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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
266
# of Listings
3
Avg # of Bedrooms
$529
Avg. $ / Sq.Ft.
$1,357,478
Med. List Price

Browse Annapolis Real Estate Listings

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Over $5M

266 Properties Found. Page 17 of 18.

***BUYER’S FAILED TO PERFORM, THEIR LOSS IS YOUR GAIN***PROPERTY LISTED BELOW APPRAISED VALUE** Welcome to 10A Ironstone Ct a beautifully maintained 3-bedroom townhome offering comfort, convenience, and the sought-after Annapolis lifestyle. This spacious home features a stunning top-level primary suite complete with a cozy fireplace, soaking tub, separate shower, and walk-in closet creating the perfect private retreat. Laundry is conveniently located on the bedroom level for everyday ease. Enjoy community amenities including a pool and clubhouse while being just minutes from Downtown Annapolis, waterfront dining, shopping, entertainment, and commuter routes. Whether you are looking to enjoy weekends by the water, local restaurants, boutique shopping, or an easy commute, this home offers the ideal blend of lifestyle and value. Competitively priced and ready for its next owner, schedule your tour today.
#MDAA2145606

ANNAPOLIS

10 IRONSTONE COURT A

3 Beds

2 Baths

1,680 Sq.Ft.

$350,000

MLS#: MDAA2145606

Welcome to a beautifully maintained home with so many amazing features! This 2 bedroom 2 bathroom 3rd floor top level unit with over 1,080 sq ft offers a spacious, open concept layout. If you are looking for a move-in-ready property that you can be proud of, then search no further! When you walk in the front door, you will first notice the open-concept living area. The living area has so much room for entertaining. A beautiful fireplace that accents the entire space. The kitchen is beautiful with a modern style, including beautiful cabinets, countertops and matching appliances. It flows into a nice extra space for an office or eat in kitchen. This open concept has a rear porch area and a peaceful wooded scenery to enjoy nature and the outdoors. Nature is offered all around this property and many ways to enjoy it. Either walking on the wooded paths, enjoying the playgrounds, working out in the fitness center or relaxing by the pool. Both bedrooms are a good size with quality closet space and space for large furniture. The main entrance to the building has an intercom system directly to each unit for gaining access. As part of the condominium fees, it covers for common area maintenance, exterior building maintenance, lawn maintenance, snow removal, trash services, water/sewer bill and more. To top it off and ensure you move in worry-free, the home has a new gas hot water heater (2026) and a washer/dryer in the unit. This home will have you beyond excited and stress-free! Do not miss your chance to own this unique property! You will have peace of mind knowing your new home was meticulously maintained and cared for. Not to mention move-in-ready! The location is ideal for commuting, as well as being in proximity to local shops, restaurants and walking distance to many amenities! It's time for you to call it HOME!
#MDAA2149028

ANNAPOLIS

501 MATHIAS HAMMOND WAY 301

2 Beds

2 Baths

1,081 Sq.Ft.

$349,900

MLS#: MDAA2149028

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.

$345,000

MLS#: MDAA2140034

Welcome to 8 Georgetown Court! This charming end of group town home offers 3 bedrooms, 1.5 bath on a quiet culdesac in the heart of Annapolis. Offering a functional layout with spacious living areas and abundant natural light, this home is perfect for both everyday living and entertaining. Enjoy generously sized bedrooms, a welcoming outdoor space, and the convenience of being just minutes from downtown Annapolis, shopping, dining, parks, and major commuter routes.Step outside to enjoy the private fenced patio, complete with a privacy fence, creating the perfect space for relaxing, entertaining, gardening, or enjoying your morning coffee. Whether you're a first time homebuyer, looking to downsize, or searching for your next investment opportunity, this home offers comfort, convenience, and value in a desirable location. Don't miss your chance to make this Annapolis gem your own!
#MDAA2149550

ANNAPOLIS

8 GEORGETOWN COURT 1-8

3 Beds

1 Baths

1,106 Sq.Ft.

$330,000

MLS#: MDAA2149550

New on site 2 days ago
Welcome to 1231 Gemini Dr Unit L, a beautifully updated top-floor residence with a rare and highly desirable lofted floor plan. Offering 1 bedroom and 1 bathroom across 1,133 sq. ft., this unit stands out as one of the largest layouts in the building and has been fully renovated to deliver a clean, modern aesthetic throughout. Soaring ceilings and recessed lighting create an open, airy feel the moment you step inside. The main living area is anchored by a stylish spiral staircase leading to the spacious loft, a versatile upper-level space ideal for a second bedroom, home office, or additional lounge area. Skylights and an additional large ceiling fan enhance the loft with natural light and comfort, while the top-floor location provides added privacy with no neighbors above. The kitchen has been completely updated with stainless steel appliances, modern wood cabinetry, and has ample storage space. Just off the kitchen and family room, a balcony offers a comfortable outdoor retreat. The main living area also features a contemporary ceiling fan, adding both style and function for warmer months. The bathroom has been refreshed with modern finishes, contributing to the home’s cohesive, upscale feel throughout. Ideally located in Annapolis, the property is just minutes from downtown, offering easy access to waterfront dining, restaurants, shopping, and local entertainment. Easy access to Route 50 and the Bay Bridge. Community amenities include trash removal, as well as access to a pool and tennis courts. Condo association is FHA approved; buyer’s lender to verify eligibility.
#MDAA2149672

ANNAPOLIS

1231 GEMINI DRIVE L

2 Beds

1 Baths

1,133 Sq.Ft.

$325,000

MLS#: MDAA2149672

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

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 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.

$309,900

MLS#: MDAA2140882

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 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

New on site 1 day ago
Beautifully Renovated 3BR/2BA Condo in Sought-After Annapolis Overlook. Welcome home to this bright and beautifully updated 3-bedroom, 2-bathroom condominium. The spacious, open-concept living area features a cozy fireplace and flows seamlessly into the dining room. In the kitchen, you will find stainless steel appliances, abundant counter and cabinet storage, and a convenient breakfast bar. The primary suite boasts a private full bathroom and direct deck access overlooking scenic green space. Designed with a split floor plan, the second bedroom sits on the opposite side of the home for optimal guest privacy, adjacent to the second full bath. The flexible third bedroom serves perfectly as a den or dedicated home office.Annapolis Overlook is a pet-friendly community offering premier amenities, including an outdoor pool and fitness room. Conveniently located with easy access to Rt. 50 and I-97, you are just minutes from Quiet Waters Park, Annapolis City Dock, Truxton Park Recreation Center, local shopping, dining, and the Chesapeake Bay.
#MDAA2150516

ANNAPOLIS

20-F AMBERSTONE COURT

3 Beds

2 Baths

1,119 Sq.Ft.

$290,000

MLS#: MDAA2150516

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