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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

265

# of Listings

3

Avg # of Bedrooms

$481

Avg. $ / Sq.Ft.

$1,292,621

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

265 Properties Found. Page 7 of 18.

Welcome to 903 Scupper Ct. Luxury living at its finest. Located close to Annapolis in the community of Broad Creek Landing. This magnificent home features almost 4300 sq. ft on the upper two levels with an additional 1500 sq. ft. of finished area in the lower level. This home was built for the executive lifestyle.
The main level includes a foyer, formal living room and dining room, large family room, gourmet kitchen with breakfast area and a separate office/library. All opening to a fabulous maintenance free deck. The upper level includes 3 large bedrooms for children and guests and 2 baths. The main bedroom/suite is comprised of a large bedroom area and sitting room. His and her closets. The main bath is absolutely beautiful. Soaking tub, large shower, his and her vanities and marble floor. The lower level is finished as a large room. This can be used for multiple adventures, as well as a full bath and access to the exterior.
The home has a brick front with maintenance free vinyl siding and aluminum facia and soffit. The roof was replaced in 2019. The upper two levels were repainted in 2024. New water heater. Everything you can ask for is in this magnificent. It is close to Annapolis, Baltimore, Washington, Rt.97 and Rt. 50. Level back yard with blooming trees and new shed!
Livability, convenience, luxury, they are all present in this home. Come and view this spectacular home!

ANNAPOLIS

903 SCUPPER COURT

4 Beds

4 Baths

5,766 Sq.Ft.

$1,050,000

MLS#: MDAA2141286

New on site 4 days ago

Stunning brick front colonial with over 6,000 total square feet featuring 4/5 bedrooms and 4½ baths across 3 finished levels on a premium lot. This home offers a sunroom, an updated eat-in kitchen with a recently installed oversized white stone island and a new refrigerator and dishwaher offering perfect space for family meals and entertaining. Enjoy a 2-story great room with a wall of windows and gas fireplace, plus a main-level office, a formal living and dining room- all with hardwood floors. The primary suite boasts hardwood floors, tray ceiling, and peaceful views of the woods. The lower level has a full bath, a recreation room, an exercise room with special rubber flooring and a potential 5th bedroom with outside entrance. The rear fenced yard backs to open space with walking paths and woods, including a patio and spacious lawn. Additional highlights include a 2-car garage with finished flooring, recent carpet and paint throughout. Located in the sought-after, community of Kingsport, offering easy access to downtown Annapolis and community routes to BWI and Washington, D.C. Community amenities include a pool, community pier, tot lot, kayak storage, and walking paths. A perfect blend of comfort, style, and outdoor enjoyment!

ANNAPOLIS

732 PEARSON POINT PLACE

5 Beds

4 Baths

5,333 Sq.Ft.

$1,025,000

MLS#: MDAA2143452

Rare waterfront redevelopment opportunity in Annapolis. The existing structure is a complete shell and requires a full renovation or rebuild. Ideal for investors, builders, or buyers looking to design and construct a custom waterfront home from the ground up.

Located along the protected waters of Oyster Cove, the property includes a deep-water pier and boat house. The existing footprint and favorable waterside placement offer strong potential to maximize views and overall design.

Convenient access to the Chesapeake Bay and close proximity to Historic Downtown Annapolis by both land and water. Enjoy boating, sailing, and easy access to surrounding waterfront destinations throughout the region.

Property is being sold strictly as-is. A unique opportunity for those ready to take on a full redevelopment project in a prime waterfront setting.

ANNAPOLIS

1254 WASHINGTON DRIVE

5 Beds

4 Baths

9,960 Sq.Ft.

$1,000,000

MLS#: MDAA2143700

Welcome to the heart of downtown Annapolis at 179 Green Street. This charming home blends timeless character with modern comfort, this is just a block from Main Street and City Dock, few block from the Naval Academy, State Capitol building, boutique shopping, and Annapolis Elementary School. Located in one of the city’s most desirable neighborhoods, it offers exceptional walkability and vibrant city living. Move in ready with a new roof, new updated kitchen, new full bathroom on main floor, new plumbing, new electrical, new basement ceiling, new fenced in yard, The main level features inviting front and enclosed side porches—perfect for morning coffee or unwinding with a glass of wine in the evening. Inside, wide-board pine floors lead to an updated L-shaped kitchen with bright white cabinetry, stainless steel appliances, and a convenient stackable washer and dryer nearby. The living room showcases rich wood wainscoting, detailed wood trim, custom built-in bookcases, and a rustic fireplace accent, creating a warm and cozy atmosphere. A dedicated dining room completes the main level, ideal for everyday living and entertaining. Upstairs, the home offers two spacious bedrooms and there is an extra versatile space featuring an exposed beam ceiling, curved built-in arch shelving, and custom cabinetry—ideal for a home office, or a den. A large bathroom showcases a Victorian-style Van Buren clawfoot tub, new LVP flooring adding timeless historic character. Outdoors, the fenced backyard provides a private retreat for entertaining or relaxing. The property also includes two oversized off-street parking spaces, offering exceptional convenience. Step into a lifestyle steeped in history and culture. Wander charming cobblestone streets to acclaimed dining, embrace sailing and local events, and enjoy the dynamic rhythm of downtown living just beyond your doorstep. This is a rare opportunity to own a true piece of Annapolis charm—schedule your private showing today. Fireplace non operational.

ANNAPOLIS

179 GREEN STREET

2 Beds

2 Baths

1,656 Sq.Ft.

$999,999

MLS#: MDAA2135874

Days on market reflects seller ability to show because of illness.
English Tudor featuring a stone front patio, covered front porch for nature lovers and bird watchers. Driveway paved and widened in 2021, extensive gardens and plantings. House surrounded by mature trees for tons of shade and privacy. Rear deck is 45 ft by 16 ft and built to hold a large hot tub. Constructed in 2016 for entertaining large gatherings. Backing to community open space the rear lawn has level play areas and room for a pool.
Drywell was replaced and expanded in 2016. Back yard has ample level space for a large pool or children play area.Two Zone HVAC systems were replaced with high efficiency systems in 2021 and 2022. Three of the four full baths were renovated in 2021. Twenty six exterior trim boards were replaced in October of 2024.
Over 4000 square feet of living space plus an oversized garage 24x25 with a floored attic space above for expansion or storage. Spacious kitchen with two Andersen French sliders to rear deck, solid cherry cabinets, quartz island with smooth cooktop and built-in exhaust fan, stainless steel appliances, Bosch dishwasher in 2024..
The great room has high cathedral ceilings, wood beams and wide plank redwood siding, floor to ceiling brick fireplace and Andersen French slider to rear deck. First floor guest room features wood flooring and access to full bath and walk-in shower. Laundry room with generous built-in shelving.
Upstairs features high-end neutral carpet, 3 bedrooms, 2 full baths and generous closet space.
Finished Lower Level has clubroom, full bath with walk-in shower, office/5th bedroom potential (needs larger window for egress) large storage room with built-in shelving.
The community has water privileges with fishing pier and canoe storage and sidewalks for dog walking or strolling the neighborhood. Convenient location for commuting to Baltimore or D.C. and 20 minutes to BWI Airport. Five miles to Downtown Annapolis for great shopping, restaurants, Naval Academy and Historic District.. Tax records has incorrect square footage and bath information.

ANNAPOLIS

553 CHOPTANK COVE COURT

5 Beds

4 Baths

3,759 Sq.Ft.

$999,997

MLS#: MDAA2117832

What’s Special "Furnished
Apartment ". Welcome to 605 Lighthouse Landing Ln, located on a quiet corner lot. This home has 6 bedrooms, 4 ½ baths, designed with an open floor plan. The great room on the first level has a den with fireplace, breakfast nook, and kitchen. Also on the first floor is the living room, foyer, dining room, and a primary bedroom with shower and soak in tub also there are two large, his and hers walk in closets. On the second level there is a primary suite and three bedrooms. The lower level comes with a complete 900 sq ft in law apartment with a primary bedroom. The fenced in yard is great for kids and pets. The large composite deck provides a great place to relax. If the power fails the Generac generator kicks in within 30 seconds, providing power to the entire house. Two large unfinished storage rooms provide more than adequate space for storage or an exercise room. All comments, data is provided by seller or seller's representatives. Buyer to confirm all & hold all parties harmless from any discrepancy data in the mls and advertising. Limited Service–Data Entry Addendum signed by seller/s must be signed by buyer/s with Purchase Contract.

ANNAPOLIS

605 LIGHTHOUSE LANDING LANE

6 Beds

4 Baths

4,041 Sq.Ft.

$998,000

MLS#: MDAA2140662

#MDAA2134724

ANNAPOLIS

105 GRISCOM SQUARE WAY

4 Beds

3 Baths

2,850 Sq.Ft.

$995,000

MLS#: MDAA2134724

New on site 4 days ago

#MDAA2140786

ANNAPOLIS

909 WHITE MARLIN WAY

5 Beds

3 Baths

4,170 Sq.Ft.

$989,900

MLS#: MDAA2140786

Priced to sell. Exceptional Value for over 3,292 finished sq ft. tucked among the trees in the gated waterfront community of Epping Forest. This spacious three-level home features vaulted tongue-and-groove wood plank ceilings, light-filled interiors, and peaceful wooded views. So many options for furniture placement and usable space.
The kitchen is designed for both everyday living and entertaining, featuring an expanded center island, abundant cabinetry, built-in shelving, and a wood-burning stove for added warmth. It opens to a flexible family room and flows into an expansive dining and living area with soaring vaulted ceilings, skylights, and a pellet stove set against a dramatic brick hearth.
Upstairs, the primary suite offers a private retreat with an en-suite bath and access to an adjoining bedroom, ideal for an office or second bedroom. The lower level features a great room, two additional bedrooms, a full bath, workshop space, and walk-out access to a shaded deck.
Epping Forest offers a unique waterfront lifestyle on the Severn River, with a private beach, a marina with boat slips, a clubhouse with a restaurant, tennis, pickleball, a playground, and year-round community events.
Ideally located just 20 minutes to BWI, 30 minutes to Washington, D.C., and Baltimore, and minutes to downtown Annapolis.

ANNAPOLIS

349 EPPING WAY

4 Beds

2 Baths

3,292 Sq.Ft.

$975,000

MLS#: MDAA2137250

Located just moments from the shoreline, 509 Chesapeake Ave presents a rare opportunity to secure a 4-bedroom, 2-bath single-family home in one of Annapolis’s most desirable waterfront-adjacent areas. Whether you’re an investor searching for your next project or a homeowner ready to create your dream coastal retreat, this property offers incredible potential.

The home features a spacious layout with four bedrooms and two full baths, providing a solid foundation for renovation and value-add improvements. With the right vision, this property could be transformed into a stunning primary residence, vacation home, or resale opportunity.

Positioned just steps from the water, enjoy the lifestyle perks of boating, dining, and all that Annapolis waterfront living has to offer. The location alone makes this a standout opportunity—properties this close to the water with this much upside are hard to find.

Ideal for buyers looking to renovate, customize, and build equity in a prime location. Bring your contractor, your vision, and unlock the full potential of this Annapolis gem.

ANNAPOLIS

509 CHESAPEAKE AVENUE

4 Beds

2 Baths

1,800 Sq.Ft.

$972,000

MLS#: MDAA2140184

Just across the street from the water in Southaven, this Annapolis home offers the kind of space and flexibility that’s increasingly hard to find. Recently updated, the main level includes a renovated kitchen with quartz countertops, dual ovens, gas cooking, stainless steel appliances, and modern cabinetry. The main level also features a living room with built-in speakers, a dining room, an optional sitting room, a half bath, garage access, and a coat closet at the front entry.

Upstairs are four well-sized bedrooms, two thoughtfully updated full baths designed with a clean, timeless aesthetic, and a laundry room. The walkout lower level remains unfinished and offers excellent storage, along with a bathroom rough-in for those who may wish to explore future expansion.

Exterior updates include a newer roof and a recently paved driveway. The attached two-car garage supports everyday needs, while the detached three-car garage offers access to an unfinished upper-level space that provides additional room to tailor to personal needs. A back deck extends off the main level, with a second deck accessible from the unfinished space above the three-car garage.

Community water access is located across the street. The Southaven community also offers a community pier and a kayak/paddleboard launch area. Set on a generous lot with ample storage and water access, 2942 Southaven Drive combines usability with the relaxed coastal character that makes this part of Annapolis so appealing.

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

2,142 Sq.Ft.

$949,900

MLS#: MDAA2131620

Prime West Annapolis Opportunity | B-1 Zoning | 13 Annapolis Street. Positioned in the heart of high-demand West Annapolis, 13 Annapolis Street presents an exceptionally rare opportunity to acquire a property with B-1 zoning flexibility in one of Annapolis’ most dynamic commercial districts. This is the kind of location where vision, creativity, and smart planning can translate into long-term value. B-1 zoning opens the door to a variety of potential uses such as boutique retail, professional offices, wellness studios, salons, galleries, cafés, creative workspaces, or thoughtfully designed mixed-use concepts (buyer to verify specific uses with the City). Whether you’re an entrepreneur looking to establish a flagship presence, a business owner seeking visibility, or an investor with a redevelopment vision, this property offers the versatility to bring those plans to life. Adding to its appeal is a feature rarely found in West Annapolis: a private driveway with abundant off-street parking, a significant advantage for clients, customers, or tenants and a true differentiator in this walkable corridor. Surrounded by beloved local restaurants, shops, and everyday conveniences, the property benefits from strong foot traffic, excellent visibility, and the vibrant energy that defines West Annapolis. Opportunities with this combination of location, zoning, and parking simply do not come along often.

ANNAPOLIS

13 ANNAPOLIS STREET

None Beds

None Baths

2,240 Sq.Ft.

$925,000

MLS#: MDAA2135402

#MDAA2140068

ANNAPOLIS

220 WEST STREET

3 Beds

2 Baths

1,540 Sq.Ft.

$924,900

MLS#: MDAA2140068

New on site 4 days ago

Tucked away on a private cul-de-sac in one of Annapolis's most coveted enclaves, this exceptional residence offers the refined living the Chesapeake Bay region is celebrated for. From the moment you arrive, beautifully manicured landscaping and an elegant facade set the tone for what awaits inside.

Hardwood floors flow throughout the main level, anchoring an open floor plan where formal and informal living spaces are thoughtfully balanced. A gracious formal living room with a fireplace provides an elegant setting for entertaining, while the informal living room, anchored by a second fireplace, offers the kind of relaxed comfort that makes a house feel like a home.

The heart of it all is a stunning two-story great room off the kitchen, where soaring ceilings soar overhead and natural light pours in from every angle; a breathtaking space that never loses its ability to impress. The chef-inspired eat-in kitchen is equally spectacular, appointed with a large center island, Corian countertops, gas cooktop, and dual wall ovens. Whether hosting an intimate dinner party or a festive gathering, this kitchen performs flawlessly. Recessed lighting throughout the main level lends a polished, gallery-like ambiance at every turn.

The coveted first-floor primary suite is a true sanctuary, offering a generous walk-in closet and the ease of single-level living at its finest. First-floor laundry adds an everyday luxury that discerning buyers will immediately appreciate.

Upstairs, two spacious bedrooms share a well-appointed full bath, while a versatile loft overlooks the living spaces below, equally suited as a private home office, library, or lounge.

The finished lower level is nothing short of spectacular. Custom built-in bookcases, a third fireplace, a full bath, and a wet bar make this space ideal for entertaining, relaxing, or hosting overnight guests in style. A whole-home generator ensures uninterrupted comfort in every season.

Outside, a paver patio and deck extend your living and entertaining space into the serene, landscaped backyard; the perfect backdrop for al fresco dining, morning coffee, or simply savoring the beauty of an Annapolis evening. A two-car garage completes this picture of thoughtful convenience.

This is Annapolis living at its finest; where classic elegance, modern comfort, and Chesapeake Bay charm converge into something truly special.

ANNAPOLIS

1604 TRAWLER LANE

3 Beds

2 Baths

4,295 Sq.Ft.

$915,000

MLS#: MDAA2143576

Lovely, well maintained marina front townhouse with great views of the Bay. Chesapeake Harbour offers a unique lifestyle that these owners have enjoyed for many years. Now it's your chance to experience it, to relax by one of the two pools, play tennis or pickleball, fish off the docks and watch spectacluar moon and sun rises and the Blue Angels from your new home. This is the only village that has it's own gym and natural gas to heat and cook with. Meet neighbors as you and your pooch walk the paths around the community or join friends for a meal at The Beacon restaurant as you watch the boats enter and depart the marina.
Chesapeake Harbour may be the perfect place for you so make an appointment to see this home soon.

ANNAPOLIS

7001 CLINTON COURT 7B

3 Beds

3 Baths

2,085 Sq.Ft.

$900,000

MLS#: MDAA2139894

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