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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

274

# of Listings

3

Avg # of Bedrooms

$510

Avg. $ / Sq.Ft.

$1,357,507

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

117 Properties Found. Page 2 of 8.

Open House Friday , 5/15 4:30-6:30PM & Saturday 5/16 12-2PM. Please join us!Adorable bungalow coming soon in sought-after West Annapolis! Super fun, walkable location—catch Navy Midshipmen football games or stroll to Chessie’s Wharf, Positano’s, Bean Rush Cafe , Always Ice Cream Company & more! Just a short distance to Downtown Annapolis for waterfront dining, shopping, and historic charm. Easy one-level living with a great fenced-in yard and a large detached garage. Professional interior photos coming soon—stay tuned!

ANNAPOLIS

607 MELVIN AVENUE

2 Beds

2 Baths

1,102 Sq.Ft.

$899,000

MLS#: MDAA2136076

New on site 3 days ago

LOCK AND LEAVE CAREFREE LIFESTYLE IN A WATERFRONT GATED COMMUNITY! DESIGNER SHOWCASE including a custom painted entry that draws you in the moment you open the door. Owner worked with a reputable interior designer to select all finishes to include designer light fixtures, gorgeous real hardwood floors, custom designed bathrooms, and so many interesting trim details. Transitional timeless design with a coastal twist. ONE OF A KIND and RARE GEM! END UNIT. Not one detail has been overlooked! And a beautiful gated waterfront and water-privileged community. BE PREPARED to be wowed when you open the front door with a top of the line renovation over $350,000. NOTICE ALL OF THE BEAUTIFUL ARCHED DOORWAYS! Bosch 3-ton with 96% gas HVAC, and Navien tankless hot water heater. All the vents were professionally cleaned after renovation. This is an opportunity that doesn't come along too often to move right into a turn-key TOTALLY RENOVATED & AND REDESIGNED BY AMAZING LOCAL DESIGNER AND CONTRACTOR!! gorgeously designed home in the exclusive community of Chesapeake Harbour. No expense has been spared to make this custom first-class from floor to ceiling. Totally redesigned and totally renovated with all permits. Custom window treatments throughout and designer light fixtures. Custom gourmet kitchen with quartz counters, stainless steel appliances, an abundance of drawer storage, perfect bar/pass through and much more! Three bedrooms and three full bathrooms. Each space offers light and invites you to relax and be happy you don't have to redo anything. Two-car garage with storage room and storage installed in ceiling of garage. Two gas fireplaces. Beautiful custom shiplap in living room and master bedroom. Multiple decks and from the top deck off master, owner loves to relax and watch the boats and bay bridge. His and her custom closets. Roofs, gutters and all trim painted in the last two weeks. Marvin windows will be installed prior to settlement in guest room and one in office.... And talk about the community, Community beach and pier and two pools, one heated and one waterfront looking out at the Bay. Tennis and pickleball courts for your fun and exercise. Don't worry about getting your steps in with all the waterfront walking paths, If you don't feel like cooking, walk on over to The Beacon with dockside seating . This is a gated community with 24/7 security and guard gate. You can have it all with the best of coastal living in this vibrant and secure community. The pictures really don't do it justice. This is the one you've been waiting for! A MUST SEE!

ANNAPOLIS

7015 CHESAPEAKE HARBOUR DRIVE 23B

3 Beds

3 Baths

2,041 Sq.Ft.

$899,000

MLS#: MDAA2145640

#MDAA2144864

ANNAPOLIS

21 WOODLAWN AVENUE

3 Beds

2 Baths

1,442 Sq.Ft.

$899,000

MLS#: MDAA2144864

New Construction in Cape St. Claire. Home construction has now started. Delivery date will be end of August or beginning of September. Days on the market began when lot was purchased. Please look at the documents section of the listing to see all standard features included with this home and all floor plans and site plan. Pictures shown in this listing are of the home now framed and a previous completed home built at 1216 Ramblewood Drive Annapolis, Md. also located in Cape St. Claire during the construction of that home. This same floor plan will be constructed on this site. Please contact listing agent with any questions.

ANNAPOLIS

1217 HAMPTON ROAD

4 Beds

2 Baths

2,700 Sq.Ft.

$896,000

MLS#: MDAA2130056

AVAILABLE TO TOUR FRIDAY, MAY 15 — CALL NOW TO SCHEDULE YOUR PRIVATE SHOWING OR VISIT THE OPEN HOUSE THIS SATURDAY!
Just in time to enjoy summer in the fabulous water-privileged community of Beechwood on the Burley. Ideally located approximately 2 miles from Downtown Annapolis, yet tucked within a quiet, tree-lined setting that feels worlds away. This spacious home offers wonderful living spaces inside and out! Versatile main level den can easily be transformed into main level bedroom suite complete with attached full bath. Meticulously maintained with numerous updates including a new roof (2025), garage doors + operating system (2025), hot water heater, whole-house generator, and more.
Launch your boat from the private community ramp with quick access to Burley Creek and the Severn River, enjoy the community pier and waterfront playground, and experience the Annapolis lifestyle at its finest — with easy access to Downtown Annapolis, City Dock, restaurants, shopping, and marinas by both boat and car.
Don’t miss the opportunity to enjoy privacy, Blue Ribbon schools, and water-oriented living in one of Annapolis’ most desirable neighborhoods. Easy access to major commuting routes make this one a 10++

ANNAPOLIS

1848 CHERRY ROAD

6 Beds

3 Baths

3,150 Sq.Ft.

$895,000

MLS#: MDAA2144280

New on site today

The home has 3 bedrooms, 2 baths, and offers 1,397 finished sq. ft. above grade, plus 367 finished sq. ft. below grade, with an additional 440 sq. ft. of unfinished storage space.
Located in the highly sought-after Murray Hill neighborhood in downtown Annapolis, this charming single-family home blends 1920s character with thoughtful modern updates and easy walkability to shops and restaurants. The home features a newly renovated kitchen (2025), original hardwood floors, and a welcoming front porch. Outdoor living includes a spacious back deck, private backyard, and beautifully landscaped gardens. Additional highlights include a bright sunroom, off-street parking, and a finished basement office space. Showings can be scheduled via email or phone.

ANNAPOLIS

7 GERMAN STREET

3 Beds

2 Baths

1,764 Sq.Ft.

$889,000

MLS#: MDAA2145808

Looking for a secluded Mountaintop home tucked away on 3.89 acres within 15 minutes from downtown Annapolis, you just found it. Unique, 4-bedroom, 3.5 bath home built in 2007. Hardwood floors, modern kitchen with granite countertops, Stainless-steel appliances and kitchen island. Fully finished basement with family room, bedroom and full bath. 2 fireplaces, one in lower-level family room and one in living room. The home also features a balcony off living room. Large deck off kitchen with roof and a large shed/barn on the property. New ashplant driveway just installed.

ANNAPOLIS

1000 GOMOLJAK LANE

4 Beds

3 Baths

3,620 Sq.Ft.

$884,990

MLS#: MDAA2143566

Charming water-privileged split-foyer residence in the desirable Beale Manor community, offering 3,145 finished square feet of thoughtfully designed living space. Recent updates include a roof replacement, a newer water heater, fresh interior paint, and beautifully refinished flooring throughout the main level, enhancing both style and peace of mind. // The traditional layout begins with a formal living room featuring large picture windows that draw in abundant natural light and flows seamlessly into the formal dining room, creating an inviting setting for gatherings. The updated eat-in kitchen is both stylish and functional, showcasing crisp white cabinetry with sleek bar pulls, a peninsula breakfast bar, black appliances including double ovens, a built-in workstation, and a bright breakfast area with sliding door access to the screened porch. Just off the kitchen, the welcoming family room is highlighted by a white-washed brick fireplace and filled with natural light, while a convenient powder room and laundry area complete the main level. // The upper level features four generously sized bedrooms, including a spacious owner’s suite with a comfortable sitting area, dual closets—one a walk-in with a custom organization system—and a private ensuite bath with a soaking tub and separate shower. A centrally located full bathroom with an extended vanity serves the additional bedrooms. The walk-out finished lower level provides exceptional versatility, offering a large recreation space, a full bathroom, a bar area with a rough-in for a sink, and a fifth bedroom ideal for a home office, gym, or guest space. // Outdoor living is equally appealing, with a screened porch overlooking the backyard, an open-air deck that steps down to a patio, and a spacious, flat, fully fenced yard backing to trees for added privacy. // Residents of Beale Manor enjoy a wealth of community amenities, including a scenic waterfront pool, a basketball court, and a whimsical pollinator garden, fostering a vibrant, connected lifestyle.

ANNAPOLIS

3135 ANCHORAGE DRIVE

5 Beds

3 Baths

3,145 Sq.Ft.

$875,000

MLS#: MDAA2134882

Tucked away in the woods on a quiet cul-de-sac, this stunning single-family home sits on a private and picturesque .77-acre lot, offering the perfect blend of tranquility and modern comfort. With 4 spacious bedrooms and 3.5 bathrooms, this home features a bright, open floor plan designed for both everyday living and entertaining.

The Spacious kitchen with windows on 2 sides and stainless appliances, flows seamlessly into the main living areas, while abundant natural light fills the home, creating a warm and inviting atmosphere throughout. The expansive primary suite is a true retreat, featuring a vaulted ceiling and a spa-like bathroom complete with skylights that bring in beautiful natural light.

Step outside to enjoy the peaceful surroundings from the large screened-in porch just off the living room, or host gatherings on the oversized deck overlooking the wooded backyard. Additional highlights include a 2-car garage and thoughtful updates throughout.

Major system upgrades provide peace of mind, including a new lifetime warranty architectural shingle roof and gutters (2023), new hot water heater (2023), and HVAC system replaced in 2018. The home was also freshly repainted in 2022, making it truly move-in ready.

This is a rare opportunity to own a beautifully updated home in a serene, private setting—while still being conveniently located to everything you need.

ANNAPOLIS

1070 FOXCROFT RUN

4 Beds

3 Baths

3,286 Sq.Ft.

$874,995

MLS#: MDAA2140616

New on site 1 day ago

#MDAA2144296

ANNAPOLIS

422 FIRST STREET

2 Beds

1 Baths

1,094 Sq.Ft.

$870,000

MLS#: MDAA2144296

Welcome to Kingsport—where timeless elegance meets waterfront living. Nestled within this coveted, water-privileged community, this exceptional 5-bedroom, 4.5-bath residence offers a seamless blend of sophistication, comfort, and everyday luxury.
A grand entry welcomes you with rich hardwoods and graceful architectural details, leading to a formal oval dining room, refined living room, and a private main-level office—perfect for today’s lifestyle. The heart of the home is a beautifully appointed gourmet kitchen, featuring a custom center island with cooktop, dual wall ovens, gleaming granite countertops, and extensive cabinetry. The space flows effortlessly into a dramatic family room, highlighted by soaring vaulted ceilings, plantation shutters, and a warm gas fireplace.
Upstairs, the primary suite is a true retreat, offering a spa-inspired bath and dual walk-in closets. An elegant en-suite bedroom and two additional bedrooms with a shared bath complete the upper level, offering both comfort and privacy.
The fully finished lower level is designed for entertaining and relaxation, featuring a spacious recreation room with a wet bar, a private guest suite, a playroom, and abundant storage.

Outdoors, a fully fenced backyard invites quiet moments and gatherings alike, with a paver patio, raised garden beds, and serene wooded views backing to scenic walking paths.

Residents of Kingsport enjoy an exceptional lifestyle with resort-style amenities including a community pool, playgrounds, hiking and biking trails, kayak launch and storage, and a picturesque pier on Crab Creek—ideal for sunset views, fishing, or peaceful afternoons by the water.

Perfectly positioned just minutes from downtown Annapolis and convenient to major commuter routes, this home offers the rare opportunity to live beautifully in one of the area’s most desirable communities.

ANNAPOLIS

730 CRISFIELD WAY

5 Beds

4 Baths

3,586 Sq.Ft.

$865,000

MLS#: MDAA2143706

New in the Market! Extensively renovated from 2022–2024, this move-in-ready, modern Colonial is a standout offering in Anchorage, an Annapolis premier water-privileged community. Set on a private, wooded half-acre lot, this 4-bedroom, 2.5-bath residence combines approximately 2,000 square feet of refined living space with a full basement. The home’s interior showcases high-end craftsmanship, including a custom kitchen with quartzite waterfall island and counter-tops, spa-inspired bathrooms, Pella windows/doors, and Spanish ceramic tiling alongside refinished hardwoods. Residents enjoy an unparalleled waterfront lifestyle with access to a 49-slip marina, boat ramp, pool, and lakeside amenities on Lake Ogleton. Perfectly positioned just minutes from Historic Downtown Annapolis, the Naval Academy, Thomas Point Preserve and Quiet Waters Park. This location provides easy commutes to Washington, DC and Baltimore. The property’s location offers a rare balance of secluded coastal living and metropolitan accessibility. Fully renovated homes in this sought-after community are rarely available at this price point—an exceptional opportunity for the discerning buyer to live the Annapolis lifestyle.

ANNAPOLIS

1126 MAINSAIL DRIVE

4 Beds

2 Baths

1,800 Sq.Ft.

$865,000

MLS#: MDAA2145432

At last, the one you've been waiting for. A beautiful home in a waterfront community. Move right in and start enjoying the Annapolis lifestyle. Anchorage is an amenity filled waterfront community in which the yearly HOA fee includes the use of a boat slip, community pool and more.
This characterful 5 bedroom 2 1/2 bath home has approximately 2,354SF of living space and has been renovated within the last 4 years. Upgrades that include HVAC, tankless hot water heater, well pump, sewer line, roof, downspouts, gutters, soffit and windows make this home a low maintenance joy. A bespoke new sunroom addition off of the kitchen includes a wood burning stove. Simply delightful!
The sparkling kitchen with a new double oven and stainless appliances has an easy flow with classically beautiful cabinetry and quartz counters. Wood floors continue through the living room and down the hall to 3 bedrooms which include the primary with ensuite bath and an additional half bath.
Downstairs there are 2 bedrooms, a full bath, laundry room, storage room and family room with a fully lined fireplace and wood stove. Garage access is through this room. In the 2 car garage you'll find 2 EV chargers. The harmonious floor plan guides you from room to room with ease.
Sitting on nearly 1/2 acre, the outdoor space won't disappoint. Entertaining is a breeze here, enjoy the spacious deck which is adjacent to the sunroom and overlooks the level, lightly treed and fenced backyard. Landscaping which has matured with the years adds to the natural charm of the property.
Two storage sheds provide plenty of storage with one facing the driveway for easy bike storage access.
The community waterfront on Lake Ogleton includes 49 deep water slips in the marina, community pool, kayak storage, boat ramp and basketball court. The Chesapeake Bay is a quick motor away and historic downtown Annapolis is minutes by car underscoring the desirability of this home's locale.
Filled with amenities and coupled with location, Anchorage is a community that truly has it all.

ANNAPOLIS

1106 MAINSAIL DRIVE

5 Beds

2 Baths

2,059 Sq.Ft.

$849,000

MLS#: MDAA2139090

Positioned as one of the best values in Kingsport, this beautifully maintained 5-bedroom, 4.5-bath home offers nearly 5,000 sq ft of finished living space and a layout ideal for both everyday living and entertaining. With comparable homes in the community trending in the mid-high $800s to $900,000 range, the current pricing presents a compelling opportunity for buyers seeking space, location, and long-term value. Ideally located just minutes from Downtown Annapolis and directly across from the community pool, clubhouse, playgrounds, dog walking area, and walking trails, this home offers both convenience and lifestyle. Inside, you’ll find hardwood flooring, a soaring two-story family room with fireplace, a gourmet kitchen with stainless steel appliances and Jenn-Air cooktop, and a private main-level office. The upper level features a spacious primary suite with two walk-in closets and a spa-style bath, along with generously sized additional bedrooms. The lower level includes a finished recreation room, a fifth bedroom or office with egress, a full bath, and additional unfinished space with potential for a media room, gym, or extended living area. The home has been well maintained, is fully functional, and offers a strong foundation for a buyer to personalize over time. Seller is offering a $10,000 concession, which may be applied toward buyer’s allowable closing costs or other permitted expenses, subject to lender guidelines. Seller is seeking clean, competitive offers aligned with current list price, and any requests for concessions should be incorporated into the overall offer terms. Property is being sold as-is. Seller requires 15–30 days to secure home of choice.

ANNAPOLIS

712 COYBAY DRIVE

5 Beds

4 Baths

4,230 Sq.Ft.

$844,995

MLS#: MDAA2143208

Love This HOME at the NEW PRICE!! Briarwood – One of Anne Arundel County’s Finest Communities… Welcome to Rosebay Court!
A mature magnolia tree and inviting covered front porch set the stage for this beautifully updated/renovated brick colonial, ideally situated on a quiet cul-de-sac. Thoughtfully finished and move-in ready, this home is prepared to welcome its new owner.
Inside, a traditional layout blends seamlessly with an open-concept feel, offering both comfort and versatility for everyday living and entertaining. The main level features a welcoming living room, a formal dining room that opens to a light-filled kitchen complete with 42” white cabinetry, complementary granite countertops, a breakfast bar, pantry, and coffee nook. A Samsung appliance suite—including a five-burner stove and French door refrigerator—adds both style and functionality.
The adjoining "great room" is another space for family & friends to gather This room impresses with vaulted ceilings, skylights, and a cozy wood-burning fireplace—perfect ambience for crisp fall and winter evenings. At the heart of this space, the breakfast nook offers table space and easy access to the outdoors -- sliding glass doors that open to a new Trex deck, ideal for relaxing, entertaining, starting your day or ending your evening... . Neutral finishes throughout this home create a fresh look and feel
Upstairs, you’ll find four spacious bedrooms, including an owner’s suite with a private bath featuring dual vanities and walk-in closet. A well-appointed hall bath and ample closet space complete the upper level.
The finished lower level offers incredible flexibility, featuring a full bathroom and level walkout access to the backyard. Whether you envision an in-law suite, guest space, home office, gym, or additional living area, this level is ready to adapt to your needs. Step outside to a newly paved patio overlooking a serene green space, surrounded by nature.
Located in a sought-after school district and just minutes from Route 50, this home offers convenient access to shopping, waterfront dining, marinas, and scenic walking paths. Enjoy easy trips to the Eastern Shore and nearby beaches.
With all new mechanicals and updates ((detailed in the disclosures)), this home offers the perfect alternative to new construction—without the wait. Move in and start enjoying your dream home this summer!
*** please note disclosure: some photos have been enhanced with virtual staging/photography ***

ANNAPOLIS

1394 ROSEBAY COURT

4 Beds

3 Baths

2,252 Sq.Ft.

$835,000

MLS#: MDAA2140978

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