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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

158

# of Listings

3

Avg # of Bedrooms

$504

Avg. $ / Sq.Ft.

$994,807

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

158 Properties Found. Page 2 of 11.

New on site 3 days ago

Welcome to an exceptional four level townhome in the coveted Village of Chesapeake Harbour in Annapolis, where every floor captures sweeping views of the Severn River and the iconic Chesapeake Bay Bridge. An elevator services all levels, offering both convenience and comfort while enhancing the ease of everyday living. Multiple balconies and decks invite you to step outside and take in sunrise over the water and evening lights shimmering across the Bay.

The main level showcases a generously sized kitchen with crisp white cabinetry, abundant storage, and a spacious center work area that anchors the space beautifully. The combined living and dining room is positioned to highlight the breathtaking backdrop and features its own fireplace, adding warmth and ambiance to the dramatic waterfront setting.

On the third level, the primary suite offers stunning water views, a private bath with a relaxing soaking tub, and a fireplace that creates a true retreat atmosphere. An additional bedroom with soaring ceiling and wonderful natural light, along with a hall bath featuring a tub shower combination, complete this level. The fourth floor provides exceptional flexibility as a third bedroom, guest retreat, or additional living space, all enhanced by balcony access and panoramic views.

The lower level functions beautifully as a welcoming family room with a cozy fireplace, ideal for relaxed evenings at home. From here, step directly out to the community boardwalk and pier, making waterfront walks and time by the water part of everyday life. Residents enjoy beautifully maintained common grounds, a community center, pools, tennis courts, and water privileges that define the Chesapeake Harbour lifestyle.

ANNAPOLIS

2215 CHESAPEAKE HARBOUR DRIVE E

3 Beds

3 Baths

3,086 Sq.Ft.

$2,300,000

MLS#: MDAA2131678

For sale , this is a huge opportunity 2 ASSETS FOR SALE , 1991-1993 West Street: 3000 sf retail building Lot Size.Discover an exceptional investment opportunity with this portfolio of two retail assets located at 1991 and 1993 West Street, Annapolis, MD.

- Property Overview:

- 1991 West St:

- Lot Size: 8,000 sq. ft.

- Zoning: BCE (Business Corridor Enhancement district)

- Features a retail building with high visibility and heavy traffic, ideal for attracting customers.

- The current tenant is willing to continue leasing or vacate if necessary, providing flexibility for potential buyers.

- 1993 West St:

- Lot Size: 4,800 sq. ft.

- This property is currently condemned, with value primarily in the land itself, offering a unique redevelopment opportunity.

Location Highlights:

- Situated in a bustling area with high foot traffic and direct proximity to Annapolis’ historic downtown, this location promises excellent visibility and accessibility for any retail business.

Important Note:

- Please do not visit the property without a scheduled appointment to ensure a smooth viewing experience.

Take advantage of this rare chance to invest in prime real estate in a thriving area. Contact us for more details or to schedule a viewing!

ANNAPOLIS

1991-1993 WEST STREET

None Beds

None Baths

3,000 Sq.Ft.

$2,099,000

MLS#: MDAA2128872

A rare opportunity for a well located worship facility on 23 acres in Cape St. Claire with exceptional frontage on Rt 50. This large complex with extensive acreage allows a congregation an unusual and great opportunity to grow or fund itself. Existing complex can be restored and used with a great opportunity for later expansion for a larger facility on the additional acreage. Selling addition acres for subdivision may be possible. Available preliminary engineering supports subdivision possibilities. This facility's main room is big enough for 175 and building boasts over 4600 total sq ft, includes a kitchen with serving bar, study, multipurpose room, foyer and reception desk, offices, and classrooms. Noteworthy architectural features include palladium windows, exposed brick, beamed ceilings and a custom staircase. The main building will require less updating and the parsonage, once used as offices, will require significant renovation. Property sold as-is, where-is. Zoning is residential and supports some commercial uses. See attached zoning table for R1 uses. All uses will require certificate of use and occupancy.

ANNAPOLIS

1016-1024 E COLLEGE PARKWAY

None Beds

None Baths

4,473 Sq.Ft.

$1,995,000

MLS#: MDAA2123582

Located in desirable Murray Hill in the heart of downtown Annapolis, this spacious newer-built Colonial-Craftsman home offers the rare combination of modern construction, architectural character, and true walkable in-town living. Built in 2014, the residence begins with a welcoming front porch and opens into a thoughtfully designed main level featuring high ceilings throughout and coffered ceilings accenting the front living and dining rooms — details that create warmth, scale, and presence rarely found in downtown homes.

The open-concept kitchen flows seamlessly into the expansive family room, where a fireplace anchors the space and elevated ceiling heights enhance light and volume. Just beyond, a three-season sunroom sits behind accordion-style glass doors, offering the flexibility to fully integrate with the main living space or remain a separate seasonal retreat. From here, windows and exterior doors open to the rear yard, creating a graceful transition between interior comfort and outdoor living.

A versatile main-level sitting room or study could potentially be a main level bedroom, with attached full bath, and dedicated laundry room providing flexibility for modern lifestyles. The finished lower level adds valuable living space with a wet bar, full bath, generous storage, and walk-out access — ideal for guests, recreation, or media use.

Upstairs, the spacious primary suite features a walk-in closet and a well-appointed bath with separate soaking tub and shower. Three additional bedrooms complete the upper level, including one en suite and two connected by a Jack-and-Jill bath. With over 3500 square feet of finished living space, the home offers a level of scale and functionality that is far larger than it appears from the street — an exceptional rarity in Murray Hill — along with the added convenience of a two-car off-street parking pad.

Enjoy a short stroll to Amos Garrett Waterside Park, catch a water taxi to City Dock or Eastport, walk to Main Street’s shops and restaurants, or dine under the stars on West Street. This coveted Murray Hill address delivers luxury, space, and lifestyle in one of Annapolis’ most sought-after neighborhood.

ANNAPOLIS

116 ACADEMY STREET

4 Beds

5 Baths

3,828 Sq.Ft.

$1,995,000

MLS#: MDAA2136136

23-acre parcel zoned primarily R-1, with some O-S. Preliminary engineering work indicates the property can be subdivided and coul support multiple residential lots. The concept drawing attached.

ANNAPOLIS

1016 E COLLEGE PARKWAY

None Beds

None Baths

23.33 acres

$1,995,000

MLS#: MDAA2123584

New on site 4 days ago

Last available opportunity for a buildable Waterfront lot on Lake Ogleton in the coveted community of Bay Ridge in Annapolis! This .22 acre lot has been in the same family for the past 58 years and is coming to market for the first time. With 57 feet of waterfrontage on the sparkling shores of Lake Ogleton, the possibilities are endless for building the waterfront home of your dreams! This property is priced to sell quickly, at $361,000 below the tax assessed value! Contact your architect and take the first step toward bringing your vision of the ideal Annapolis lifestyle on the water! The sought-after Bay Ridge Community features a plethora of amenities, including a community pool with a clubhouse that overlooks the beautiful waters of the Bay, community beaches on both the River and the Bay, and a community Marina with a newly renovated clubhouse. Off-the-water activities include enjoying the basketball court, playground, ball fields, pickleball courts, common areas, and year-round community activities. Walk or ride your bike for miles along the water and enjoy all the benefits of the Bay Ridge lifestyle. There is no other place like it! Located just minutes from downtown Annapolis and Eastport, which offer the perfect balance of small-town charm and big world sophistication. Traveling or commuting is just as convenient by easily accessing Rt. 50 and 97, which provides direct access to Baltimore, BWI, Ft. Meade/NSA, and Washington, DC, or head over the Bay Bridge to the Eastern Shore for a quick beach vacation.

ANNAPOLIS

48 E LAKE DRIVE

None Beds

None Baths

0.22 acres

$1,895,000

MLS#: MDAA2137314

New on site today

No sign on property.
Welcome to 1303 Windsor Ridge Lane, a luxury residence offering exceptional comfort, privacy, and resort-style amenities. Nestled on a private 3.71 acre lot within the sought-after Windsor community and Broadneck school district, this home provides a rare sense of tranquility with no neighboring homes in sight. The backyard is a true oasis, designed for both entertaining and everyday enjoyment. Highlights include a heated saltwater pool with waterfall features and automatic cover, an outdoor kitchen, a pavilion with automatic screens, a cozy fireplace, and TV hookup—perfect for relaxing day or night. Lush landscaping and the home’s elevated setting further enhance privacy. The architectural roof of the home was replaced in 2024. Inside, the open floor plan with 9' ceilings is filled with natural light from abundant windows. The chef’s kitchen features upgraded finishes including Viking double oven, Viking 6 burner gas cooktop, Futuro top-of-the-line island range hood, white cabinetry, quartz countertops, glass backsplash and 2 custom built pantry closets. Off one side of the kitchen, you'll find the spacious family room with a gas fireplace, dining room, cozy living room with a 2 sided gas fireplace shared with the sunroom, a study and half bath. You'll enjoy the Sonos sound system throughout the home. On the other side of the kitchen is a guest suite with a private bath, laundry room, a spacious bonus room and the 3 car epoxy coated garage. Dual staircases lead you to the second floor which has 4 bedroom suites. The primary suite serves as a luxurious retreat overlooking the backyard, complete with a sitting area and spa-like ensuite bath featuring a walk-in shower, soaking tub, double vanity and additional make-up vanity area. Each ensuite bathroom has been fully renovated with fresh and modern finishes. The fully finished lower level offers exceptional versatility with a gym, theater, bar, additional living space, a full bath, and an extra room that can serve as an additional bedroom. This home is located adjacent to Windsor Farm Elementary School and just minutes from Rt. 50 offering easy access to Annapolis, Washington, D.C. and the beach. Whether you’re seeking a peaceful retreat, an entertainer’s dream, or a family-friendly home, 1303 Windsor Ridge Lane delivers it all. You will appreciate the meticulous details and beauty of this exceptional property.

ANNAPOLIS

1303 WINDSOR RIDGE LANE

5 Beds

6 Baths

7,936 Sq.Ft.

$1,890,000

MLS#: MDAA2136918

Discover a rare deep-water retreat on peaceful Burley Creek, an inviting waterfront home where contemporary architecture, warm natural textures, and the serenity of nature come together in a way that instantly feels like a getaway. With soaring vaulted ceilings, natural wood accents, dramatic stacked-stone fireplaces, and sunlight spilling in from every angle, the home offers a cozy, ski-chalet ambiance, only here, the views are of still water, quiet mornings, and the deep blue of 10’ mean low water.

Tucked into a lovely setting yet just minutes from downtown Annapolis, this refreshed three-bedroom, three-bath contemporary offers one bedroom on each level, creating ideal separation and flexibility for guests, multi-generational living, or weekend retreats. The interior has been thoughtfully updated throughout, including fresh paint on every level and new LVP flooring that adds a soft, modern touch while enhancing the warm architectural lines of the home. Expansive windows and sliding doors draw in natural light and frame sweeping views of the creek, bringing the outdoors in and making every room feel connected to the water.

The main level is the heart of the home, where the dramatic stone fireplace rises to meet the vaulted ceiling and creates a gathering space that feels both elevated and deeply comfortable. The dining area and living room flow seamlessly onto the outdoor decks, offering multiple places to enjoy morning coffee, read a book, or simply breathe in the calm that surrounds the property. The kitchen and breakfast area provide direct access to the outdoors and enjoy tile flooring that complements the clean, modern updates found throughout the rest of the home.

Each floor offers its own bedroom and full bath. The lower level is bright and welcoming with a renovated full bathroom and a walkout directly to the waterfront lawn, ideal for guests, a studio, or a home office. The main level bedroom sits near a beautifully updated full bath featuring new flooring, vanity, and lighting. The upper-level primary suite feels like a private retreat of its own. A spacious walk-in closet provides ample storage, while the ensuite bath, complete with an elevated soaking tub that feels like something out of Old Hollywood adds a touch of whimsy and charm. The open dual-vanity area and tucked-away water closet function beautifully while keeping the suite’s retreat-like feel intact.

Outside, the property shines with multiple decks, quiet sitting areas, and a gently sloping lawn leading to the water’s edge. The private dock, with an impressive 10' MLW, can accommodate up to five boats, an exceptional feature rarely found in Annapolis at any price point. Electric and potable water at the dock, with 30 AMP hook up. Boaters will appreciate both the depth and flexibility, with the potential to rent one or more slips for added income if desired.

Whether you're hosting waterfront gatherings, relaxing by one of the two stunning stacked-stone fireplaces, or unwinding on one of the many peaceful outdoor spaces, this home offers a lifestyle that balances luxury, comfort, and natural beauty. Warm, inviting, architecturally unique, and designed to embrace the water from every angle, this property offers a one-of-a-kind opportunity to enjoy deep-water living in a setting that feels like a year-round retreat.

A truly exceptional Annapolis offering where luxury design, cozy chalet ambiance, and premier boating features meet in perfect harmony.

ANNAPOLIS

1836 BURLEY LANE

3 Beds

3 Baths

2,016 Sq.Ft.

$1,695,000

MLS#: MDAA2132644

Stunning Waterfront Coastal Retreat on Oyster Creek with Breathtaking Sunsets! This exceptional 4-bedroom, 4-bathroom home is perfectly situated on the shores offering unique views of the Chesapeake Bay and Oyster Creek from nearly every room. Step inside to discover the open design, highlighting a gourmet kitchen designed for both beauty and function, featuring granite countertops, stainless steel appliances, and breakfast bar. The open-concept living and dining areas flow easily out to the multi-level waterfront decking, ideal for entertaining or simply enjoying the peaceful surroundings. The luxury primary suite is a true sanctuary, complete with a private waterfront deck, spa-like bathroom featuring a walk-in shower, soaking tub, and a generous walk-in closet. The third-level living space includes a full bath and offers endless possibilities—perfect as a media room, guest suite, or home office with elevated views.
Outside, a private pier with a 20,000 lb boat lift invites you to explore the water with ease. Whether you're boating, fishing, or just soaking in the serene creekfront setting, this property offers the ultimate coastal lifestyle. Don’t miss this rare opportunity to own a slice of waterfront paradise on Oyster Creek. Property is in a Special Tax District. - $2,274.75 annually.

ANNAPOLIS

3300 SHORE DRIVE

4 Beds

4 Baths

2,798 Sq.Ft.

$1,650,000

MLS#: MDAA2116986

PHOTOS TO BE UPDATED THROUGHOUT BUILDING PROCESS!! This is a rare opportunity to own a newly built, beautifully designed home on a large lot in an established neighborhood-with nature at your doorstep and everything Annapolis has to offer just minutes away. This home is estimated to be completed in March, 2026. With a stunning Colonial architectural style, this beautiful home offers 5-bedrooms and 4.5-baths and sits on the last available lot in the Twin Hills neighborhood which is 1.4 acres and borders lush trees and a preservation area. It offers a rare blend of privacy, openness and a connection to nature. Whether you are hosting friends or enjoying a quiet night in, the thoughtful layout makes everyday living feel seamless and relaxed.

As you step inside, you are greeted by an inviting open floor plan with an abundance of light throughout that seamlessly connects the open-concept gourmet kitchen to the family room, creating an ideal space for both entertaining and everyday living. The kitchen features stainless steel appliances, including double wall ovens, cooktop and built-in microwave, complemented by a spacious island and quartz countertops. The Morning Room (Breakfast Room) and Conservatory offers light filled retreats year round. You will also find five generously sized bedrooms, each designed with comfort in mind. The primary suite is a true retreat, with a spacious sitting room and dual walk-in closets in addition to a luxurious en-suite bathroom featuring a soaking tub, walk-in shower, and dual vanities as well as dual water closets! The family room features 10’ ceilings and a relaxing gas fireplace to keep you warm in the cooler nights! The full basement, with an outside entrance, provides extra entertaining spaces with a extensive recreation room, true fifth bedroom and full bath as well as an unfinished area which leaves endless possibilities for customization, whether you envision a home theater, gym, or additional living space. The bedroom floor laundry adds a touch of practicality to daily routines, while the cozy family room off the kitchen serves as the heart of the home, perfect for relaxation and connection. The side-entry garage accommodates three vehicles and a generous amount of storage space, ensuring convenience and ease of access.

This residence is not just a home; it's a lifestyle choice that embodies luxury, comfort, and modern living. Experience the perfect blend of sophistication and warmth in this remarkable new construction home, where every detail has been thoughtfully curated for your enjoyment. All of this with an Annapolis address (and a close proximity to the water and fine restaurants Annapolis has to offer) to add to the joy you will feel from choosing this as your next home. Howmar Homes is a local builder dedicated to treating every house as if it were his own. With no shortcuts taken, each home reflects true care and craftsmanship you can see and feel in every detail. An optional inground pool has already been approved and has been cited on property for future or present consideration. If you act quickly, you can still select final finishings. Don’t miss your chance! Schedule your showing today!

ANNAPOLIS

1907 MACKIEBETH COURT

5 Beds

4 Baths

5,437 Sq.Ft.

$1,575,000

MLS#: MDAA2125858

Greet neighbors from the front porch or entertain them on the private, fenced rear patio. This classically designed home offers high ceilings, two gas fireplaces, updated kitchen and baths and a floor plan that allows for intimate gatherings or lavish dinner parties. Light floods all the rooms including the 4 upper level(3 ensuite) bedrooms, one with a balcony. The laundry is conveniently located on the upper level; the lower level offers a cozy fireplace, full bath and separate entry. There is a two car garage (with electric car charger)off a rea driveway that can accommodate 3-4 additional vehicles. And when the snow melts you will be awed by the professionally designed gardens and outdoor living spaces.
All this within walking/biking distance to local shops, restaurants and events.
Downsizing? There is ample storage! Moving up? The flexible floorplan can accommodate your changing lifestyle. Come see for yourself.

ANNAPOLIS

1109 BOUCHER AVENUE

4 Beds

4 Baths

3,779 Sq.Ft.

$1,545,000

MLS#: MDAA2136296

Incredible Opportunity in the Heart of Eastport!

Beautifully remodeled Victorian located on the Eastport Peninsula. Features include a welcoming front porch, wood floors, and a chef’s kitchen with Viking appliances, a 6-burner stove, and vented hood. Windows and roof were replaced in 2025; roof includes new gutter guards. Energy-efficient appliances, including a gas on-demand water heater, have earned this home an Energy Star Certificate from BGE.

Flexible heating and cooling options with radiator heat and five mini-split units providing a total of 48,000 BTUs for heating and cooling. Skylights feature solar shades, and the fully encapsulated crawl space enhances year-round comfort and efficiency.

Upper level offers two bedrooms, each with a full bath, plus a full-size washer and dryer.

Enjoy a private, fully fenced backyard (new fence 2020) with mature native trees and landscaping—perfect for relaxing or entertaining. The detached accessory structure offers endless possibilities: office, studio, hobby room, or gym. And don't forget.....there is an off street driveway !!

This property is move-in ready—just bring your personal touch!

ANNAPOLIS

120 CHESAPEAKE AVENUE

2 Beds

2 Baths

2,130 Sq.Ft.

$1,449,000

MLS#: MDAA2130442

#MDAA2136350

ANNAPOLIS

2154 CHESAPEAKE HARBOUR DRIVE

3 Beds

3 Baths

2,350 Sq.Ft.

$1,385,000

MLS#: MDAA2136350

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 End Unit at the standard price, however, 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.

ANNAPOLIS

208 SELLEW ROAD

3 Beds

3 Baths

3,100 Sq.Ft.

$1,375,000

MLS#: MDAA2119308

There are so many option available for this property in the heart of Historic Annapolis. You may want to convert the entire home back to one living unit. You may want to live in one, long-term rent the other two or short term rent one. You may choose that it be be used for a couple/single person to live in one apt and rent out 2 or have a multigenerational combined family living in 1, 2 (while renting 1) or all 3. There are so many possibilities to enjoy this amazing property. This is 3 fully finished levels and units above grade. The basement level houses the storage area, HVAC and shared laundry area. All of the units are fully furnished with kitchen appliances, items, dishware, glassware, beds, linens, furniture, you name it, it is there and conveys. This is steps away from the Naval Academy. The main level entry has a hallway with stairwell to the upper level units and access to the man level unit Apt 1 and the basement. Apt 1 offers a foyer, eat-in kitchen, full bath, living room, bedroom and access to the rear patio fenced in area. The 2nd level has Apt 2 with a living room, kitchen, bath, 2 bedrooms and access to the rear patio area. The third upper level offers a full bath, galley kitchen, bedroom and large living area with space for a table, couch and mor furnishings. All units have the old time charm with modern components. All three units offer high ceilings. This is a very popular property so bear with us as we want to accommodate all showing requests. The most advance notice you can give the better. There may be times when all 3 may not be able to be seen on the same day. There is a virtual tour where you can walk through the entire property, zoom in and out and see the whole house from your phone or computer. This is also listed as Residential MLS# MDAA2132242. Parking info is loaded in the documents section. Unit schedule: Unit 1 can be seen 1.2 to 1.9 and other days with notice. Unit 2 is available to be seen 1.2 to 1.22. Unit 3 is available to be seen the whole month of January.

ANNAPOLIS

165 KING GEORGE STREET

4 Beds

None Baths

2,649 Sq.Ft.

$1,375,000

MLS#: MDAA2132270

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