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
361
# of Listings
3
Avg # of Bedrooms
$481
Avg. $ / Sq.Ft.
$1,098,732
Med. List Price

Browse Annapolis Real Estate Listings

67 Properties Found. Page 5 of 5.

New on site 2 days ago
Experience the best of both nature and city living in this spacious top-floor unit at Annapolis Overlook. With nearly 1,400 sq ft, this 2-bedroom, 2-bathroom home offers high ceilings, generous living space, a cozy fireplace, and a balcony overlooking a wooded setting—yet it's just minutes from Downtown Annapolis! You'll enjoy easy access to restaurants, shopping, and entertainment, as well as close proximity to the U.S. Naval Academy and local schools. Quick access to Route 50 and the Bay Bridge makes commuting a breeze.

Recent upgrades include a new HVAC unit installed in Fall 2023 and new energy-efficient patio doors, installed in 2023 and new toilets. The home also features updated vanities, mirrors, and fresh paint throughout. Don’t miss this opportunity for a top-floor unit in an incredibly convenient location! Secured front door access and assigned parking spaces complete the package.
#MDAA2116574

ANNAPOLIS

40 HEARTHSTONE COURT K K

2 Beds

2 Baths

1,376 Sq.Ft.

$284,900

MLS#: MDAA2116574

Great new Price!!       Isn't this how you always envisioned retirement!!
A premiere life of luxury overlooking the shores of the Chesapeake Bay!  Brand new hardwood flooring throughout the entire unit and complete interior painting.  Lovely end unit with extra windows that allows for wonderful natural light throughout.  Tranquil setting/views overlooking the beautiful wooded common grounds. Private Florida room can be utilized as a screened porch or enclosed for year round use.  
Monthly fee includes ALL utilities, daily meal, weekly housekeeping, concierge service, taxes, insurance, even repairs or replacement of all appliances, HVAC, plumbing/electric, nothing to do but move right in and enjoy life while all daily needs are included in the monthly fee!
#MDAA2096604

ANNAPOLIS

7101 BAY FRONT DRIVE 400

1 Beds

1 Baths

1,000 Sq.Ft.

$275,000

MLS#: MDAA2096604

Are you ready to relax and let someone else do the cooking and cleaning?  Now is your opportunity!  One monthly payment takes care of food, cleaning, ALL utilities, taxes, insurance, maintenance, everything is included in the monthly fee!! There's even medical staff on duty 24 hours a day/seven days a week.  And it's all located within a luxurious Annapolis retirement community.
Enjoy immense social opportunities with your peers in an upscale private and secure setting overlooking the shores of the Chesapeake Bay!  Brand new hardwood flooring throughout the entire unit and complete professional interior painting.  Lovely end unit with extra windows that allows for wonderful natural light throughout.  Tranquil setting/views overlooking the beautiful wooded common grounds. Florida room can be utilized as a screened porch or in the fall, it can closed up for year round use.  
Monthly fee includes ALL utilities, daily meal, weekly housekeeping, concierge service, taxes, insurance, even repairs or replacement of all appliances, HVAC, plumbing/electric, nothing to do but move right in and enjoy life while all daily needs are included in the monthly fee!
#MDAA2110104

ANNAPOLIS

7101 BAY FRONT DRIVE 400

1 Beds

1 Baths

1,000 Sq.Ft.

$275,000

MLS#: MDAA2110104

Are you ready to relax and let someone else do the cooking and cleaning?  Now is your opportunity!  One monthly payment takes care of food, cleaning, ALL utilities, taxes, insurance, maintenance, everything is included in the monthly fee!! There's even medical staff on duty 24 hours a day/seven days a week.  And it's all located within a luxurious Annapolis retirement community for those 60+.
Enjoy immense social opportunities with your peers in an upscale private and secure setting overlooking the shores of the Chesapeake Bay!  Brand new hardwood flooring throughout the entire unit and complete professional interior painting.  Lovely end unit with extra windows that allows for wonderful natural light throughout.  Tranquil setting/views overlooking the beautiful wooded common grounds. Florida room can be utilized as a screened porch or in the fall, it can closed up for year round use.  
Monthly fee includes ALL utilities, daily meal, weekly housekeeping, concierge service, taxes, insurance, even repairs or replacement of all appliances, HVAC, plumbing/electric, nothing to do but move right in and enjoy life while all daily needs are included in the monthly fee!
#MDAA2116362

ANNAPOLIS

7101 BAY FRONT DRIVE 400

1 Beds

1 Baths

1,000 Sq.Ft.

$275,000

MLS#: MDAA2116362

New on site 3 days ago
Updated 3 Bedroom/2 Bathroom Condo in Sought-After Fairwinds Community! 

Welcome to this beautifully maintained and move-in ready  home located in the highly desirable Fairwinds community. This home offers the perfect blend of comfort, convenience, and style with thoughtful upgrades throughout.

Interior Features Include:
Warm hardwood floors throughout the entire condo. 
Updated Kitchen and Bathrooms 
Windows replaced in 2003
New HVAC in 2024
New Roof 2024
Washer & Dryer replaced in 2016
Kitchen renovated in 2003
Culligan Water Filter on Kitchen Sink
** Condo fee includes gas, water and sewage utilities

This home offers a functional layout perfect for everyday living or entertaining. The Fairwinds community is known for its peaceful atmosphere, beautifully maintained grounds, and unbeatable location close to shopping, dining, and major commuter routes.

Whether you’re a first-time buyer, looking to downsize, or seeking a turnkey investment, this condo checks all the boxes.  
 Schedule your private tour today and discover why Fairwinds is one of the area's most sought-after communities!
#MDAA2115166

ANNAPOLIS

217 VICTOR PARKWAY H 217H

3 Beds

2 Baths

1,189 Sq.Ft.

$275,000

MLS#: MDAA2115166

Welcome to 38 Pleasant St! This renovated 2-bedroom, 1-bath townhome is located in downtown Annapolis and could be the perfect starter home or investment property. Renovations in 2021 included a new kitchen with stainless steel GE appliances, new flooring, HVAC, and a hot water heater. The main level features a living room, dining room, and kitchen that leads out to a fenced-in yard. The upper level includes 2 bedrooms, a full bath, and a laundry room. Windows have been replaced.

This home is centrally located in downtown Annapolis, within close proximity to the USNA, St. John's College, the cultural district, the City Dock, waterfront, shops, restaurants, and government buildings. Whether you're looking for an affordable home in Annapolis or considering a weekend getaway, this is the perfect choice.

This townhouse is not part of an HOA or condo association and is completely move-in ready. Don't wait!
#MDAA2105312

ANNAPOLIS

38 PLEASANT STREET

2 Beds

1 Baths

840 Sq.Ft.

$259,900

MLS#: MDAA2105312

New on site 2 days ago
Welcome to 204 Victor Parkway in the fairwinds condo community in Annapolis, This move-in ready 2 bed 2 bathroom condo is spacious and functional, this home has been meticulously maintained and offers a blend of simple living while maximizing your location needs. This condo is on the second level and has its own balcony, The primary bedroom host an en suite bathroom plus a modern vanity that can be used for various ideas. The Fairwinds community provides an abundance of amenities, including a large outdoor pool, tennis courts, multiple playgrounds, picnic areas, and expansive open spaces for residents to enjoy. Ideally located just minutes from Quiet Waters Park, local shopping centers, marinas, and Downtown Annapolis, you'll have easy access to all the best that Annapolis has to offer, including a short drive to the  U.S. Naval Academy. 
*Condo includes water & gas utilities. *
#MDAA2111984

ANNAPOLIS

204 VICTOR PARKWAY G 204G

2 Beds

2 Baths

970 Sq.Ft.

$250,000

MLS#: MDAA2111984

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