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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
270
# of Listings
3
Avg # of Bedrooms
$517
Avg. $ / Sq.Ft.
$1,448,219
Med. List Price

Browse Annapolis Real Estate Listings

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Over $5M

270 Properties Found. Page 18 of 18.

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

1312 Square Ft Condo in Fairwinds of Annapolis ***NEW HVAC November 2024*** NEW LIGHTING 2024***NEW ELECTRICAL PANEL 2026 ***New shower glass door in master bathroom >>>Popular Fairwinds Condo is a great place to live!! Two Bedroom Two Bath WITH DEN condominium ! Newer stainless steel appliances ! Freshly painted 2026 ! Luxury Vinyl thru living areas and carpet in bedrooms! Lots of closets and storage! Free storage in another building ! Master bedroom has full bath ! Updated kitchen ! New light fixtures including eyeball lights! Granite countertops in kitchen! Stack washer/dryer in unit. Awesome enclosed patio for private electric grilling! Amenities in Fairwinds include swimming pool, tennis courts and tot lot. Fabulous condo and flexible seller is anxious to sell!!
#MDAA2139798

ANNAPOLIS

5 SILVERWOOD CIRCLE 1

2 Beds

2 Baths

N/A

$269,999

MLS#: MDAA2139798

Ground Floor Living! Absolutely stunning & fully remodeled condo in Fairwinds of Annapolis. Featuring 2 bedrooms and 2 full bathrooms, this condo shows as well as any condo you will find in the entire community. The unit boasts brand new LVP flooring, beautiful white Shaker cabinets, stunning new quartz counters, new SS appliances, 2 spectacularly remodeled bathrooms, brand new lighting throughout, and entire unit freshly painted. In unit laundry with custom made "Kenneth Alexander" barn door. It will be hard to find a more finely appointed condo in the entire association!
#MDAA2139322

ANNAPOLIS

205 VICTOR PARKWAY D 205D

2 Beds

2 Baths

972 Sq.Ft.

$269,999

MLS#: MDAA2139322

Renovated Annapolis Condo | Private Patio | Community Amenities | Move-In Ready Renovated in 2022 and move-in ready, this 1,300+ sq ft ground-floor condo in the Fairwinds community offers an open-concept layout, recessed lighting, updated kitchen with stainless steel appliances, tiled bathrooms, Electrolux front-load washer and dryer, custom finishes, and walk-in closet. Step outside to a private patio overlooking green space, offering a quiet place to enjoy your morning coffee or relax at the end of the day. The monthly condo fee covers exterior building maintenance, lawn care, snow removal, and trash. Fairwinds offers a pool, four tennis courts, two playgrounds, pet stations, and an athletic field. Conveniently located near Giant, CVS, Starbucks, and Dunkin on Bay Ridge Road, with Quiet Waters Park nearby and historic downtown Annapolis less than 7 miles away. Easy access to Route 50 and Route 97 for commuters heading toward DC, Baltimore, Fort Meade, and surrounding areas. One-year home warranty included at closing. Seller open to closing cost assistance with an acceptable offer.
#MDAA2142108

ANNAPOLIS

7 SILVERWOOD CIRCLE 3

2 Beds

2 Baths

N/A

$247,500

MLS#: MDAA2142108

Welcome to easy Annapolis living! This beautifully updated 2-bedroom, 1-bath condo offers the perfect blend of style, comfort, and convenience. Tucked away at the rear of the community, this home enjoys a private, wooded setting with large windows that fill the space with natural light and create a peaceful retreat from the everyday. The open-concept floor plan is designed for modern living, featuring updated flooring, fresh paint, and a spacious living area that flows seamlessly into the kitchen. The kitchen boasts granite countertops, stainless steel appliances, ample cabinetry, and a large breakfast bar perfect for casual dining, entertaining, or working from home. The generous primary bedroom features two large closets and ample storage, while the second bedroom offers flexibility as a guest room, home office, or fitness space. Step outside to the oversized private patio, an ideal spot to enjoy morning coffee, unwind after work, or entertain friends while surrounded by mature trees. Residents enjoy access to community amenities, including a pool available for a nominal seasonal fee. Ideally located just minutes from Downtown Annapolis, Quiet Waters Park, shopping, dining, commuter routes, and major highways, this home offers convenient access to both Washington, D.C. and Baltimore. Whether you’re a first-time buyer, downsizing, or searching for a low-maintenance lifestyle, this move-in-ready condo is one you won’t want to miss.
#MDAA2147778

ANNAPOLIS

19 HERITAGE COURT C

2 Beds

1 Baths

960 Sq.Ft.

$235,000

MLS#: MDAA2147778

Builder Special ... Vacant Lot ready for your vision for a small and functional single family home that would be super close to downtown. The parcel is partially fenced and has an existing paved driveway that leads to a one car carport that was once used by the owners of the adjoining lot. Buyer responsible for feasibility study, or lot use interpretation request, with the City of Annapolis Planning and Zoning Department for consideration and approval to construct a SFR.
#MDAA2142490

ANNAPOLIS

LOT 6 GILMER STREET

None Beds

None Baths

0.11 acres

$99,000

MLS#: MDAA2142490

Level lot, 2017 perc evaluation indicated a possible home up to a 2,500 sq ft . Buyer to verify all information.
#MDAA455886

ANNAPOLIS

1012 CARRS ROAD

None Beds

None Baths

0.16 acres

$98,000

MLS#: MDAA455886

ONLINE AUCTION: This auction takes place on the Ashland Auction Group Website Bidding Platform Bidding begins 5/1/2026 @ 10:00 AM. Bidding ends 5/5/2026 @ 12:45 PM. List Price is Suggested Opening Bid. Deposit: $10,000. This +/- 10,000 ft² parcel of land is located in Annapolis, MD within Anne Arundel County. It is just minutes away to Fishing Creek and Thomas Point Park. It offers easy access to major traffic artery Forest Dr. This property is vacant.
#MDAA2139482

ANNAPOLIS

3338 ARUNDEL ON THE BAY ROAD

None Beds

None Baths

0.23 acres

$50,000

MLS#: MDAA2139482

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Buyers resources
7 Reasons to Work with a Realtor
7 Principles For Home Buying Success
Getting a Mortgage To Buy a Home
Home Hazards Awareness
Key Items For Home Inspection
Questions When Buying a Condo
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Sellers resources
8 reasons to work with a realtor
Calculating Capital Gains
Checklist for Better Showing
Cleaning Home For Sale
Improving Odds Of an Offer
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Selling Your Home for More $$

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