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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

281

# of Listings

3

Avg # of Bedrooms

$505

Avg. $ / Sq.Ft.

$1,384,229

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

281 Properties Found. Page 6 of 19.

Set on a private .75-acre lot backing to the 14th hole of the Navy Golf Course, this exceptional home is located in a prime Broadneck School District location just minutes from Downtown Annapolis. The backyard is what truly sets this property apart. With a screened-in porch, fire pit, multiple seating areas, basketball and pickleball court, full playground, and expansive lawn, it feels more like your own private park than a typical backyard. Whether hosting a crowd, watching the kids play, or enjoying a quiet evening outdoors, this is really a magical setting. Inside, 9-foot ceilings, generous room sizes, custom finishes, and abundant natural light create comfortable living spaces throughout. A main-level bedroom and full bath offer flexibility for guests or multi-generational living. The walk-out lower level includes a family room, bar, office, gym, and dedicated playroom. Additional features include Hardiplank siding, a two-car garage, and ample side parking for several cars in the driveway. A voluntary Pendennis Mount HOA of just $50 per year provides water access on the Severn River near the Severn Inn. Homes offering this combination of outdoor space, recreation, privacy, and convenience are few and far between.

ANNAPOLIS

1903 BALTIMORE ANNAPOLIS BOULEVARD

6 Beds

4 Baths

5,532 Sq.Ft.

$1,295,000

MLS#: MDAA2148048

Hard Hat Tours are now available by appointment! Early buyers have the opportunity to customize their home's finish colors and materials. Don't wait! Construction is moving along and the builder will make selections for any unreserved homes.
This listing is for an interior home on Lot 6. Sturbridge Homes is offering a generous pre-construction incentive package for early buyers. Submit your deposit now to lock in current pricing and have the ability to customize your home! Sales Center appointments are available now.
Welcome to Towne Row - A community of 18 Luxury Townhomes in the Annapolis Town Center Corridor.
A Towne Row home is superior in every way. The craftsmanship and expansive spaces are apparent immediately. Notice the contemporary exterior, rooftop terrace for entertaining and stargazing, and two-car garage. Savor the spacious kitchen and luxurious owner's suite, privately situated on its own level, and the high-end materials and fixtures throughout. Live graciously and vertically on four generous levels, whisked up and down by your private elevator. This is Towne Row, your haven, your showplace, your new home. It's like none other in Annapolis. Features include: 3,100 Square Feet of Living Space, 3 Bedrooms + Den, 3 Full Baths, 2 Half Baths, Expansive Gourmet Kitchen With Walk-out Deck, Private Elevator, Elegant, Spacious Owner's Suite on Its Own Level, Quartz Countertops Throughout, Four Levels of Finished Living Space, Rooftop Deck With Space for Hot Tub, Two-car Garage, Energy Star & LEED Gold Certified

Location, location, location. Living at Towne Row puts you in the heart of the bustling Annapolis Town Center corridor. You have instant access to an array of upscale and casual restaurants, boutiques and shops, favorite grocery stores, sophisticated fashion and home goods retailers, fitness clubs, movie theaters, and essential services. Plus, you'll be minutes from the Annapolis historic district, endless waterways, nearby marinas, and a short drive to Baltimore and Washington, D.C. It's luxury living and convenience beyond compare.

Lot dimensions, floor plans, and square footage figures are approximate. Architectural renderings are samples only and may not reflect the exact product. Sellew Rd. has not been built and may not appear on some mapping apps. Map to 2555 Riva Rd. for the approximate location.

ANNAPOLIS

108 SELLEW ROAD

3 Beds

3 Baths

3,100 Sq.Ft.

$1,295,000

MLS#: MDAA2135966

New on site 2 days ago

Hard Hat Tours are now available by appointment! Early buyers have the opportunity to customize their home's finish colors and materials. Don't wait! Construction is moving along and the builder will make selections for any unreserved homes.
This listing is for an interior home on Lot 16. Sturbridge Homes is offering a generous pre-construction incentive package for early buyers. Submit your deposit now to lock in current pricing and have the ability to customize your home! Sales Center appointments are available now.
Welcome to Towne Row - A community of 18 Luxury Townhomes in the Annapolis Town Center Corridor.
A Towne Row home is superior in every way. The craftsmanship and expansive spaces are apparent immediately. Notice the contemporary exterior, rooftop terrace for entertaining and stargazing, and two-car garage. Savor the spacious kitchen and luxurious owner's suite, privately situated on its own level, and the high-end materials and fixtures throughout. Live graciously and vertically on four generous levels, whisked up and down by your private elevator. This is Towne Row, your haven, your showplace, your new home. It's like none other in Annapolis. Features include: 3,100 Square Feet of Living Space, 3 Bedrooms + Den, 3 Full Baths, 2 Half Baths, Expansive Gourmet Kitchen With Walk-out Deck, Private Elevator, Elegant, Spacious Owner's Suite on Its Own Level, Quartz Countertops Throughout, Four Levels of Finished Living Space, Rooftop Deck With Space for Hot Tub, Two-car Garage, Energy Star & LEED Gold Certified

Location, location, location. Living at Towne Row puts you in the heart of the bustling Annapolis Town Center corridor. You have instant access to an array of upscale and casual restaurants, boutiques and shops, favorite grocery stores, sophisticated fashion and home goods retailers, fitness clubs, movie theaters, and essential services. Plus, you'll be minutes from the Annapolis historic district, endless waterways, nearby marinas, and a short drive to Baltimore and Washington, D.C. It's luxury living and convenience beyond compare.

Lot dimensions, floor plans, and square footage figures are approximate. Architectural renderings are samples only and may not reflect the exact product. Sellew Rd. has not been built and may not appear on some mapping apps. Map to 2555 Riva Rd. for the approximate location.

ANNAPOLIS

109 SELLEW ROAD

3 Beds

3 Baths

3,300 Sq.Ft.

$1,265,000

MLS#: MDAA2149300

#MDAA2147138

ANNAPOLIS

128 STILLY WAY

5 Beds

4 Baths

4,692 Sq.Ft.

$1,250,000

MLS#: MDAA2147138

New on site 2 days ago

Enjoy living in the heart of Eastport, where charming streets, waterfront parks, and a vibrant dining scene create one of Annapolis' most coveted lifestyles. This inviting home on a private cul-de-sac with just 4 houses combines comfortable living spaces with exceptional indoor-outdoor flow, all within walking distance of local shops, restaurants, marinas, and downtown Annapolis.

Thoughtfully designed, the main level offers a wonderful balance of open gathering spaces and cozy retreats. The combined living and dining room is filled with natural light from high ceilings and skylights and opens directly to the expansive deck overlooking the backyard. At the heart of the home, the kitchen with center island flows seamlessly into the family room, where a fireplace creates a warm ambiance and easy access to the large screened porch and deck encourages effortless indoor-outdoor living. A newly renovated powder room provides privacy and convenience for family and guests.

Upstairs, the primary suite provides a peaceful retreat featuring an ensuite bath with skylight, walk-in shower, and walk-in closet. Two additional bedrooms share a hall bath and are bathed in natural light, with one showcasing soaring ceilings.

The lower level offers exceptional versatility with a spacious recreation room centered around a countertop area with full-size refrigerator, making it ideal for movie nights, game days, or hosting. A full bath, stackable laundry area, and a bonus room that makes an excellent office, or hobby space complete this level.

Outside, the fenced backyard provides privacy and space for gatherings with family and friends, while the expansive deck and screened porch create inviting spaces to relax and enjoy the seasons.

Stroll the artful and nautical streets to five-star restaurants, neighborhood pubs, and hidden street-end parks. You'll find yourself just moments from downtown Annapolis and the Naval Academy. Eastport and Annapolis offer the perfect balance of small-town charm and world-class sophistication, with convenient access to Routes 50 and 97 for easy commuting to Baltimore, BWI Airport, Fort Meade, NSA, and Washington, D.C. Welcome Home!

ANNAPOLIS

4 KELLY COURT

3 Beds

3 Baths

2,450 Sq.Ft.

$1,250,000

MLS#: MDAA2148640

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 two 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

One-Level Luxury Living in the Heart of Downtown Annapolis.
Experience penthouse living at the highly sought-after 141 West Residence. This beautifully appointed 2-bedroom, 2.5-bath condominium offers a seamless, turnkey lifestyle with an open, light-filled floor plan enhanced by floor-to-ceiling windows and premium finishes throughout. Step outside to the expansive, unique, private terrace, an inviting outdoor retreat ideal for dining, entertaining, or simply relaxing under the retractable awnings on sunny afternoons.

Designed for both comfortable everyday living and effortless entertaining, the gourmet kitchen features high-end appliances, gas cooking, a large island with great work space,, and wine storage. A bright private 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—offer exceptional comfort for owners and guests alike.

Two assigned parking spaces convey with the property. Located just steps from Annapolis' acclaimed restaurants, boutique shopping, waterfront attractions, and cultural amenities, this exceptional penthouse offers the very best of luxury, convenience, and one-level living in downtown Annapolis.

ANNAPOLIS

141 WEST STREET 401

2 Beds

2 Baths

1,354 Sq.Ft.

$1,195,000

MLS#: MDAA2145410

Nestled in the highly sought-after Homewood community, just a short walk from downtown Annapolis, this beautifully maintained and turnkey home offers the perfect blend of in-town convenience and suburban tranquility. Tucked away on a quiet private street and set on an expansive 16,723-square-foot lot, the property is surrounded by lush, manicured landscaping, creating a serene and private retreat. The outdoor living spaces are truly exceptional—featuring a raised vegetable and flower planters, a welcoming firepit area, a 2 car garage, and a fully private backyard where the gentle sounds of happily chirping birds set the tone for peaceful relaxation or effortless entertaining. A charming brick screened-in porch extends the living space, providing the perfect setting to enjoy the outdoors in comfort. Inside, the home is in pristine, move-in ready condition and filled with natural light that pours in through well-placed windows. The fully renovated interior offers 4 BR and 2.5 baths, with hardwood flooring throughout the first and second levels. The spacious primary suite impresses with vaulted ceilings, a walk-in closet, and a luxurious whirlpool Jacuzzi tub. The main level features a welcoming entry foyer, a cozy living room with a brick wood-burning fireplace, and a dining room that seamlessly opens to the screened porch through Anderson French doors—ideal for indoor-outdoor living. The kitchen is thoughtfully updated with beautiful wood cabinetry and modern appliances. On the first floor is an expansive, light-filled office with an adjacent library—perfect for working from home or easily adaptable as an additional bedroom. The fully finished basement offers both interior and exterior access, along with a utility room equipped with a Trane HVAC system, a French drain system, and abundant shelving for storage. Combining privacy, thoughtful upgrades, and an unbeatable location, this home truly offers the best of both worlds—and is not to be missed.

ANNAPOLIS

2 ISAACS STREET

4 Beds

2 Baths

2,232 Sq.Ft.

$1,175,000

MLS#: MDAA2142378

New on site 2 days ago

#MDAA2148526

ANNAPOLIS

20 SHAW STREET

3 Beds

2 Baths

1,500 Sq.Ft.

$1,150,000

MLS#: MDAA2148526

With just one look, you will fall in love! 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

1,650 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

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