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

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47 Properties Found. Page 3 of 4.

0.65-acre corner lot along Bestgate Road in Annapolis with frontage on both Bestgate and Willey. Zoned R2, allowing for a single-family detached home. Public water and sewer connections are available through Anne Arundel County. Buyers will need to apply for service, obtain a connection permit, and pay the applicable capital facility charge along with any contractor installation costs. The existing well and septic are assumed to be nonfunctional. All site engineering, utility applications, and permitting will be the responsibility of the buyer. Convenient location near Route 50, downtown Annapolis, and area shopping. Excellent opportunity for a custom home project or long-term hold in a highly accessible central corridor.
#MDAA2129812

ANNAPOLIS

668 N BESTGATE ROAD

None Beds

None Baths

0.65 acres

$325,000

MLS#: MDAA2129812

Welcome to effortless living in one of Annapolis' most sought-after locations. With new systems like the **new price**Welcome to effortless living in one of Annapolis' most sought-after locations. With new systems like the efficient gas furnace and hot water heater, this well-maintained 2-bedroom, 2-bathroom condominium offers 1,065 square feet of comfortable living space with one standout feature that sets it apart: main-level access. In a building with no elevator, this ground-floor location means you'll never climb a single flight of stairs—ideal for those seeking accessibility and convenience. Step outside your front door onto a charming patio where you can enjoy your morning coffee or unwind after a day exploring everything Annapolis has to offer. This private outdoor space adds a welcoming touch to everyday living. The real magic lies in what's just beyond your doorstep. You're within walking distance or a short drive to the Annapolis Historic District, where cobblestone streets lead to the Maryland State House, boutique shops, and acclaimed restaurants. Stroll down to City Dock for waterfront dining and sailing culture, or catch a game at Navy-Marine Corps Memorial Stadium. The U.S. Naval Academy is practically in your backyard—making this an exceptional opportunity for parents of midshipmen seeking a convenient pied-à-terre during their student's four years at the Academy. Daily conveniences are equally close at hand: grocery stores, houses of worship, the hospital and easy transportation connections to Washington, D.C. for work or weekend adventures are here. With modest association fees and no-frills ownership, this condo delivers exceptional value in a location where proximity to history, culture, and community commands a premium. Whether you're downsizing, investing, or establishing a local home base, this main-level gem offers the freedom to live well in one of the Mid-Atlantic's most charming cities.
#MDAA2140882

ANNAPOLIS

2001 WARNERS TERRACE N 102

2 Beds

2 Baths

1,065 Sq.Ft.

$317,000

MLS#: MDAA2140882

Experience the Baywoods lifestyle from Unit #202, a beautifully located 1BR/1.5BA cooperative residence in the sought-after Baywoods community of Annapolis. Nestled along the beautiful Chesapeake Bay, Baywoods offers residents the perfect blend of waterfront beauty, maintenance-free living, and a vibrant retirement lifestyle. Unit #202 is ideally located in the North Tower, just steps from the elevator and conveniently situated on the same floor as the Bistro, making dining and socializing easily accessible. Relax and enjoy peaceful wooded views from the spacious all-season enclosed patio, offering a private and serene setting year-round. Residents enjoy access to a wide range of amenities, dining venues, wellness programs, social activities, walking paths, and future care services—all within a scenic Annapolis setting. Call the listing agent for details on the cooperative ownership structure, buyer qualifications, monthly fees, and to schedule a private tour. Discover why so many residents choose Baywoods to enjoy the Chesapeake Bay lifestyle while maintaining independence and peace of mind.
#MDAA2147982

ANNAPOLIS

7101 BAY FRONT DRIVE 202

1 Beds

1 Baths

1,000 Sq.Ft.

$315,000

MLS#: MDAA2147982

Welcome to Tidewater Colony, one of Annapolis' most sought-after condo communities! This wonderful 2-bedroom, 1.5-bath condo offers an exceptional opportunity to own an affordable home in a prime Annapolis location (just outside city limits, so NO CITY TAXES), minutes from the U.S. Naval Academy, Navy-Marine Corps Memorial Stadium, Anne Arundel Medical Center, downtown Annapolis, major commuter routes, shopping, dining, and more! Step inside to discover an inviting open-concept floor plan enhanced by vaulted ceilings, a spacious family room featuring custom built-in bookcases and a cozy gas fireplace, creating the perfect setting for relaxing evenings at home. The adjoining dining area provides seamless access to a private deck (with composite decking), ideal for enjoying your morning coffee or unwinding with an evening cocktail. The generously sized primary bedroom offers vaulted ceilings, a walk-in closet and direct access to the full bath, while a second bedroom, convenient half bath, and in-unit laundry provide comfort and functionality. Move in with confidence knowing that the major systems have already been updated, including a brand-new HVAC system (2026) and newer stainless steel kitchen appliances. Enjoy a low-maintenance lifestyle with outstanding community amenities, including a swimming pool, tennis court, walking trails, fitness center, clubhouse and Water and Sewer are included in your condo fees! Whether you're a first-time homebuyer, downsizing, or looking for an ideal Annapolis retreat, this home offers the perfect combination of value, convenience, and lifestyle. Don't miss your chance to make this exceptional condo your own. Schedule your private showing today and experience all that Tidewater Colony and Annapolis have to offer!
#MDAA2142656

ANNAPOLIS

2015 GOV THOMAS BLADEN WAY 303

2 Beds

1 Baths

1,007 Sq.Ft.

$315,000

MLS#: MDAA2142656

Serenity Meets Convenience at The Reserve in Heritage Harbour, a premier 55+ community! What sets this unit apart from every other in the building is its unique relationship with the outdoors. As the only unit featuring a private brick patio with direct walk-out access to the parking lot and sidewalks, it bridges the gap between condo living and the autonomy of a villa. For the pet owner, it means no more navigating elevators or hallways at 6:00 AM; for the traveler, it means unloading luggage is a breeze. It is the gold standard for accessibility and ease, seamlessly blending indoor comfort with the outdoors. Inside, the home shines with fresh paint and gleaming hardwood floors. The open-concept living and dining areas flow naturally to the patio, creating an expansive feel for entertaining. The kitchen features 42-inch cabinetry, Corian countertops, and a four-burner gas stove with a grill insert, plus a sun-drenched bistro breakfast nook. The primary suite is a true sanctuary, featuring brand-new plush carpeting and a unique sunroom sitting area—ideal for a home office or reading nook. The spa-like ensuite boasts a new walk-in shower, granite counters, and a vessel sink. Practicality is built-in with a spacious walk-in closet, a dedicated laundry room with a new washer/dryer, and an extra storage cage in the building’s basement. Heritage Harbour Living: Living here grants access to The Lodge, the community’s social heartbeat. Enjoy world-class amenities including: indoor and outdoor pools & fitness center, tennis, pickleball, bocce, and a community golf course, woodworking shop, arts room, and a well-stocked library, private kayak launch on the South River. 90+ clubs and a robust social calendar. Located just minutes from Downtown Annapolis with easy access to Routes 50 and 97, this home offers the perfect balance of peaceful retreat and urban accessibility. Don’t miss this rare opportunity for true single-level living in a vibrant, amenity-rich enclave.
#MDAA2135514

ANNAPOLIS

940 ASTERN WAY 102A

1 Beds

1 Baths

1,073 Sq.Ft.

$310,000

MLS#: MDAA2135514

Welcome to effortless waterfront living in the sought-after Severn House community! This charming 1-bedroom, 1-bath condo offers the perfect blend of tranquility and Annapolis lifestyle—whether you're paddleboarding out for your morning coffee, hopping on the water taxi for an evening in town, or enjoying sunset cruises from your own rented boat slip. Spend your days lounging by the waterfront pool, hosting crab feasts with friends, or simply soaking in the peaceful surroundings. Tucked away on the third floor and backing to woods, this unit offers rare privacy and a quiet retreat from the buzz of downtown—while still being just minutes away. The condo fee covers gas, water, sewer, and basic cable—making for easy, low-maintenance living (just pay electric). A dedicated basement storage unit adds extra convenience. Located close to Eastport Shopping Center, restaurants, coffee shops, the gym, and the farmers market, this is your opportunity to enjoy the best of coastal Annapolis living—every single day.
#MDAA2140406

ANNAPOLIS

796 FAIRVIEW AVENUE F 796 F

1 Beds

1 Baths

756 Sq.Ft.

$308,000

MLS#: MDAA2140406

Spring has arrived, and this beautifully updated 3-bedroom, 2-bath condo offers the perfect opportunity to enjoy the best of the Annapolis lifestyle. Located on the 3rd floor, this light-filled home combines modern upgrades, comfort, and unbeatable access to outdoor recreation and waterfront attractions. Inside, the open-concept living, dining, and kitchen area creates a warm and inviting flow, complete with a cozy fireplace—perfect for relaxing after a day on the water or exploring the city. The renovated kitchen (2022) features granite countertops, farmhouse sink, stainless steel appliances, and contemporary cabinetry designed for both everyday living and entertaining. Brand-new windows (2021) fill the home with natural light. The spacious primary suite includes a private en-suite bath and direct access to a walkout patio overlooking the community pool—an ideal spot for morning coffee, evening sunsets, or enjoying the spring breeze. Generous closet space throughout and updated bathroom finishes add to the home’s appeal. For buyers who love the outdoors, this location is exceptional. Just minutes away, enjoy scenic walking and biking trails, waterfront views, picnic areas, dog-friendly spaces, and seasonal outdoor activities at Quiet Waters Park, a local favorite with over 300 acres of trails and water access. You’re also moments from Historic Downtown Annapolis, Spa Creek, Back Creek marinas, waterfront dining, kayaking, sailing, and Chesapeake Bay attractions, making it easy to enjoy the coastal lifestyle that makes Annapolis so desirable. Community amenities include a swimming pool and convenient pet stations for easy living. Whether you're looking for a primary residence, a low-maintenance coastal retreat, or a home close to parks and the waterfront, this condo offers outstanding value and location. Now is the perfect time to make your move—schedule your private showing today and experience spring in Annapolis at its best.
#MDAA2129788

ANNAPOLIS

10 SANDSTONE COURT L

3 Beds

2 Baths

1,333 Sq.Ft.

$305,000

MLS#: MDAA2129788

Perhaps the finest Annapolis has to offer...A premiere, resort style retirement living option for those 60+ Time to let someone one else take care of the daily cooking and cleaning, you only need to relax, socialize with your friends and enjoy all Annapolis, Md has to offer! One monthly fee takes care of ALL utilities, daily meal, weekly cleaning, taxes, insurance, garage parking, maintenance/replacement of all appliances and HVAC. You've earned this!
#MDAA2128842

ANNAPOLIS

7101 BAY FRONT DRIVE 301

1 Beds

1 Baths

1,000 Sq.Ft.

$300,000

MLS#: MDAA2128842

This fabulous 3 bed/2 full bath condo has been renovated and is in the perfect location of amenity rich Fairwinds of Annapolis! Featuring fresh paint throughout, all new flooring (carpet and LVP), new windows and shades, new interior doors and a brand-new primary bath! This home is incredibly spacious, being one of the largest units, with lots of storage and a very flexible floorplan. Offering an owner's suite, full size washer/dryer in unit, updated eat-in kitchen, relaxing courtyard views and more! Fairwinds is close to wonderful restaurants, downtown Annapolis as well as shopping and services nearby. Community amenities include a swimming pool, tennis courts, tot lot and a picnic area with grills. Additionally, water, gas (heat and cooking) as well as biweekly foyer/stairwell cleanings are covered by the condo fee. If you have been waiting to find a large 3 bedroom, 2 bath condo, this is the home for you!
#MDAA2147576

ANNAPOLIS

140 GEORGETOWN ROAD 10

3 Beds

2 Baths

1,670 Sq.Ft.

$299,999

MLS#: MDAA2147576

Welcome to this fully renovated penthouse condo in the highly desirable Annapolis Overlook community. This spacious 2-bedroom, 2-bath residence features soaring 10-foot ceilings in the main living area, creating an airy, open feel filled with natural light, along with a cozy wood-burning fireplace perfect for cooler evenings. The thoughtfully designed open-concept layout flows seamlessly from the living and dining spaces to the covered balcony — protected on three sides for year-round enjoyment — while the incredible cross breeze throughout the home makes temperate months especially enjoyable indoors. Inside, nearly every surface has been updated with brand-new finishes, including luxury vinyl plank flooring, new carpet, new soft-close cabinetry, quartz countertops, stainless steel appliances, fresh paint, and fully renovated bathrooms. The spacious primary suite offers a walk-in closet and private en suite bath for added comfort and convenience. Residents of Greystone Court enjoy secured building entry, beautifully maintained common grounds and green space, a fantastic outdoor pool, fitness center, and abundant guest parking. The unit also includes two parking spaces — one assigned and one permit parking space. Ideally located with easy access to Downtown Annapolis, Washington D.C., and all major commuter routes, this home also places you moments from shopping, dining, and everyday conveniences. Modern, move-in ready, and perfectly located — this is condo living at its best.
#MDAA2144856

ANNAPOLIS

40 GREYSTONE COURT L L

2 Beds

2 Baths

1,229 Sq.Ft.

$299,900

MLS#: MDAA2144856

Welcome to 930 Astern Way — a completely renovated spacious 1-bedroom, 1½-bath condominium located in the sought-after 55+ community of Heritage Harbour. This bright and inviting unit offers modern comfort and low-maintenance living. The open layout creates an airy feel, with abundant natural light flowing throughout the home. The generously sized bedroom includes a private full bath, while the additional half bath is perfect for guests. Whether you’re relaxing at home or entertaining friends, this condo provides both comfort and style. One of the standout features of this building is the incredible convenience: residents enjoy access to a gym located right in the building, along with both an indoor pool and an outdoor pool — allowing you to swim and stay active year-round without ever leaving your immediate community. Beyond the building, Heritage Harbour offers unmatched resort-style amenities at the Lodge, including another indoor and outdoor pool, fitness center, golf course, tennis and pickleball courts, kayak storage, walking paths, on-site restaurant, woodworking shop, community library, and countless clubs and social activities. This vibrant waterfront community is known for its active lifestyle and welcoming atmosphere. If you’re looking for bright, updated living combined with exceptional amenities and convenience, 930 Astern Way delivers it all.
#MDAA2145386

ANNAPOLIS

930 ASTERN WAY 510

1 Beds

1 Baths

1,152 Sq.Ft.

$299,900

MLS#: MDAA2145386

Welcome to this fully renovated, single level condo on the 2nd floor of the building. One of the most recently updated 2-bedroom unit in the community, featuring brand-new flooring throughout and a gorgeous new kitchen with granite countertops, new stainless steel appliances, and other modern finishes. The open-concept living area is spacious and inviting. Community amenities include an outdoor pool, exercise room, and recreational clubroom. Reserved/assigned parking is available for two vehicles.
#MDAA2142030

ANNAPOLIS

10 SANDSTONE COURT G

2 Beds

2 Baths

1,103 Sq.Ft.

$298,500

MLS#: MDAA2142030

Welcome to 302-H Hilltop Lane, a beautifully maintained home that offers a perfect blend of comfort, convenience, and low-maintenance living , close to water, boating activities, concert venues.and more. Freshly painted 2BR/2BA condo in sought-after North Green Condominiums! Features a spacious living room filled with natural light, an inviting kitchen complete with stainless steel appliances, ample cabinetry, hardwood floors throughout, tile foyer/kitchen/enclosed balcony, newer microwave, Whirlpool washer/dryer, new sliding glass door. The fully enclosed glass balcony provides additional year-round living space for relaxing, entertaining, or enjoying morning coffee. This bright, open floor plan offers a separate dining area and spacious bedrooms. Community pool, lawn maintenance included, and convenient access to downtown Annapolis, shopping, dining, major highways, and BWI Airport. Move-in ready and maintenance-free living at its best!
#MDAA2148338

ANNAPOLIS

302 HILLTOP LANE H

2 Beds

2 Baths

1,082 Sq.Ft.

$275,000

MLS#: MDAA2148338

New on site 1 day ago
Welcome to the sought-after North Green Condominiums in Annapolis! This spacious top-floor, two-level penthouse loft condo offers an open and versatile floor plan designed for comfortable living and entertaining. The kitchen features granite countertops, stainless steel appliances, and ceramic tile flooring. Both full bathrooms were beautifully remodeled in 2024 and showcase stylish, modern finishes. The expansive loft provides endless possibilities as a home office, family room, exercise area, guest retreat, or hobby space. Step outside to your private balcony, the perfect place to enjoy your morning coffee or unwind after a long day. Recent updates include a main-level HVAC system replaced in 2022 and an upper-level HVAC system replaced in 2019. Residents enjoy outstanding community amenities, including a pool and entertainment area. Ideally located close to everything Annapolis has to offer, including downtown Annapolis, Truxtun Park, waterfront attractions, shopping, dining, and major commuter routes. This move-in-ready penthouse combines space, style, convenience, and an unbeatable location.
#MDAA2147614

ANNAPOLIS

300 HILLTOP LANE I

2 Beds

2 Baths

1,321 Sq.Ft.

$275,000

MLS#: MDAA2147614

Nestled in the charming Fairwinds on Severn community, this inviting 2-bedroom, 2- full bathroom garden level condo offers a perfect blend of comfort and convenience. Step inside to discover a traditional floor plan adorned with recessed lighting, creating a warm ambiance. The ample dining area flows seamlessly into a cozy living space, ideal for gatherings. Cook and entertain with ease in this well-equipped updated kitchen featuring stainless appliances, maple cabinets & granite counter-tops. Super spacious primary suite with built-in vanity, multiple closets and en-suite full bath w/ tiled walk-in shower. Slider off of living room leads you to a private walk-out terrace patio - ideal for pets & entertaining. Brand new gas HVAC! Outside, the community amenities beckon with a refreshing in-ground pool, tennis courts, and picnic areas, perfect for leisurely afternoons. There are plenty of unassigned parking spots in the huge parking lot, while you can reserve a spot for an annual fee (current spot is 161). With easy access to local parks and shopping, this location is a true gem. The condo fee covers essential services like gas, water, trash, and snow removal, ensuring a hassle-free lifestyle. Experience the comfort of home in this delightful condo and enjoy all that Annapolis & the Chesapeake Bay have to offer!
#MDAA2141140

ANNAPOLIS

16 SILVERWOOD CIRCLE 1

2 Beds

2 Baths

1,313 Sq.Ft.

$275,000

MLS#: MDAA2141140

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