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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
272
# of Listings
3
Avg # of Bedrooms
$428
Avg. $ / Sq.Ft.
$925,284
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

73 Properties Found. Page 1 of 5.

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

$160,000

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

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

Excellent opportunity to fulfill your dream of constructing your own dream custom home. This lot is located in a beach community with lots of creeks. Enjoy the lazy days on or by the water with lots of activities. Make this a second home to just relax and enjoy being away from the hustle and bustle of city life. The property is currently not connected to public water or sewer but are slated for future development making this a great piece of property to buy and hold or start your planning with the utility option for a future date.
#MDAA2111916

ANNAPOLIS

1221 CREEK DRIVE

None Beds

None Baths

0.26 acres

$55,000

MLS#: MDAA2111916

Welcome to 1848 Milvale located in the Saint Margarets area of Annapolis. As you enter the home you are struck by the beautiful wide views of Mill Creek, the open floor plan, and architectural details. The dining room and living room have gorgeous coffered ceilings, cherry hardwood floors, extensive millwork, floor-to-ceiling windows, and French doors that overlook the saltwater pool, spa, and creek. The kitchen offers a huge central island, wolf range, and custom cabinetry. Off the kitchen is the family room... it's striking with its vaulted barrel ceiling, custom built-ins, bar area, gas fireplace, and curved bank of windows centering again on the views of Mill Creek. The home has 2 main-floor bedroom suites with attached baths. The waterside bedroom has a poolside door and views of the creek while the front bedroom has serene views of the cornfields across the road facing East. One of the architectural highlights of the home is the stairwell tower with its impressive wide girth access to two distinct upper-level areas. Flooded with light, the high ceiling with clerestory windows first lands at the hall library-study. This cozy nook opens to a multi-purpose suite that can be used as a 3rd bedroom, a nursery, a 2nd family room, or an often-needed teen hangout area. The tower takes a turn to the left and accesses the primary bedroom and adjoining waterside office. The primary bedroom provides his and her walk-in closets, a huge spa bath with a soaking tub, heated floors, a walk-in shower, and laundry. Off of the primary bedroom is a handsome office with custom cabinets, a gas fireplace, and a deck to enjoy your morning coffee or a sunset cocktail. The lower level is the fifth-bedroom suite. This room is both the seller's workout room and wine cellar. The utility room has a wash sink, great for gardening, and houses the water treatment systems and 2 Geo-Thermal systems. The home has beautiful hardscaping with irrigation, and a rock garden water feature in the front of the home, and in the back, there is 148 ft of water frontage with a handsome Belgium stone seawall. The pier is "like new" with 2 slips, a 15,000 lb. boat lift, and 8 MLW. The pier is in a NO WAKE ZONE on weekends .. Located on one of the most sought-after roads in Annapolis and known for its privacy and country-like living, Milvale Road winds along the banks of Mill Creek in Saint Margarets surrounded by farmland and corn fields. A perfect place to unwind and enjoy the best sunsets around! Available from December 1, 2024-June 1, 2025
#MDAA2074056

ANNAPOLIS

1848 MILVALE ROAD

5 Beds

5 Baths

5,855 Sq.Ft.

$25,000

MLS#: MDAA2074056

Severn River Luxury Estate – 6-Month Furnished Rental in Annapolis. Available Fall 2025 through Spring 2026. Escape the chill of northern winters and enjoy the temperate beauty of the Mid-Atlantic from this luxurious waterfront estate in Annapolis, Maryland. Overlooking the Severn River and the iconic U.S. Naval Academy, this elegant retreat offers the perfect blend of relaxation, recreation, and refined living. Set on a private property with sweeping water views, this fully furnished home is ideal for a six-month stay, whether you're working remotely, entertaining guests, or simply recharging in a stunning setting. Enjoy pickleball on your private court, sunset walks along the water, dinners in downtown Annapolis just minutes away, or quiet mornings on one of the home's multiple verandas. Inside, you’ll find: * A grand formal dining room * Gourmet kitchen with top-of-the-line appliances, walk-in pantry, and dining area * Main-level office and cozy two-sided fireplace in family room * Multiple living and family rooms, including a club/game room over the garage * Private pier, in-ground pool, and outdoor entertaining space The second level features a luxurious primary suite with spa-like bath, water views, and a private veranda. Additional ensuite bedrooms and a spacious bonus room with balcony provide plenty of flexibility for guests, office space, or relaxation. A third-floor bedroom suite with sitting area and bath offers even more space and privacy, while the finished basement includes a bedroom, full bath, workout room, rec room, and walk-out access to the backyard. This is not just a rental—it’s a seasonal lifestyle upgrade in one of the East Coast’s most scenic and storied towns. Live well. Entertain often. Relax deeply. Welcome to your seasonal waterfront escape.
#MDAA2119338

ANNAPOLIS

1932 CARROLLTON ROAD

8 Beds

8 Baths

9,315 Sq.Ft.

$23,000

MLS#: MDAA2119338

Experience waterfront living in this exceptional 5 bedroom, 4 1/2 bath home, perfectly positioned to capture breathtaking panoramic views of the South River and unforgettable sunsets. Designed for comfort and style, this residence features an open-concept layout with a spacious living room highlighted by a stone wood-burning fireplace. The kitchen boasts a very large granite island with seating. The sitting area just off of the living room is the perfect place to reflect while taking in the sparkling water views. The primary suite offers a luxurious escape with a spa-inspired bath and stunning river views. Two bedrooms and 1 1/2 bath on the main level are perfect for overnight guests. Spacious finished lower level with full bath, fireplace and walk out to waterside decking perfect to extend entertaining outdoors. A protected private pier with deep water, multiple slips, and a jet ski lift invites endless waterfront adventures. The dock can accommodate a sailboat at the end of the pier or the big slip. This South River waterfront is truly one-of-a-kind. Property is available furnished or unfurnished. Landlord will consider including all utilities and furnishings for $7500 per month.
#MDAA2129844

ANNAPOLIS

125 ISLAND VIEW DRIVE

5 Beds

4 Baths

3,105 Sq.Ft.

$6,500

MLS#: MDAA2129844

Amazing waterfront residence on the Chesapeake Bay with almost 360 degree water views of the Chesapeake Bay, Fishing Creek, and South River. Enjoy a quiet and friendly neighborhood with private beaches and a pier for your boat across the street. Never hassle with bay bridge traffic and enjoy a unique location which is 5 miles to downtown Annapolis, 5 minutes to major retail and restaurants, and a 45 minute drive to downtown Baltimore and Washington DC. The open floor plan provides a great room with cathedral ceilings, hardwood floors, an updated gourmet kitchen, a dining area, and a wood burning fireplace all with panoramic bay views of the bay bride and Thomas Point Light House. A deck off the great room provides a perfect spot to enjoy the bay breeze, to watch the water life of the Chesapeake, and to see spectacular sights of the stars and moon over the bay at night. Up a few steps, you will find the large master bedroom with en-suite bath, large walk-in closet, and views of Fishing Creek through large windows. 2 additional bedrooms, a 2nd full bath, and laundry closet complete this level. Ground level foyer, 2-car attached garage, and storage shed complete the property. 2+ year lease preferred. See agent notes for Tenant responsibility.
#MDAA2117630

ANNAPOLIS

3563 NARRAGANSETT AVENUE

3 Beds

2 Baths

2,082 Sq.Ft.

$6,000

MLS#: MDAA2117630

Stunning 2017 build Pendennis Mount home. Immediate availability. Cul de sac locale, two car garage, two car driveway. Water and bridge views from multiple bedrooms. Open concept main level boasts Plantation shutters, moulding, architectural details galore. Dark wood wide plank flooring throughout main level. Gorgeous dining area with two skylights and wall of windows, access to Trex deck. Kitchen features shaker style cabinets in white gloss, contrast island with seating. Frigidaire Gallery steel appliance suite including convection oven, and gas stovetop, beveled subway tile backsplash and accents. Family room has gas fireplace, built in shelving with matched granite tops. Formal sitting room could be utilized as office, playroom, etc. Entire house bathed in natural light; side stairwell creates spectacular sight lines. Upper level includes gracious primary en suite bedroom with walk in closet. Wide plank hardwood floors continue along upper level landing, and into primary bedroom. Three additional bedrooms, all carpeted. Shared hall bath with tub. All four bedrooms feature Plantation shutters, ceiling fans, ample closet space. Lower level has soaring ceilings, second family room. Fifth bedroom OR home office space, attached full bath. Could function as an au pair, in- law, or guest space - coded entry on exterior door with access to back yard. Incredible amounts of storage space with clever, multi- tiered design. Play set included. Walk to neighborhood parks, Jonas Green Park. A short jaunt to all that downtown Annapolis has to offer, convenient to multiple commuter routes. Fantastic! Some photos are virtually staged. Basic landscaping, septic maintenance included. 7-8 month lease term ideal, to end by late July 2026. No smoking. Pets (up to two) considered on a case by case basis; non-refundable pet deposit if $500 per pet. Please reach out with any questions.
#MDAA2131366

ANNAPOLIS

1923 HARRINGTON PLACE

5 Beds

3 Baths

3,234 Sq.Ft.

$5,800

MLS#: MDAA2131366

Discover the perfect blend of privacy, lifestyle, and location on the highly coveted Annapolis Neck peninsula. Set on more than half an acre with no HOA, this light-filled, fully updated home delivers the everyday comfort of a modern retreat—just minutes from Quiet Waters Park, the South River, and everything Downtown Annapolis has to offer. Step inside to an inviting, open layout designed for both relaxing and entertaining. The renovated kitchen features Calacatta quartz countertops, a navy-and-white cabinetry design, and stainless steel appliances, flowing seamlessly into the dining space and out onto a spacious rear deck overlooking a tree-lined, private yard—ideal for cookouts, gatherings, and evenings by the firepit. A versatile main-level flex room offers space for a home office, gym, or game room. Upstairs, you’ll find four oversized bedrooms including a serene owner’s suite with walk-in closet and updated bath. Laundry is conveniently located on the bedroom level. The finished lower level adds even more usable space with a rec room, full bath, and walkout access—perfect for guests, hobbies, or extended living. Enjoy abundant parking, room for your boat or outdoor gear, and the freedom that comes with no community restrictions. You're moments from the 340-acre Quiet Waters Park, multiple marinas, local beaches, water access points, and the vibrant dining, shopping, and waterfront scene of Eastport and Historic Annapolis. Whether you're looking for a primary residence, a weekend escape, or a flexible, fully furnished option ready for immediate enjoyment, 920 Old Annapolis Neck Road offers a rare opportunity to live the Chesapeake Bay lifestyle without sacrificing privacy, space, or convenience. Schedule your tour today and experience why this peninsula is one of Annapolis’ most desirable places to call home.
#MDAA2127670

ANNAPOLIS

920 OLD ANNAPOLIS NECK ROAD

4 Beds

2 Baths

2,552 Sq.Ft.

$4,998

MLS#: MDAA2127670

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

3,078 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

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.

$4,500

MLS#: MDAA2129406

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

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

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