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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
253
# of Listings
3
Avg # of Bedrooms
$405
Avg. $ / Sq.Ft.
$830,016
Med. List Price

Browse Annapolis Real Estate Listings

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$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

253 Properties Found. Page 14 of 17.

Just across the street from the water in Southaven, this Annapolis home offers the kind of space and flexibility that’s increasingly hard to find. Recently updated, the main level includes a renovated kitchen with quartz countertops, dual ovens, gas cooking, stainless steel appliances, and modern cabinetry. The main level also features a living room with built-in speakers, a dining room, an optional sitting room, a half bath, garage access, and a coat closet at the front entry. Upstairs are four well-sized bedrooms, two thoughtfully updated full baths designed with a clean, timeless aesthetic, and a laundry room. The walkout lower level remains unfinished and offers excellent storage, along with a bathroom rough-in for those who may wish to explore future expansion. Exterior updates include a newer roof and a recently paved driveway. The attached two-car garage supports everyday needs. A back deck extends off the main level. Community water access is located across the street. The Southaven community also offers a community pier and a kayak/paddleboard launch area. Set on a generous lot with ample storage and water access, 2942 Southaven Drive combines usability with the relaxed coastal character that makes this part of Annapolis so appealing.
#MDAA2131660

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

2,142 Sq.Ft.

$4,950

MLS#: MDAA2131660

Discover the charm of this exquisite Colonial-style home nestled in the desirable Oyster Harbor community. This stunning 3-bedroom, 2.5-bathroom residence boasts 1,584 sq. ft. of meticulously maintained living space, featuring solid hardwood floors and an inviting family room that seamlessly connects to the kitchen-perfect for entertaining. Enjoy cozy evenings by the brick fireplace or bask in natural light from the skylights and double-pane windows. The kitchen is equipped with modern appliances, including a built-in microwave, dishwasher, and electric oven, ensuring culinary delights are just a step away. The main floor laundry adds convenience to your daily routine. Step outside to your private oasis, where a 34-foot waterfront on Oyster Creek awaits. With a private dock site, you can indulge in fishing, kayaking, or simply soaking in the serene bay views. The bulkheaded lot offers a perfect blend of nature and leisure, with a stone driveway providing ample parking. Oyster Harbor is more than just a home; it's a lifestyle. Enjoy community amenities such as a beach, boat ramp, and pier/dock, all while being surrounded by lush parks and top-rated schools. With easy access to public services and a vibrant neighborhood atmosphere, this property is a rare find. Available for lease starting August 1, 2025, with flexible terms from 12 to 24 months, this home includes water and trash removal in the rent. Don't miss your chance to experience the perfect blend of comfort and community in this exceptional property!
#MDAA2113692

ANNAPOLIS

1330 WASHINGTON DRIVE

3 Beds

2 Baths

1,584 Sq.Ft.

$4,500

MLS#: MDAA2113692

BEAUTIFUL COLONIAL HOME ON QUIET CUL DE SAC, SURROUNDED BY 34 LUXURY HOMES. THIS HOME HAS BEEN METICULOUSLY MAINTAINED. GOURMET KITCHEN. SUNROOM. MASTER BEDROOM WITH SPACIOUS EN SUITE BATH. OFFICE. 2 FAMILY ROOMS, 1 WITH GAS FIREPLACE. FORMAL DINING ROOM. HUGE STORAGE ROOM WITH SHELVING INCLUDED. 2 CAR GARAGE. BEAUTIFUL PATIO. ENTERTAINERS DELIGHT! AVAILABLE DECEMBER 1, 2025!
#MDAA2129808

ANNAPOLIS

612 SAMANTHA COURT

4 Beds

2 Baths

4,592 Sq.Ft.

$4,300

MLS#: MDAA2129808

Nestled in the charming Boucher Place community, this exquisite end-of-row townhouse offers a luxurious lifestyle defined by elegance and comfort. Built in 2011, this carriage house-style residence boasts a sophisticated blend of modern design and timeless appeal, making it the perfect sanctuary for those who appreciate the finer things in life. As you approach the property, you are greeted by beautifully maintained sidewalks and inviting street lights that illuminate the path to your new home. The cement siding not only enhances the aesthetic appeal but also ensures durability and low maintenance, allowing you to spend more time enjoying your luxurious surroundings. Step inside to discover a spacious 1,800 square feet of thoughtfully designed living space. This home features three generously sized bedrooms and three and a half bathrooms, providing ample room for relaxation and privacy. The warm ambiance is complemented by a cozy gas fireplace, perfect for creating a welcoming atmosphere during cooler months. The heart of the home is the gourmet kitchen, equipped with high-end stainless steel appliances, including a built-in microwave, dishwasher, and electric stove. Whether you are a culinary enthusiast or prefer casual dining, this kitchen is designed to inspire. The open layout seamlessly connects the kitchen to the living area, making it an ideal space for entertaining or enjoying quiet evenings at home. Additional highlights include a partially furnished interior that exudes style and comfort, along with a convenient detached garage that offers two spaces for your vehicles. The property also includes essential amenities such as common area maintenance, parking, and trash removal, ensuring a hassle-free living experience. Available for lease starting November 15, 2025, with flexible terms ranging from six to eighteen months, this residence invites you to embrace a lifestyle of luxury and convenience. Experience the perfect blend of modern living and classic charm in this exceptional townhouse, where every detail has been meticulously crafted to create a true sense of home. Don't miss the opportunity to make this exquisite property your own.
#MDAA2129406

ANNAPOLIS

19 BOUCHER PLACE

3 Beds

3 Baths

1,800 Sq.Ft.

$4,300

MLS#: MDAA2129406

This much desired, "Everest" unit on the 3th floor features many upscale upgrades, two master bedroom suites, powder room, gleaming bamboo hardwood floors (no carpet), office/den, plantation shutters, custom lighting throughout, custom paint, 10 ft ceilings, open living/dining floor space, stone and granite countertops, upgraded appliances, double oven, large laundry room, new HVAC system, closet organizers, extra storage cage, balcony, and more. Located on the desired retail boulevard side with city feel of all Town Center activities. Enjoy evening on your balcony with spectacular seats to the Summer Friday evening concerts. Amenities include two assigned garage spaces, concierge services, fitness center, rooftop pool, etc. Live and walk to the best that the Annapolis Town Center offers - Whole Food Market, Target, fabulous restaurants, banking, and Annapolis best restaurants and bars. Minutes from Historic Downtown Annapolis, Annapolis Mall, Anne Arundel Medical Center and easy access to Route 50 and Highway 97. MUST SEE UNIT!
#MDAA2131606

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 309

2 Beds

2 Baths

1,681 Sq.Ft.

$4,200

MLS#: MDAA2131606

Rare opportunity to experience Chesapeake Harbour at its finest in this exquisitely renovated waterfront terrace-level condo.in a Gated community with 24/7 security. Every inch of this 2-bedroom, 2-spa-bath residence have been thoughtfully reimagined to deliver designer elegance and modern comfort. From the crown moldings and engineered lighting to the custom tilework and bidet-equipped spa bathrooms with heated floors, no detail has been overlooked. Enjoy a gourmet kitchen featuring stone counters, premium cabinetry, and upscale appliances, complemented by new flooring throughout and deluxe plantation shutter with light filtering option window treatments ,. Both bathrooms offer high-end vanities and soft-close vanities , with upend quality plumbing fixtures for a spa-like retreat feel. Step outside to a fully furnished patio and greet the day with breathtaking sunrises over the Chesapeake Bay. with view all the way to bay bridge and eastern shore . Whether you're entertaining or unwinding, this home offers a rare blend of serenity and sophistication — all just steps from the water with hidden beach , and two(2) community swimming pools, pickleball and Tennis courts and spectacular landscaping.
#MDAA2130344

ANNAPOLIS

2125 QUAY VILLAGE COURT T1

2 Beds

2 Baths

1,270 Sq.Ft.

$4,200

MLS#: MDAA2130344

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

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

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. NOTE: If tenant prefers unfurnished, that can be arranged.
#MDAA2125248

ANNAPOLIS

122 BAY VIEW DRIVE

4 Beds

3 Baths

2,200 Sq.Ft.

$3,950

MLS#: MDAA2125248

Professional photos coming soon- Come see this stunning property that has it all! Open concept kitchen, walk-in pantry, stainless appliances, huge pantry, gas stove. Harwood floors throughout main level, bathroom on every level, bonus loft space above garage. True master bedroom with lots of light and will fit king sized bedroom suite. Double sink master bathroom with sunk in tub. Huge private yard behind garage. Plenty of parking and parking on the street as well. Credit must be at least a 650, must make 3x the rent amount and pets case by case.
#MDAA2128406

ANNAPOLIS

1833 DREW STREET B

3 Beds

3 Baths

1,616 Sq.Ft.

$3,900

MLS#: MDAA2128406

**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

2,737 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

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.
#MDAA2130262

ANNAPOLIS

617 S CHERRY GROVE AVENUE

3 Beds

2 Baths

2,000 Sq.Ft.

$3,500

MLS#: MDAA2130262

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

1,512 Sq.Ft.

$3,500

MLS#: MDAA2128478

Prime Annapolis location! Negotiable rent terms for tenant who will respect the home. All the amenities & conveniences plus amazing community! Clean, Bright, Spacious, Ready to move in as soon as January 1st! 3 ensuite bedrooms offering privacy & lots of closet space! Rarely available for rent. Main level entrance with bonus room (additional fam room, home office, gym, rec room..) plus half bath. Oversized 2 car garage plus 2 additional parking passes for the community. Level 1 offers gourmet kitchen open to dining area & spacious family room with fireplace &walk out to balcony plus another 1/2 bath. Upper level 1 has laundry room, 2 spacious bedrooms - each with large full baths. The primary bedroom has huge walk in closet, full bath with double sink vanity and large shower. Bedroom #2 is spacious with another full bath, bathtub/shower combo & large closet! Upper level offers spacious bonus/rec/.office/gym/play area with access to upper level balcony, 3rd bedroom & 3rd full bath. Walk to Annapolis Town Center, Whole Foods, Coopers Hawk and Tatte - the new French Bakery boasting the most delectable coffee and fresh tasty meal and snack options all day long. Close commute to the Naval Academy and other prime Annapolis locations. Private, quiet community yet only minutes from major roads & interstates. This move in Ready 3 bedroom 3 full plus 2 half bath home boasts all the amenities and upgrades you have been waiting for! Bright Cheery, Spacious, fresh and ready for you!
#MDAA2132066

ANNAPOLIS

803 FRANCIS HARRIS PLACE

3 Beds

3 Baths

2,032 Sq.Ft.

$3,500

MLS#: MDAA2132066

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