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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

282

# of Listings

3

Avg # of Bedrooms

$504

Avg. $ / Sq.Ft.

$1,381,763

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

282 Properties Found. Page 9 of 19.

Charming water-privileged split-foyer residence in the desirable Beale Manor community, offering 3,145 finished square feet of thoughtfully designed living space. Recent updates include a roof replacement, a newer water heater, fresh interior paint, and beautifully refinished flooring throughout the main level, enhancing both style and peace of mind. // The traditional layout begins with a formal living room featuring large picture windows that draw in abundant natural light and flows seamlessly into the formal dining room, creating an inviting setting for gatherings. The updated eat-in kitchen is both stylish and functional, showcasing crisp white cabinetry with sleek bar pulls, a peninsula breakfast bar, black appliances including double ovens, a built-in workstation, and a bright breakfast area with sliding door access to the screened porch. Just off the kitchen, the welcoming family room is highlighted by a white-washed brick fireplace and filled with natural light, while a convenient powder room and laundry area complete the main level. // The upper level features four generously sized bedrooms, including a spacious owner’s suite with a comfortable sitting area, dual closets—one a walk-in with a custom organization system—and a private ensuite bath with a soaking tub and separate shower. A centrally located full bathroom with an extended vanity serves the additional bedrooms. The walk-out finished lower level provides exceptional versatility, offering a large recreation space, a full bathroom, a bar area with a rough-in for a sink, and a fifth bedroom ideal for a home office, gym, or guest space. // Outdoor living is equally appealing, with a screened porch overlooking the backyard, an open-air deck that steps down to a patio, and a spacious, flat, fully fenced yard backing to trees for added privacy. // Residents of Beale Manor enjoy a wealth of community amenities, including a scenic waterfront pool, a basketball court, and a whimsical pollinator garden, fostering a vibrant, connected lifestyle.

ANNAPOLIS

3135 ANCHORAGE DRIVE

5 Beds

3 Baths

3,145 Sq.Ft.

$875,000

MLS#: MDAA2134882

New on site 1 day ago

Tucked among mature trees in the sought-after community of Annapolis Roads, this beautifully updated home offers the perfect blend of privacy, modern upgrades, and timeless charm. Set on a picturesque wooded lot, the property welcomes you with a massive wraparound porch—an ideal place to enjoy your morning coffee, entertain guests, or unwind while taking in the peaceful views of the surrounding trees.

Inside, a dramatic two-story foyer with soaring 30-foot ceilings and a stunning staircase creates an unforgettable first impression. Gleaming hardwood floors flow throughout the main level, complemented by thoughtful updates and designer finishes that make this home truly move-in ready.

The spacious main level offers excellent flow for both everyday living and entertaining. Large windows fill the home with natural light while showcasing the beautiful wooded setting. The oversized family room and gathering spaces create a warm and inviting atmosphere for family and friends.

Upstairs, the expansive primary suite serves as a private retreat, featuring a generous bedroom, large walk-in closet, and a beautifully renovated spa-like bathroom complete with a separate water closet. Three additional well-sized bedrooms and a second fully updated bathroom provide plenty of space for family, guests, or a home office. New carpeting throughout the upper level adds a fresh, modern touch.

The unfinished lower level offers endless possibilities, featuring a rough-in for a future bathroom and ample space to create additional living areas, a recreation room, gym, or guest suite. The attached two-car garage provides convenience and additional storage.

Recent improvements include a newer HVAC system, updated bathrooms, fresh finishes, and numerous upgrades throughout, allowing buyers to move in with confidence.

Perfectly sited to enjoy the best of Annapolis Roads, the property offers access to an exceptional waterfront lifestyle. Residents enjoy a sandy beach with sweeping Chesapeake Bay views, waterfront pavilion, playground, firepit, community dock, boat ramp, walking trails through Ogleton Woods and numerous community events. Nestled between Lake Ogleton and the Chesapeake Bay, Annapolis Roads is known for its winding roads, wooded lots and abundance of preserved green space and water access. There is no HOA—the community operates as a special tax district with fees included in the property taxes. Ideally located just minutes from downtown Annapolis, shopping, dining and major commuting routes.

A rare opportunity to own a beautifully updated home in one of Annapolis’ most desirable waterfront communities.

ANNAPOLIS

2701 OGLETON ROAD

4 Beds

2 Baths

2,976 Sq.Ft.

$874,000

MLS#: MDAA2140686

Welcome to Kingsport—where timeless elegance meets waterfront living. Nestled within this coveted, water-privileged community, this exceptional 5-bedroom, 4.5-bath residence offers a seamless blend of sophistication, comfort, and everyday luxury.
A grand entry welcomes you with rich hardwoods and graceful architectural details, leading to a formal oval dining room, refined living room, and a private main-level office—perfect for today’s lifestyle. The heart of the home is a beautifully appointed gourmet kitchen, featuring a custom center island with cooktop, dual wall ovens, gleaming granite countertops, and extensive cabinetry. The space flows effortlessly into a dramatic family room, highlighted by soaring vaulted ceilings, plantation shutters, and a warm gas fireplace.
Upstairs, the primary suite is a true retreat, offering a spa-inspired bath and dual walk-in closets. An elegant en-suite bedroom and two additional bedrooms with a shared bath complete the upper level, offering both comfort and privacy.
The fully finished lower level is designed for entertaining and relaxation, featuring a spacious recreation room with a wet bar, a private guest suite, a playroom, and abundant storage.

Outdoors, a fully fenced backyard invites quiet moments and gatherings alike, with a paver patio, raised garden beds, and serene wooded views backing to scenic walking paths.

Residents of Kingsport enjoy an exceptional lifestyle with resort-style amenities including a community pool, playgrounds, hiking and biking trails, kayak launch and storage, and a picturesque pier on Crab Creek—ideal for sunset views, fishing, or peaceful afternoons by the water.

Perfectly positioned just minutes from downtown Annapolis and convenient to major commuter routes, this home offers the rare opportunity to live beautifully in one of the area’s most desirable communities.

ANNAPOLIS

730 CRISFIELD WAY

5 Beds

4 Baths

3,586 Sq.Ft.

$865,000

MLS#: MDAA2143706

Our Adams model with a 2' extenstion will be built at this beautiful location near Duvall Creek. Home is priced at the base house only - act fast to choose the options and additions to make this home your own. Photos are of the model with optional In-Law Suite.
Contact Listing Agent to schedule appointment.

ANNAPOLIS

3268 KITTY DUVALL DRIVE

4 Beds

2 Baths

2,474 Sq.Ft.

$849,990

MLS#: MDAA2147542

New on site 3 days ago

Welcome to 1848 Carriage Road, a timeless gem that is beautifully situated in the highly sought-after Lindamoor community. Just a short stroll from the community beach and only a few streets from both neighborhood docks, this home offers the perfect blend of water accessibility, convenience, and undeniable charm.

Step inside to discover a warm and inviting main level filled with large windows and natural light. The spacious living room flows seamlessly into the dining area and kitchen, creating an ideal layout. Designed for easy living, the home functions like a rancher, with three generous sized, sun-filled bedrooms, two bathrooms and everything you need on the main level. The kitchen opens onto a deck overlooking a spacious, wooded backyard — perfect for gardening, entertaining, pets, or play.

The fully finished walk-out lower level significantly expands the living space and offers exceptional flexibility. With direct access from the garage and a large sliding door to the backyard, this level features a spacious family room, a separate sitting area perfect for a media room or home office, a large fourth bedroom, and a full bathroom. Abundant storage and versatile spaces provide endless possibilities for guests, fitness, recreation, or work-from-home needs.

Ideally located just minutes from historic downtown Annapolis, you'll enjoy easy access to waterfront restaurants, boutique shopping, marinas, and year-round cultural events, along with convenient commuting routes to both Washington, D.C. and Baltimore.

Offered at an attractive price and ready for its next owners, this is a rare opportunity to enjoy the lifestyle and amenities that make Lindamoor one of Annapolis’ desirable waterfront communities.

Don't miss your chance to make this charming property your new home.

ANNAPOLIS

1848 CARRIAGE DRIVE

4 Beds

3 Baths

2,622 Sq.Ft.

$849,000

MLS#: MDAA2148380

New on site 2 days ago

Experience the very best of downtown Annapolis living at Acton's Landing. Ideally located just a block from the waterfront and within easy walking distance of City Dock, Main Street, the Naval Academy, restaurants, shops, and marinas, this sought-after community offers an exceptional opportunity to enjoy a truly walkable Annapolis lifestyle.
Acton's Landing is known for its distinctive residences, where no two floor plans are exactly alike. Residents enjoy secure entry, elevators, a fitness center, library, beautifully maintained common spaces, and inviting outdoor gathering areas. The building has also undergone significant recent improvements, including a full interior refresh and exterior rehabilitation.
This light-filled residence offers over 1,400 square feet of comfortable one-level living. Large windows fill the home with natural light, while the open floor plan creates inviting spaces for both everyday living and entertaining. The updated kitchen features peninsula seating and opens seamlessly to the dining and living areas. Two private balconies provide additional outdoor living space.
The thoughtfully designed floor plan includes two spacious bedroom suites, each with its own updated bathroom and generous closet space, along with a dedicated home office and an additional half bath for guests. The living area includes a custom built-in entertainment center and a 55-inch Samsung (2024) television. Recent owner improvements include fresh interior paint, a new HVAC system, new hot water heater, new dishwasher, and an under-sink water filtration system, allowing the next owner to move in and immediately enjoy the home. Whether you're enjoying waterfront strolls, dining al fresco, summer concerts, or the shops and restaurants that make Annapolis such a special place to live, Acton's Landing places it all just outside your door.

ANNAPOLIS

66 FRANKLIN STREET 412

2 Beds

2 Baths

1,479 Sq.Ft.

$849,000

MLS#: MDAA2149170

NEW PRICE, UPDATED SQUARE FOOTAGE + NEW PHOTOS ADDED — INCREDIBLE OPPORTUNITY! Boasting 1,549 sq. ft. of finished historic charm, this 1905 Homewood treasure sits on a rare, oversized 0.26-acre lot—offering space and flexibility nearly impossible to find this close to City Dock. While the main house charms with high ceilings, refinished hardwoods, and a light-filled 3-seasons wrap-around porch, the true crown jewel is the backyard oasis. Surrounded by stunning, mature trees, the sprawling lawn features an existing 1-car garage ripe for transformation. Bring your vision to easily rebuild this structure into a premier Accessory Dwelling Unit (ADU), income-producing apartment, or a private home office oasis. Walk to the Navy Stadium, local cafes, and the Poplar Trail. With room to grow, update, and build equity, this is a rare Annapolis footprint waiting for your personal touch!

Note on Square Footage: Finished square footage has been updated to 1,549 sq. ft. based on recent agent measurements. Public tax records currently reflect inaccurate historical data (1,442 sq. ft.) and do not fully capture the complete finished living area.

ANNAPOLIS

21 WOODLAWN AVENUE

3 Beds

2 Baths

1,549 Sq.Ft.

$849,000

MLS#: MDAA2144864

Pure Privacy on this wooded paradise here in Annapolis. Situated on a private, 1.42 acre lot, you're going to love the sun-filled family room and adjacent sunroom. The kitchen has been remodeled with gorgeous, wooded cabinetry, granite counters and high-end appliances. There is a formal living and dining room for all of your functions. The basement has been waterproofed and is walk-out level and ready to be finished. There are three bedrooms upstairs with an open office/loft area. Explore nature or just enjoy the hummingbirds from the back deck and porch. Close to everything, but feels miles away!

ANNAPOLIS

1812 CROSSPOINTE DRIVE

3 Beds

2 Baths

2,792 Sq.Ft.

$845,000

MLS#: MDAA2143460

#MDAA2144296

ANNAPOLIS

422 FIRST STREET

2 Beds

1 Baths

1,094 Sq.Ft.

$835,000

MLS#: MDAA2144296

Welcome home to this one of a kind three bedroom, two and a half bath rancher on a double lot in sought after Cape St Claire. One level living at it's finest, with a huge sunroom with vaulted ceiling on one wing, and the bedrooms on the other wing of this sprawling rancher. This property has been lovingly maintained by the owners, with the addition of the sunroom, powder room, laundry room, and part of the garage in more recent years. The 600 square foot light filled sunroom is the focal point of the house now, with wonderful built in bookshelves and entertainment center. The original family room has a wood burning fireplace, and makes a cozy den or office. Stainless appliances and table space in the kitchen with French doors leading to the stone patio out back. The living room and dining room have ample space for gatherings. In the bedroom wing of the house find the primary bedroom with an attached full bath and two more ample bedrooms share the hall full bath. Recent updates include; in 2020 - Fast Care Floor System installed in garage & driveway resurfaced, in 2023 a new roof, in 2025 new well pump, updated electric to code, one new air conditioner, new stainless steel liner in fireplace , & new oil tank, and in 2026 - new faucets in kitchen and master bath****** Cape St Claire amenities include, beaches, fishing/crabbing pier, boat ramp, playgrounds, marina, & more. Broadneck School District. Close to shops and restaurants. Mins from Downtown Annapolis, and easy access for commuter routes to Washington, Baltimore, and close to Ft Meade. Great location, minutes from downtown Annapolis, and good commuter location with quick access to Rt 50 & I-97 close to Washington or Baltimore

ANNAPOLIS

1047 LITTLE MAGOTHY VIEW

3 Beds

2 Baths

2,892 Sq.Ft.

$825,000

MLS#: MDAA2146800

Open House Sunday 12-2 Welcome to Winchester On The Severn. One of Annapolis's most established waterfront community's. This home provides mature landscaping with a canopy of lovely trees and bushes both in the front and rear yard. Covered front porch! You will be pleased to enter a spacious foyer. Main level bedroom with a full bath to the left. A few steps up to the open floor plan with spacious living room that feeds into the dining room. Be prepared to enjoy the screened porch off the dining room. A wonderful spot to relax and enjoy the back yard. The eat in kitchen is filled with light! Comfortable family room is complimented with a wood burning fireplace. And you can also walk out from the family room to the back yard! The basement is dry and has a new 2025 heat pump. The 3 additional bedrooms have fresh paint. The larger bedroom is en-suite. Ready to know about the neighborhood? Amenities include private beach on the Severn River, marina, boat ramp, multiple piers, dog beach, beach pavilion, and the Chase Creek swim club. Nearby is the B&A trail. You may not want to leave the home but if you do it is a short ride to Annapolis and all major routes. Welcome. Enjoy

ANNAPOLIS

1518 WINCHESTER ROAD

4 Beds

3 Baths

2,249 Sq.Ft.

$825,000

MLS#: MDAA2147986

Love This HOME at the NEW PRICE!! Briarwood – One of Anne Arundel County’s Finest Communities… Welcome to Rosebay Court!
A mature magnolia tree and inviting covered front porch set the stage for this beautifully updated/renovated brick colonial, ideally situated on a quiet cul-de-sac. Thoughtfully finished and move-in ready, this home is prepared to welcome its new owner.
Inside, a traditional layout blends seamlessly with an open-concept feel, offering both comfort and versatility for everyday living and entertaining. The main level features a welcoming living room, a formal dining room that opens to a light-filled kitchen complete with 42” white cabinetry, complementary granite countertops, a breakfast bar, pantry, and coffee nook. A Samsung appliance suite—including a five-burner stove and French door refrigerator—adds both style and functionality.
The adjoining "great room" is another space for family & friends to gather This room impresses with vaulted ceilings, skylights, and a cozy wood-burning fireplace—perfect ambience for crisp fall and winter evenings. At the heart of this space, the breakfast nook offers table space and easy access to the outdoors -- sliding glass doors that open to a new Trex deck, ideal for relaxing, entertaining, starting your day or ending your evening... . Neutral finishes throughout this home create a fresh look and feel
Upstairs, you’ll find four spacious bedrooms, including an owner’s suite with a private bath featuring dual vanities and walk-in closet. A well-appointed hall bath and ample closet space complete the upper level.
The finished lower level offers incredible flexibility, featuring a full bathroom and level walkout access to the backyard. Whether you envision an in-law suite, guest space, home office, gym, or additional living area, this level is ready to adapt to your needs. Step outside to a newly paved patio overlooking a serene green space, surrounded by nature.
Located in a sought-after school district and just minutes from Route 50, this home offers convenient access to shopping, waterfront dining, marinas, and scenic walking paths. Enjoy easy trips to the Eastern Shore and nearby beaches.
With all new mechanicals and updates ((detailed in the disclosures)), this home offers the perfect alternative to new construction—without the wait. Move in and start enjoying your dream home this summer!
*** please note disclosure: some photos have been enhanced with virtual staging/photography ***

ANNAPOLIS

1394 ROSEBAY COURT

4 Beds

3 Baths

2,252 Sq.Ft.

$825,000

MLS#: MDAA2140978

New on site 1 day ago

#MDAA2149354

ANNAPOLIS

76 OLD MILL BOTTOM ROAD N 205

3 Beds

3 Baths

1,729 Sq.Ft.

$825,000

MLS#: MDAA2149354

The sellers are offering $10,000.00 towards purchasers closing costs.
Phenomenal home at a great price! This is a must see!
Nestled in the highly desirable Annapolis Roads community on the mouth of Lake Ogleton, this distinctive home offers exceptional indoor and outdoor living spaces, timeless architectural details, and access to some of Annapolis' most sought-after waterfront amenities. Private spaces abound. From the beautiful screened family room, to the covered deck, ivy covered brick walled patio, sun room, there is always a quiet area to relax.
The many windows provide natural light throughout.
Major systems and appliances recently updated include the furnace (3 years), dishwasher, two air conditioning units( approximately 9 years), washer and dryer. Updated windows.
Extensive hardscaping surrounds the property, creating multiple inviting outdoor spaces. The sunroom is a standout feature, showcasing hand-hewn beams, custom built-in cabinetry, and a wall of Cape Cod-style windows that fill the space with natural light.
Throughout the home include custom lighting highlights built-in shelving, cabinetry, and workspaces. The spacious primary suite features an ensuite bath with a jetted tub, walk-in closet, and an additional shoe closet. A second jetted tub is located in the upper-level hall bath.
Residents enjoy access to Annapolis Roads' exceptional amenities, including a private beach, bayfront pavilion, playground, fire pit, community pier, kayak/SUP storage, boat ramp, hiking trails, and a variety of neighborhood events throughout the year.
A unique opportunity to enjoy the charm, character, and community lifestyle that make Annapolis Roads such a special place to call home.

ANNAPOLIS

2644 QUEEN ANNE CIRCLE

3 Beds

3 Baths

3,000 Sq.Ft.

$820,000

MLS#: MDAA2146714

Nestled in the charming Boucher Place community, this exquisite end-of-row townhouse offers a perfect blend of coastal and traditional architectural styles, creating a warm and inviting atmosphere. Built in 2013, this residence boasts 1,800 square feet of thoughtfully designed living space, ideal for those seeking comfort and elegance. The kitchen is a chef's dream, featuring upgraded countertops, a spacious island, and high-end stainless steel appliances, including a gas range and built-in microwave. The combination of hardwood on the main level, throughout adds a touch of sophistication, while plush carpeting in the bedrooms ensures a cozy retreat. The home features three generously sized bedrooms, each designed with comfort in mind. The primary suite is a true sanctuary, complete with a walk-in closet and a luxurious en-suite bathroom featuring a tub shower. Enjoy the warmth of the gas fireplace in the family room, creating a perfect ambiance for relaxation. Thoughtful details such as ceiling fans and window treatments enhance the home's comfort and style. Step outside to your private outdoor oasis, where a roof top balcony, deck, and patio await, perfect for enjoying morning coffee or evening gatherings. The beautifully landscaped courtyard view adds to the serene atmosphere, making it an ideal spot to unwind. This property also includes a detached two-car garage with rear entry, ensuring convenience and ample storage. The paved driveway and well-maintained sidewalks enhance the overall appeal of the home. As part of the Boucher Place community, residents benefit from included association services such as lawn maintenance, snow removal, and insurance, allowing for a low-maintenance lifestyle. Experience the perfect blend of luxury and comfort in this stunning townhouse, where every detail has been carefully curated to create a welcoming home. Embrace the exclusive lifestyle that awaits you in this beautiful property. New Roof in 2024 and new hardwoods in 2025.

ANNAPOLIS

19 BOUCHER PLACE

3 Beds

3 Baths

1,800 Sq.Ft.

$819,000

MLS#: MDAA2142690

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