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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

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Over $5M

265 Properties Found. Page 8 of 18.

GREAT OPPORTUNITY! Huge building offers two levels with office on main level (currently rented @$4500 a month and office on upper level is vacant and ready for you to run your business as the other is rented or just have them both rented. Close to Annapolis Mall, Route 50 and much more!
#MDAA2135848

ANNAPOLIS

2563 FOREST DRIVE

None Beds

None Baths

20,173 Sq.Ft.

$899,999

MLS#: MDAA2135848

*** A must-see opportunity in the desirable Eastport Peninsula! This unique property features two attached dwellings in one, offering exceptional flexibility and income potential. The original dwelling, once a charming church, has been thoughtfully converted into a 2-bedroom, 1.5-bath home with an open-concept main level full of character and charm. The second dwelling, located at the rear, is a cozy cottage complete with 1 bedroom, loft, and kitchen —perfect for rental income, guests, or extended family. A truly special property with endless possibilities—don’t miss it!
#MDAA2131796

ANNAPOLIS

200 CHESAPEAKE AVENUE

3 Beds

2 Baths

2,942 Sq.Ft.

$899,900

MLS#: MDAA2131796

New on site 2 days ago
OPEN SATURDAY the 9th 11-1. Floor plan coming soon. Four bedroom with the fourth being a flex space office/guest room.
#MDAA2141488

ANNAPOLIS

1100 BAY RIDGE AVENUE

4 Beds

2 Baths

1,720 Sq.Ft.

$899,000

MLS#: MDAA2141488

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 foundation that was just completed 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.
#MDAA2130056

ANNAPOLIS

1217 HAMPTON ROAD

4 Beds

2 Baths

2,700 Sq.Ft.

$896,000

MLS#: MDAA2130056

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.
#MDAA2134882

ANNAPOLIS

3135 ANCHORAGE DRIVE

5 Beds

3 Baths

3,145 Sq.Ft.

$895,000

MLS#: MDAA2134882

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.
#MDAA2139090

ANNAPOLIS

1106 MAINSAIL DRIVE

5 Beds

2 Baths

2,059 Sq.Ft.

$875,000

MLS#: MDAA2139090

Welcome to this wooded paradise here in Annapolis. Situated on a private, 1.42 acre lot, you're going to love the sun-filled family room and adjacent sunroom. The kitchen has been remodeled with gorgeous, wooded cabinetry, granite counters and high-end appliances. There is a formal living and dining room for all of your functions. The basement has been waterproofed and is walk-out level and ready to be finished. There are three bedrooms upstairs with an open office/loft area. Explore nature or just enjoy the hummingbirds from the back deck and porch. Close to everything, but feels miles away!
#MDAA2143460

ANNAPOLIS

1812 CROSSPOINTE DRIVE

3 Beds

2 Baths

2,792 Sq.Ft.

$875,000

MLS#: MDAA2143460

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.
#MDAA2140616

ANNAPOLIS

1070 FOXCROFT RUN

4 Beds

3 Baths

3,286 Sq.Ft.

$874,995

MLS#: MDAA2140616

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.
#MDAA2143706

ANNAPOLIS

730 CRISFIELD WAY

5 Beds

4 Baths

3,586 Sq.Ft.

$865,000

MLS#: MDAA2143706

New on site 3 days ago
Welcome to this beautifully maintained, newer Colonial (built in 2021) offering the perfect blend of modern design and peaceful privacy in Annapolis. Featuring 5 bedrooms and 3.5 baths, this home delivers the feel of new construction—without the wait. Step inside to discover 9-foot ceilings and a bright, open-concept layout ideal for both everyday living and entertaining. The gourmet eat-in kitchen boasts a spacious island, seamlessly connecting to the inviting family room highlighted by a cozy gas fireplace. A convenient main-level bedroom adds flexibility for guests or multigenerational living. Upstairs, you’ll find a generously sized laundry room and a luxurious primary suite complete with a private ensuite bath. The fully finished basement expands your living space with a large recreation area, den, and full bath—perfect for work, play, or relaxation. Enjoy the outdoors from the newly built 18x18 deck overlooking a flat, half-acre lot that offers exceptional privacy. The backyard is thoughtfully designed with an above-ground pool and a dedicated fire pit area—ideal for gatherings year-round. A newly completed walk and bike path nearby provides easy access to Sandy Point, downtown Cape St. Claire, and Anne Arundel Community College—an incredible amenity for an active lifestyle. Tucked just around the corner from Cape St. Claire, this property offers added space and seclusion while remaining close to everything Annapolis has to offer. Schedule your private showing today and experience all this exceptional home has to offer!
#MDAA2143596

ANNAPOLIS

1402 INSEY RD

5 Beds

3 Baths

3,181 Sq.Ft.

$859,900

MLS#: MDAA2143596

SAVINGS OPPORTUNITY! DON'T FORGET TO ASK US ABOUT THE SELLER 2-1 RATE BUYDOWN! RENOVATED EASTPORT GEM With MODERN COASTAL FINISHES! ABOUT THE HOME: 3 levels of luxury living featuring 4 Bedrooms and 3.5 Bathrooms. Open-concept main level with New Hickory hardwood floors and designer lighting throughout. THE GOURMET KITCHEN: Custom white Shaker cabinetry, modern black hardware, Quartz countertops, oversized center island, and premium stainless appliances with gas cooking. THE PRIMARY SUITE: A rare main-level primary retreat with walk-in closet and spa-like bath featuring custom tile work and glass-enclosed shower. THE FLEXIBLE LOWER LEVEL: Fully finished walk-up basement with a 4th bedroom/office, family room with wood accent wall, and a custom full bath—perfect for a guest or in-law suite. THE EXTERIOR: Iconic white picket fence in front, with cozy front porch, and a private rear yard with beautiful wood privacy fence is expanded by an additional 736 SF (included in sale). New Andersen 100 series windows, Hardie Plank siding, and new hardscaped paths. PARKING: Private driveway with 2 off-street parking spaces. LOCATION: Unbeatable walkability to Downtown Annapolis, Maritime activities, and local favorites. See Annapolis City site for details on the Eastport Choice Neighborhood Initiative! Enjoy all that Eastport has to Offer! Don't Let This One Get Away! Make your Appointment Today! Active Ring Camera on Property.
#MDAA2142230

ANNAPOLIS

152 JEFFERSON STREET

4 Beds

3 Baths

2,282 Sq.Ft.

$850,000

MLS#: MDAA2142230

Significant Price Improvement!! A rare opportunity! Priced to sell, won't last long. Welcome to this beautifully maintained 5 bed, 4.5 bath, colonial home situated on almost a half of acre and only 2 blocks to the Chesapeake Bay where you can hear the sounds of the ships passing by in your backyard! Located in the very desirable and relaxed Oyster Harbor Community. This move-in ready home features: over 3,100 finished sqft, 2 primary suites with private full baths which makes it perfect for multi-generational living. The main level is filled with natural light, cathedral ceilings, and an open layout. The main level primary suite offers a spacious bedroom with costume shutters, a walk-in closet with extra room for storage, and a oversized walk-in shower with floor to ceiling tile, multiple shower heads, and a bench. The upper level features the second primary suite with a full bath, 2 additional bedrooms and another full bath. The huge lower level has multiple rooms including a large rec room that can fit a pool table, games and a bar area, plus a family room or theatre room, a 5th bedroom, and a full bath! There is even space for a kitchenette! The lower level has outside access which would make it perfect for an in-law suite. The backyard is fully fenced in and perfect for summertime entertaining! When spring hits you will be surrounded by green trees; the lot next to the home is a preserved lot. This home is nestled between Oyster Creek, Fishing Creek, and the Chesapeake Bay. Oyster Harbor offers the best of Coastal Maryland living—just minutes from historic downtown Annapolis, top-rated restaurants, shopping, and commuter routes. Quiet Waters Park is only minutes away with walking trails, dog park and beach, concerts, ice skating, and so much more! Walking distance to Thomas Pointe Park. The Coast Guard is just down the street. This home is MOVE-IN READY AND A MUST-SEE!
#MDAA2138708

ANNAPOLIS

3280 ARUNDEL ON THE BAY ROAD

5 Beds

4 Baths

3,144 Sq.Ft.

$850,000

MLS#: MDAA2138708

New on site 4 days ago
Tucked away along a quiet private road, 278 Cape Saint John Road greets you with an understated charm that quietly hints at something far more extraordinary beyond. At first glance, the home feels quaint and unassuming—but as you turn onto the driveway, marked by its whimsical dragonfly mailbox, the experience begins to unfold. Surrounded by lush, manicured greenery, the approach is nothing short of enchanting. Towering glass windows at the main entrance reflect the natural beauty that envelops the property, creating a seamless connection between the home and its serene surroundings. Step inside, and you’re immediately captivated by a breathtaking floor-to-ceiling glass wall that frames the expansive living room. Here, soaring cathedral ceilings elevate the space, while an elegant staircase rises gracefully to the second floor, setting the tone for the home’s architectural beauty. Wander further, and the home reveals itself like a collection of carefully curated surprises. Around each corner, a new feature awaits: a stylish wet bar perfect for entertaining, a thoughtfully designed laundry room, a full bath complete with a luxurious soaking tub, two massive rooms you can use your imagination . A secondary staircase adds both convenience and character, leading seamlessly back to the main level. The living spaces are as generous as they are inviting. Three oversized bedrooms offer comfort and retreat, complemented by a newly renovated bathroom and an updated kitchen designed for both everyday living and effortless hosting. Custom closets add a touch of tailored sophistication, while a sun-drenched entertainment room provides the perfect setting for gatherings or quiet afternoons alike. The home’s spacious foyer welcomes you toward the front entrance, where vibrant flowerbeds and mature trees create a natural sense of privacy—an intimate escape that feels worlds away. And yet, this tranquil haven is ideally located just minutes from the charm and energy of Annapolis, with the Cape Saint John community beach and boat ramp just around the corner. This is more than a home—it’s a hidden retreat where elegance, comfort, and nature exist in perfect harmony.
#MDAA2143268

ANNAPOLIS

278 CAPE ST JOHN ROAD

3 Beds

3 Baths

2,500 Sq.Ft.

$850,000

MLS#: MDAA2143268

Nestled on 2 private acres in Annapolis, this expansive custom-built Cape Cod offers incredible potential for those looking to create their dream home. Featuring a spacious layout, the home includes a main-level primary suite complete with a large walk-in closet, private water closet, and a generous en-suite bath. The inviting family room provides the perfect gathering space and opens to a beautiful stone patio accessible from both the family room and primary bedroom—ideal for indoor-outdoor living. Multiple fireplaces throughout the home, including one in the full-footprint unfinished basement, add warmth and character while offering endless possibilities for future expansion. While the property does require some updates and is being sold as-is, its impressive size, desirable location, and solid custom construction make it a rare opportunity to invest in a truly special home.
#MDAA2142688

ANNAPOLIS

1918 MACKIEBETH COURT

4 Beds

3 Baths

5,117 Sq.Ft.

$849,900

MLS#: MDAA2142688

Priced at $845,000 and positioned as one of the best values in Kingsport, just minutes from Downtown Annapolis, this beautifully maintained 5-bedroom, 4.5-bath home offers nearly 5,000 sq ft of finished living space, exceptional curb appeal, and a thoughtfully designed layout ideal for both everyday living and entertaining. Located directly across from the community pool, clubhouse, playgrounds, and dog walking area, the home offers a combination of convenience and lifestyle that is rarely available at this price point. 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 storage. Included floor plans provide a clear view of the home’s functional layout and flow across all levels, highlighting the spacious room sizes and versatile use of space. Step outside to a beautifully landscaped backyard featuring a brick paver patio surrounded by gardens, creating a peaceful and inviting setting perfect for hosting dinners, BBQs, morning coffee, or relaxing at the end of the day. Well maintained over the years, the home is priced to reflect its features while offering an excellent opportunity for a buyer to personalize and add value in a highly desirable Kingsport location. Seller is seeking clean, competitive offers aligned with current list price, and requests for concessions should be incorporated into the overall offer terms. Recent comparable sales suggest value relatively above the current list price. Seller is ready to make a move and has directed for the home to be sold. Seller requires up to 30 days to secure home of choice.
#MDAA2143208

ANNAPOLIS

712 COYBAY DRIVE

5 Beds

4 Baths

4,230 Sq.Ft.

$845,000

MLS#: MDAA2143208

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