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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

266

# of Listings

3

Avg # of Bedrooms

$529

Avg. $ / Sq.Ft.

$1,357,478

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

266 Properties Found. Page 6 of 18.

#MDAA2147138

ANNAPOLIS

128 STILLY WAY

5 Beds

4 Baths

4,138 Sq.Ft.

$1,250,000

MLS#: MDAA2147138

Foreclosure opportunity in sought-after Annapolis! Spacious 4BR/3.5BA Colonial with over 4,500 sq ft of living space. Features include multiple living areas, large kitchen footprint, finished lower level, and generous bedroom sizes. Private backyard with in-ground pool ready to be restored. Excellent potential for renovation or investment. Convenient to shopping, dining, major routes, and downtown Annapolis. Sold strictly AS-IS.

Schedule your showing now!

ANNAPOLIS

371 CARRIAGE PARK WAY

4 Beds

3 Baths

6,724 Sq.Ft.

$1,218,375

MLS#: MDAA2133126

Escape to your New Sanctuary on a 1.17 Acre Lot. Welcome to the Birch Model, one of our premier homes designed for those who desire the best in space, style, and comfort. This home offers everything you need for luxurious living.
UP TO 5 Bedrooms: Perfect for large families or those who enjoy hosting guests, each bedroom is spacious and thoughtfully designed.
UP TO 4.5 Bathrooms: Enjoy the convenience of four full bathrooms and a powder room, providing ample space and privacy for everyone.
Extra Storage Space: Keep your home organized with plenty of storage throughout, including a dedicated storage room!
Walk-In Pantry: A spacious pantry provides ample storage for all your kitchen essentials and more.
Butler’s Bar: Entertain in style with a dedicated butler’s bar, perfect for serving drinks and hors d’oeuvres.
Dedicated Office: An ideal space for working from home, studying, or managing household affairs.
Open and Inviting Layout: The Birch Model features a seamless flow between the kitchen, dining, and living areas, perfect for both everyday living and entertaining.
Luxurious Owner’s Suite: Retreat to your private haven, featuring a spacious bedroom, a spa-like en suite bathroom, and a large walk-in closet.
Optional Upgrades and Customizations: Personalize your Birch Model with a variety of finishes, fixtures, and additional features to make it truly your own.
The Birch Model offers unparalleled luxury and space, making it the perfect home for those who want it all. Discover what makes this home truly exceptional. Contact us today to schedule a tour and learn more about available customization options!

ANNAPOLIS

1353 YORKTOWN ROAD

4 Beds

3 Baths

3,100 Sq.Ft.

$1,199,999

MLS#: MDAA2147894

Tranquility and nature awaits you in this timeless all-brick estate, thoughtfully designed for both everyday living and MULTI-GENERATIONAL l flexibility — offering the rare feeling of living in your own private retreat while still being just minutes from the heart of Annapolis. With over 5,500 square feet, multiple private living areas, and the potential for dual primary-style suites, this home is perfectly suited for extended family living, an au pair setup, long-term guests, or evolving household needs.

A long private drive opens to a circular driveway welcoming you home to a picturesque landscape filled with mature trees and open space. Complete with a three-car garage and separate shed, there’s plenty of room for vehicles, hobbies, storage, and weekend projects.

Your home unfolds with beautifully designed living space, where hardwood floors, freshly painted interiors, abundant natural light, and generous room sizes create a warm and inviting atmosphere. The main level offers two spacious living areas, both with cozy fireplaces, a formal dining room, and a private office that could easily function as a main-level bedroom — creating additional flexibility for guests or multi-generational living needs.

The second level features four spacious bedrooms and three full baths, along with a large bonus room over the garage offering endless possibilities for a playroom, studio, secondary living area, or potential second primary suite. The expansive primary retreat is complete with its own fireplace and large private bath featuring a soaking tub, separate shower, and dual vanity.

The third upper level provides two additional bedrooms and a full bath, creating a private retreat ideal for guests, an au pair suite, or extended family.

The finished lower level adds even more versatility with a large recreation room, exercise space, abundant storage, and walkout access to a second patio leading to the generous backyard.
The lower backyard offers a secluded setting perfect for bonfires, s’mores, and evenings gathered with friends and family under the trees.
Your outdoor experience continues with an expansive deck overlooking 2.25 private acres of surrounding woodland — an ideal setting for summer dinners, quiet mornings with coffee, or simply decompressing while listening to nature. Fresh eggs await from your very own chicken coop — and the chickens can convey if buyers wish.

Perfectly positioned for your private oasis, yet just minutes from Annapolis, the Naval Academy, commuter routes, and local shopping.

A rare opportunity to enjoy space, privacy, flexibility, and nature while staying connected to everything the Annapolis area has to offer.

ANNAPOLIS

962 COACHWAY

6 Beds

4 Baths

5,889 Sq.Ft.

$1,199,000

MLS#: MDAA2138664

NEW PRICE! Welcome to 805 Spa rd., an amazing investment opportunity in the desirable Murray Hill community in Annapolis! Murray Hill is probably the best residential neighborhood in the city with single-family homes, and walkable to downtown. This 9-bedroom, 4.5 bath, triplex home has been completely renovated! There is ample parking for up to 8 cars. This home offers rental potential with 3 separate units under 1 roof. This property could be short or long-term rental investment, a multi-generational home, or owner-occupied housing hack, which enables the owner to live in one side and rent out the other sides to pay and qualify for the mortgage. There are 3 units, Unit 1 has 4 beds, 2.5 baths, unit 2(in the back) has 3 beds, 1bath, and the basement has 2 bed, 1 ba. All have separate entrances. The entire house has been completely renovated with all new wiring, plumbing, 3 new kitchens and 4.5 new baths, new HVAC,2nd unit new hot water heater, sprinkler system all units, granite counter tops, stainless steel appliances, all new flooring throughout and enclosed porch with all new windows.

ANNAPOLIS

805 SPA ROAD

5 Beds

None Baths

2,800 Sq.Ft.

$1,198,000

MLS#: MDAA2141884

NEW PRICE! Welcome to 805 Spa rd., an amazing investment opportunity in the desirable Murray Hill community in Annapolis! Murray Hill is probably the best residential neighborhood in the city with single-family homes, and walkable to downtown. This 9-bedroom, 4.5 bath, triplex home has been completely renovated! There is ample parking for up to 8 cars. This home offers rental potential with 3 separate units under 1 roof. This property could be short or long-term rental investment, a multi-generational home, or owner-occupied housing hack, which enables the owner to live in one side and rent out the other sides to pay and qualify for the mortgage. There are 3 units, Unit 1 has 4 beds, 2.5 baths, unit 2(in the back) has 3 beds, 1bath, and the basement has 2 bed, 1 ba. All have separate entrances. The entire house has been completely renovated with all new wiring, plumbing, 3 new kitchens and 4.5 new baths, new HVAC,2nd unit new hot water heater, sprinkler system all units, granite counter tops, stainless steel appliances, all new flooring throughout and enclosed porch with all new windows.

ANNAPOLIS

805 SPA ROAD

9 Beds

4 Baths

2,800 Sq.Ft.

$1,198,000

MLS#: MDAA2141866

#MDAA2148526

ANNAPOLIS

20 SHAW STREET

3 Beds

2 Baths

1,500 Sq.Ft.

$1,150,000

MLS#: MDAA2148526

Open Friday, July 10th from 4-6:30 PM! Vacation every day in your stunning two-level condo with exceptional views and amazing privacy! Wonderful open floor plan and walls of glass make you feel like you are on a boat and create outstanding views from every room. Exceptional features include smart technology throughout, a wood-burning fireplace, soaring ceilings, GE Cafe appliances (new in 2024), electric blinds, separate dining area with a glass wall that beautifully reflects the water and accentuates the gorgeous natural light. Designer-selected tones throughout the home reflect the changing moods of the outdoors — soft greys and grey blues echo the water and sky, while subtle sunrise-inspired oranges and purples bring warmth and character to the interiors. Cherry wood floors and rich wood accents create a seamless connection between indoor living and the surrounding waterfront setting. The unit has been redesigned to increase the storage, creating ample closet space. Every day is a new opportunity to experience an incredible sunrise over the Chesapeake Bay Bridge and Eastern Shore, follow the tankers and watch the boat races. Chesapeake Harbour is a gated waterfront resort with outstanding water access, including private beaches, boat launch, and great piers for gathering with friends and neighbors to watch the races or cast a fishing line. Choose which of the two waterside community pools suits your mood (one is heated), enjoy a game of tennis on the multiple available courts, or launch your boat or board from the sandy beach and glide across the water. Take one of the many community paths to the marina (slips at Chesapeake Harbour Marina are available for a fee and NOT part of the HOA) or stop in for drinks or dinner at The Beacon harborside restaurant. Better still, stay home where you have the best view in the community and just relax. This amazing haven is located within a few short minutes of fun Eastport, Downtown Annapolis and its many offerings, dozens of scrumptious close-by neighborhood restaurants, 5 minutes from multiple breathtaking parks (Quiet Waters, Thomas Point, EO Moyer, Carr's), and it truly feels like a world away from it all! Bonus-100% turnkey-furniture included! Ask for more details!

ANNAPOLIS

2127 BEACH VILLAGE COURT 202

3 Beds

3 Baths

1,750 Sq.Ft.

$1,150,000

MLS#: MDAA2146926

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!

ANNAPOLIS

120 KINGSWOOD ROAD

5 Beds

3 Baths

3,748 Sq.Ft.

$1,150,000

MLS#: MDAA2147546

Enjoy luxury one-level living in the heart of downtown Annapolis in this unique, penthouse condo with a one-of-a-kind, beautifully landscaped, expansive terrace. The condo includes two bedrooms plus an office or 3rd bedroom, 2.5 bathrooms and an open floor plan. Leave the cars in your secure two garage parking spaces, and walk to dinner, the waterfront, the Naval Academy, concerts, Maryland Hall for the Arts, and City Dock. This condo offers a seamless, turnkey lifestyle anchored by an open, light-filled floor plan enhanced by floor-to-ceiling windows and premium finishes throughout. The private terrace is an inviting outdoor retreat ideal for dining, entertaining, or simply relaxing under the retractable awnings on sunny afternoons. The gourmet kitchen is designed for both everyday living and effortless entertaining and features high-end appliances, gas cooking, a large island with ample work space, and dedicated wine storage. A sun-filled office that doubles as a 3rd bedroom, provides the perfect work-from-home space, while the spacious primary suite and second bedroom—thoughtfully positioned on the opposite side of the residence for added privacy—provide exceptional comfort for owners and guests alike. Welcome to 141 West Street where one level luxury living, a private penthouse terrace, two garage parking spaces, and a walk-everywhere location come together to offer benefits that are difficult to duplicate anywhere else in downtown Annapolis.

ANNAPOLIS

141 WEST STREET 401

2 Beds

2 Baths

1,354 Sq.Ft.

$1,149,000

MLS#: MDAA2145410

Enjoy unobstructed views of Saltworks Creek from this ideally situated home in the sought-after, water-privileged community of Severn Grove—just minutes from downtown Annapolis. Thoughtfully designed across three spacious levels, the home offers an open, light-filled floor plan that seamlessly blends everyday comfort with effortless entertaining, all defined by picturesque water views. The main level features warm wood flooring, a welcoming living room with a fireplace, and a well-appointed kitchen anchored by a large island and accented with plantation shutters. A main-level bedroom with a full bath and a separate office provide flexible living options. Step outside to multiple decks and a screened porch—perfect for relaxing or hosting while taking in the peaceful surroundings. Upstairs, three additional bedrooms include a water side primary suite with sweeping water views. A cozy library with custom bookcases and its own fireplace creates an ideal space for reading or working from home. Finishing out the second floor is a full bathroom and two bedrooms....one with water views. The fully finished lower-level lives like a private guest suite, complete with a bedroom, full bath, kitchen, spacious living area, and walk-out access—offering exceptional versatility for extended visits or multigenerational living. Additional features include off-street parking and access to Severn Grove’s exceptional amenities, including a clubhouse, beach, water access/marina, and kayak storage. With its flexible layout, scenic setting, and prime location, this home offers a rare opportunity to enjoy the best of waterfront living.

ANNAPOLIS

1812 SHORE DRIVE

5 Beds

4 Baths

3,240 Sq.Ft.

$1,149,000

MLS#: MDAA2138462

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!

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.

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.

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.

ANNAPOLIS

767 BON HAVEN DRIVE

5 Beds

4 Baths

3,255 Sq.Ft.

$1,100,000

MLS#: MDAA2140440

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Buyers resources

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Selling Your Home for More $$

Buyers resources

BUYERS RESOURCES

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SELLERS RESOURCES

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