fairwinds Community!

Welcome to this beautifully maintained and move-in ready home located in the highly desirable Fairwinds community. This home offers the perfect blend of comfort, convenience, and style with thoughtful upgrades throughout.

Interior Features Include:
Warm hardwood floors throughout the entire condo.
Updated Kitchen and Bathrooms
New HVAC in 2024
New Roof 2024
Windows replaced
Washer & Dryer replaced
Kitchen renovated
Culligan Water Filter on Kitchen Sink
** Condo fee includes gas, water, sewage utilities and community pool.

This home offers a functional layout perfect for everyday living or entertaining. The Fairwinds community is known for its peaceful atmosphere, beautifully maintained grounds, and unbeatable location close to shopping, dining, and major commuter routes.

Whether you’re a first-time buyer, looking to downsize, or seeking a turnkey investment, this condo checks all the boxes.
Schedule your private tour today and discover why Fairwinds is one of the area's most sought-after communities!

ANNAPOLIS

217 VICTOR PARKWAY H 217H

3 Beds

2 Baths

1,189 Sq.Ft.

$275,000

MLS#: MDAA2115166

New on site 1 day ago

Great location just off Bay Ridge Rd, in walking distance to Giant Food, hair salon, restaurants & other convenient stores, Near bus service, and the historic district. Fresh , neutral painting, with white trim, Pergo flooring & neutral carpet. Unique, rare floorplan with a office (or den), and a separate dining room,with recessed lighting, that has a large, "feature" window that lets the light in!
Light, bright and airy, living area has a slider to the exterior patio, with a greenspace view, and a separate mechanical room. The bedrooms have a split floor plan with one on each end of the apartment. HVAC is about 2010, Frig about 2020, stove about 2007, dishwasher age unk, but only used less than 5 times!
The condo fee, which is $408.19/ mo INCLUDES gas heat, hot water, and provides access to tot lot/playground, community pool, and tennis. Come see!

ANNAPOLIS

9 SILVERWOOD CIRCLE 6

2 Beds

1 Baths

1,136 Sq.Ft.

$260,000

MLS#: MDAA2117130

Welcome to 38 Pleasant St! This renovated 2-bedroom, 1-bath townhome is located in downtown Annapolis and could be the perfect starter home or investment property. Renovations in 2021 included a new kitchen with stainless steel GE appliances, new flooring, HVAC, and a hot water heater. The main level features a living room, dining room, and kitchen that leads out to a fenced-in yard. The upper level includes 2 bedrooms, a full bath, and a laundry room. Windows have been replaced.

This home is centrally located in downtown Annapolis, within close proximity to the USNA, St. John's College, the cultural district, the City Dock, waterfront, shops, restaurants, and government buildings. Whether you're looking for an affordable home in Annapolis or considering a weekend getaway, this is the perfect choice.

This townhouse is not part of an HOA or condo association and is completely move-in ready. Don't wait!

ANNAPOLIS

38 PLEASANT STREET

2 Beds

1 Baths

840 Sq.Ft.

$259,900

MLS#: MDAA2105312

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