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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
276
# of Listings
3
Avg # of Bedrooms
$515
Avg. $ / Sq.Ft.
$1,434,627
Med. List Price

Browse Annapolis Real Estate Listings

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Over $5M

71 Properties Found. Page 5 of 5.

Welcome to 120 Kingswood Road, a sanctuary offering privacy, comfort and charm tucked away on a secluded 3.00 +/- acre lot. Located in one of Annapolis' most peaceful cul-de-sacs, this home immediately impresses with a long, level, trail-like driveway, leading to a show stopping reveal of contemporary style living at its finest. Enjoy winter waterviews of Saltworks Creek and soak in the wonders of nature from the cozy porch, one of two bedroom balconies, expansive main level back deck (2023) or large paver patio.  An abundance of square footage, offering 3 levels of living space including a large recreation room off of the updated kitchen, separate dining room, 5 bedrooms, 3 ½ baths, and finished walk out basement. The grand primary ensuite is the wow factor, with stand-alone fireplace, vaulted ceiling and updated bathroom with separate dressing room (2026). The remaining 4 bedrooms (one with a fireplace) do not disappoint continuing the connection to the outdoors offering natural light and expansive woodland views.   Lovingly maintained, this home offers peace of mind with the roof installed in 2021, HVAC in 2026, owned water treatment/conditioning system in 2024, updated radon mitigation system in 2025, and new wall to wall carpet in the living room and stairs in 2026.  The 2 freestanding wood stoves and 2 wood burning insert fireplaces are sold as is.  No HOA and an ideal, rarely offered location, minutes from downtown, Route 50, I 97, and everything Annapolis has to offer. Welcome home!
#MDAA2147546

ANNAPOLIS

120 KINGSWOOD ROAD

5 Beds

3 Baths

3,748 Sq.Ft.

$1,150,000

MLS#: MDAA2147546

Striking modern craftsman located in Eastport! This beautifully constructed home boasts 3 levels of living space including the finished basement with great room, bonus room and full bath. The community of Green Acres is a private, water privileged neighborhood with a waterfront park just steps from the home. Located on Back Creek the residents enjoy boat slips, canoe/kayak storage and vibrant community gatherings. The inviting front porch with balcony above welcomes you as you step onto the property. The high ceilings, plethora of windows for natural light and wide open floor plan set the tone for this wonderful home. The main level features a thoughtful layout and elegant details including a formal living room and dining room which flows to the stunning 2 story Family room with coffered ceiling. The adjacent breakfast nook and gourmet kitchen boasts a massive island; perfect for entertaining. The sunroom off the kitchen is an ideal location to relax or entertain and offers a smooth transition to access the outdoor patio; perfect for alfresco dining. Head upstairs to enjoy the spacious Primary bedroom ensuite with coved ceiling, walk-in closet and luxurious spa-like bathroom. 3 additional bedrooms on this level, one with a spacious balcony overlooking the front yard, provides plenty of space for family and friends. The quaint community of Green Acres provides a community waterfront common area to gather, swim, fish, launch a kayak or tie up a small vessel. The close proximity to downtown Eastport encourages you to stroll the artful and nautical streets to amenities like; five-star restaurants, pubs and shopping. Not to mention you are merely steps away from downtown Annapolis and Naval Academy by either walking across the Spa Creek drawbridge or motoring in the water taxi. From this location, you are also close to some of the Bay's best cruising and fishing areas. Attractive destinations such as Baltimore's Inner Harbor, St. Michael's, Oxford, and Solomon's Island are only a short cruise away. Annapolis offers the perfect balance of small-town charm and big world sophistication. Located just 5 miles to Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft.Meade/NSA and Washington, DC. Welcome Home!
#MDAA2136882

ANNAPOLIS

819 JANICE DRIVE

4 Beds

3 Baths

4,043 Sq.Ft.

$1,125,000

MLS#: MDAA2136882

This gorgeous townhome nestled in the sought-after community of Uptown at Murray Hill, in the heart of downtown Annapolis' West Street Arts District and just steps away from restaurants, pubs, galleries and boutiques. A classic brick façade and covered front porch overlook a charming city garden. Inside, the home is professionally decorated with elegant Pottery Barn furnishings and thoughtfully curated finishes throughout. The entry level features a flex space with French doors—ideal for guests, a home office, or bedroom—along with a convenient powder room. Upstairs, the main living level showcases rich hardwood flooring and an open, light-filled layout perfect for everyday living and entertaining. The bright kitchen is a true centerpiece, complete with granite countertops, stainless steel appliances, a pantry, and a breakfast counter with seating beneath stylish pendant lighting. A sliding glass door opens to the balcony, extending your living space outdoors for grilling. The kitchen flows seamlessly into the dining area highlighted by a designer chandelier, and onward to the inviting living room with a cozy gas fireplace. The primary suite offers a peaceful retreat with luxury vinyl plank flooring, a spacious California-style walk-in closet, and a beautifully appointed ensuite bath featuring dual vanities, generous counter and cabinet space, and a glass-enclosed step-in shower with built-in bench. A large guest bedroom and a hall bath with tub/shower provide comfortable accommodations for family or visitors. The top floor adds exceptional versatility with a game room and lounge area, complete with a wet/dry bar, powder room, and direct access to a private deck—perfect for entertaining or relaxing evenings at home. Additional highlights include a garage and off-street parking. Ideally located with easy access to Rt. 50, Navy–Marine Corps Memorial Stadium, the United States Naval Academy, the Severn River, and all the shops, dining, and waterfront charm of Annapolis, this exceptional home offers the very best of Annapolis living.
#MDAA2136426

ANNAPOLIS

219 WEST STREET

3 Beds

2 Baths

2,080 Sq.Ft.

$1,125,000

MLS#: MDAA2136426

Tucked within the gated waterfront community of Epping Forest, this charming Craftsman bungalow captures the ease and appeal of Annapolis waterfront living with the rare advantage of true one-level living. Perfectly positioned on one of the community’s largest and flattest lots, the property offers a difficult-to-find combination of privacy, outdoor space, and low-maintenance comfort just moments from the Severn River and downtown Annapolis. Inside, the three-bedroom, two-bath residence is filled with warmth and character. Heated floors provide year-round comfort, while dual fireplaces, including one gas and one wood-burning, create inviting gathering spaces throughout the home. The sun-filled great room features transom windows, abundant natural light, and French doors that open seamlessly to the outdoor living areas, creating an effortless connection between indoors and out. The surrounding grounds have been thoughtfully designed to embrace every season of Chesapeake Bay living. Mature landscaping, a dedicated vegetable garden, outdoor fireplace, cedar outdoor shower, and expansive patio create a setting equally suited for quiet mornings or entertaining after a day on the water. Seasonal winter views of the Severn River further enhance the property’s appeal and reinforce its connection to the waterfront lifestyle that defines Annapolis and Anne Arundel County. Life in Epping Forest extends far beyond the home itself. Residents enjoy access to one of Annapolis’ most established and sought-after waterfront communities, complete with a private clubhouse with waterfront dining, deep-water marina, sandy beach, boat ramp, tennis courts, scenic walking trails, and a vibrant calendar of neighborhood events and clubs. The location also offers convenient access to downtown Annapolis, the U.S. Naval Academy, Washington, D.C., Baltimore, and major commuter routes. This is a rare opportunity to own a turnkey home in one of Annapolis’ premier gated waterfront communities, where the Chesapeake Bay lifestyle is part of everyday living. Epping Forest is a Special Tax District. Annual tax: $1,583.64. Community is governed by binding Rules and Regulations.
#MDAA2145574

ANNAPOLIS

310 EPPING WAY

3 Beds

2 Baths

2,036 Sq.Ft.

$1,100,000

MLS#: MDAA2145574

Discover luxurious living in this exceptional 5-bedroom, 4-bathroom home nestled on a full acre in an exclusive WATER ACCESS community. This meticulously crafted residence seamlessly blends elegant design with modern comfort, offering the perfect retreat for those seeking both tranquility and sophistication. The expansive one-acre lot offers endless possibilities for outdoor enjoyment, including gardening, relaxing on the rooftop deck, or sitting under the ceiling fans on the large front porch. Each of the five spacious bedrooms offers comfort and style, while four full bathrooms feature premium tile work, modern vanities, and spa-like amenities. All the while, enjoying the water access community amenities that offer boating, fishing, and waterfront recreation just moments from your doorstep. Easy access to local restaurants, shopping, and major roadways.
#MDAA2140440

ANNAPOLIS

767 BON HAVEN DRIVE

5 Beds

4 Baths

3,255 Sq.Ft.

$1,100,000

MLS#: MDAA2140440

Stately brick traditional in sought-after Bowen Manor community. - Turn key,move- in ready just minutes from Historic Annapolis, major commuter routes, and marinas. Offering spacious, bright living throughout. Built with numerous custom upgrades and additions by the original owner, this beautifully maintained residence combines timeless elegance with thoughtful design and very low maintenance From the moment you open the handsome front doors, you'll appreciate the rich Brazilian cherry hardwood floors,elegant crown molding and timeless architectural details throughout this beautiful home. A private first-floor office with French doors and a sunny window provides the perfect space for working from home, reading or a quiet retreat. Designed for both comfortable living and entertaining, the chef's kitchen features gas cooking, center island, and generous gathering space flowing seamlessly into the inviting family room with a cozy gas fireplace. The luxurious primary suite offers a private sitting room, tray ceilings, and an generous walk- in closet. Four spacious bedrooms provide room for family and guests alike. Bedroom level laundry room. The walkout lower level is ideal fro expansive family room, second gas fireplace, and access to a wonderful brick patio area - perfectly suited for a future hot tub installation. Generous amounts of storage, the insulated under- deck drainage system helps keep the patio protected from rain. Additional highlights include all TVs convey, security system, and electric air filtration system. Perfectly located with convenient access to BWI Airport and just 15 minutes to the Beltway, this exceptional property offers comfort, convenience, and enduring quality. A warm and welcoming home you'll proudly call "Home Sweet Home"
#MDAA2145756

ANNAPOLIS

216 BOWEN COURT

4 Beds

4 Baths

4,032 Sq.Ft.

$1,100,000

MLS#: MDAA2145756

Backs to Quiet Waters Park! This spacious and elegant home offers 4 bedrooms, 3.5 bathrooms and approximately 4,400 sq. ft. of living space, with the option to expand to 5,300 sq. ft. by adding a fourth level. The gourmet kitchen features double wall ovens (with the upper oven including an air-fry option), a 36-inch gas cooktop and the choice of a cabinetry hood or stainless-steel chimney hood. Additional highlights include a sunroom. These are to-be-built homes, allowing buyers to make all selections and personalize their finishes.
#MDAA2138688

ANNAPOLIS

116 STILLY WAY

4 Beds

3 Baths

4,400 Sq.Ft.

$1,099,990

MLS#: MDAA2138688

Waterfront home nestled in the serene enclave of Kitty Creek; located right off the South River with easy access to the Chesapeake Bay. This recently updated home offers the perfect blend of luxury, comfort, and waterfront living. Inside, you’re welcomed by refinished hardwood floors and abundant natural light. The updated kitchen features new GE stainless steel appliances and opens to a cozy living room with a wood-burning fireplace and direct access to the deck; ideal for dining under the stars overlooking the peaceful backyard and creek. A main-level laundry/mudroom with side entrance and ramp adds everyday convenience.The primary suite is a true retreat, featuring a waterfront-facing design with a private balcony and updated en-suite bath. Three additional bedrooms with new carpet offer flexibility for guests, a home office, or growing needs. The fully finished walkout lower level provides a private in-law suite with its own entrance, full kitchen, large updated bath, and laundry hookup; perfect for extended stays or entertaining. Outside, enjoy 50 feet of waterfront with a private dock slip, kayak rack, and a spacious .41-acre lot offering plenty of room to relax, garden, or play. Ideally located with easy access to Annapolis, BWI, and DC, this home offers the best of peaceful waterfront living in Annapolis and everyday convenience.
#MDAA2143898

ANNAPOLIS

996 HEADWATER ROAD

4 Beds

3 Baths

2,288 Sq.Ft.

$1,099,500

MLS#: MDAA2143898

New on site today
Don’t miss this rarely available 4-bedroom, 2.5-bath Colonial in the highly sought-after, water-privileged community of Amberley. Fresh paint and abundant natural light create a warm and inviting atmosphere throughout. The kitchen is filled with natural light and offers gray-toned cabinetry, recessed lighting, a sunny breakfast area, and peaceful tree-lined views. Perfect for both everyday living and entertaining, the spacious family room offers a cozy gas fireplace with a charming brick surround, custom built-ins, and direct access to the rear covered porch. Overlooking picturesque Whitehall Creek, this tranquil outdoor retreat provides the perfect setting to gather with friends or unwind while taking in the serene waterfront scenery at any time of day. Just beyond is a versatile formal dining area framed by lovely front lawn views. Whether hosting memorable dinners, creating a cozy sitting room, or using the space as a private home office, this room offers flexibility while enjoying a peaceful scenery. A nearby powder room and laundry room add convenience and functionality. Retreat upstairs to the spacious primary suite, where large windows adorned with plantation shutters fill the room with natural light. The walk-in closet is thoughtfully outfitted with a custom organization system, while the en-suite bath offers a tiled walk-in shower, creating a comfortable and private retreat at the end of the day. Three additional bedrooms, each with ample closet space, share a well-appointed hall bath with a tub/shower combo, completing the upper level. The unfinished lower level provides abundant storage space and shelving with the possibility for future expansion if finished. An attached two-car garage, complete with a built-in workshop, is ideal for hobbyists, DIY enthusiasts, or extra storage needs. An extended driveway offers ample off-street parking for 4+ cars. With nature as your backdrop, this spectacular 29,500 sq ft lot is an entertainer's dream. Create your own private oasis with breathtaking riverfront views and a meandering pathway leading to your private boat slip. Enjoy endless opportunities to relax or entertain outdoors, from cozy evenings around the firepit on the brick patio to peaceful mornings surrounded by mature trees that provide beauty, privacy, and a serene setting year-round. Amberley's exceptional amenities further enhance this waterfront lifestyle. Residents enjoy access to three community piers with 45 boat slips, kayak and dinghy racks, a kayak launch pier, and a boat ramp. In addition, more than 15 acres of preserved forest and open fields offer walking trails and scenic vistas, making this a truly special place to call home.
#MDAA2141328

ANNAPOLIS

700 N HOLLY DRIVE

4 Beds

2 Baths

2,072 Sq.Ft.

$1,099,000

MLS#: MDAA2141328

Spacious and elegant, this 4-bedroom, 4.5-bath home offers approximately 4,400 sq. ft., with the option to expand to 5,300 sq. ft. with a fourth level. The gourmet kitchen features double wall ovens (upper with air-fry), a 36" gas cooktop, and choice of cabinetry or stainless steel hood. Enjoy a sunroom, cozy fireplace, 9-foot ceilings on all levels, and a finished basement with full bath. Energy-efficient upgrades include a tankless water heater and two-zone HVAC. Private setting near Quiet Waters Park. Fully furnished model available. Estimated move-in July/August.
#MDAA2134880

ANNAPOLIS

113 STILLY WAY

4 Beds

4 Baths

4,700 Sq.Ft.

$1,079,990

MLS#: MDAA2134880

Rare waterfront redevelopment opportunity in Annapolis. The existing structure is a complete shell and requires a full renovation or rebuild. Ideal for investors, builders, or buyers looking to design and construct a custom waterfront home from the ground up. Located along the protected waters of Oyster Cove, the property includes a deep-water pier and boat house. The existing footprint and favorable waterside placement offer strong potential to maximize views and overall design. Convenient access to the Chesapeake Bay and close proximity to Historic Downtown Annapolis by both land and water. Enjoy boating, sailing, and easy access to surrounding waterfront destinations throughout the region. Property is being sold strictly as-is. A unique opportunity for those ready to take on a full redevelopment project in a prime waterfront setting.
#MDAA2143700

ANNAPOLIS

1254 WASHINGTON DRIVE

5 Beds

4 Baths

9,960 Sq.Ft.

$1,000,000

MLS#: MDAA2143700

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