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
359
# of Listings
3
Avg # of Bedrooms
$479
Avg. $ / Sq.Ft.
$1,097,034
Med. List Price

Browse Annapolis Real Estate Listings

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

359 Properties Found. Page 20 of 24.

New on site 3 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 4 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 3 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

Open House Sunday, May 18th, 1-3 pm. Great Townhome at the Saltaire in Annapolis. 2 bedroom, 1.5 Bath with a fireplace and large back deck. Well priced in a popular community with a community pool, across from the Annapolis Recreation Center.
#MDAA2115488

ANNAPOLIS

290 HILLTOP LANE M

2 Beds

1 Baths

1,024 Sq.Ft.

$249,950

MLS#: MDAA2115488

Welcome to the heart of downtown Annapolis, where city living meets historic charm! This 3-bedroom, 1 Full and 1 Half-bathroom, townhome offers an incredible opportunity to be just 2 blocks away from the Capitol building, shopping, restaurants, and the picturesque waterfront filled with boats. Convenience is key with parking included, allowing you to explore the vibrant downtown area with ease. Kitchen appliances are also included in the sale, making this property quicker for you to move in and enjoy. Don't miss this rare opportunity to own a piece of Annapolis for under $250,000! This charming townhome is your ticket to experiencing the vibrant downtown lifestyle Annapolis has to offer or add another rental property to your portfolio.
#MDAA2112570

ANNAPOLIS

63 TOWN PINES COURT

3 Beds

1 Baths

1,037 Sq.Ft.

$225,000

MLS#: MDAA2112570

New on site 3 days ago
Seize the opportunity to own a cleared, water-view lot in the community of Highland Beach, an incorporated municipality, Located just minutes from Downtown Annapolis, this lot provides easy access to schools, shopping, and dining. The community beach is only steps away, offering picturesque water views. Sewer hook-up is available at the street.
#MDAA2114238

ANNAPOLIS

3210 BRUCE

None Beds

None Baths

0.14 acres

$165,000

MLS#: MDAA2114238

Welcome to the sought-after community of Cape St. Claire! This lot is being offered as an addition to a home for sale. Please contact the county for possible development.
#MDAA2116560

ANNAPOLIS

1167 GREEN HOLLY DRIVE

None Beds

None Baths

0.21 acres

$165,000

MLS#: MDAA2116560

BUSINESS SALE ONLY- Fantastic opportunity to own this turnkey and well established restaurant in the heart of downtown Annapolis. Approximately 1500SF with 20 dine-in seat capacity. Fully equipped kitchen ready for any menu. Downtown Annapolis boasts a vibrant and diverse restaurant scene, seamlessly blending historic charm with modern culinary offerings. This location has excellent visibility on the popular Main St. Beer & Wine license available. Landlord approval of new tenant is required. Showings by appointment only.
#MDAA2105548

ANNAPOLIS

138 MAIN STREET

None Beds

None Baths

N/A

$150,000

MLS#: MDAA2105548

Fantastic opportunity to build your dream home in Annapolis! This lot is conveniently located near stores, retaurants and route 50. Lot is owned by the house next door so they are currently using it as an extended yard.
#MDAA2103344

ANNAPOLIS

GILMER STREET

None Beds

None Baths

0.11 acres

$120,000

MLS#: MDAA2103344

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

*****Where Creek Road ends there are 8 lots, then this lot is available for purchase, then 8 more lots and Creek Road picks back up. This lot sits in the middle of 17 lots. All infrastructural would need to be completed by buyer. ****** This 0.41 acre lot is water privilege community with beach, boat dock, boat slips, boat ramp and more. Public sewer hook up available is available in the community . Well would be the water source, See disclosures for lot location.
#MDAA2064060

ANNAPOLIS

1227 CREEK DRIVE

None Beds

None Baths

0.41 acres

$79,900

MLS#: MDAA2064060

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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
Questions When Choosing a Realtor
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
Preparing Home for photoshoot
Selling Your Home for More $$

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