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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
296
# of Listings
3
Avg # of Bedrooms
$470
Avg. $ / Sq.Ft.
$1,067,632
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

65 Properties Found. Page 2 of 5.

Waterfront home in Oakwood Community w/ unsurpassed views of S. River and Bay. Newly renovated gourmet kitchen w/ island. Main level 2 BR 1 bath. Spacious open living area, F/R with wood-burning F/P. Hard wood FL through out. 2-Car garage w/ lots of workspace and storage. New 100 foot pier. Tranquil location, steps from Thomas Point Park. Pets case.
#MDAA2114138

ANNAPOLIS

3730 THOMAS POINT ROAD

4 Beds

2 Baths

1,932 Sq.Ft.

$5,050

MLS#: MDAA2114138

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.

$5,000

MLS#: MDAA2113692

This charming Murray Hill single family home features 3 bedrooms and 2 .5 bathrooms. A brick 2 story cape cod style house with an open concept floorplan with hardwood floors, granite countertops and stainless steel appliances. The primary suite is large with 2 closets and a completely renovated bathroom. There is a full basement with a bonus room, storage, laundry, and a separate workshop area. There is also a large fenced in back yard with a paver patio and a brick paved driveway for off street parking. 2 blocks to the water and a 10 minute walk to Main Street. Restaurants & coffee shops are right around the corner. Pets will be considered on a case-by-case basis with additional pet rent of $45.00 per month.
#MDAA2122836

ANNAPOLIS

18 STEELE AVENUE

3 Beds

2 Baths

2,370 Sq.Ft.

$4,850

MLS#: MDAA2122836

*** FULLY FURNISHED HOME!!!! ALL YOU NEED TO BRING IS YOUR SUITCASE! SPACIOUS 4 BEDROOM 2 BATH HOME THAT HAS BEEN NEWLY RENOVATED. LEASE TERM IS NEGOTIABLE. PETS CASE BY CASE.
#MDAA2124352

ANNAPOLIS

134 S HOMELAND AVENUE

4 Beds

2 Baths

2,675 Sq.Ft.

$4,750

MLS#: MDAA2124352

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.

$4,500

MLS#: MDAA2123566

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.

$4,400

MLS#: MDAA2116374

159 Conduit Street - a charming residence located in the heart of Annapolis, MD. This home boasts four spacious bedrooms and two full bathrooms, offering ample space for comfort and relaxation. The kitchen is a chef's dream, equipped with a range, refrigerator, dishwasher, and a microwave/range hood. The convenience of an in-house washer, dryer, and disposal system adds to the ease of living. This home is not just about comfort, it's about lifestyle. Its prime location allows you to enjoy the vibrant downtown scene of Annapolis, with everything you need just a short walk away. Experience the perfect blend of comfort, convenience, and city living in this beautiful home. Pets only considered smaller breed with $35.00 added per month as pet rent.
#MDAA2124588

ANNAPOLIS

159 CONDUIT STREET

4 Beds

2 Baths

1,888 Sq.Ft.

$4,200

MLS#: MDAA2124588

Lovely 4 bed, 2.5 bath Contemporary home nestled within the highly desirable water privileged community of Cape St. John. This charming residence offers a wonderful opportunity to experience an active lifestyle of living near the water without compromising on affordability. With its welcoming ambiance and convenient location, this home presents an excellent choice for those seeking a serene retreat near the water. This well-maintained home features updated HW flooring, 2-story great room with lots of natural light, and an efficient wood burning fireplace as it's focal point. Dramatic Cathedral Ceilings brings this 2-story great room alive! Updated Gourmet Kitchen has granite countertops, recessed lighting, SS appliances, double wall ovens, built-in microwave, under the counter lighting, and pantry. There is an Island which provides additional seating as well. You can host large dinner parties in the formal dining room which spills over into the great room or onto the large deck. There are two sliding doors leading out to the expansive, private deck w/Seasonal views of the South River. Property backs to trees giving you a feeling of living in the woods. Upstairs you will find a nice sized Primary suite w/ensuite bath, large walk-in closet and waterview from your private balcony. There are 2 other spacious bedrooms on this floor, the 3rd one has a 2nd balcony overlooking the deck also providing seasonal water views. The office / 4th bedroom is conveniently located on the main floor. Full walkout basement w/additional entertaining space & storage area would make a nice home gym or theatre room. On the basement level you will find a nice sized laundry room with plenty of additional storage. There is a patio located under the deck and accessible from the walk out basement as well. New Prodigy Insulated siding and doors were installed in (2018). While this home may not be directly on the waterfront, you'll find that the beach is only a short stroll down the street (Cape Saint John Rd, right on on Valleyview, left on Dogwood, entrance to park on left). Tenants have access to private beach, boat ramp, picnic area, playground allowing you to indulge in many water activities easily. Close to shopping, restaurants, health facilities, major routes and minutes to downtown Annapolis. Come experience Cape St. John's friendly atmosphere! APPLY ON RENTSPREE using link in this listing. Please Note: Owners are highly allergic to cats and unfortunately, they will not be accepting any applications for tenants with cats.
#MDAA2124036

ANNAPOLIS

2983 POPLAR TRAIL

4 Beds

2 Baths

3,276 Sq.Ft.

$4,200

MLS#: MDAA2124036

Street level storefront/office with tremendous visibility at the gateway to the West Annapolis shopping & business district. See photos of the superior interior finish. Neighborhood has a village type vibe featuring other boutique stores, offices and restaurants with easy access from Rt. 50. Walkable to the Historic District, USNA & Navy Marine Corps Memorial Stadium. 4 other commercial tenants & 2 residential tenants in the adjacent building at 4 Annapolis Street share the rear parking lot. Street level space has approximately 1,200 sf. Lower level has approximately 1,200 sf with direct walkout access to the 30+ space surface parking lot. Tenant pays electric, oil heat, cable and splits the quarterly water/sewer bill with the adjacent tenant...One Petticoat Lane. Landlord pays for grounds & parking lot maintenance, snow, ice & trash removal. Unique opportunity for an existing business requiring quick possession of superior built-out space.
#MDAA2116236

ANNAPOLIS

2 ANNAPOLIS STREET

None Beds

None Baths

11,456 Sq.Ft.

$4,000

MLS#: MDAA2116236

Luxury Living, Minutes from Historic Downtown Annapolis! Premium two-level condo with ground-level entrance and over 2,500 sq. ft. of luxury living. Features include soaring 10 ft. ceilings, a dramatic two-story living room, and a versatile loft family room/den. Gourmet kitchen offers granite countertops, breakfast bar, and upgraded appliances. Three large bedrooms with fully renovated baths, ample storage, and extra closet space throughout. Outdoor living includes an upper deck and lower patio backing to woods for privacy. Plenty of sophisticated space to share and just minutes to the Naval Academy—perfect for families or roommates seeking comfort and convenience. Ideally located close to historic downtown Annapolis, shopping, dining, and Routes 50/97.
#MDAA2124292

ANNAPOLIS

803 LATCHMERE COURT 104

3 Beds

3 Baths

2,598 Sq.Ft.

$4,000

MLS#: MDAA2124292

Spacious 4-bedroom, 3.5-bathroom home featuring gleaming hardwood floors on the main level and a beautifully updated kitchen perfect for entertaining. The finished basement provides additional living space, while the private, fully fenced backyard offers a peaceful outdoor retreat. Enjoy your morning coffee or an evening drink on the large deck. Convenient 2-car garage. Very convenient location to local shops, restaurants, the DC commuter bus, and major highways.
#MDAA2121746

ANNAPOLIS

1807 GREEN TOP COURT

4 Beds

3 Baths

2,574 Sq.Ft.

$3,850

MLS#: MDAA2121746

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

Welcome to Bay Highlands in Annapolis! This open, light-filled home is spacious and inviting. You'll love the airy living room with high ceilings and skylights, as well as a gas fireplace and wrap-around balcony (there's even a porch swing)! The primary suite includes a private balcony and ensuite bath as well as a fabulous walk-in closet. Use the loft as a 4th bedroom, office, or game room. A well-appointed kitchen includes stainless appliances, and plenty of counter and storage space; adjoining the kitchen is convenient upper-level laundry. The entry level of this contemporary home includes two large recreation areas; the back room could also be used as a bedroom and has walkout backyard access as well as a third full bathroom. The peaceful screened in porch is perfect for crab feasts, game nights or a cozy afternoon reading spot. With garage parking and additional driveway space, there's plenty of room for vehicles as well as storage. The community of Bay Highlands has access to a dock and boat ramp, and landlord is happy to arrange for boat ramp access. Pets considered on a case-by-case basis! Please note: minimum 650 credit score and qualifying income required.
#MDAA2122856

ANNAPOLIS

3241 HENSON AVENUE

4 Beds

3 Baths

2,346 Sq.Ft.

$3,800

MLS#: MDAA2122856

Welcome to this absolute gem in the Eastport area of Annapolis, MD. This 4 bedroom / 2 bath main house was built in 1912, but has a lot of modern updates. Beautiful wood floors in the main level open-concept Living Room. A huge open kitchen with upgraded appliances and a double oven and an oversized kitchen Island with tons of storage. You will find a washer and dryer in the basement. A Large 13,000+sf lot offers room for off street parking and a beautiful patio and pond in the back yard. The property is completely fenced in, front and back. This home is within walking distance to all of the shops, dining and waterfront that Eastport has to offer.
#MDAA2123056

ANNAPOLIS

915 JACKSON STREET

4 Beds

2 Baths

2,076 Sq.Ft.

$3,795

MLS#: MDAA2123056

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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