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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
401
# of Listings
3
Avg # of Bedrooms
$449
Avg. $ / Sq.Ft.
$1,097,261
Med. List Price

Browse Annapolis Real Estate Listings

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$3M - $5M

Over $5M

136 Properties Found. Page 1 of 10.

This stunning log home on 2.48 scenic acres (with the potential to subdivide) offers the perfect blend of rustic elegance and thoughtful upgrades. Surrounded by lush landscaping, the property provides treetop views and a glimpse of the water during the winter months. The impressive two-story living room showcases a dramatic wood-burning fireplace and flows effortlessly into the dining area and the gourmet kitchen, which features granite countertops, a breakfast bar, ample cabinet space, and all major appliances. Three generously sized bedrooms are located on the main level, each with gleaming hardwood floors. The primary suite includes a ceiling fan, walk-in closet, a spa-like bathroom with a soaking tub and separate shower, and private access to the deck. Upstairs, a sunlit loft with oversized skylights offers flexible space for a home office, family room, or den and includes a full bathroom. The finished basement adds even more living space, with a spacious recreation room featuring wall-to-wall carpeting and recessed lighting, a fourth bedroom, a laundry area, and plenty of storage. Outdoor living is just as inviting, with a large rear deck that backs to wooded privacy and a welcoming front paver walkway and deck. The driveway provides ample parking, and the home is just a short walk from community beach access. Ideally located near major highways and downtown Annapolis, this home offers tranquil surroundings with convenient access to shopping, dining, and everyday necessities.
#MDAA2113476

ANNAPOLIS

2977 SOUTHAVEN DRIVE

4 Beds

4 Baths

3,200 Sq.Ft.

$1,000,000

MLS#: MDAA2113476

NEW PRICE! Live the Annapolis lifestyle just close enough to enjoy in-town living, but tucked away in a quiet little enclave avoiding all the noise and parking challenges in town. The current homeowner refers to Primrose Hill as a serene little gem. Walk to coffee shops and dining hot spots, launch the boat or hop on the water taxi right up the street. This distinguished Georgian-style home offers the best of both worlds peaceful, private living with unparalleled access to the city's most desirable amenities. The HOA cares for the lawn and snow removal, just lock and leave and head out of town stress free! Originally the model home for the community, every inch of this residence reflects elevated design and attention to detail a discerning buyer would expect. The timeless Georgian brick front exudes classic charm, while the interior reveals a sophisticated, modern aesthetic. A sleek, designer kitchen with upgraded appliances flows effortlessly into an open-concept main living area ideal for entertaining or relaxed everyday living. The inviting family room is anchored by custom built-ins and a gas fireplace, adding warmth and architectural interest. This 5-bedroom, 4.5-bath home is designed for comfort and style. The upper-level features four spacious bedrooms, including a luxurious owners suite with cathedral ceilings, an expansive walk-in closet, and a spa-inspired bathroom retreat. Bedroom two boasts its own private ensuite, offering flexibility for guests or multigenerational living. A conveniently located upstairs laundry enhances everyday functionality. The fully finished lower level includes a generous recreation room and a versatile bonus roomperfect for a home gym, office, or guest bedroom. A rare two-car garage with additional driveway parking adds convenience, especially valuable in this in-town location. Residents enjoy exclusive access to nearby amenities such as the Pip Moyer Recreation Center with tennis and pickleball courts, fitness classes and a swim club. The park like setting and intentional green spaces serve as the perfect backdrop for weekly neighborhood wine nights and social gatherings throughout the year fostering a welcoming and connected sense of community. This location provides a quick commute to DC and Baltimore. CHECK OUT THE VIRTUAL TOUR
#MDAA2113794

ANNAPOLIS

52 PRIMROSE HILL LANE

5 Beds

4 Baths

3,978 Sq.Ft.

$999,999

MLS#: MDAA2113794

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.
#MDAA2108296

ANNAPOLIS

711 GENESSEE STREET

4 Beds

3 Baths

3,148 Sq.Ft.

$999,900

MLS#: MDAA2108296

Recently updated colonial with all new custom kitchen cabinets, stainless appliances, dual oven w/gas cooktop. Family room with built in surround sound speakers-bring your own equipment. Primary suite with custom bath large shower with dual heads, nice soakiing tub, border-lighted mirror and a towel warming bar. Laundry closet on 2nd floor. Parrtial unfinished basement with utilities plus space for a possible movie/man cave. Attached oversized 2 car garage with extra storage area. 3 car-plus garage 10' doors 13' ceilings, car lift-great for those do-it-yourself folks, tons of space above to finish for rooms-in-law/teenage apartment! House sits on a double lot space for a pool? Plenty of room for boats, RV's or other toys? Access to back of lot by a gravel driveway
#MDAA2111664

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

2,142 Sq.Ft.

$999,900

MLS#: MDAA2111664

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!
#MDAA2073518

ANNAPOLIS

7015 CHESAPEAKE HARBOUR DRIVE 23B

3 Beds

3 Baths

2,041 Sq.Ft.

$985,000

MLS#: MDAA2073518

***BEST VALUE!!*** Discover this 𝒃𝒆𝒂𝒖𝒕𝒊𝒇𝒖𝒍 𝒇𝒊𝒗𝒆-𝒃𝒆𝒅𝒓𝒐𝒐𝒎, 𝒕𝒉𝒓𝒆𝒆-𝒂𝒏𝒅-𝒂-𝒉𝒂𝒍𝒇-𝒃𝒂𝒕𝒉 𝒄𝒐𝒍𝒐𝒏𝒊𝒂𝒍 on a spacious corner lot in sought-after Mulberry Hill. Perfectly located at the forefront of neighborhood growth, this home offers instant luxury with incredible future potential! Enjoy a 𝒘𝒆𝒍𝒄𝒐𝒎𝒊𝒏𝒈 𝒄𝒐𝒗𝒆𝒓𝒆𝒅 𝒇𝒓𝒐𝒏𝒕 𝒑𝒐𝒓𝒄𝒉, 𝒓𝒆𝒂𝒓 𝒅𝒆𝒄𝒌, 𝒂𝒏𝒅 𝒂𝒏 𝒐𝒗𝒆𝒓𝒔𝒊𝒛𝒆𝒅 𝒕𝒉𝒓𝒆𝒆-𝒄𝒂𝒓 𝒈𝒂𝒓𝒂𝒈𝒆. Inside, you’ll love the 𝒉𝒂𝒓𝒅𝒘𝒐𝒐𝒅 𝒇𝒍𝒐𝒐𝒓𝒔, 𝒇𝒓𝒆𝒔𝒉 𝒑𝒂𝒊𝒏𝒕, 𝒄𝒓𝒐𝒘𝒏 𝒎𝒐𝒍𝒅𝒊𝒏𝒈, 𝒂𝒏𝒅 𝒓𝒆𝒄𝒆𝒔𝒔𝒆𝒅 𝒍𝒊𝒈𝒉𝒕𝒊𝒏𝒈 throughout. The main level boasts a formal living and dining room, plus a cozy family room with a 𝒈𝒂𝒔 𝒇𝒊𝒓𝒆𝒑𝒍𝒂𝒄𝒆. The 𝒖𝒑𝒅𝒂𝒕𝒆𝒅 𝒌𝒊𝒕𝒄𝒉𝒆𝒏 features granite counters, a center island, stainless steel appliances, and a bright bay-window breakfast nook. Upstairs, the 𝒑𝒓𝒊𝒎𝒂𝒓𝒚 𝒔𝒖𝒊𝒕𝒆 is a true retreat with hardwood floors, a private bath, and a bonus room. Three additional bedrooms with new carpet and an updated full bath complete the upper level. The 𝒇𝒊𝒏𝒊𝒔𝒉𝒆𝒅 𝒘𝒂𝒍𝒌-𝒖𝒑 𝒍𝒐𝒘𝒆𝒓 𝒍𝒆𝒗𝒆𝒍 offers a versatile rec room, a fifth bedroom perfect for an office or guest room, and a full bath. All this in a 𝒒𝒖𝒊𝒆𝒕 𝒄𝒐𝒎𝒎𝒖𝒏𝒊𝒕𝒚 𝒋𝒖𝒔𝒕 𝒎𝒊𝒏𝒖𝒕𝒆𝒔 𝒇𝒓𝒐𝒎 𝒕𝒉𝒆 𝑵𝒂𝒗𝒂𝒍 𝑨𝒄𝒂𝒅𝒆𝒎𝒚, 𝒈𝒐𝒍𝒇 𝒄𝒐𝒖𝒓𝒔𝒆, 𝒂𝒏𝒅 𝒆𝒗𝒆𝒓𝒚𝒕𝒉𝒊𝒏𝒈 𝑨𝒏𝒏𝒂𝒑𝒐𝒍𝒊𝒔 𝒉𝒂𝒔 𝒕𝒐 𝒐𝒇𝒇𝒆𝒓. Don’t miss this incredible opportunity!
#MDAA2119682

ANNAPOLIS

1825 JOHNSON ROAD

5 Beds

3 Baths

3,028 Sq.Ft.

$979,900

MLS#: MDAA2119682

***BEST VALUE!!*** 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!
#MDAA2098830

ANNAPOLIS

1825 JOHNSON ROAD

5 Beds

3 Baths

3,028 Sq.Ft.

$979,900

MLS#: MDAA2098830

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.
#MDAA2101062

ANNAPOLIS

15 PRESIDENT POINT DRIVE B2

2 Beds

2 Baths

1,260 Sq.Ft.

$975,000

MLS#: MDAA2101062

Welcome to this absolute gem in the Eastport area of Annapolis, MD. This 4 bedroom / 2 bath main house was built in 1912, but has a lot of modern updates. A Large 13,000+ sq.ft. Lot offers room for off street parking and a beautiful patio and pond in the back yard. Make your way thru the back yard to a 2 story building perfect for an office / art studio, complete with it's own kitchen and bathroom. This is a truly unique property that wont last long !
#MDAA2119368

ANNAPOLIS

915 JACKSON STREET

4 Beds

2 Baths

1,956 Sq.Ft.

$975,000

MLS#: MDAA2119368

Stunning contemporary in Winchester on the Severn featuring abundant windows that provide lovely views. Enjoy multi-level decks, patios, and custom hardscaping, complete with a private putting green and hot tub. Main level includes foyer, large sunroom, living room with stone fireplace - dining room combination, kitchen with granite countertops, main bedroom with adjoining full bath, 2 additional bedrooms and full bath in hall. The lower level includes another sunroom with exit to the rear yard, recreation room, study, and another very spacious room (potential 4th bedroom) with super bath and side exit. A real beauty! The Winchester on the Severn community offers a voluntary association fee of $260 per year for access to amenities, including a private beach, dock, canoeing, playground, and covered picnic pavilion . The community also has 2 different areas with boat slips that when available can be rented for an additional fee. The Chase Creek Swim Club is also nearby and joinable for an additional fee.
#MDAA2116724

ANNAPOLIS

1534 CIRCLE DRIVE

4 Beds

3 Baths

2,316 Sq.Ft.

$975,000

MLS#: MDAA2116724

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.
#MDAA2108900

ANNAPOLIS

1534 CIRCLE DRIVE

5 Beds

3 Baths

3,230 Sq.Ft.

$975,000

MLS#: MDAA2108900

Price Reduction: 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.
#MDAA2108692

ANNAPOLIS

1141 MAINSAIL DRIVE

4 Beds

2 Baths

2,176 Sq.Ft.

$970,000

MLS#: MDAA2108692

Welcome to 3 Constitution Square in the desirable Murray Hill/Spa West neighborhood of Annapolis. This charming, updated 3 bedroom, 2 bath home features an open floor plan with America cherry hardwood floors. The stunning kitchen with LG appliances is the place to create an amazing meal. Custom wood cabinets, marble countertops, LG appliances- including a magnetic induction stove and an under sink 3 stage water filter are just a few of the thoughtful additions you will find in this kitchen designed for the home chef. A family room off of the kitchen opens to a deck and the backyard. Retreat to the primary suite with a perfectly appointed bathroom with glass stall shower. Bedroom 2 and 3 have access to the hall bathroom with deep soaking tub. The lower level offers a versatile den/office or second family room, a recreation room and large utility space. Step outside to the beautifully landscaped, fenced backyard. Enjoy a summer BBQ or gardening in the raised beds. Just moments from Amos Garret Park, catch the water taxi to downtown or launch your kayak for a paddle. This home offers easy access to Annapolis shops, restaurants and waterfront attractions- combining comfort, style and location in one perfect package. Other features of this home include: * Generac whole house generator * BGE Home Performance Energy Star gold award, * basement waterproofing * fully encapsulated attic * 10'x12' insulated shed
#MDAA2120272

ANNAPOLIS

3 CONSTITUTION SQUARE

3 Beds

2 Baths

1,903 Sq.Ft.

$950,000

MLS#: MDAA2120272

Nestled in sought-after Kingsport, this impeccably maintained residence offers a rare combination of comfort, style, and convenience. Kingsport residents enjoy exclusive access to a private pool, community dock, and beautifully landscaped walking trails—perfect for morning jogs, evening strolls, or weekend paddle-boarding adventures. This expansive home features five generously sized bedrooms and four and a half bathrooms, thoughtfully designed to accommodate both daily living and entertaining. The fully finished basement offers flexible space ideal for a media room, home gym, guest suite, or playroom. Inside, the open-concept floor plan flows effortlessly, enhanced by an abundance of natural light, high ceilings, and elegant architectural details. At the heart of the home, the updated gourmet kitchen boasts modern appliances, ample counter space, and stylish finishes—making it a dream for both casual cooks and culinary enthusiasts. The adjoining living and dining areas create a welcoming space for gatherings of any size. Step outside to a serene slate patio, perfectly positioned for outdoor dining, entertaining, or simply unwinding with a glass of wine as the sun sets. Eco-conscious buyers will appreciate the hidden rear solar panels, delivering significant energy savings while preserving the home’s clean exterior aesthetic. With top-tier amenities just steps from your front door and community pride that’s second to none, 712 Pearson Point Place is more than a home—it’s a lifestyle. Don’t miss your chance to experience the very best of Kingsport living.
#MDAA2113996

ANNAPOLIS

712 PEARSON POINT PLACE

5 Beds

4 Baths

5,184 Sq.Ft.

$950,000

MLS#: MDAA2113996

Charming Brick Colonial in Prime Annapolis Location! Welcome to this beautifully maintained 2-story brick home on sought-after Ebb Point Ln in Annapolis, MD. Perfectly situated just minutes from the U.S. Naval Academy, Annapolis Mall, and downtown waterfront attractions, this home offers the best of convenience and charm. Boasting 4 spacious bedrooms and 3.5 baths, including a desirable main-level primary suite with a walk-in closet and a private ensuite bath, this home is designed for both comfort and functionality. The main level features a bright and airy formal living room and dining room, along with a large family room complete with built-in cabinetry and a cozy gas fireplace—ideal for entertaining or quiet evenings at home. Enjoy cooking in the well-appointed kitchen with ample counter space and direct access to the wood deck, perfect for outdoor dining and summer gatherings. The partially finished basement offers great potential for a rec room, home office, or gym. Additional highlights include a 2-car garage, a paved driveway, and mature landscaping that enhances the home’s curb appeal. Located in the highly regarded Anne Arundel County Public Schools district—zoned for Rolling Knolls Elementary, Bates Middle School, and Annapolis High School. Don’t miss this rare opportunity to own a classic Annapolis home with timeless character and modern conveniences in a prime location!
#MDAA2116784

ANNAPOLIS

244 EBB POINT LANE

4 Beds

3 Baths

3,103 Sq.Ft.

$950,000

MLS#: MDAA2116784

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