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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

310

# of Listings

3

Avg # of Bedrooms

$440

Avg. $ / Sq.Ft.

$996,943

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

310 Properties Found. Page 18 of 21.

Experience your own piece of paradise. Enjoy this fully furnished, well appointed home in a river front community. 4 bedrooms 3 baths close to the end of a quiet street. See the South River from your front yard and second floor kitchen deck. Close to Maryland's state capital, commuter routes and plenty of restaurants and shopping.

ANNAPOLIS

122 BAY VIEW DRIVE

4 Beds

3 Baths

2,200 Sq.Ft.

$4,300

MLS#: MDAA2125248

Absolutely Gorgeous Historic Annapolis home , full of the charm and style yet completely restored with all of the modern conveniences . Close to everything 1 block from main street.....City Dock, Bar, Restaurants...... across from City Hall, Close to spa creek ..... Come sit back and enjoy the Annapolis life style.

Pets allowed with non refundable pet fee of $250 per Pet and $50 a month pet rent per pet

Parking permits are required now by the city. Must apply for them
https://www.annapolisparking.com/ or through a specific webpage https://www.annapolis.gov/1824/New-Residents

ANNAPOLIS

151 DUKE OF GLOUCESTER STREET

4 Beds

3 Baths

1,990 Sq.Ft.

$4,100

MLS#: MDAA2116374

Charming corner lot home for rent on the coveted Eastport Horn Point peninsula in Annapolis, MD. This cozy residence features 4 bedrooms and 2 fully renovated baths, separate dining and front entry sunporch which provides a comfortable living space for its occupants. With a small but efficient kitchen, rear deck, and mini split air and heating with natural gas radiator heat backup, and unfinished basement, this home offers convenience and comfort in a most desirable location near downtown and Eastport eateries! Don't miss out on the opportunity to make this lovely house your new home.

Small pets considered on a case-by-case basis with additional monthly pet rent. This is a non-smoking unit. No groups please.

ANNAPOLIS

530 FIRST STREET

4 Beds

2 Baths

1,200 Sq.Ft.

$4,095

MLS#: MDAA2127894

697 Giddings, 3 levels of Modern luxury in the heart of West Annapolis. Designed by Hammond Wilson Architects and built by Bayview Builders. This townhome is loaded with high end finishes. Custom kitchen with Quartz Countertops, stainless steel top of the line appliances. The lower level has a full bath and rec room that could be used as a 3rd bedroom. Open modern floor plan with hardwood floors throughout. Pella Double-Pane windows which helps keeps the street noise to a minimum. French doors lead to a nice sized patio perfect for any outdoor activity. Shops and restaurants right outside your front door. Restaurants include InGrano, (fine dining), Chessies Wharf by RAR Brewing, Evelyn's Cafe, Bean Rush Coffee shop and Always Ice Cream. Walkable to downtown, Naval Academy and stadium. Water access 5 blocks away. Easy access to RT 50/97. Pets case by case, rent includes 2 parking spot. Electric car charging available.

ANNAPOLIS

697 GIDDINGS AVENUE

2 Beds

2 Baths

1,523 Sq.Ft.

$4,000

MLS#: MDAA2128808

Beautiful 2 BR/2 Bath condo w/many extras in the most luxurious, secure building in downtown Annapolis. Great southern views, natural light, sliding glass doors, plantation shutters in all rooms, wood floors, gourmet kitchen , stainless appliances & granite counters, Pool, Hot Tub, Fitness Center, 24/7 live concierge/security person in lobby. Two Underground Garage Spaces with remote door openers included.
Rent includes most utilities. Available June 1st, 2025
Luxury living in the heart of Annapolis, just blocks to Downtown City Dock attractions and restaurants.

ANNAPOLIS

5 PARK PLACE 624

2 Beds

2 Baths

1,270 Sq.Ft.

$3,850

MLS#: MDAA2110354

**PROFESIONAL PHOTOS COMING SOON**
Spacious and inviting, this Annapolis home offers over 3,000 sq. ft. of living space in a prime location-- a short commute to downtown Annapolis and the Naval Academy. Available NOW!
The main level provides an easy flow between the kitchen, dining, and living areas, with plenty of natural light throughout. A bonus room off the back of the kitchen adds extra space for relaxing, entertaining, or working from home, and it overlooks a private tree-lined backdrop.
Upstairs you’ll find a comfortable primary suite with its own bath and walk-in closet, along with two additional bedrooms, a full bath, and a loft area perfect for study or play. The finished lower level includes a large recreation room with access to the backyard, an additional full bath, laundry, and ample storage.
Two reserved parking spots are included.
Conveniently located near shops, restaurants, commuter routes, and only a short drive to the Naval Academy, this home is ready for you to move in and enjoy.

ANNAPOLIS

428 CRANES ROOST COURT

3 Beds

3 Baths

3,076 Sq.Ft.

$3,650

MLS#: MDAA2124994

One of the largest homes in Atlantis features 5 bedrooms and 4 1/2 baths!!! Over 3000 sq ft with finished basement and 1 car garage.

Access to Tot Lot and larger kid playground. Access to the community pier for fishing, crabbing, and kayaking. Community does bi-weekly food trucks. 4 kayaks will be left at the house for tenants to use. The pier access is a 5 min walk, 1 street over.
Pets are considered case by case. Pet rent $25 per month. No groups please. Minimum credit score 675.

ANNAPOLIS

946 AQUA COURT

5 Beds

4 Baths

N/A

$3,600

MLS#: MDAA2128710

GREAT OPPORTUNITY! Close to everything to include Annapolis Mall and much more! Top level huge office with several tons of opportunity!

ANNAPOLIS

2563 FOREST DRIVE

None Beds

None Baths

20,173 Sq.Ft.

$3,500

MLS#: MDAA2065382

NEW PRICE!!! Charming Murray Hill Beauty — 4BR/3BA in the Heart of Annapolis!

Fall in love with this spacious and beautifully maintained home in one of Annapolis’ most sought-after neighborhoods! Featuring four generous bedrooms and three full baths, this classic Murray Hill residence blends historic charm with modern comfort.

Enjoy the warmth of sun-filled living spaces, gleaming hardwood floors, and architectural details throughout. The kitchen opens to inviting dining and living areas—perfect for entertaining or relaxing at home. The basement provides plenty of storage, while the one-car garage and two additional driveway spaces make parking easy (a true bonus in downtown Annapolis!).

Step outside and take in tree-lined streets, friendly neighbors, and walkable access to all that Annapolis has to offer—dining, shopping, the waterfront, and city events just minutes away.

Available for $3,850/month — this Murray Hill treasure offers space, charm, and the quintessential Annapolis lifestyle.

ANNAPOLIS

10 CONSTITUTION AVENUE

4 Beds

3 Baths

1,930 Sq.Ft.

$3,500

MLS#: MDAA2125866

Excellent rental opportunity in Village Greens of Annapolis. This spacious three-level townhouse has been meticulously maintained and is ready for a renter. Upon entry, you will be greeted by hardwood floors and neutral paint colors throughout. The lower level has a large living area, powder room, and access to the two-car garage. Upstairs you will find spacious and comfortable main-level living with a second living room. The kitchen is perfect for any chef, you will enjoy an open concept which is great for entertaining. The kitchen is complete with granite countertops, stainless steel appliances, gas cooking, an island with bar seating, plenty of cabinetry, and a pantry. There is room for a large dining table and a breakfast nook. The dining area also has a cozy, double-sided gas fireplace! Off of the main level is an outdoor deck, perfect for morning coffee or watching a sunset while enjoying the double-sided fireplace. You will find all three bedrooms on the third level of the townhouse and two full bathrooms. All bedrooms have vaulted ceilings and plenty of windows for ample natural lighting. The primary bedroom has a walk-in closet and a bathroom with a dual vanity. The back portion of the neighborhood to access the garage and driveway is gated which makes for added privacy. This townhouse has a two-car garage with electric vehicle charging capability and a spacious driveway. There is also extra, on-street parking in the front of the home. Village Greens is about a five-minute walk to restaurants like Ledo Pizza, and Shika Sushi. You will also be close to convenience stores, shopping, and recreation like Quiet Waters Park! Downtown Annapolis and the United States Naval Academy are a short drive away. Commuters will enjoy quick access to interstate routes, Washington DC, Baltimore, and BWI! Make your appointment to see this one today. Pets are case by case, 680+ credit score required.

ANNAPOLIS

617 S CHERRY GROVE AVENUE

3 Beds

2 Baths

2,000 Sq.Ft.

$3,500

MLS#: MDAA2130262

Coming soon! Townhouse in the amenity rich Chesapeake Harbour is ready for you! 2 car garage. Master suite features gas fireplace, deck with water views, walk-in closets, luxurious bathroom equipped with new over-sized walk-in shower and jacuzzi tub. Community amenities to include pools, beaches, piers, kayak launch, and tennis courts! Private Marina and water front restaurant located in this gated community.

No pets allowed per condo association rules and regulations. No groups please. Minimum credit score of 650 required.

ANNAPOLIS

7025 CHESAPEAKE HARBOUR DRIVE 18B

3 Beds

2 Baths

2,188 Sq.Ft.

$3,495

MLS#: MDAA2128712

#MDAA2129972

ANNAPOLIS

1411 STONECREEK ROAD

4 Beds

2 Baths

1,920 Sq.Ft.

$3,450

MLS#: MDAA2129972

Stunning Oyster Harbor Rental – Coastal Charm Meets Comfort

This gorgeous rental blends comfort, charm, and the best of coastal living. Nestled in the highly desirable Oyster Harbor community, residents enjoy water privileges and access to a sandy beach, picnic area, fishing pier, and playground—all just a short walk from the front door. Additional amenities include a community marina, boat ramp, and storage racks for kayaks and paddle boards, creating the ultimate waterfront lifestyle just minutes from downtown Annapolis.

The home itself is designed for both entertaining and everyday enjoyment. An enormous screened-in porch and a spacious, fully fenced backyard provide plenty of room to garden, relax in a hammock, or host gatherings. After a day at the beach, the outdoor shower is the perfect convenience.

Inside, the property features three bedrooms, two full bathrooms, and hardwood floors throughout the main level. The home comes fully furnished for a move-in ready experience, with the option to remove furnishings at the time of application.

Don’t miss the opportunity to live in this beautiful home and vibrant waterfront community—where comfort, charm, and lifestyle come together seamlessly.

ANNAPOLIS

1252 CREEK DRIVE

3 Beds

2 Baths

1,555 Sq.Ft.

$3,250

MLS#: MDAA2126456

#MDAA2128480

ANNAPOLIS

508 HARBOR DRIVE

4 Beds

1 Baths

2,400 Sq.Ft.

$3,250

MLS#: MDAA2128480

#MDAA2126402

ANNAPOLIS

780 FAIRVIEW AVENUE F F

2 Beds

1 Baths

1,000 Sq.Ft.

$3,250

MLS#: MDAA2126402

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