One of the most popular communities provided by {{page_data.agentName}}

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
276
# of Listings
3
Avg # of Bedrooms
$515
Avg. $ / Sq.Ft.
$1,434,627
Med. List Price

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Over $5M

276 Properties Found. Page 14 of 19.

Brand New Lower Price! $7,000 Closing Cost Assistance or interest rate buy-down! Located in the water-privileged community of Cape St. Claire in Annapolis, this Dutch Colonial offers a practical layout, recent updates, and a private outdoor setting. Located within the Broadneck School District (Buyer to verify with local school board). The home features a traditional floor plan with multiple living areas, allowing for flexible use of space for everyday living, entertaining, and work-from-home needs. Recent interior improvements include fresh paint, bathroom upgrades, and newer vinyl plank flooring, providing a clean, updated feel. Major system updates include a newer roof and water heater, helping reduce the likelihood of immediate maintenance expenses. Set on a 0.21-acre shaded lot with established trees, the property offers natural privacy and a comfortable outdoor environment. An outbuilding provides additional storage or workspace. The 1-car garage and large driveway accommodate parking up to 4+/- vehicles. Cape St. Claire is a well-established, water-privileged community known for its access to the Chesapeake Bay lifestyle. Residents have access to multiple private community beaches, boat ramps, fishing piers, playgrounds, and open recreational areas. The Little Magothy River is located approximately five blocks away, providing convenient access for kayaking, boating, and fishing. Conveniently located near Route 50, offering access to Annapolis, Baltimore, and Washington, D.C. Some Photos are virtually enhanced; see captions.
#MDAA2147582

ANNAPOLIS

1075 SUN VALLEY DRIVE

4 Beds

2 Baths

2,274 Sq.Ft.

$574,900

MLS#: MDAA2147582

Welcome to 206 Wesley Brown Ln! This spacious townhome has been lovingly maintained by the original owner. Rooftop views and effortless flow welcome you to elevated living in Admirals Square. This four level townhome is just minutes from downtown Annapolis with easy access to Route 50 and I-97, offering both convenience and lifestyle. This home features 3 spacious bedrooms, 3 full baths, and 2 powder rooms across a flexible, well-designed layout. Wide plank oak floors run throughout the main living spaces, adding warmth and continuity to the home’s clean, modern design. The heart of the home is a beautiful kitchen with quartz countertops and stainless steel appliances. The kitchen, dining, and living areas flow seamlessly together, creating a cohesive space that is ideal for both everyday living and entertaining. Upstairs, the loft level opens to a beautiful and private rooftop terrace. This indoor-outdoor space is perfect for hosting friends and truly extends your living space in a way that feels both functional and special. Additional highlights include a one car garage, private driveway, and ample street parking for guests, a rare and valuable combination in this area. Turnkey, stylish, and designed for how people actually live, this home offers the best of low maintenance luxury in one of Annapolis’ most desirable communities.
#MDAA2144158

ANNAPOLIS

206 WESLEY BROWN LANE

3 Beds

3 Baths

2,174 Sq.Ft.

$569,999

MLS#: MDAA2144158

Welcome to 2638 Foremast Aly in Annapolis - a beautifully appointed townhome offering stylish finishes, functional living space, and an unbeatable location! This spacious home features 3 bedrooms, 2 full baths, and 2 half baths, thoughtfully designed across multiple levels with tall ceilings and gorgeous hardwood floors that create a bright, open feel throughout. The heart of the home is the inviting kitchen and living area, complete with a cozy fireplace that adds warmth and charm to the space. Upstairs, you’ll find spacious bedrooms, including a comfortable primary suite, along with the convenience of bedroom-level laundry. Step outside to enjoy the upgraded composite back deck; the perfect low-maintenance space for relaxing, entertaining, or enjoying quiet evenings outdoors. Parking is effortless with a 2-car garage plus two additional driveway spaces. Updates include a new water heater (2026), wifi controlled under cabinet lighting, and gutter guards! Ideally located in Annapolis with easy access to shopping, dining, commuter routes, and all the charm of the historic waterfront city, this move-in ready home combines comfort, style, and convenience in one exceptional package!
#MDAA2146076

ANNAPOLIS

2638 FOREMAST ALLEY

3 Beds

2 Baths

2,020 Sq.Ft.

$569,000

MLS#: MDAA2146076

Elegant brick and siding split-foyer residence offering 4 bedrooms and 3 renovated full bathrooms on a beautifully sized 0.21-acre lot. The thoughtfully designed upper level features a sun-filled living room, formal dining area, well-appointed brand new kitchen with new appliances, and seamless access to the rear deck—perfect for refined indoor-outdoor living. Three bedrooms and two full baths complete the main level. The lower level is highlighted by a private primary suite with a generously renovated full bathroom, providing an ideal owner’s retreat or guest quarters, along with a spacious family/recreation room, laundry area, and mechanical room. Luxury vinyl flooring extends throughout both levels, complemented by windows in excellent condition. Major updates include the roof and HVAC system. Serviced by well and public sewer. A well-maintained home offering comfort, privacy, and timeless appeal.
#MDAA2134820

ANNAPOLIS

721 FAIRWAY DRIVE

4 Beds

3 Baths

2,080 Sq.Ft.

$568,000

MLS#: MDAA2134820

Charming cedar sided chalet style set in the wooded and beach access community of Cape St Claire. Enter into a dramatic cathedral ceiling living and dining space with skylights, looking through to a three season clerestory windowed addition where you will welcome family and friends. Sliders from the tall window surrounded sun room open onto a deck with room for feasts and relaxing. Memories are made here. An island and deep pantry in the kitchen with a plant window for your herbs to thrive provide plenty of storage. Generous bedroom and updated bath on the main level offer convenience and privacy. Upstairs two bedrooms are separated by a second full bath. Extensive landscaping with perennials lets you enjoy nature's blooms with little fuss. A fenced garden on the sunny side of the house is waiting to provide perfect tomatoes, cukes, peppers or vivid flowers for your table. Recent updates include replaced and stained cedar siding on one wall and trim throughout. Entry porch has been refreshed as well as decking replaced on deck off sunroom. A new roof, new washer and dryer, new and upgraded alarm system top off the new luxury vinyl plank on the main level.
#MDAA2144128

ANNAPOLIS

1189 HIGHVIEW DRIVE

4 Beds

2 Baths

2,500 Sq.Ft.

$565,000

MLS#: MDAA2144128

Stunning Oyster Harbor – Coastal Charm Meets Comfort This gorgeous property blends comfort, charm, and the best of coastal living. Nestled in the highly desirable Oyster Harbor community, residents enjoy water privileges and access to a sandy beach, picnic area, fishing pier, and playground—all just a short walk from the front door. Additional amenities include a community marina, boat ramp, and storage racks for kayaks and paddle boards, creating the ultimate waterfront lifestyle just minutes from downtown Annapolis. The home itself is designed for both entertaining and everyday enjoyment. An enormous screened-in porch and a spacious, fully fenced backyard provide plenty of room to garden, relax in a hammock, or host gatherings. After a day at the beach, the outdoor shower is the perfect convenience. Inside, the property features three bedrooms, two full bathrooms, and hardwood floors throughout the main level. Don’t miss the opportunity to live in this beautiful home and vibrant waterfront community—where comfort, charm, and lifestyle come together seamlessly.
#MDAA2145374

ANNAPOLIS

1252 CREEK DRIVE

3 Beds

2 Baths

1,555 Sq.Ft.

$565,000

MLS#: MDAA2145374

Location Location location!! Modern rancher style home located near everything Annapolis has to offer! It's just minutes to Downtown Annapolis. The House is much bigger than it looks. A beautiful fenced in backyard with a composite decking awaits for outdoor entertaining. This house also features 5 bedrooms and two full bath. This home is almost 2,000 sf. finished. Entire home was fully renovated in 2025. The finished basement features a laundry room, family room, 2 spacious bedrooms, and one full bathroom. The whole top level features 3 bedrooms, one full bath, open concept style kitchen with island that opens to the dining space and large living room. New HVAC, plumbing and electrical system. Move-in ready, fully furnished!! This home really offers a wonderful opportunity to enjoy Annapolis living — just minutes from shopping, dining, and commuter routes.
#MDAA2130284

ANNAPOLIS

1002 TYLER AVENUE

5 Beds

2 Baths

1,920 Sq.Ft.

$550,000

MLS#: MDAA2130284

Beautifully updated and filled with thoughtful improvements, this Cape Cod in Annapolis combines model-like interiors, a recently finished lower level, and inviting outdoor living just minutes from the Chesapeake Bay. Blooming perennial landscaping and a covered front porch create a warm welcome, while inside, a deceptively spacious open concept floor plan showcases hardwood flooring, recessed lighting, and a soft neutral palette that carries throughout the home. The living room is bright and airy, highlighted by a partial vaulted ceiling accented with skylights that fill the space with natural light. Just beyond, the renovated kitchen blends style and function with stainless steel appliances, a tile backsplash, abundant cabinetry, roll-out shelving, and a swing-out pantry designed for effortless organization. A dedicated dining area with a modern light fixture completes the main living space with a polished touch. The main level includes a spacious bedroom with a walk-in closet featuring a built-in organization system. Also on this level is a beautifully renovated full bath complete with a double sink vanity, stylish finishes, and a tiled tub and shower surround. Nearby, the laundry room provides storage shelving and convenient access to the backyard. Upstairs, two generously sized bedrooms share an updated full bath with a tiled shower enclosed by frameless glass. One of the upper level bedrooms is enhanced by a charming shiplap accent wall and a cozy window seat, adding character and a tucked-away place to relax. The recently finished lower level expands the living space with a comfortable family room featuring durable wood-look tile flooring, a versatile bonus room, and a sizable storage area. Outdoor spaces are equally inviting, with a deck and patio overlooking the spacious backyard, creating room to entertain, relax, or enjoy the surrounding greenery. A storage shed with a garage door adds functionality, while major updates including the roof and water heater offer additional peace of mind. This location places you moments from some of Annapolis’ most scenic waterfront recreation, including Sandy Point State Park with its sandy beach, marina, fishing and crabbing access, and sweeping Chesapeake Bay Bridge views. Jonas Green Park, Quiet Waters Park, and Thomas Point Park are also nearby, offering trails, kayaking, waterfront overlooks, and endless opportunities to enjoy the natural beauty of the Annapolis area.
#MDAA2145366

ANNAPOLIS

1470 LOG INN ROAD

3 Beds

2 Baths

1,465 Sq.Ft.

$550,000

MLS#: MDAA2145366

Opportunity awaits in sought-after St. Margarets! This 3-bedroom, 1-bath home with hardwood floors, situated on a gorgeous 1-acre lot offering plenty of space and potential. Solid built home they don't make houses like this any longer, needs updating, making it the perfect chance to bring your ideas and renovate to your personal taste. Most major systems updated within last 10 years. Whether you are looking for an investment opportunity or a property to create your dream home, this one has endless possibilities. Home is being sold strictly “AS IS.” Home warranty included.
#MDAA2144750

ANNAPOLIS

1509 DUVALL ROAD

3 Beds

1 Baths

1,512 Sq.Ft.

$550,000

MLS#: MDAA2144750

Welcome to Village Greens — Where Annapolis Living Reaches Its Full Potential. Tucked along a tree-lined streetscape that delivers that quintessential Annapolis vibe, this stunning 3 BR, 2.5 BA luxury townhome checks every box. Step inside to an open concept main level where rich hardwood floors flow beneath soaring ceilings, plantation shutters grace every window, and modern updated lighting plus freshly painted spaces adds a polished, contemporary feel throughout. Upstairs, vaulted ceilings continue to impress. The primary suite is a true retreat — custom walk-in closet, soaring ceilings, walk-in shower, soaking tub, and a double bowl owner's vanity. Gorgeous LVP flooring runs throughout the upper level, combining beauty with durability. A true basement with windows sets this home apart — bright and full of possibilities, with a plumbing rough-in already in place for a future bath. Outside, gated rear access leads to private resident parking pads and garages, keeping the neighborhood's gorgeous streetscape beautifully uninterrupted. Minutes to Route 50 puts Baltimore, D.C., and the Eastern Shore within easy reach — yet you're squarely in the heart of Annapolis, minutes from world-class waterfront dining, the iconic City Dock, Quiet Waters Park, and everything that makes this city so beloved. Fresh crabs, sailing, brick streets, and the Naval Academy — this is the Annapolis lifestyle, beautifully lived. Schedule your tour today!
#MDAA2145726

ANNAPOLIS

607 S CHERRY GROVE AVENUE

3 Beds

2 Baths

2,008 Sq.Ft.

$550,000

MLS#: MDAA2145726

HERITAGE HARBOUR! It's the perfect size! 2 Bedrooms. 2 full Baths. Den. Sun Room Addition. Deck (2025). HVAC (2025). Architectural Shingle Roof (2021). HHCA's site touts the community as... an established community in Annapolis, offering beautiful wooded lots and featuring a wide variety of recreational, cultural, social, and educational activities for its residents. Residents can participate in over 90 activities, clubs and committees. The center of community activities is the Lodge, which features a welcoming atrium, an auditorium, indoor and outdoor pools, fitness center, library, boutique, activities room, woodwork shop, game rooms, coffee corner and meeting rooms. Behind the Lodge, residents enjoy a picnic area, horseshoes, bocce ball and kayaking on our waterfront on the South River. We also offer multiple tennis and pickleball courts, a nine-hole golf course, a pro shop, a clubhouse dining room, a pier with boat slips and RV and boat storage on a lot in the community. Residents enjoy the convenience of regular bus trips to shopping centers and special bus trips to cultural destinations, as well as volunteer drivers for medical appointments. Our pet-friendly community of active residents always welcomes newcomers!
#MDAA2143166

ANNAPOLIS

2550 GOLFERS RIDGE ROAD

2 Beds

2 Baths

1,661 Sq.Ft.

$550,000

MLS#: MDAA2143166

Welcome to 102 Vanguard Lane, an elegant gated community offering a home with refined finishes and comfort in the heart of Annapolis. Rich hardwood floors throughout the main level, while the kitchen impresses with granite countertops and a brand-new refrigerator. Custom plantation shutters & blinds; upgraded lighting & more! Exterior w/ Hardiplank siding & beautiful deck off kitchen that includes an amazing indoor/outdoor fireplace! This beautifully updated home showcases brand-new paint and new carpet throughout, creating a pristine, move-in-ready experience. Thoughtfully refreshed and designed for both everyday luxury and memorable gatherings, this home offers an exceptional lifestyle just minutes from Annapolis dining, shopping, and waterfront attractions. A rare opportunity to enjoy comfort, style, and location—all in one exceptional property.
#MDAA2134520

ANNAPOLIS

102 VANGUARD LANE

4 Beds

3 Baths

2,000 Sq.Ft.

$549,999

MLS#: MDAA2134520

This exceptional 5th-floor condo offers a one-of-a-kind, unique floor plan with breathtaking panoramic views and an abundance of natural light from its sunny southern exposure. Featuring two generously sized bedrooms with expansive closets, this upscale residence combines comfort and style. Inside, you’ll find beautiful hardwood floors (no carpet), soaring 10-foot ceilings, elegant granite countertops throughout and NEW appliances. The freshly painted interiors are complemented by custom window treatments that add both privacy and sophistication. Step outside to your private balcony and enjoy sweeping views of the surrounding area. Two assigned parking space for convenience. Building Amenities: Rooftop pool with panoramic vistas. State-of-the-art fitness center. Elegant club rooms for gatherings and relaxation. Concierge service for a luxurious living experience Ideally located in the vibrant Annapolis Town Center, this condo puts you within walking distance of premier shopping, dining, and entertainment options. Whether you're enjoying a meal at one of the area's finest restaurants or exploring local boutiques, everything you need is just moments away. This is a must-see home that blends modern living with the best of Annapolis! Don't miss out on the chance to call this spectacular property yours.
#MDAA2139908

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 513

2 Beds

2 Baths

1,485 Sq.Ft.

$549,000

MLS#: MDAA2139908

Motivated seller! New price reflects home and pool "as is." This spacious split-level home offers an exceptional combination of comfort and functionality. The main level features an updated kitchen with adjoining dining area, creating a welcoming space for meals and gatherings. A stunning 400-square-foot sunroom addition provides year-round enjoyment and opens directly to an expansive 400-square-foot composite deck, perfect for entertaining or relaxing outdoors. The primary suite includes a private ensuite bathroom, while two additional bedrooms and a full hall bath complete the upper level. The walk-out lower level offers incredible flexibility with a spacious family room, a separate living room featuring a wood-burning fireplace, two additional bedrooms, and a convenient half bath—ideal for guests, a home office, or multi-generational living. Outside, you'll finddriveways on both sides of the house, with parking for up to four vehicles. There are two storage sheds for all your tools and equipment, and a portable generator that conveys with the property and is capable of powering approximately three-quarters of the home. Pool, pool equipment and home convey "as is." Mortgage savings may be available for buyers of this listing.
#MDAA2146744

ANNAPOLIS

1115 SKYWAY DRIVE

5 Beds

3 Baths

1,480 Sq.Ft.

$540,000

MLS#: MDAA2146744

Nestled in the sought-after Southwoods community just off West Street, this beautifully updated single-family home offers the perfect blend of comfort, style, and convenience with easy access to everything Annapolis has to offer. Inside, luxury vinyl plank flooring flows throughout the inviting two-story floor plan featuring arched entryways, a cozy fireplace, and flexible living spaces designed for today’s lifestyle. The updated kitchen shines with white cabinetry, Corian countertops, stainless steel appliances, pantry storage, and a convenient breakfast bar with seating, all opening to a sunny morning room and family room ideal for everyday living and entertaining. A main-level office or flex space, along with a powder room, adds versatility and function. Upstairs, the spacious primary suite features a private bath, while two additional bedrooms share a well-appointed hall bath. Enjoy outdoor living with a welcoming front porch, private backyard, deck, and off-street driveway parking — all in a location that puts shopping, dining, Historic Annapolis, commuter routes, and waterfront attractions just moments away.
#MDAA2146440

ANNAPOLIS

1529 RITCHIE LANE

3 Beds

2 Baths

1,524 Sq.Ft.

$539,000

MLS#: MDAA2146440

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