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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
359
# of Listings
3
Avg # of Bedrooms
$479
Avg. $ / Sq.Ft.
$1,097,034
Med. List Price

Browse Annapolis Real Estate Listings

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$3M - $5M

Over $5M

127 Properties Found. Page 8 of 9.

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!
#MDAA2108536

ANNAPOLIS

7024 CHANNEL VILLAGE COURT T2

2 Beds

2 Baths

1,177 Sq.Ft.

$535,000

MLS#: MDAA2108536

Enjoy resort-like living at Chesapeake Harbour, a gated community filled with amenities and beautiful water views of the Chesapeake Bay! This desirable 2 bedroom, 2 bathroom ground-floor unit offers access to dual covered terraces, a wood-burning fireplace, and updates throughout. The kitchen features new countertops and a new refrigerator as well as recently updated sink, stove, dishwasher, and cabinets. The owner's suite provides its own terrace entrance plus a walk-in closet and en-suite bath with double-sink vanity. This community offers a marina with a waterfront restaurant, summertime Tiki bar, two pools - including one that is bayfront- plus tennis courts, a private beach, pier, storage for your canoe or kayak, and onsite security. Ideal location just three miles from Historic Annapolis, near commuter corridors to DC and Baltimore, and just 30 minutes from BWI airport. Come and enjoy the abundant amenities and the convenience of living in the waterfront community of Chesapeake Harbour!
#MDAA2101380

ANNAPOLIS

7022 CHANNEL VILLAGE COURT T2

2 Beds

2 Baths

1,277 Sq.Ft.

$535,000

MLS#: MDAA2101380

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.

$535,000

MLS#: MDAA2116088

Welcome to 1019 Timber Creek Drive—an updated 4-bedroom, 2-bath home nestled in a quiet, tree-lined Annapolis neighborhood just minutes from downtown and Eastport. Inside, you’ll find fresh paint, new carpet, and a bright layout featuring hardwood floors, a cozy wood-burning fireplace, and newly renovated bathrooms. The kitchen offers modern appliances and plenty of storage, while the spacious bedrooms provide flexibility for family, guests, or a home office. Enjoy peace of mind with a new high-efficiency HVAC system and newer Samsung washer/dryer. The private backyard backs to trees and offers space to relax or entertain, plus there are two off-street parking spots. Timber Creek is a close-knit community with a tot-lot playground and low HOA fees. Just moments from Quiet Waters Park, local shops, and all the charm of Annapolis—this is a move-in-ready gem you don’t want to miss.
#MDAA2109642

ANNAPOLIS

1019 TIMBER CREEK DRIVE

4 Beds

2 Baths

1,826 Sq.Ft.

$535,000

MLS#: MDAA2109642

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.

$535,000

MLS#: MDAA2112714

NEW PRICE & OPEN Saturday, 5/31, 11-1! Welcome to this beautifully maintained 3-bedroom, 2.5-bath home in one of Annapolis’s most amenity-rich waterfront communities. Nestled between Oyster Creek, Fishing Creek, and the Chesapeake Bay, Oyster Harbor offers the best of coastal Maryland living—just minutes from historic downtown Annapolis, top-rated restaurants, shopping, and commuter routes. This move-in ready home features a long list of updates, including a brand-new roof, new granite countertops, new dishwasher and recent mechanical improvements: a new heat pump and A/C compressor (2024), and new refrigerator, stove, washer, and dryer (2019). The fully fenced backyard boasts water peeks, a hot tub, and a spacious deck surrounded by beautiful landscaping—ideal for entertaining or quiet evening relaxation. Inside, the layout includes a welcoming living area, functional kitchen with plenty of cabinet space, and a light-filled dining area. Upstairs, the primary suite includes a private full bath, with two additional bedrooms and a full bath. But what truly sets this home apart are the amazing resort-style amenities: private community beach with swimming area and sea nettle nets, three marinas , fishing pier, boat ramp, kayak racks, beach volleyball, and playgrounds! Whether you’re looking for a full-time residence or a weekend retreat, this home and its community offer something truly special: a waterfront neighborhood that embraces recreation, relaxation, and the Chesapeake lifestyle.
#MDAA2114714

ANNAPOLIS

3331 ARUNDEL ON THE BAY ROAD

3 Beds

2 Baths

1,364 Sq.Ft.

$535,000

MLS#: MDAA2114714

Beautifully Updated & Move-In Ready! Nestled in a quiet and peaceful Annapolis community, this charming home is packed with recent upgrades—including a brand new architectural shingle roof, a newly constructed and freshly stained deck, and a new front door—all completed within the past six months. Inside, you’ll find fresh paint throughout and warm, inviting spaces that flow effortlessly. The enclosed sun porch with durable Trex decking offers a relaxing retreat year-round, while the spacious deck is perfect for outdoor entertaining. Centrally located with easy access to shops, dining, and commuter routes, this home combines comfort, style, and convenience. Don’t miss your chance to call it home!
#MDAA2113536

ANNAPOLIS

1406 CATLYN PLACE

3 Beds

2 Baths

2,414 Sq.Ft.

$535,000

MLS#: MDAA2113536

Location! Location! Resort living between two rivers in this lovely split level home! Twenty year homeowner never stopped improving the home, including recent architectural roof, HVAC with humidity control, home water filtration system, and a jumbo 75 gallon hot water heater. Oak patterned laminate floors throughout provide a warm & classy feel. The upper floor offers three bedrooms that are enhanced by a remodeled full bath. A galley kitchen is a chef’s delight, and leads to a custom rear door that takes you down to the patio and lush garden. The fully finished lower level, considered “below grade”, has several large sunlit windows and opens to a spacious living room with French doors that open to a handsome stone deck for grilling, entertaining, or just relaxing with a book. Two additional large rooms with beds and closets share a full bath. The large rear yard has a stained wooden fence, beautiful greenery, and a generous 10’ x 20’ storage shed. Driveway for you boat or vehicles. Nearby Safe Harbor Marina in Eastport offers premium resort amenities with a family atmosphere: boating, tennis, pickleball, swimming, and a poolside Cafe and Tiki bar. Also a few blocks walk from home is the Annapolis Athletic Club, offering an array of fitness classes, personal trainers, varied strength & cardio machines, massage, and locker rooms with lounge. Luxurious steam room & sauna, and showers with towel service end the ideal workout. All of the day’s activities will enhance your appetite for deluxe dining at nearby seafood & steak restaurants. The Historic District, City Dock Market House, and United States Naval Academy are a mile walk or bike ride. Or head the other direction 1 &1/2 miles to Quiet Waters Park to enjoy the 340 acres of trails, paddle boarding/kayaking, picnic pavilions, or nationally renowned Dog Park along the South River. Annapolis has a vibrant arts community hosting exhibits at local galleries and cafes, as well as the Maryland Hall for the Creative Arts, which is home to the Annapolis Symphony Orchestra, ballet, and jazz/rock concerts. Your home is walking distance to the City treasure, Truxton Park, with an active tennis and pickleball community playing on remodeled and lighted courts. The park has a large swimming pool with adjacent children’s waterfalls and a covered pavilion. Wooded walking/jogging trail leads to Spa Creek. Boater’s use a twin boat ramp that offers easy access to scenic Spa Creek, cruising past the historic Annapolis Yacht Club into the mouth of the glorious Severn River & Chesapeake Bay. Conveniently located 23 miles from Baltimore International Airport & Amtrak, and 30 miles from the White House, world class travel, museums, and entertainment are at your doorstep! Priced below condos with high monthly fees or townhomes with HOA…hurry it won’t last!
#MDAA2100100

ANNAPOLIS

1022 TYLER AVENUE

5 Beds

2 Baths

1,854 Sq.Ft.

$534,900

MLS#: MDAA2100100

Looking for a rare opportunity in desirable Annapolis? Here’s your chance to scoop up a single-family home on a lot in Eastport, just steps from downtown and surrounded by high-value properties. The home is a 2 bedroom 1-bathroom fixer-upper being sold strictly As-Is. Whether you’re looking to renovate, rebuild, or invest, you can’t beat this location. Walk to shops, restaurants, and the waterfront, and enjoy the Annapolis lifestyle. Opportunities like this don’t come around often — bring your vision and make it yours!
#MDAA2111786

ANNAPOLIS

912 WINDSOR AVENUE

2 Beds

1 Baths

576 Sq.Ft.

$525,000

MLS#: MDAA2111786

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.

$524,900

MLS#: MDAA2114934

ANNAPOLIS lifestyle in this 3 Level Cape Cod, boasting 5 Bedrooms and 2 full Bathrooms. The Beautiful interior showcases contemporary finishes and a thoughtful layout that maximizes both style and functionality. The custom kitchen with quartz countertops, stainless-steel appliances and attractive cabinetry enhances your cooking and gathering experience. Complete with a traditional floor plan and modern finishes that will WOW you the moment you walk through the door. The bathrooms have been tastefully refreshed adding modern elegance to this classic home. Freshly painted, new carpet and laminate wood plank flooring throughout. The expansive yard provides the perfect setting for outdoor activities, entertainment, and a place for pets to play in the rear fenced yard. Conveniently located in ANNAPOLIS, close to Fine Dining, Fun Eateries, Nightlife Entertainment, Water Sports, Historic sites and major routes. Don't miss this opportunity to make this your lovely home.
#MDAA2116470

ANNAPOLIS

86 SUMMERFIELD DRIVE

5 Beds

2 Baths

2,340 Sq.Ft.

$524,900

MLS#: MDAA2116470

Welcome to 2004 Quay Village Court, Unit T2—a stunning 2-bedroom, 2-bath terrace-level condo nestled in the resort-style community of Chesapeake Harbour! With its prime location and newly updated kitchen, this home is move-in ready, offering the perfect gateway to luxurious coastal living. The spacious primary suite features an ensuite bath, a walk-in closet, and direct access to a private patio—your personal oasis for peaceful mornings or cozy evenings. The beautifully renovated kitchen, completed in 2023, boasts stainless steel appliances, quartz countertops, and a wine bar, with a slider leading to an additional patio area for seamless indoor-outdoor living. The foyer entry welcomes you to a sunken dining room that flows into a bright living room with a wood-burning fireplace. Step outside to the main patio and enjoy a view of the landscaped lawn and pool—a serene setting perfect for entertaining or unwinding. New HVAC installed in 2023. The second bedroom offers ample closet space and a large window, with a nearby full bath ideal for guests. Additional conveniences include an in-unit stacked washer and dryer, reserved parking for residents, and abundant visitor parking just steps away. As a resident of Chesapeake Harbour, you’ll enjoy a wealth of amenities, including a deep-water marina with direct Bay access, a private sandy beach, crabbing and fishing piers, two fenced outdoor pools (one heated), four tennis courts with pickleball, kayak rentals, walking paths, picnic areas and a waterfront bar/restaurant, Beacon. With 24-hour gated security and convenient access to Quiet Waters Park, local shopping, fine dining, and all that Annapolis has to offer, this is luxury living at its finest! Don’t miss your opportunity to call this extraordinary property home—schedule your showing today!
#MDAA2101798

ANNAPOLIS

2004 QUAY VILLAGE COURT T2

2 Beds

2 Baths

1,221 Sq.Ft.

$524,900

MLS#: MDAA2101798

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.
#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

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!
#MDAA2109724

ANNAPOLIS

903 NOAH WINFIELD TERRACE 303

2 Beds

2 Baths

1,516 Sq.Ft.

$520,000

MLS#: MDAA2109724

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