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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
318
# of Listings
3
Avg # of Bedrooms
$463
Avg. $ / Sq.Ft.
$1,069,668
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

71 Properties Found. Page 2 of 5.

***Tenant Occupied 24 hour notice on all showings****Welcome to 106 Annapolis St. in sought after West Annapolis. This Hammond Wilson designed luxury Penthouse Unit is a one-of-a-kind rental option in a sought after Annapolis location. The 2 bedrooms PLUS Den/3rd Bedroom is loaded with high end finishes. Bright custom Kitchen features Quartz countertops, KitchenAid Stainless Steel Appliances. Open floor plan, wide plank hardwood floors throughout the unit. Primary bedroom with ensuite bathroom, porcelain tile and dual vanity. Unit has 2 different balconies that overlook Annapolis St. Rent includes 2 parking spaces in garage below building. Building has an elevator or use the stairs. Unbeatable location, right in the heart of West Annapolis. Shops, restaurants (RAR Chessie's Wharf, Evelyn's and Ingrano), coffee and Ice Cream shop just steps outside the front door. Close to USNA & Stadium walk to Downtown and easy access to Rt. 50. Pets on Case by Case. Available 11/7/25
#MDAA2127104

ANNAPOLIS

106 ANNAPOLIS STREET 203

2 Beds

2 Baths

1,406 Sq.Ft.

$4,600

MLS#: MDAA2127104

Views of the Great Chesapeake Bay come with this updated and upgraded Oyster Creek waterfront. Shared pier with a large boat slip, community beach and boat ramp for easy water access to the Bay. No smoking house and no pets allowed.
#MDAA2113692

ANNAPOLIS

1330 WASHINGTON DRIVE

3 Beds

2 Baths

1,584 Sq.Ft.

$4,500

MLS#: MDAA2113692

Welcome to Eastport! This exquisitely restored 1945 Cape Cod boasts modern amenities, four bedrooms, and two full bathrooms. Available with lovely antique furnishings to sleep up to 8 people. The expansive, fenced backyard boasts a deck and patio. You'll love the charm, the glorious gardens, and the proximity to all that Annapolis has to offer. Walk to restaurants, shops, and yacht clubs! This is the iconic Eastport experience you've been dreaming of. Welcome home!
#MDAA2128478

ANNAPOLIS

922 JACKSON STREET

4 Beds

2 Baths

2,184 Sq.Ft.

$4,500

MLS#: MDAA2128478

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.
#MDAA2125248

ANNAPOLIS

122 BAY VIEW DRIVE

4 Beds

3 Baths

2,200 Sq.Ft.

$4,300

MLS#: MDAA2125248

Welcome to this exquisite home nestled conveniently close to downtown Annapolis and Eastport. This former four bedroom model home with 2 car garage is most likely the largest house in Ambridge. The home has been freshly painted and carpeted and is situated on a nice corner lot in this premier community with downtown Annapolis in one direction and Quiet Waters Park in the other. Features include over 3,500 square feet on all three levels and 2,400 + finished square feet on first and second level. (The two car garage is not included in the 3,500 square feet.) Floor plans are attached. Sunny open floor plan featuring large kitchen with white cabinetry, granite and pantry, plus stainless steel refrigerator (8/2023, $2,400). Family room has wood burning fireplace and custom built-in cabinetry. Dining room also has custom built-in cabinetry with bump out window and newer chandelier. Hardwood throughout first level. Two level foyer. Large upper level features an open sitting area with skylight leading to four bedrooms including primary bedroom and bath. Fully unfinished lower level offers 1,100 square feet and awaits your finishing touches. Will sell some furniture upon request. Easy access to commuting routes to Baltimore, Washington D.C., and/or Fort Meade. Newer HVAC system (2021), irrigation system, new garbage disposal, and security system. Owner Agent. There is no sign on the property. Listing MDAA2123438 is the Sale listing for this property.
#MDAA2123566

ANNAPOLIS

919 BERWICK DRIVE

4 Beds

2 Baths

2,292 Sq.Ft.

$4,200

MLS#: MDAA2123566

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.
#MDAA2127894

ANNAPOLIS

530 FIRST STREET

4 Beds

2 Baths

1,200 Sq.Ft.

$4,150

MLS#: MDAA2127894

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
#MDAA2116374

ANNAPOLIS

151 DUKE OF GLOUCESTER STREET

4 Beds

3 Baths

1,990 Sq.Ft.

$4,100

MLS#: MDAA2116374

Feel like you're on vacation every day at home in this beautiful 3 bedroom, 2 bathroom, 1370 SF condo at Severn House in Eastport. Enjoy watching sailboats from your couch or relaxing at the community waterfront pool. Love your spacious water view balcony, perfect for entertaining friends. The living room opens to the dining room and balcony, providing a lovely flow for gatherings. With 3 bedrooms, you have the flexibility for an office or extra guest room. You'll appreciate the convenience of a full-size washer and dryer in your condo. The community offers a pool, boat slips, and park-like grounds, creating a serene environment. The owner covers monthly condo fees and provides a 2 parking spaces with guest parking available on a first-come, first-serve basis up to 10 days at a time. Owner is able to leave some furniture if tenant requests. Please note, Severn House does not permit pets. The owner is open to a 12-36 month lease, which is available online, and the condo can be ready for you by November 1. No Smoking. Welcome to your New Home! Check out our video tour too!
#MDAA2128924

ANNAPOLIS

772 FAIRVIEW AVENUE C 772 C

3 Beds

2 Baths

1,370 Sq.Ft.

$4,000

MLS#: MDAA2128924

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.
#MDAA2128808

ANNAPOLIS

697 GIDDINGS AVENUE

2 Beds

2 Baths

1,523 Sq.Ft.

$4,000

MLS#: MDAA2128808

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.
#MDAA2128710

ANNAPOLIS

946 AQUA COURT

5 Beds

4 Baths

N/A

$3,850

MLS#: MDAA2128710

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.
#MDAA2125866

ANNAPOLIS

10 CONSTITUTION AVENUE

4 Beds

3 Baths

1,930 Sq.Ft.

$3,850

MLS#: MDAA2125866

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.
#MDAA2110354

ANNAPOLIS

5 PARK PLACE 624

2 Beds

2 Baths

1,270 Sq.Ft.

$3,850

MLS#: MDAA2110354

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.
#MDAA2128712

ANNAPOLIS

7025 CHESAPEAKE HARBOUR DRIVE 18B

3 Beds

2 Baths

2,188 Sq.Ft.

$3,695

MLS#: MDAA2128712

**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.
#MDAA2124994

ANNAPOLIS

428 CRANES ROOST COURT

3 Beds

3 Baths

3,076 Sq.Ft.

$3,650

MLS#: MDAA2124994

GREAT OPPORTUNITY! Close to everything to include Annapolis Mall and much more! Top level huge office with several tons of opportunity!
#MDAA2065382

ANNAPOLIS

2563 FOREST DRIVE

None Beds

None Baths

20,173 Sq.Ft.

$3,500

MLS#: MDAA2065382

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