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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
392
# of Listings
3
Avg # of Bedrooms
$453
Avg. $ / Sq.Ft.
$1,135,816
Med. List Price

Browse Annapolis Real Estate Listings

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Over $5M

392 Properties Found. Page 16 of 27.

WOW! Nestled along the Chesapeake Bay, this waterfront residence offers views of the community marina and the open water beyond. Situated in the sought-after gated community of The Village of Chesapeake Harbour, this beautifully updated two-bedroom, two-bath home combines modern elegance with coastal charm. Step into the welcoming foyer, where an open-concept design unfolds with a soothing color palette freshly painted in 2022. Custom shades, including select electric-controlled options, add both privacy and convenience. The living and dining area boasts striking wood-look porcelain tile flooring, seamlessly blending gray and blue hues that echo the shimmering waters just beyond. Crown molding adds a refined touch, while the living room’s fireplace creates a cozy retreat. A three-panel sliding glass door leads to the expansive patio—larger than others in the community—where you can unwind in a private setting while soaking in the serene water views. The well-appointed kitchen is both stylish and functional, featuring stainless steel appliances, including a recently replaced dishwasher, range, and microwave. An antiqued glass tile backsplash reflects natural light, creating a luminous atmosphere, while a pantry provides ample storage. Another triple-panel sliding glass door opens to a front patio, making this space feel bright and airy. The primary bedroom is a tranquil haven, offering direct patio access through yet another sliding glass door, providing serene water views. The en-suite bath is a luxurious retreat with a double vanity topped with granite, a water closet, and a floor-to-ceiling tiled shower. A spacious walk-in closet with a built-in organizational system completes this private sanctuary. Down the hall, the second bedroom is generously sized, accompanied by an updated full bath with a modern vanity. A sleek, stacked washer and dryer are tucked away in the laundry room, rounding out the home’s well-designed layout. Storage is plentiful, with custom-built closet systems enhancing organization throughout. For peace of mind, the brand-new HVAC system was upgraded in 2025, including an added air purifier. Ample space is available for residents and guests in the unassigned parking lot. The community offers resort-style living with premier water access and exceptional amenities. Enjoy dining at the on-site Beacon Waterfront Galley & Bar, take a dip in one of two pools with bay views, or relax on the private sandy beach. Outdoor enthusiasts will love the fishing piers, kayak launch, and scenic walking and biking trails. Tennis courts and a picnic area provide additional recreation options. Electric car charging stations offer convenience. Boaters will appreciate the Chesapeake Harbour Marina, featuring 81 wet slips with fresh water, electricity, and WiFi, as well as a full-service yacht facility. Ideally situated near Historic Downtown Annapolis, Chesapeake Harbour provides a peaceful retreat while remaining within commuting distance of Baltimore and Washington, D.C. Experience coastal living at its finest—where the water meets effortless luxury. Property Updates: Porcelain tile flooring, dishwasher, range and microwave, washer & dryer, blinds, kitchen faucet and disposal, kitchen backsplash, interior paint, full bath vanity, closet built-ins, HVAC updates, and more!
#MDAA2116088

ANNAPOLIS

7024 CHANNEL VILLAGE COURT T2

2 Beds

2 Baths

1,177 Sq.Ft.

$525,000

MLS#: MDAA2116088

Beautifully maintained and move-ready 3BR/2.5BA expanded home located on a spacious lot in the quiet neighborhood of Cape Saint Claire. Parking is just steps from the front door into your forever home. Step into the main floor living space boasting tons of natural light, vaulted ceilings, hard wood floors, and an open floor plan. The main floor features a large family room with a brick wood burning fireplace, a spacious dining area, a half bath, and a stunning kitchen. The kitchen features beautiful wood cabinets finished with crown moldings, high-end stainless steel appliances including an electric cooktop and a wall oven, beautiful granite countertops, a double stainless sink under a window, and an island with a raised breakfast bar. Make your way to the second floor featuring two primary sized bedrooms with hardwood flooring, and a full bath. On the lower level is the third bedroom, a full bath with a large walk-in shower, storage, and laundry. From the main floor step outside to a large wood deck that overlooks a yard filled with green space, landscaping, adult trees, and two sheds. This home is move-in ready with so much to offer new homeowners and is located in close proximity to shopping, restaurants, and commuter routes.
#MDAA2118566

ANNAPOLIS

1178 IDYLEWILD DRIVE

3 Beds

2 Baths

2,016 Sq.Ft.

$525,000

MLS#: MDAA2118566

Stunning 3 BR/2 FBA "St. Michael" condo main level w/ garage across the hall in sought after Four Seasons at St Margarets in 55+ community. Gourmet kitchen - granite counters, upgraded cabinets, recessed lighting, 1 yr old refrigerator, breakfast area and desk, hardwoods. The unit has a wonderful open flow and has just been freshly painted, 2021 Furnace, upgraded carpet, and relaxing patio. This unit offers a driveway, garage and extra storage. Amazing community amenities w/ beautiful clubhouse, fitness room, party room, billiards & cards, pool! Great location to everything in Annapolis & Eastern Shore.
#MDAA2117512

ANNAPOLIS

1509 FERAL DAE LANE 102

3 Beds

2 Baths

1,757 Sq.Ft.

$525,000

MLS#: MDAA2117512

Price Reduced! Welcome to 746 Warren Drive Annapolis, Maryland —nestled just a block and a half from Back Creek in the highly desirable Greenacres community of Eastport. This charming 5-bedroom, 1.5-bath home sits on a generous lot along a quiet street, offering both privacy and water access. Enjoy first-floor living with a freshly painted interior and exterior, brand new carpet throughout the finished basement and stairs, and abundant natural light pouring in from the beautiful bay window with newly installed side windows. A dedicated office space on the lower level makes working from home a breeze. Step outside to a spacious rear deck—perfect for entertaining—overlooking newly landscaped grounds with fresh sod and updated exterior lighting. The home also features solar panels, off-street parking, and multiple updates within the past couple of weeks. Located in a water-privileged community with access to a large waterfront green space, and close to local restaurants and marinas, this home delivers the ultimate Eastport lifestyle. Don’t miss your chance to live steps from the water in one of Eastport’s most sought-after neighborhoods. **The total finished square footage including basement is not reflected correctly on the MLS. **
#MDAA2109984

ANNAPOLIS

746 WARREN DRIVE

5 Beds

1 Baths

1,200 Sq.Ft.

$524,900

MLS#: MDAA2109984

Building One Nearly Sold Out - Model Home Now For Sale! Bright, spacious unit showcasing gorgeous design upgrades throughout. Start an exciting new chapter in this amenity-rich 55+ community conveniently located minutes to downtown Annapolis, retail shopping, waterfront dining and Bay Bridge. Reserved parking space included. Turnkey luxury, private balcony... Tour this incredible Model Home today!
#MDAA2095514

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 207

2 Beds

2 Baths

1,318 Sq.Ft.

$523,655

MLS#: MDAA2095514

Welcome to 316 Burnside Street, Unit #208 — a charming one-bedroom, one-bath condominium nestled in the heart of Annapolis. This inviting residence features beautiful luxury vinyl plank flooring, a recently installed water heater (2024), and central A/C for year-round comfort. This flexible layout offers additional sleeping accommodations with a Murphy bed in the dining area and a sleeper sofa. Residents will enjoy access to a rooftop pool with stunning water views, perfect for relaxing or entertaining. Ideally located near vibrant shops, restaurants, and waterfront attractions, this home offers the best of Annapolis living. Don't miss the opportunity to make it yours!
#MDAA2112714

ANNAPOLIS

316 BURNSIDE STREET 208

1 Beds

1 Baths

768 Sq.Ft.

$520,000

MLS#: MDAA2112714

Experience the best of Heritage Harbour in this rarely available penthouse condo—one of the most spacious units in the building! This stunning two-story home is packed with premium features, offering 2 large bedrooms, each with a walk-in closet, 2.5 bathrooms, and ample storage space. Gleaming hardwood floors flow throughout the open floor plan, where the kitchen overlooks the family room, complete with a cozy wood-burning fireplace. Step outside onto your private balcony patio, the perfect retreat on beautiful days. Bonus: A reserved garage parking space conveys with the unit! This exceptional building includes indoor and outdoor pools and a fully equipped gym for your convenience. Plus, Heritage Harbour’s world-class amenities are second to none, featuring: ✅ Indoor & outdoor pools ✅ Hot tub & sauna ✅ Golf course ✅ Tennis & pickleball courts ✅ On-site restaurant ✅ Boat slips & kayak racks ✅ RV/boat storage ✅ The Lodge/Community Center—offering endless social and recreational activities Don’t miss this opportunity to enjoy luxury, space, and an unbeatable 55+ lifestyle in Heritage Harbour!
#MDAA2109828

ANNAPOLIS

930 ASTERN WAY 609

2 Beds

2 Baths

1,926 Sq.Ft.

$519,900

MLS#: MDAA2109828

Move-In Ready! This beautifully updated home features an updated kitchen with modern appliances, a fully renovated bathroom, new washer & dryer, new hot water heater, new HVAC system, refinished hardwood floors, and a new roof. Additional highlights include a wood-burning fireplace, a spacious screened-in rear porch, and a one-car garage that is currently in the process of being converted back into a functional garage. The entire house will also be fully repainted prior to settlement. Located within walking distance to Truxton Park and Annapolis public transit, this home offers convenience, comfort, and charm.
#MDAA2108848

ANNAPOLIS

9 EDELMAR DRIVE

4 Beds

2 Baths

936 Sq.Ft.

$519,900

MLS#: MDAA2108848

Bright, spacious unit at second floor elevation showcases stylish design upgrades throughout! Start an exciting new chapter in this amenity-rich 55+ community conveniently located mere minutes to downtown Annapolis, retail shopping, waterfront dining and Bay Bridge. Reserved parking space included. Turnkey luxury includes window treatments, full-size washer/dryer and more! Building One nearly sold out - tour this stunning new home today!! Virtual staging used to demonstrate the space & layout.
#MDAA2110762

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 107

2 Beds

2 Baths

1,318 Sq.Ft.

$519,090

MLS#: MDAA2110762

Welcome to this Wonderful home very close to Annapolis & the properties to be in a private area but close proximity to be in the City of Annapolis! Located in close proximity to restaurants , shopping, and entertainmemt . You will enjoy summer evenings dining - out in the over large deck out back! The Home offers an open floor plan that leads you to entertaining with a spacious living room, Dining Room & Remodeled Kitchen with Granite counter tops and New stainless steel Appliances. The dining & Living room boasts beautiful refinished hardwood flooring and Open to a Kitchen . The primary bedroom offers private Full remodeled bath with access to shower In addition to 2 others great size bedrooms and a Full renovated bathroom! Relax in the finished basement that offers large rec room, Additional bedroom/office/playroom and full renovated 3rd bath! You will love this home! Ready for your buyer to move-in!!
#MDAA2101268

ANNAPOLIS

1971 DOMINOE ROAD

4 Beds

3 Baths

2,160 Sq.Ft.

$519,000

MLS#: MDAA2101268

Stunning Penthouse in Four Seasons at St. Margaret’s – A Premier 55+ Community! Discover luxury and convenience in this beautifully maintained penthouse unit, nestled in the sought-after Four Seasons at St. Margaret’s. Designed for effortless living, this home features an elevator-equipped building, garage and an inviting open floor plan with soaring vaulted ceilings. Step inside to find gorgeous wood flooring extending through the foyer, living, dining, kitchen, and hallway areas. The updated kitchen boasts granite countertops, stainless steel appliances (2020), a stove with a convection oven option, pantry cabinets with roll-out shelving (2020), and under-cabinet lighting (2020)—perfect for both everyday cooking and entertaining. The spacious primary suite offers a walk-in closet with a built-in safe and a remodeled en-suite bath (2020) featuring a jetted soaking tub, new vanity, countertops, flooring, and a walk-in shower with seat & grab bars and a remote bidet. The hallway bath also includes a bidet and custom tilework. The second bedroom and loft provide flexible space, with carpeting replaced in 2020. Additional highlights include: ✅ Front-load washer/dryer (2020) in a dedicated laundry room with cabinetry ✅ New windows (2021) with a lifetime warranty ✅ Extra storage under the loft stairs ✅ Surge protector added to the main electrical panel ✅ One-car garage with shelving and interior access ✅ Brand-new furnace and A/C unit (2024) and water heater (2019) Enjoy resort-style amenities, including a swimming pool, fitness center, library, meeting/game room, billiard room, community kitchen, and spacious gathering areas. Relax outdoors on the main patio or upper deck overlooking the pool. This exceptional home blends modern upgrades with a vibrant, active lifestyle. Schedule your private tour today! Note: This unit is also available to rent.
#MDAA2109724

ANNAPOLIS

903 NOAH WINFIELD TERRACE 303

2 Beds

2 Baths

1,516 Sq.Ft.

$515,000

MLS#: MDAA2109724

Welcome Home to 901 Chesterfield Road!! This Beautifully updated Single family home located in Annapolis has the space you need to create a life you desire. Boasting an array of sleek finishes throughout this 5 Bedroom, 3 Bathroom home has so much to offer!! The main level offers an open concept layout featuring spacious living room, dining area, 3 entry level bedrooms, 2 full bathrooms, and sunroom. The kitchen boasts S/S appliances, white shaker cabinets, Quartz counters and MORE! All bathrooms have been updated with new ceramic tile, and all new bathroom fixtures! The basement has been fully finished to include 2 additional bedrooms, 3rd full bathroom, and utility room. Off street private parkin and SO MUCH MORE!! Book your private showing today before its gone!!
#MDAA2114934

ANNAPOLIS

901 CHESTERFIELD ROAD

5 Beds

3 Baths

2,457 Sq.Ft.

$514,900

MLS#: MDAA2114934

New Phase at Element at Mill Creek! Building B, The Banyan, is already half-sold, featuring lounge areas, party room, 2-story clubroom, upper & lower terraces, and more! Start your exciting new chapter in this amenity-rich 55+ community located minutes to downtown Annapolis, shopping, waterfront dining and Bay Bridge. Spacious home with large private balcony boasts desirable southern exposure and showcases stylish design upgrades throughout. Includes true chefs kitchen, huge owners closet, reserved parking. Low condo fee. Tour this stunning home and the building's incredible amenities today!
#MDAA2115854

ANNAPOLIS

76 OLD MILL BOTTOM ROAD N 308

1 Beds

2 Baths

1,076 Sq.Ft.

$511,400

MLS#: MDAA2115854

Nestled in the sought-after Four Seasons Community, this luxurious penthouse condo offers an exceptional living experience for those aged 55 and better. Located in a premier active adult community, this top-floor residence boasts soaring ceilings and an open-concept design, accentuated by a stylish loft that overlooks the main living area. Spanning 1,516 square feet, the condo features two generously sized bedrooms and two full, modern bathrooms, providing ample space and privacy. The gourmet kitchen is a chef’s dream, equipped with stainless steel appliances, granite countertops, and a breakfast bar that seamlessly flows into the bright and airy living and dining areas with balcony access. Expansive windows flood the space with natural light and the versatile loft space, accessible by a sleek staircase, is perfect for a home office, art studio, or cozy reading nook. The primary suite is a true retreat, complete with a spacious walk-in closet and an en-suite bathroom featuring dual vanities, a jetted soaking tub, and a glass-enclosed shower. The second bedroom, ideal for guests or family, is conveniently located near the second full bathroom. Hardwood floors, designer fixtures, and custom finishes throughout elevate the elegance of this sophisticated home. Residents of this exclusive 55+ community enjoy a low-maintenance lifestyle with access to premium amenities such as a fitness center, game room, library, outdoor pool and beautiful, well-maintained grounds. Just minutes from Annapolis’ vibrant downtown, the condo offers easy access to boutique shopping, fine dining, and the city’s renowned waterfront attractions, including the U.S. Naval Academy and historic sailing harbors. With private garage parking and elevator access, this penthouse condo combines luxury, convenience, and the best of Annapolis living for an unparalleled retirement retreat.
#MDAA2105660

ANNAPOLIS

903 NOAH WINFIELD TERRACE 303

2 Beds

2 Baths

1,516 Sq.Ft.

$505,000

MLS#: MDAA2105660

An incredible find; Welcome home to 577 Francis Nicholson Way, a rarely available end unit townhome residence in the highly desirable Tidewater Community! With fresh carpet on the main & upper floors along with new roof (1 year old), newer HVAC (under 2 years old), and newer hot water heater, move in complete peace of mind! Past the hardwood laden foyer, the kitchen flows with hardwoods, granite countertops, stainless steel appliances, and a breakfast nook perfect for morning coffee. The hardwoods continue through the dining room which flows to a fresh-carpet laden family room complete with gas fireplace and sliding door to the deck & backyard. Upstairs the primary bedroom shines with natural light on the vaulted ceiling, and it's ample size compliments the walk-in closet. An en-suite primary bathroom is ready for your personalized touches. The second bedroom, also with new carpet, is past the hallway second-full bathroom. A fully finished basement has a sizable living room and graciously spaced third bedroom equipped with full bathroom. To round out this incredible offering is Tidewater Colony's incredible community amenities complete with pool, tennis courts, club house, community center, and so much more!
#MDAA2118986

ANNAPOLIS

577 FRANCIS NICHOLSON WAY

3 Beds

3 Baths

2,024 Sq.Ft.

$504,000

MLS#: MDAA2118986

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