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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
384
# of Listings
3
Avg # of Bedrooms
$476
Avg. $ / Sq.Ft.
$1,085,905
Med. List Price

Browse Annapolis Real Estate Listings

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

384 Properties Found. Page 11 of 26.

Commercially zoned C-1 pad site available adjacent to McDonald's and Wendy's. Just shy of 1 acre. Public Utilities. Great visibility from Rt. 50. Build your office building, a restaurant, retail center, mixed use building, residential apts or condos over ground floor commercial, etc. See documents section for more information.
#MDAA2018250

ANNAPOLIS

1440 WHITEHALL ROAD

None Beds

None Baths

0.92 acres

$749,900

MLS#: MDAA2018250

Nestled in a tranquil corner of Annapolis, this expansive ¾-acre property offers a rare combination of privacy, natural beauty, and opportunity. With serene water views and a peaceful setting, the generous lot size may allow for subdivision—offering the flexibility to build a second home while retaining the existing residence or reimagine the space entirely. Ideally situated near local marinas and the Annapolis sailing school, this location is perfect for boating enthusiasts. Residents can enjoy the quiet surroundings while being just minutes from downtown Annapolis’ renowned dining, shopping, and waterfront attractions. A truly special offering in one of Maryland’s most desirable areas. See residential listing. MLS is MDAA2108602. See property boundary maps and tons of title info in the document section.
#MDAA2108878

ANNAPOLIS

7033 BEMBE BEACH ROAD

None Beds

None Baths

0.78 acres

$749,900

MLS#: MDAA2108878

Nestled in a tranquil corner of Annapolis, this expansive ¾-acre property offers a rare combination of privacy, natural beauty, and opportunity. With serene water views and a peaceful setting, the generous lot size may allow for subdivision—offering the flexibility to build a second home while retaining the existing residence or reimagine the space entirely. Ideally situated near local marinas and the Annapolis sailing school, this location is perfect for boating enthusiasts. Residents can enjoy the quiet surroundings while being just minutes from downtown Annapolis’ renowned dining, shopping, and waterfront attractions. A truly special offering in one of Maryland’s most desirable areas. See Land Listing as well. MLS is MDAA2108878. See property boundary maps and tons of title info in the document section.
#MDAA2108602

ANNAPOLIS

7033 BEMBE BEACH ROAD

2 Beds

1 Baths

792 Sq.Ft.

$749,900

MLS#: MDAA2108602

1.485 acre RLD zoned parcel/ lot available adjacent to McDonald's, Wendy's. Potential uses include daycare, veterinarian, assisted living, club, group home, kennel, plant nursery, produce stand, etc. All utilities are available. Easy access on and off of Rt. 50. Refer to documents section.
#MDAA2018258

ANNAPOLIS

1444 WHITEHALL ROAD

None Beds

None Baths

1.49 acres

$749,900

MLS#: MDAA2018258

Step into Luxury Living in this beautiful ground level 2 bedroom 2 bathroom condominium at 5 Park Place, Annapolis' most coveted address. You'll be delighted from the moment you approach the impressive building and impressed again and again by all of the features and amenities that are included for you here. Step inside the grand lobby and your own front door is just a few short steps away! Inside find an open flowing floor plan with everything you could want, all on one level! The living room is spacious and features a handsome gas fireplace, hardwood flooring and sliding glass door to your very own private balcony. The balcony includes space for seating and is a rare find in the building! Enjoy the elegant kitchen with solid wood cabinets, stainless steel appliances and gleaming granite countertops. Enjoy meals in the dining area or by the breakfast bar. The guest suite is large and features 2 closets and direct access to the convenient guest bathroom. The primary suite is neutral and oversized with a wonderfully large walk-in closet and full primary bathroom with double sinks. 2 Garage parking spots are included as well as a valuable bonus garage storage space! Park Place residents enjoy so many conveniences including an outdoor pool, impressive gym, party room, billiards room, several decorated spaces and meeting rooms, a outdoor paths, dog park area, dedicated building manager, a trolly to take you Downtown and more! See it today!
#MDAA2100262

ANNAPOLIS

5 PARK PLACE 102

2 Beds

2 Baths

1,208 Sq.Ft.

$748,000

MLS#: MDAA2100262

This stunning penthouse in an exclusive 55+ community offers low-maintenance living a few minutes from Annapolis. The expansive fourth-floor corner unit offers a quiet respite from everyday life. Nine-foot upgraded tray ceilings and plank flooring add an elegant touch throughout. LVL flooring throughout the unit. The gourmet kitchen is an entertainer's dream with a huge island, stunning countertops, tile backsplash, and tons of quality cabinetry. Upgraded kitchen appliances. Kitchen faucets are "touchless". Samsung high-efficiency washer/dryer included. The living and dining area offers room for large seating areas for relaxing in front of the game and a dedicated space for gracious dining. Pendant lights over kitchen peninsula, dining room Two bedrooms each feature an ensuite bath with high-quality finishes and a spa-like feel. The two bedrooms are separated with a long hallway for optimum privacy, and each has customized closets in the owner suite step in, spare bedroom. Also custom shelving in the pantry and guest bathroom. There are two bonus living spaces that can be used for additional sleeping areas, exercise/media room, or offices. Custom-built cabinets in the space next to "owners' suite". Three ceiling fans included. The Element at Mill Creek offers a fitness center, golf/sports simulator, and walking trails. Pickleball courts and a dog park are in the works. With a secure entry, garage parking, and elevator access, life is safe and easy! Assigned garage space (#CG-24) is included and valued at $25,000. Assigned storage cage (#26) is included. You will be a hop, skip, and a jump from Annapolis and restaurants and waterfront activities. You will have quick access to Route 50 and major arteries.
#MDAA2113036

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 411

2 Beds

2 Baths

1,723 Sq.Ft.

$740,000

MLS#: MDAA2113036

Come see this great 3 bedroom, 3.5 bath rancher set on 2 acres located in the highly sought after neighborhood of Rolling hills located close to Historic Annapolis and convenient to shopping, restaurants and health care! The beautiful spacious kitchen is a welcoming place for entertaining and is complete with a large island with a cooktop with a downdraft, stainless steel appliances that include a wall oven and built-in microwave, dishwasher and refrigerator and TONS of counter space. The kitchen also has plenty of room for a large kitchen table. Next to the kitchen is the large dining room with its crystal chandelier, huge bay window to let in all of the light and also has chair molding. Also off of the kitchen is the laundry room that doubles as a powder room as well. There is where you will find the door out to the large 2-car garage. The kitchen also has a door out to the deck with steps down to your new amazing IDEAL backyard, where you will find out why the neighborhood is called Rolling Hills. The views are over the top! Back inside, the family room is spacious and has the door out to the 3-season room where you can enjoy views of the backyard again, and you'll love the vaulted ceiling with a ceiling fan, surrounded with windows and a slider out to the deck again. The main level also has the primary suite with an en suite bathroom , ceiling fan and 2-closets. The 2nd bedroom is also on the main level plus a 2nd full bathroom for guests. The lower level has the 3rd bedroom with a ceiling fan and 3rd full bathroom that has an expansive custom built shower with a seamless glass enclosure, pedestal sink and custom tile throughout. The lower level also has a HUGE 2nd family room with porcelain tiled flooring to look like hardwood, wood-burning stove, recessed lighting, crown molding and a slider out to the large covered concrete patio. The lower level also has a large storage room. There is also a separate 2nd storage room that can be accessed from the outside. It could be used for a home gym, more storage, workshop, you name it! All of this and you will feel like you live in the country while still being so close to major commuting routes, Annapolis Mall, Naval Academy, Downtown waterfront, etc.... Check out the virtual tour!
#MDAA2114392

ANNAPOLIS

515 CORBIN PARKWAY

3 Beds

3 Baths

2,540 Sq.Ft.

$735,000

MLS#: MDAA2114392

Situated in a prestigious Annapolis neighborhood, experience the epitome of luxury living in this stunning 2-bedroom, 2-bathroom Park Place unit, with an east-facing view overlooking the pool area. Immerse yourself in the area's rich history, with iconic landmarks just a short stroll away. Enjoy a variety of dining experiences, from charming cafes to high-end restaurants, all within walking distance. For added convenience, take advantage of the complimentary shuttle bus service where you will also find vibrant entertainment venues and the bustling downtown City Dock, awaiting your exploration. This unit is elegantly designed with hardwood floors, beautiful window treatments, and plush carpeting in the bedrooms. The kitchen features granite countertops, stainless steel appliances, oak cabinetry, and new lighting in the dining area. The primary bedroom includes a luxurious walk-in closet with wall-to-wall carpeting and additional storage space, ensuring a comfortable living experience. Upgrades are found throughout the unit and the entire building, adding to your personal comfort. This unit also includes two basement garage parking spaces. Indulge in the numerous amenities Park Place offers, such as a 42-foot outdoor pool, hot tub, gourmet outdoor grilling areas, a dog park, a party room, an exercise room, a library with a book exchange, and even an area for a garden. The social committee ensures a lively community with various planned events. Enjoy peace of mind with excellent 24/7 live concierge service and security in the lobby. Many utilities are included in the condo fee, making this an exceptional value. Embrace the quintessential Annapolis lifestyle, where luxury meets history, and modern amenities blend seamlessly with timeless charm. Don't miss your chance to make this extraordinary Park Place unit your own!
#MDAA2109420

ANNAPOLIS

5 PARK PLACE 527

2 Beds

2 Baths

1,270 Sq.Ft.

$729,900

MLS#: MDAA2109420

Major Price improvement!!1 Enjoy stunning views of Spa Creek, St. Mary's, and the Annapolis skyline from this ideally located sun filled 3rd-floor condo, next door to the Annapolis Yacht Club’s Activity Center and Pool. This spacious 2-bedroom unit features an open-concept design with a cozy fireplace and a large, open balcony, perfect for relaxing on chaise lounges or dining al fresco. The condo complex offers a wealth of amenities, including a pool, grilling area, clubroom, and a fitness studio with showers, 1 assigned parking spot all set against the backdrop of a scenic marina. Take a leisurely stroll to the best restaurants, bars, and shops in Eastport and downtown Annapolis, or hop on the water taxi for a charming ride around the bay. This is waterfront living at its finest! Condo bylaws require a 15-day right of refusal. Possibility of buying a boat slip directly out front at marina. Unit is offered fully Furnished!!!
#MDAA2110198

ANNAPOLIS

301 BURNSIDE STREET B 302

2 Beds

1 Baths

822 Sq.Ft.

$725,000

MLS#: MDAA2110198

Discover the perfect blend of comfort and convenience at The Residence at Park Place in Annapolis. This two-bedroom, two-bathroom condo spans 1,292 square feet with an open layout and includes two secure garage parking spots. Ideally located just a short drive from Washington, D.C., Baltimore, and BWI Airport, it offers easy access to major hubs while being within walking distance of Historic Annapolis, the U.S. Naval Academy, and local dining favorites like Sailor Oyster Bar and Rams Head Tavern. Building amenities include a refreshing outdoor pool, a fitness center, and secure access, providing both convenience and peace of mind. Priced at below market, this property is an excellent opportunity to enjoy vibrant city living in one of Maryland’s most sought-after areas. The furnishings in the images have been virtually staged to help you picture the home’s full potential and layout possibilities. Contact your real estate professional for a private tour.
#MDAA2095846

ANNAPOLIS

5 PARK PLACE 430

2 Beds

2 Baths

1,292 Sq.Ft.

$720,000

MLS#: MDAA2095846

This rare and luxurious brick front end unit townhome offers 4 levels of perfection! Located in the gated community of The Vineyards of Annapolis, this is one of the largest homes in the community at over 3,100 square feet featuring a bump out on three levels, allowing ample sunlight to flow throughout. The main level is highlighted by a recent kitchen renovation that includes modern quartz counters, KitchenAid appliances with gas range, and a stylish herringbone tile backsplash. The tall ceilings, plentiful windows, open floor plan and hardwood floors in the living and dining room are the perfect combination to feel warm and inviting. The living room features one of two gas fireplaces (the other in the lower level) and access to the low maintenance, composite deck. Upstairs, the expansive primary suite offers vaulted ceilings, hardwood floors, a sitting area, and a generously sized walk-in closet. As you enter the luxurious ensuite bath you will find the perfect place to relax and unwind with dual vanities, a soaking tub, and a separate shower. Two additional bedrooms and a full hallway bath completes the upper level. The bonus loft space can serve as an additional bedroom, office, hobby room, or more. Downstairs you will find a versatile family room, an additional bonus room suitable as a fifth bedroom or office, and a full bathroom, giving you ample living space all around. The lower level includes convenient access to the attached two-car garage and a quaint brick patio, perfect for morning coffee. Don't forget about the convenient location due its ease of access to Route 50 and 97 and its proximity to many restaurants and shopping, including the Annapolis Towne Centre. This beautiful gem has it all!
#MDAA2115120

ANNAPOLIS

2714 CABERNET LANE

4 Beds

3 Baths

3,105 Sq.Ft.

$700,000

MLS#: MDAA2115120

PRIVATE WATER COMMUNITY! 5 BEDROOM 2.5 FULL BATH BRICK HOME SITS ON .42 ACRE LOT IN SOUGHT AFTER HILLSMERE ESTATES! FRESHLY PAINTED THROUGHOUT! UPPER LEVEL HARDWOOD FLOORS HAVE BEEN REFINISHED! UPDATED KITCHEN W/ SS APPLIANCES, QUARTZ COUNTER TOPS, TILED BACKSPLASH, TABLE SPACE W/ BREAKFAST BAR & RECESSED LIGHTING. LIVING ROOM HAS BRICK FIREPLACE AND MANTEL, HARDWOOD FLOORS, BAY WINDOW W/ PLANTATION SHUTTERS. DINING ROOM & BONUS SUNROOM IS SURROUNDED BY WINDOWS W/ PLANTATION SHUTTERS & 2 SETS OF FRENCH DOORS W/ ACCESS TO SIDE DECK AND EXT REAR PATIO. PRIMARY EN-SUITE HAS LIGHTED CEILING FAN, PRIVATE POWDER ROOM AND SLIDER DOOR W/ ACCESS TO REAR PATIO. 2 ADDITIONAL SPACIOUS BEDROOMS W/ HARDWOOD FLOORS. BEDROOM 3 HAS IN CLOSET AN ALL IN ONE WASHER/DRYER COMBO. THIS CAN BE REMOVED, BUT GIVES BUYER OPTION TO HAVE A RENTAL ON EACH LEVEL. HALLWAY BATHROOM W/ UPDATED TILED TUB SHOWER AND FLOORS. LOWER LEVEL HAS ADDITIONAL KITCHEN W/ TOASTER OVEN, MICROWAVE, SS REFRIGERATOR, MOVABLE ISLAND W/ CABINETS AND COUNTER TOP BURNERS. FAMILY ROOM HAS BRICK FIREPLACE AND MANTEL. TABLE SPACE . FULL BATHROOM W/ TUB SHOWER. 2 ADDITIONAL BEDROOMS AND LAUNDRY ROOM W/ BUILT IN CLOSET AND SHELVES. EXT SHED AND FENCED IN REAR YARD. FLAT ROOF 2025 AND EXT CHIMNEY REFINISHED. SWIMMING POOL AND SOCCER FIELD DIRECTLY ACROSS THE STREET. THIS COMMUNITY HAS AN OPTIONAL IMPROVEMENT ASSOCIATION FOR $25/YEAR BUT NOT REQUIRED. HILLSMERE COMMUNITY HAS LOTS OF AMMENITIES!
#MDAA2113704

ANNAPOLIS

130 GREAT LAKE DRIVE

5 Beds

2 Baths

2,014 Sq.Ft.

$699,900

MLS#: MDAA2113704

Move-in ready ! 404 Beach Drive is a warm and inviting gracious home nestled in the beautiful Hillsmere Estates/Hillsmere Shores water privileged community offering access to two beachfront playgrounds, private beaches, picnic area, marina club, a boat ramp, canoe/kayak storage, boat slips, beach pavilions, volleyball courts and a community pool. New Samsung stove, over the range microwave, and dishwasher and new flooring in the family room. A truly welcoming retreat of comfort, tranquility and convenience just minutes to Quiet Waters Park, the public library, public and private schools, shopping, restaurants, downtown City Dock/Historic Annapolis and the United States Naval Academy. A great place to call home!
#MDAA2103872

ANNAPOLIS

404 BEACH DRIVE

3 Beds

3 Baths

1,976 Sq.Ft.

$699,900

MLS#: MDAA2103872

New on site 1 day ago
Ideally located in the heart of the Historic Annapolis, this beautifully maintained 2-bedroom, 1.5-bath home is just a short walk from Church Circle and one block from a waterfront park—perfect for launching your paddleboard or catching a water taxi for a quick ride to Eastport. With Spa Creek just steps away and Main Street, West Street restaurants, the City Dock, Naval Academy, and Murray Hill all within walking distance, this is in-town Annapolis living at its best. Inside, the main level showcases beautiful hardwood floors and a seamless flow from the living room to the dining area and into a fully updated kitchen featuring quartz countertops, stainless steel appliances, and a four-burner gas range. Tucked away in a closet within the kitchen is a discreet laundry area, offering convenience without sacrificing space or style. A recently renovated half bath completes the main level. Upstairs, you’ll find two spacious bedrooms and a fully updated full bath. The private backyard patio, enclosed by fencing and shaded by a mature magnolia tree, offers a serene space for morning coffee or evening entertaining. There's even enough room to store your kayak or paddleboard, making it easy to enjoy the nearby water access at Acton Cove. This home has seen numerous recent updates, including recently updated sewer lines, roof, electrical, and plumbing. The mechanical systems are all relatively new, making this a truly move-in-ready home. Tucked away on a quiet street, 104 South Street offers some of the most convenient parking in the Historic District. With quick access to Routes 450, 50, and 97, this home offers the perfect blend of historic character, modern updates, and unbeatable location. Furniture is negotiable.
#MDAA2117318

ANNAPOLIS

104 SOUTH STREET

2 Beds

1 Baths

1,032 Sq.Ft.

$699,000

MLS#: MDAA2117318

Don't miss this opportunity to get a turn-key home, in a wonderful water oriented community of Admiral Heights! Features include a wood burning fireplace, hardwood floors, open kitchen with breakfast bar, living room, dining room with sliding glass doors to the deck overlooking the fenced backyard, with lots of room to play. Lower level family room, guest bath, laundry room, garage & access to tall concrete floor crawl space for storage and utilities. On the upper level there are hardwood floors, 3 bedrooms and a full bath. Community is near the Navy Stadium, downtown Annapolis, the public library & more! Easy access to all routes of travel, Rt.50, Rt. 97
#MDAA2114966

ANNAPOLIS

13 WAINWRIGHT DRIVE

3 Beds

1 Baths

1,456 Sq.Ft.

$695,000

MLS#: MDAA2114966

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