One of the most popular communities provided by {{page_data.agentName}}

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

274

# of Listings

3

Avg # of Bedrooms

$510

Avg. $ / Sq.Ft.

$1,357,507

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

274 Properties Found. Page 13 of 19.

Welcome to 3320 Arundel on the Bay Road—where relaxed coastal living meets thoughtful design in the water-privileged community of Oyster Harbor. This beautifully maintained and upgraded 3-bedroom, 3.5-bath coastal-style home offers the perfect blend of indoor comfort and outdoor enjoyment.
Inside, you’ll find an upgraded and inviting open plan design complemented by a cozy wood-burning fireplace, and three ensuite bedrooms, each with a private bath. The finished lower level offers full daylight and a walk-out slider to a private paver patio. A versatile studio apartment with quarts counter tops and bright white cabinetry, is ideal for guests, rental income, or a private workspace—with its own separate entry.
Step outside and experience the home’s exceptional exterior features. The premium IPE wood dining deck and front stairs provide a durable and stylish space for entertaining or relaxing, enhanced by a clear-view vinyl-clad railing system. The property includes five parking spaces, multiple brick paver walkways, a private entry to the studio, a brick patio with garden beds, and two rear storage sheds, including a walk-in shed with a window. Every detail is designed for both function and coastal curb appeal.
Living in Oyster Harbor means enjoying unmatched access to the Chesapeake lifestyle. This sought-after waterfront community borders Oyster Creek, Fishing Creek, and the Chesapeake Bay, offering multiple shoreline access points for boating, paddling, and soaking in the views. Residents enjoy a private sandy beach with designated swimming areas, sea nettle nets, picnic spots, BBQ areas, and a gazebo perfect for gatherings.
For boating enthusiasts, the community features three marinas with 30–40 slips, boat ramps, multiple piers, and docking locations. There’s even a dedicated fishing pier, dinghy racks, and floating dock spaces for small craft like kayaks, paddleboards, and Sunfish sailboats. Whether you’re crabbing, fishing, or simply enjoying the water, this community checks every box.
This is more than just a home—it’s a gateway to a vibrant coastal lifestyle in one of Annapolis’ most vibrant water-access neighborhoods. Come home to your get-away lifestyle!

ANNAPOLIS

3320 ARUNDEL ON THE BAY ROAD

3 Beds

3 Baths

1,812 Sq.Ft.

$600,000

MLS#: MDAA2141892

** 2 Silopanna Court ** stands out as one of the most compelling options in Annapolis within this price range; easily walkable to downtown for famous Annapolis eats, shopping, and entertainment.

Tucked away on a quiet cul-de-sac just minutes from downtown Annapolis, this 2,000± square foot home offers the rare combination of privacy, meaningful upgrades, and everyday convenience. The shaded backyard is a summer favorite spot for your hammock or firepit with s'mores.

Since 2021, major improvements have already been handled for you, including a new roof, windows and sliders, vinyl siding with upgraded gutters, HVAC system, water heater, and fully updated kitchen and bathrooms... giving buyers confidence in both condition and long-term value.

The layout offers 4 bedrooms and 2.5 baths with a natural flow that allows you to live comfortably day-to-day while still having that work-from-home dedicated space.

Set on a manageable, low-maintenance lot with no HOA, this is an ideal fit for those who want space and freedom without added restrictions. Extend the driveway, add a garage, put in a swing set, or a tree-house. Heck, add both! This is a great place to make it exactly what you want it to be

With its location just minutes from downtown Annapolis dining, water access, and commuter routes, the home delivers both accessibility and a tucked-away feel.

This home is waiting for you! Turn key and ready to move in. Or consider it as an investment property and enjoy the fruits of the demand from the US Naval Academy, traveling nurses, or LTR.

ANNAPOLIS

2 SILOPANNA COURT

4 Beds

2 Baths

2,000 Sq.Ft.

$599,900

MLS#: MDAA2141372

1701 Delage Lane presents an exceptional opportunity for investors, contractors, or buyers ready to renovate and build instant equity. This large four-bedroom home with one and a half baths is full of potential, making it ideal for those with vision and creativity seeking to transform a property into something truly special.
Situated on a generously sized lot in an established neighborhood, the home offers a solid foundation for a complete renovation or reimagining. Whether you're looking to customize your next residence or take on your next investment project, the possibilities here are abundant.
Enjoy a prime location just minutes from historic downtown Annapolis, the United States Naval Academy, area marinas, waterfront attractions, shopping, and dining. Commuters will appreciate convenient access to major routes connecting to Baltimore, Washington, D.C., and Fort Meade.
Bring your contractor and imagination—this is a rare chance to create value in one of Annapolis’s most desirable locations. Property is being sold strictly as-is.

ANNAPOLIS

1701 DELAGE LANE

4 Beds

1 Baths

1,960 Sq.Ft.

$599,000

MLS#: MDAA2145174

Motivated Sellers!! Price Just Improved!!

Rare Opportunity in an Amazing Annapolis Neighborhood!

Welcome to 79 Windwhisper. A beautiful 4 bedroom, 2500 sq foot, 3.5 bath home with an office, located in one of Annapolis’ most desirable neighborhoods. This well-maintained property offers numerous recent updates, including new carpet, hardwood flooring on main level, updated bathrooms, flooring, fresh paint interior and exterior, a new refrigerator, and a new dishwasher, making it move-in ready.

The home features a fully finished basement, providing plenty of additional living or entertainment space, along with the convenience of a garage.

Enjoy the Chesapeake lifestyle with a private neighborhood marina just a short walk away, perfect for kayaking and paddleboarding. Outdoor lovers will also appreciate being less than 2 miles from Quiet Waters Park, offering trails, waterfront views, and year-round recreation.

Ideally located near the U.S. Naval Academy and just 3 miles from Historic Downtown Annapolis, you’ll have easy access to waterfront dining, shopping, and local events.

Professional landscaping is already scheduled and fully paid for, with improvements to be completed in April, adding even more curb appeal to this wonderful property.

Don’t miss this rare opportunity to own in an exceptional Annapolis location!

ANNAPOLIS

79 WINDWHISPER LANE

4 Beds

3 Baths

2,560 Sq.Ft.

$599,000

MLS#: MDAA2138392

There is no lifestyle quite like life at the Villages of Chesapeake Harbour! Your coastal lifestyle awaits in this beautifully renovated main-level residence within the sought-after gated waterfront community of Chesapeake Harbour. Offering tranquil marina views and resort-style amenities just minutes from downtown Annapolis, this sun-filled home blends charm, comfort, and low-maintenance living. (Property can be adapted to be handicap accessible too!) Light pours through the open-concept living and dining spaces, anchored by a cozy shiplap-accented fireplace. The updated kitchen features tasteful granite countertops and backsplash, white bead board cabinetry, SS appliances, breakfast bar seating, a dedicated coffee station, and peaceful marina views right from the kitchen sink. Sliding glass doors lead to the private patio overlooking the marina with direct access to scenic waterfront walking trails, perfect for morning coffee walks by the water. The spacious primary suite offers patio access, a large walk-in closet, and a spa-like bath with a jetted soaking tub. A generously sized second bedroom features convenient access to a dual-entry full bath. Luxury vinyl plank flooring, crown molding, recessed lighting, and shiplap accents add warmth and coastal character throughout. Enjoy Chesapeake Harbour’s exceptional amenities, including a private beach, marina (with ability to rent a boat slip), multiple pools (one heated & one overlooking the Chesapeake Bay), tennis & pickleball courts, walking trails around the water, and the community restaurant and bar The Beacon... the perfect spot to grab an orange crush and a bite to eat after a long day on the water. Waterfront living awaits you!

ANNAPOLIS

7044 HARBOUR VILLAGE COURT T1

2 Beds

2 Baths

1,250 Sq.Ft.

$595,000

MLS#: MDAA2144650

Welcome to 709 Skippers Lane, a rare and versatile Live/Work townhome in the sought‑after Village Greens community—one of the only homes in the development offering this unique zoning flexibility. With 3,016 sq. ft. of beautifully finished space, this contemporary residence blends upscale living with the opportunity to operate a boutique business, studio, or professional office right from home. Step inside to discover a thoughtfully upgraded interior featuring designer touches, abundant natural light, and an open-concept layout ideal for modern living. The gourmet kitchen, spacious dining area, and inviting living room create a warm and functional environment perfect for everyday comfort or entertaining. The home offers three spacious bedrooms, two full baths, and two half baths, including a serene primary suite with generous closet space and a well-appointed en‑suite bath. Every level has been meticulously maintained, reflecting pride of ownership throughout. A new AC unit was installed in Oct 2025. The garage is painted and that floor has high temp epoxy. The street-level commercial space—previously home to a boutique yarn and knitting shop—opens the door to endless possibilities. Whether you envision a specialty retail shop, creative studio, office, or an expanded living area, this flexible zone empowers you to live, work, and play without compromise. Perfectly positioned just minutes from historic downtown Annapolis, major commuter routes, shopping, dining, and the waterfront, this home offers the ideal blend of convenience and charm. Sellers to offer a one year home warranty for the buyer at time of settlement

ANNAPOLIS

709 SKIPPERS LANE

3 Beds

2 Baths

3,016 Sq.Ft.

$590,000

MLS#: MDAA2132646

Major Price Reduction w/ Some Closing Help! Located in the water-privileged community of Cape St. Claire in Annapolis, this Dutch Colonial offers a practical layout, recent updates, and a private outdoor setting.

The home features a traditional floor plan with multiple living areas, allowing for flexible use of space for everyday living, entertaining, and work-from-home needs. Recent interior improvements include fresh paint, bathroom upgrades, and newer vinyl plank flooring, providing a clean, updated feel.

Major system updates include a newer roof and water heater, helping reduce the likelihood of immediate maintenance expenses.

Set on a 0.21-acre shaded lot with established trees, the property offers natural privacy and a comfortable outdoor environment. An outbuilding provides additional storage or workspace.

The 1-car garage and large driveway accommodate parking up to 4+/- vehicles.

Cape St. Claire is a well-established, water-privileged community known for its access to the Chesapeake Bay lifestyle. Residents have access to multiple private community beaches, boat ramps, fishing piers, playgrounds, and open recreational areas.

The Little Magothy River is located approximately five blocks away, providing convenient access for kayaking, boating, and fishing.

The property is located within the Broadneck school district (buyer to verify), a factor many buyers consider when evaluating location.

Conveniently located near Route 50, offering access to Annapolis, Baltimore, and Washington, D.C.

ANNAPOLIS

1075 SUN VALLEY DRIVE

4 Beds

2 Baths

2,274 Sq.Ft.

$589,900

MLS#: MDAA2140126

Welcome to this beautiful 2 bedroom 2 bath coveted end unit condo in the sought-after gated Chesapeake Harbour community, This home is a rare find, offering the perfect blend of privacy, natural light, and outdoor space. Inside, the additional square footage an end unit offers creates an open floor plan bathed in sunlight, thanks to windows on three sides. The living spaces are airy and inviting, with seamless flow from the cozy living room to the dining area and updated kitchen. You'll love the thoughtful details, including hardwood floors, a fireplace for those cooler evenings, and scenic views that bring the outdoors in. This home is ideally located to enjoy watching the sunrise over Chase Pond and the Bay with your morning coffee or tea. Later in the day the oversized wrap-around deck invites you to relax, entertain, or simply soak in the tranquil surroundings and watch the sunset over the Marina. Chesapeake Harbour is a vibrant, amenity-rich community with access to 2 pools, 2 tennis and pickle ball courts, kayaking, walking trails and a marina, all just minutes from downtown Annapolis. Whether you're a boating enthusiast or simply crave the coastal lifestyle, this property checks all the boxes. Don’t miss your chance to own this one-of-a-kind retreat. Schedule your tour today and experience Chesapeake Harbour living at its finest!

ANNAPOLIS

2110 CHESAPEAKE HARBOUR DRIVE 101

2 Beds

2 Baths

1,237 Sq.Ft.

$585,000

MLS#: MDAA2138114

Nestled in the charming community of Arundel on the Bay, this delightful ranch-style home offers a perfect blend of comfort and convenience. With 3 spacious bedrooms and 2.5 bathrooms, this residence boasts an inviting open floor plan, ideal for both relaxation and entertaining. The heart of the home features a cozy family room with a wood-burning stove, and a bar that seamlessly connects to an eat-in kitchen including a double oven and a large pantry. Step outside to discover a 0.34-acre corner lot complete with a deck and fire pit, perfect for outdoor gatherings. The property also includes 2 driveways for ample parking and a shed for additional storage. Enjoy the benefits of community living with access to a private beach, boat dock, playground and picnic areas, all just a short stroll away. The Chesapeake Bay is at your fingertips, offering opportunities for boating, kayaking, fishing, and leisurely days by the water. Residents appreciate the proximity to local parks, schools, stores and just minutes from downtown, enhancing the overall quality of life. With a strong sense of community and well-maintained common areas, this home is not just a place to live, but a place to thrive. Experience the warmth and charm of Arundel on the Bay just in time for summer!

ANNAPOLIS

3448 COHASSET AVENUE

3 Beds

2 Baths

2,160 Sq.Ft.

$585,000

MLS#: MDAA2142830

#MDAA2134820

ANNAPOLIS

721 FAIRWAY DRIVE

4 Beds

3 Baths

2,080 Sq.Ft.

$585,000

MLS#: MDAA2134820

***Major Price Reduction***Enjoy luxury condo living in this first-floor 2-bedroom, 2-bath home. Featuring gleaming hardwood floors, spacious and bright layout, and a stylish kitchen, this residence combines comfort and convenience. Park Place offers exceptional amenities including 24/7 concierge service, a pool, fitness center, meeting and party rooms, library, and a rear outdoor patio with a kitchen and grilling area—perfect for entertaining. The unit comes with a storage space as well as parking. Additional perks include a dog park and easy access to restaurants and shopping. A fabulous in-town location you won’t want to miss. Welcome home!

ANNAPOLIS

5 PARK PLACE 107

2 Beds

2 Baths

1,272 Sq.Ft.

$575,000

MLS#: MDAA2138356

Don’t miss this beautifully updated, move-in-ready condo in the highly sought-after, amenity-rich community of Chesapeake Harbour, offering serene marina views and the perfect backdrop to relax and watch the boats drift by. This inviting home is bright and cheery and features neutral paint and carpeting. There are two spacious bedrooms with two full baths. The open-concept living and dining areas create an effortless flow for both everyday living and entertaining and opens up to a deck that overlooks the marina. The updated kitchen showcases granite countertops and ample cabinetry, while the cozy wood-burning fireplace adds warmth and charm to the living space. Chesapeake Harbour offers resort-style living with 24/7 gated security, two pools, tennis courts, a private sandy beach, and scenic walking paths. Enjoy the convenience of a water taxi to Historic Annapolis or dine waterside at The Beacon, located right within the community. Experience low-maintenance coastal living at its finest, this is the one you’ve been waiting for.

ANNAPOLIS

7004 CHANNEL VILLAGE COURT 102

2 Beds

2 Baths

N/A

$575,000

MLS#: MDAA2143832

New on site 2 days ago

Large, beautifully maintained contemporary home in the sought-after Stone Creek community of Annapolis. Professional photos of this bright and airy property are coming soon.
Features of this 4-bedroom, 3.5-bathroom home include:
Renovated Interior: Recently painted throughout with an open-concept layout, remodeled kitchen and bathrooms, and vinyl plank flooring in the living and dining rooms.
Chef’s Kitchen: Features granite countertops, extensive cabinet space, and a breakfast bar that opens to a great room with a fireplace.
Primary Suite: Includes double closets and a recently remodeled primary bath.
Upgraded Systems: Newer roof and windows, with an HVAC unit installed in 2018.
Outdoor Living: A sliding door leads to a gorgeous new deck and mature landscaping, perfect for entertaining.
Lower Level: The basement includes a large laundry room, a full bath, and two rooms; the main family room area is framed and ready for completion.
Community Amenities: Access to a community center, in-ground pool, and tennis courts.
The property is conveniently located near major highways and downtown Annapolis, offering an easy commute to Washington D.C., Baltimore, and Fort Meade.

ANNAPOLIS

15 LANDINGS COURT

4 Beds

3 Baths

1,736 Sq.Ft.

$575,000

MLS#: MDAA2145304

New on site 4 days ago

Opportunity awaits in sought-after St. Margarets! This 3-bedroom, 1-bath home with hardwood floors, situated on a gorgeous 1-acre lot offering plenty of space and potential. Solid built home they don't make houses like this any longer, needs updating, making it the perfect chance to bring your ideas and renovate to your personal taste. Most major systems updated within last 10 years. Whether you are looking for an investment opportunity or a property to create your dream home, this one has endless possibilities. Home is being sold strictly “AS IS.” Home warranty included.

ANNAPOLIS

1509 DUVALL ROAD

3 Beds

1 Baths

1,512 Sq.Ft.

$575,000

MLS#: MDAA2144750

Welcome to 206 Wesley Brown Ln! Rooftop views and effortless flow welcome you to elevated living in Admirals Square. This four level townhome is just minutes from downtown Annapolis with easy access to Route 50 and I-97, offering both convenience and lifestyle. This home features 3 spacious bedrooms, 3 full baths, and 2 powder rooms across a flexible, well-designed layout. Wide plank oak floors run throughout the main living spaces, adding warmth and continuity to the home’s clean, modern design. The heart of the home is a beautiful kitchen with quartz countertops and stainless steel appliances. The kitchen, dining, and living areas flow seamlessly together, creating a cohesive space that is ideal for both everyday living and entertaining. Upstairs, the loft level opens to a beautiful and private rooftop terrace. This indoor-outdoor space is perfect for hosting friends and truly extends your living space in a way that feels both functional and special. Additional highlights include a one car garage, private driveway, and ample street parking for guests, a rare and valuable combination in this area. Turnkey, stylish, and designed for how people actually live, this home offers the best of low maintenance luxury in one of Annapolis’ most desirable communities.

ANNAPOLIS

206 WESLEY BROWN LANE

3 Beds

3 Baths

2,174 Sq.Ft.

$574,999

MLS#: MDAA2144158

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