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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

358

# of Listings

3

Avg # of Bedrooms

$482

Avg. $ / Sq.Ft.

$1,113,127

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

133 Properties Found. Page 1 of 9.

Welcome to 711 Genessee Street – where modern luxury meets the heart of Annapolis charm. Located in the coveted West Annapolis School District, this newer construction stunner (built in 2021) offers the perfect blend of upscale finishes, smart design, and unbeatable location—all within walking distance to shops, dining, and everything you love about Annapolis living.
Step inside to find a main level designed for both everyday comfort and effortless entertaining. The open-concept layout is grounded by wide plank wood flooring, enhanced by custom moldings, and anchored by a cozy gas fireplace. The chef’s kitchen is a standout feature, boasting 42” custom cabinetry, quartz countertops, a top-of-the-line appliance package, and a gas cooktop—perfect for everything from weekday meals to weekend gatherings. Custom oak stairs and railings tie the space together with warmth and character.
Upstairs, retreat to your primary suite complete with cathedral ceilings and a spa-like ambiance. The upper level continues the upscale feel with 9-foot ceilings and custom tray ceilings, creating a spacious, airy vibe throughout the bedrooms and baths.
The fully finished lower level adds even more versatility, featuring a large recreation room, an additional bedroom, a full bath, and plenty of storage space—ideal for guests, hobbies, or a second living area.
Outside, enjoy a welcoming front porch that invites morning coffee and neighborhood chats, while the rear paver patio offers the perfect spot for outdoor dining or summer soirées. The fully fenced-in backyard is a private escape, ready for pets, play, or peaceful lounging.
Don't miss your chance to own this thoughtfully upgraded, move-in ready gem in one of Annapolis' most desirable neighborhoods. 711 Genessee Street is more than a home—it’s a lifestyle upgrade.

ANNAPOLIS

711 GENESSEE STREET

4 Beds

3 Baths

3,148 Sq.Ft.

$999,900

MLS#: MDAA2108296

Welcome to 1141 Mainsail Drive, a renovated Classic Colonial style home located in the sought-after Waterfront Community of Anchorage. This 4-bedroom, 2.5-bathroom property has undergone over $200,000 in renovations over the past 20 years while preserving its classic colonial charm. This beautiful corner lot has a newly repaved driveway, a 2-car garage and is only a block away from the amenities which include a 49-slip marina, a boat ramp, an outdoor pool, racks for kayak and paddle boards and a half basketball court.
Many improvements have been done throughout the home including a total refurbishing of the hardwood floors (main level and upper level), fresh paint, upgraded kitchen with marble countertops and stainless-steel appliances, gas line, renovated bathrooms, replacement of windows, roof, siding, gutters, finished basement and water proofing (French drain), laundry room with 2021 washer and dryer, furnace, water heater, well pump, sump pump, sewer line and more.
The tall symmetrical windows in the main level invite light into this classic colonial style layout with a newly painted double-sided masonry wood burning fireplace and an open-layout kitchen. The main level includes a foyer, powder room, family room, living room, dining room and kitchen. The eat-in-kitchen flows seamlessly into “the heart of the home”, the casual dining area and family room, creating an open and inviting space for everyday living. The French doors from the casual dining area lead to a rear brick patio for outdoor entertainment. The 2-car garage is attached to the home with direct entrance into the main level. The upper level features 4-bedrooms, 2-upgraded bathrooms and a den/home office nook. The lower level is a fully finished basement with space for a recreation room, home office and/or fitness area. Also, there is a renovated Laundry / Utility Room with an additional storage space.
Do not miss this opportunity to purchase a renovated colonial in Anchorage as they are a rare find and especially at this price point. Anchorage is a small community (106-homes), with no cut through streets, and mature landscaping. This .34-acres property is 3.5-miles from downtown historic Annapolis, 1-mile from the 340-acre Quiet Waters Park, 35-miles from Washington D.C. and 32-miles from Baltimore.

ANNAPOLIS

1141 MAINSAIL DRIVE

4 Beds

2 Baths

2,176 Sq.Ft.

$985,000

MLS#: MDAA2108692

***Be at the forefront of the Neighborhood Property Expansions and Enjoy the Future Appreciation of
this stunning five-bedroom, three full and one-half bath colonial is located in the Mulberry Hill community. Situated on a large corner lot, this home boasts a covered front porch, rear deck and attached three-car garage. Inside, you will find beautiful hardwood floors, recessed lighting, crown molding and fresh paint throughout. The main level features a formal living room, separate dining room and step-down family room with a gas fireplace and mantel. The spacious, table-space kitchen boasts granite countertops, center island, stainless steel appliances and a bay-window breakfast nook. Upstairs, the primary suite offers a luxurious retreat with hardwood floors, a private bath and a bonus room. Three additional bedrooms with new carpet and an updated full hall bath complete the upper level. The finished, walk-up lower level offers a versatile recreation room, a flexible fifth bedroom, perfect for use as a home office, den or guest room and a full bathroom. Located in a quiet setting, just minutes from the Naval Academy and the Naval Academy Golf Course, yet close to everything that Annapolis has to offer, this home is truly a dream come true!

ANNAPOLIS

1825 JOHNSON ROAD

5 Beds

3 Baths

3,028 Sq.Ft.

$985,000

MLS#: MDAA2098830

Welcome to this 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 coast 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!New Bosch HVAC, and 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 !! 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. 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. WAS TEMP OFF THE MARKET NOVEMBER TO NOW!

ANNAPOLIS

7015 CHESAPEAKE HARBOUR DRIVE 23B

3 Beds

3 Baths

2,041 Sq.Ft.

$985,000

MLS#: MDAA2073518

Eastport Waterfront Condo – 2BR/2BA – 1250 sq ft. 2 outdoor decks – 1 with amazing full city and waterfront view. Open Concept Living Room with cooks kitchen. Living Room has hardwood floors and fireplace. Newer windows and sliding doors with blinds. Full size front loader washer/dryer. Designer style Bathrooms. Community has pool, pier and tennis courts. Walk to town and live the life. Sorry no pets. Non-smoking unit.

ANNAPOLIS

15 PRESIDENT POINT DRIVE B2

2 Beds

2 Baths

1,260 Sq.Ft.

$975,000

MLS#: MDAA2101062

Waterfront Living in Epping Forest with Stunning Views!

Nestled in the exclusive, gated community of Epping Forest, this beautifully maintained 2-bedroom, 2.5-bath home offers serene water views and a relaxed yet sophisticated lifestyle. Designed for effortless living, the open floor plan features 10-foot ceilings, gleaming hardwood floors, and a cozy fireplace in the Great Room. The expansive gourmet kitchen flows seamlessly into the all-season sunroom, complete with dedicated HVAC and stunning water vistas. A convenient half bath and laundry room complete the main level.

Upstairs, the grand owner’s suite boasts an oversized walk-in closet, a spa-like bathroom, and a private deck overlooking the water—perfect for morning coffee or evening sunsets. A spacious guest bedroom (or ideal office/den) with a charming full bath completes the upper level.

Outside, a fully fenced yard provides a secure space for furry friends to play freely. Off-street parking is plentiful, a rare and highly sought-after feature in this private enclave.

Epping Forest is more than a neighborhood—it’s a lifestyle. This vibrant waterfront community offers a marina with direct Severn River access, a private beach, clubhouse with a restaurant, boat club, fishing tournaments, tennis, volleyball, basketball, and year-round social events like oyster roasts, dock parties, summer camps, and holiday celebrations, including spectacular July 4th fireworks.

Located just minutes from major highways, shopping, and Historic Downtown Annapolis, this is a rare opportunity to experience the best of waterfront living. Come discover the charm of Epping Forest and make it your home!

ANNAPOLIS

336 SEVERN ROAD

2 Beds

2 Baths

1,708 Sq.Ft.

$975,000

MLS#: MDAA2110674

Incredible PRIVATE oasis, in sought after community of Winchester on the Severn. One of a kind home, surrounded by protected lands. One of the highest and largest lots in the community, overlooking the wooded glen. Custom hardscaping with multi level decks, and numerous stone patios. Enjoy the tiered golf putting green and the outdoor spa hot tub! There are 2 beautiful sunroom additions on the back of the house, allowing nature to flow in. The windows and french style doors through-out affording light to flow and tree top views. Quality interor features include hardwood and marble flooring, custom cherry built-ins, in-law/au pair suite (that could serve as a optional second primary suite), featuring interior and exterior entry. Double covered carport parking and additioanl parking in driveway for several vehicles. Vaulted beamed ceilings, masonry fireplace and more! Community has a voluntary association of $260/yr. for use of community water amenities. Chase Creek Swim Club within walking distance. Explore miles of trails on foot or by bike, on the nearby Annapolis Baltimore Trail.

ANNAPOLIS

1534 CIRCLE DRIVE

5 Beds

3 Baths

3,230 Sq.Ft.

$975,000

MLS#: MDAA2108900

New on site today

Stunning contemporary home in Winchester on the Severn featuring abundant windows that provide private treetop views. Situated at one of the highest elevations, the property is surrounded by parkland and overlooks wooded areas. Enjoy multi-level decks, stone patios, and custom hardscaping, complete with a private putting green and hot tub. The community offers a voluntary association fee of $260 per year for access to amenities, including a private beach, dock, boat slips, canoeing, and a beach club. The Chase Creek Swim Club is also nearby. A true gem!

ANNAPOLIS

1534 CIRCLE DRIVE

5 Beds

3 Baths

2,316 Sq.Ft.

$975,000

MLS#: MDAA2116724

Welcome to this bright and beautiful 4-bedroom, 2.5-bath colonial tucked in the trees with timeless curb appeal and room to grow.
From the moment you pull into the wide driveway and see the wraparound front porch, you'll feel right at home.
Step inside to find freshly updated spaces filled with natural light—wood floors, neutral paint, and a welcoming layout that flows effortlessly from room to room. The main level includes a spacious living room, formal dining area, and a sun-soaked family room with floor-to-ceiling windows that bring the outside in.
The kitchen is a true highlight with sleek white cabinetry, updated appliances, and a wall of windows overlooking the backyard—ideal for morning coffee or prepping meals while enjoying the view. Upstairs, all four bedrooms are generously sized, including a serene primary suite with a private bath. The bathrooms are updated and well-maintained.
Outside, the large back deck and wraparound porch provide the perfect setting for outdoor dining, relaxing with a book, or entertaining friends. The 2-car garage adds convenience and extra storage space. And to top it off, you’ll have access to the newly renovated Bay Ridge pool club—your own nearby getaway during the warmer months.
This home offers a peaceful setting, stylish updates, and plenty of space to make your own. Don’t miss it!

ANNAPOLIS

1206 SOUTHWIND COURT

4 Beds

2 Baths

2,964 Sq.Ft.

$975,000

MLS#: MDAA2113764

Welcome to 712 Pearson Point Place—The best lot location in Kingsport! This beautifully maintained property is ideally situated in a sought-after pool and dock community with scenic walking paths. Featuring five spacious bedrooms, four bathrooms, fully finished basement, and a stylish, functional layout, this home offers both comfort and elegance. Enjoy light-filled living spaces, a well-appointed/updated kitchen, and inviting outdoor area perfect for relaxing or entertaining. With top-tier community amenities just steps away, this is Kingsport living at its finest!

ANNAPOLIS

712 PEARSON POINT PLACE

5 Beds

4 Baths

5,184 Sq.Ft.

$970,000

MLS#: MDAA2113996

Price Reduction to this former model home in Kingsport! Step into an inviting two story foyer that sets the tone for the entire residence! This home offers a blend of elegance and functionality. Many updates have been done by current homeowners. A three story, three-sided brick home on a corner lot that emanates timeless elegance. This home has two inviting front porches for relaxation. Entering the two story foyer with marble floor, you will see framed mirrors, and a Juliet balcony. A formal living room, hardwood floors, and one of three gas fireplaces. A bay window for your grand piano, or to sit with morning coffee. The dining room, includes a mirrored wall, and hardwood floors. A half bath with marble tile floor is off the living room. An open concept kitchen, family room, laundry room and pantry are situated towards the back of the home. The kitchen is an entertainer's dream with a large two level granite island with cooktop, hardwood floors, and a double wall oven for your holiday baking! A walk-in pantry with ample shelving. The family room has floor to ceiling windows, hardwood floors, and the second gas fireplace situated next to built in glass shelves. The family room looks out on a private enclosed fenced back yard with a two level gray slate patio to enjoy the gardens.
On the second level, you will find a split hallway with hardwood floors. The primary bedroom, includes an attached bathroom which was updated in March 2022; a soaking tub with jets and a walk-in shower with dual shower heads, dual sink vanities, quartz counter tops. The primary bedroom, has a ten foot tray ceiling, ceiling fan, recessed lighting, wainscoting, two walk-in closets, and a sitting area for relaxing. There are three other bedrooms on the upper level, the largest of the three features a private porch, hardwood floors, private bath with tub/shower, and ceramic tile floor. Perfect for visitors. Another bedroom features built-in bookshelves. The last of the four bedrooms overlooks the upstairs porch.
The lower level is fully finished. A family room with built in counter w/cabinets, wainscoting, an egress window. Another room serves as a bonus room or flex room that could be used as a fifth bedroom, and is currently used as a gym, with a wall of mirrors, built-in counter with shelving and drawers. There is also a home office that is a homeowners dream, with built in bookcases, shelving to store your books, and the third gas fireplace. Another room currently used for storage, can be used for hobbies, or to store your wine. A full bathroom is also located on the lower level. Crown molding throughout enhances the character of this home.
Two new Air Conditioner Units- August 2017 and July 2019. Duct cleaning - March 2024, New Roof-Oct.-2019, Hardwood floors on main floor and stairs were refinished-May 2024. Kitchen counter to match kitchen island granite w/new sink April 2025. Sound surround throughout the house to include the outdoor patio. Central Vac, Sprinkler System, 75 Gallon Hot Water Tank- February 2022, Hot/cold water faucet in the garage, Security system.
A community pool, two tot lots, walking trails, water access to Church Creek, dock, kayak launch, and kayak storage.
Convenient to Rt.50/97 to D.C., Baltimore, Bay Bridge and beaches. 3.2 miles to Naval Academy, and historic downtown Annapolis.

ANNAPOLIS

709 PILOT HOUSE DRIVE

4 Beds

4 Baths

4,494 Sq.Ft.

$959,900

MLS#: MDAA2111234

New on site 1 day ago

🏡 1367 Cedar Avenue – Modern Comfort Meets Coastal Charm

Set on a beautifully landscaped corner lot just two blocks from Fishing Creek, this 5-bedroom, 3.5-bath updated craftsman colonial in Arundel on the Bay is the kind of home that instantly makes you feel at ease. Think breezy porch mornings, backyard cookouts, and friendly neighborhood waves—it’s Annapolis living at its best.

The welcoming slate front porch leads you into a light-filled main level with an open-concept layout that’s perfect for entertaining or simply enjoying everyday life. The expanded gourmet kitchen is the heart of the home, featuring quartz countertops, stainless appliances, a big island/breakfast bar, Restoration Hardware lighting, and custom soft-close cabinetry. Off the foyer, a cozy window seat invites you to curl up with a book or a coffee. The main-level office (or 5th bedroom!) faces the front and includes custom built-in cabinetry—ideal for guests, work-from-home days, or creative projects.

Upstairs, you’ll find four generous bedrooms with custom-designed closets, plus a newly added Kohler walk-in Jacuzzi tub in the hall bath—perfect for relaxing soaks or added accessibility.

Downstairs, the fully finished lower level adds even more flexibility with a spacious rec room, full bath, laundry, workshop, and a large storage room—everything you need, right where you need it.

Step outside and the fun continues! The fenced backyard was designed for gathering and play, featuring a custom HardiePlank deck with a built-in grill, storage bar, and room to lounge or entertain. There’s a Wi-Fi-controlled irrigation system, a professionally manicured lawn, and an expanded stamped concrete driveway. The oversized garage includes smart built-in storage, and the 20kW whole-home generator ensures you’re never left in the dark.

This smart home also includes a Nest thermostat, video doorbell, dual-zone HVAC, and automatic lighting—because convenience is a luxury too.

Living in Arundel on the Bay means more than just enjoying the beach and pier (though they’re pretty great). With a boat ramp, kayak racks, playground, basketball court, and community events like paddleboard yoga, movie nights, and summer beach parties, this neighborhood is as fun and welcoming as they come.

ANNAPOLIS

1367 CEDAR AVENUE

5 Beds

3 Baths

3,036 Sq.Ft.

$949,000

MLS#: MDAA2116610

Living in Shearwater is truly a dream, offering the perfect blend of leisure, recreation, and waterfront serenity. This exclusive gated community boasts top-tier amenities, including a deep water marina, dinghy floating dock, kayak launch, pickleball, tennis, racquetball courts, and a stunning waterfront pool. Conveniently located, it's an easy, nice walk, bike ride, or water taxi trip to downtown. For outdoor enthusiasts, kayaking right from your doorstep adds to the unparalleled lifestyle. This beautifully appointed waterfront terrace condominium provides the convenience of one-level living with 1855 sq. ft. of thoughtfully crafted space, ensuring comfort and southwest exposure. The Kitchen includes a handsome kitchen bar, perfect for entertaining friends or enjoying a glass of wine while cooking up your favorite meal. The sleek, modern design is complemented by high-end induction cooking, offering precision and efficiency for the discerning home Chef. Well-appointed walk-in pantry. A sliding glass door in the kitchen leads to an ample alfresco area ideal for entertaining and grilling. The generous living room invites relaxation with a cozy wood-burning fireplace. Cozy nook with window seat . The roomy laundry room provides additional storage. Private office nook off the Primary suite, perfect nook for working from home, managing daily tasks, tucked away for privacy yet conveniently accessible. Observe blue herons, egrets, ducks, and bald eagles from your garden terrace. There are boat slips available depending on size and water depth. The cost of $62 per foot of overall boat length per year. Most slips are 15-18 wide. Depth ranges 6-8 ft MLW. Power and water included. The marina includes 34 slips owned by the Shearwater Association, as well as 28 slips that are deeded to Condominium Owners. Other facilities owned by the Association include 13 spaces for dinghies and 42 spaces for kayaks. Electricity and water are available to all users of the marina facilities at no charge. Dinghies $195 per year - Kayaks $100 per year. LCE slip owners may also rent their slips to other condominium owners or tenants. Contact the Dockmaster for all information regarding resident and guest slip availability. Spa Creek is one of the most sought-after waterways in all of Annapolis, taking you to downtown Ego Alley. Perfect spot to watch the Parade of Lights in December, a tradition in Annapolis. And best of all, it's nestled along the waterfront, offering peaceful mornings and golden hour views and the kind of lifestyle that turns every day into a getaway.

ANNAPOLIS

3 SPA CREEK LANDING A

2 Beds

2 Baths

1,855 Sq.Ft.

$948,000

MLS#: MDAA2112968

• Eclectic downtown location with 8 on-site parking spaces
• Unit has a reception/bullpen area, 5 offices, a kitchen that seats 4, copy/fax room and 2 restrooms (one with shower)
• Upgraded finishes and systems throughout
• Close proximity to Maryland State House, Circuit Court, State Office Buildings, United States Naval Academy, Annapolis City Dock, and St. John’s College
• Walking distance to Rams Head Bar & Grill, El Toro Bravo, Level, Tsunami, and various retail shops and services
• Taxes for the unit are $10,040 annually
• MX zoning, permitting uses of office, retail, restaurants, galleries, and laboratories.

ANNAPOLIS

79 WEST STREET 1

None Beds

None Baths

N/A

$940,000

MLS#: MDAA2110468

New on site 4 days ago

An incredible opportunity with endless potential awaits! This 3-bedroom, 3-bath home sits on an elevated 3 acres, offering expansive views of Mill Creek and is surrounded by mature trees for a serene, private setting. Whether you're looking to enjoy the existing solidly built home, renovate, or expand - this property provides the space and flexibility to create your dream retreat. Take advantage of water views without the cost of waterfront taxes! Three marinas are just minutes from your doorstep, making this an ideal location for boating enthusiasts. Built by a member of the renowned Willard family, whose craftsmanship helped shape the Chesapeake Bay deadrise fishing boat, this property carries a rich history and offers a rare chance to create something truly special. The home itself features hardwood floors, beamed ceilings, and a screened-in porch - all positioned to capture the scenic surroundings. With a little thinning of the underbrush, you’ll have stunning water views from most rooms! Looking for even more potential? The adjoining lot (Lot #1) is 90% approved. Both properties have met all health department requirements, with the final piece being a public water extension along the existing house frontage. The subdivision is not at record plat and has been taken as far as the current owner is willing to go but all of the legwork to get it to this point will convey.
This is more than just a home—it’s a unique opportunity to craft your dream estate in a prime Annapolis location. Don’t miss out—schedule your showing today to explore the possibilities!

PLEASE NOTE: The home does have a moisture issue, and the HVAC system is not currently functioning. Call agent for more info. Documentation for the subdivision efforts can be emailed. The property does fall within the Chesapeake Bay critical area. Per the proposed subdivision plat a forest conservation easement would be imposed with the approval of the subvision. The home is being sold strictly as-is, where is. Any inspections for buyer's information only.

ANNAPOLIS

1634 ORCHARD BEACH ROAD

3 Beds

3 Baths

2,868 Sq.Ft.

$930,000

MLS#: MDAA2116058

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