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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
274
# of Listings
3
Avg # of Bedrooms
$510
Avg. $ / Sq.Ft.
$1,357,507
Med. List Price

Browse Annapolis Real Estate Listings

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Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

54 Properties Found. Page 3 of 4.

Beautifully maintained 3-level townhome in the desirable Annapolis Overlook community in Annapolis! This spacious home offers approximately 1,680 sq ft with 3 bedrooms, 2.5 baths, and a functional layout designed for comfortable living. The main level features a bright living area, separate dining space, and an updated kitchen with ample cabinet storage and room for entertaining. Upstairs you’ll find generously sized bedrooms including a primary suite with private bath and great closet space. Enjoy low-maintenance living in a well-established community conveniently located near downtown Annapolis, the Naval Academy, shopping, restaurants, and major commuter routes. The 21403 area is known for its coastal lifestyle, outdoor recreation, and close proximity to the Chesapeake Bay.  Perfect for first-time buyers, investors, or anyone looking for easy living in a prime Annapolis location!
#MDAA2140034

ANNAPOLIS

40 IRONSTONE COURT J

3 Beds

2 Baths

1,680 Sq.Ft.

$359,999

MLS#: MDAA2140034

This colonial home, built in 1950, blends classic appeal with modern comfort. Spanning 1,584 square feet, this detached residence features four spacious bedrooms and two full bathrooms, making it an ideal retreat for those seeking both space and style. Venture inside to discover a warm and inviting interior adorned with carpet and hardwood floors. The eat-in kitchen, designed for both functionality and social gatherings, offers ample table space, perfect for casual dining or entertaining. The bathrooms feature a convenient tub-shower combination, providing a relaxing oasis after a long day. The unfinished full basement presents a blank canvas for customization, whether you envision a home gym, workshop, or additional storage. Outside, the property features a well-maintained front and rear yard, ideal for outdoor activities or serene relaxation. Parking is a breeze with off-street options or a driveway. This home is conveniently located with easy access to local dining, market and shopping. So, don't miss this opportunity to make his home your own
#MDAA2144184

ANNAPOLIS

7 CARVER STREET

4 Beds

2 Baths

1,584 Sq.Ft.

$350,000

MLS#: MDAA2144184

NEW KITCHEN just installed! The eat-in kitchen has been updated with NEW tall, white kitchen cabinetry w/brushed bronze handles, NEW upgraded quartz countertops,NEW lighting, freshly painted, and boasts all stainless steel appliances including a gas range, french door refrigerator, dishwasher, and microwave—all installed within the past year. Enjoy Annapolis living with a community pool and fitness center—right at home! This beautiful townhome-style condo features a sprawling top-floor Owner’s Suite with a private bath, soaking tub, separate shower, double vanity, and oversized walk-in closet. The second level offers two additional large bedrooms and a full bath, ideal for guests, family, roommates, or a home office. Recent upgrades include a brand-new roof, newer gas HVAC (approx. 1.5 yrs), full-size washer & dryer (approx. 2 yrs), and newer stain-resistant carpet with pad. The main level shines with luxury vinyl tile flooring for a modern, low-maintenance lifestyle. Convenient main-level half bath. Reasonable condo fees cover the pool, fitness center, roof, fencing, and lawn care—truly lock-and-leave living. Ideally located just minutes from downtown Annapolis, this home includes one reserved parking space plus one additional parking permit. Comfort, convenience, and carefree living—all in one place. 🏡✨
#MDAA2143694

ANNAPOLIS

50 HEARTHSTONE COURT E

3 Beds

2 Baths

1,620 Sq.Ft.

$350,000

MLS#: MDAA2143694

Just Reduced + $5000 closing cost credit towards this move-in ready condo in the sought-after Riva Trace community! Freshly painted with brand-new carpet throughout, this home features a bright solarium, a spacious primary bedroom with a walk-in closet, and a primary bath complete with a soaking tub and separate shower. All appliances convey, making this home truly turnkey. Step outside to enjoy your own private patio. The Riva Trace community offers an impressive array of amenities, including scenic walking paths, picnic areas, pickleball and tennis courts, a baseball field, basketball court, and a community pier—perfect for enjoying the outdoors and staying active. Conveniently located just minutes from downtown Annapolis, with quick access to major commuter routes.
#MDAA2136078

ANNAPOLIS

2702 SUMMERVIEW WAY 103

2 Beds

2 Baths

1,285 Sq.Ft.

$349,999

MLS#: MDAA2136078

Welcome to this beautiful 2-bedroom, 2-bath condo in the highly sought-after Tidewater Colony community of Annapolis. Inside, you’ll find 9-foot ceilings, luxury vinyl plank floors, custom blinds, and a modern kitchen with granite countertops, gas cooking, and a built-in microwave. The spacious primary suite features a double vanity and a luxurious bath with separate shower and soaking tub. Additional highlights include high-efficiency HVAC and a dedicated laundry room with full-size washer and dryer. Enjoy resort-style living with access to the clubhouse, fitness center, pool, tennis courts, playground, and walking trails. Perfectly positioned just minutes from downtown Annapolis and Anne Arundel Medical Center, with easy commuter access to Route 50 and Route 97. A prime location paired with comfort and convenience—this one checks all the boxes.
#MDAA2136790

ANNAPOLIS

2006 PEGGY STEWART WAY 204

2 Beds

2 Baths

1,046 Sq.Ft.

$335,000

MLS#: MDAA2136790

Welcome to this home nestled in the heart of Annapolis. Offering a blend of comfort, functionality, and convenience, this property features spacious living areas, abundant natural light, and a layout designed for everyday living and entertaining. Enjoy a generous backyard perfect for relaxing or hosting gatherings, along with easy access to local shopping, dining, marinas, parks, and major commuter routes. Located just minutes from downtown Annapolis and the Chesapeake Bay, this home provides the ideal balance of charm, accessibility, and lifestyle. Property is being sold as is. Don’t miss the opportunity to make this Annapolis gem your own.
#MDAA2144702

ANNAPOLIS

121 CONLEY DRIVE

3 Beds

1 Baths

1,280 Sq.Ft.

$330,000

MLS#: MDAA2144702

LOCATION, LOCATION, LOCATION!! Your Beautiful Home awaits in The Heart of Annapolis!! Brand New Carpet, New HVAC (2021) Inside and Outside Unit, Corian Counter's and even an Awesome Wooded View from your Private Balcony! Community Pool, Pickel Ball, Community Center, Exercise Room and so much more!!! Be in your new home in just 2 weeks, With preferred vendors!!
#MDAA2144778

ANNAPOLIS

631 ADMIRAL DRIVE 302

2 Beds

2 Baths

1,341 Sq.Ft.

$329,900

MLS#: MDAA2144778

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

1 Year home warranty offered by the seller (a $500 value)! 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.

$318,000

MLS#: MDAA2135514

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, 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

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

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.

$305,000

MLS#: MDAA2144856

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

Perched on the top floor of the sought-after Fairwinds of Annapolis community, this beautifully updated condo offers a quiet retreat with no neighbors above and serene courtyard views. Surrounded by mature trees and thoughtfully landscaped common areas, residents enjoy a well-maintained setting complete with a pool, tennis courts, tot lots, snow removal, picnic areas for grilling, bike and kayak storage racks. Inside, the home has been updated throughout with stylish luxury vinyl plank flooring, creating a cohesive and modern feel. The spacious living room is filled with natural light and features a sliding glass door that opens to a private deck overlooking the courtyard. The deck is enhanced with new acacia wood decking and provides an ideal spot to relax or unwind. The living area flows seamlessly into the dining room, making everyday living and entertaining effortless. The kitchen combines function and style with stainless steel appliances, including a gas range with a double oven, along with a comfortable breakfast area for casual dining. Tucked at the end of the hall, the spacious primary bedroom offers a peaceful retreat with a walk-in closet, a second closet, and a private en-suite bath. Two additional generously sized bedrooms share a well-appointed hall bath, providing flexibility for guests, family, or a home office. An in-unit laundry room adds everyday convenience. Thoughtful updates enhance the home’s appeal, including new toilets, updated electrical components, and a newly installed range and microwave. Additional upgrades such as new window blinds and updated cabinet pulls add a polished finishing touch. Parking is easy with ample unassigned spaces available, along with the option to secure a reserved parking decal for an additional fee. In addition to the community amenities, residents enjoy a vibrant mix of local Annapolis amenities including charming waterfront dining and boutique shopping in historic downtown and scenic strolls along the City Dock. Outdoor enthusiasts can take advantage of nearby parks, the Chesapeake Bay, easy access to bike trails, and a variety of community events and farmers markets. Combining thoughtful updates, a functional layout, and a quiet top-floor location, this home offers comfortable living in a vibrant and amenity-rich community.
#MDAA2138752

ANNAPOLIS

21 SILVERWOOD CIRCLE 11

3 Beds

2 Baths

1,670 Sq.Ft.

$300,000

MLS#: MDAA2138752

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

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