One of the most popular communities provided by {{page_data.agentName}}

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

274

# of Listings

3

Avg # of Bedrooms

$510

Avg. $ / Sq.Ft.

$1,357,507

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

274 Properties Found. Page 9 of 19.

New on site today

The home has 3 bedrooms, 2 baths, and offers 1,397 finished sq. ft. above grade, plus 367 finished sq. ft. below grade, with an additional 440 sq. ft. of unfinished storage space.
Located in the highly sought-after Murray Hill neighborhood in downtown Annapolis, this charming single-family home blends 1920s character with thoughtful modern updates and easy walkability to shops and restaurants. The home features a newly renovated kitchen (2025), original hardwood floors, and a welcoming front porch. Outdoor living includes a spacious back deck, private backyard, and beautifully landscaped gardens. Additional highlights include a bright sunroom, off-street parking, and a finished basement office space. Showings can be scheduled via email or phone.

ANNAPOLIS

7 GERMAN STREET

3 Beds

2 Baths

1,764 Sq.Ft.

$889,000

MLS#: MDAA2145808

Looking for a secluded Mountaintop home tucked away on 3.89 acres within 15 minutes from downtown Annapolis, you just found it. Unique, 4-bedroom, 3.5 bath home built in 2007. Hardwood floors, modern kitchen with granite countertops, Stainless-steel appliances and kitchen island. Fully finished basement with family room, bedroom and full bath. 2 fireplaces, one in lower-level family room and one in living room. The home also features a balcony off living room. Large deck off kitchen with roof and a large shed/barn on the property. New ashplant driveway just installed.

ANNAPOLIS

1000 GOMOLJAK LANE

4 Beds

3 Baths

3,620 Sq.Ft.

$884,990

MLS#: MDAA2143566

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

Tucked away in the woods on a quiet cul-de-sac, this stunning single-family home sits on a private and picturesque .77-acre lot, offering the perfect blend of tranquility and modern comfort. With 4 spacious bedrooms and 3.5 bathrooms, this home features a bright, open floor plan designed for both everyday living and entertaining.

The Spacious kitchen with windows on 2 sides and stainless appliances, flows seamlessly into the main living areas, while abundant natural light fills the home, creating a warm and inviting atmosphere throughout. The expansive primary suite is a true retreat, featuring a vaulted ceiling and a spa-like bathroom complete with skylights that bring in beautiful natural light.

Step outside to enjoy the peaceful surroundings from the large screened-in porch just off the living room, or host gatherings on the oversized deck overlooking the wooded backyard. Additional highlights include a 2-car garage and thoughtful updates throughout.

Major system upgrades provide peace of mind, including a new lifetime warranty architectural shingle roof and gutters (2023), new hot water heater (2023), and HVAC system replaced in 2018. The home was also freshly repainted in 2022, making it truly move-in ready.

This is a rare opportunity to own a beautifully updated home in a serene, private setting—while still being conveniently located to everything you need.

ANNAPOLIS

1070 FOXCROFT RUN

4 Beds

3 Baths

3,286 Sq.Ft.

$874,995

MLS#: MDAA2140616

New on site 1 day ago

#MDAA2144296

ANNAPOLIS

422 FIRST STREET

2 Beds

1 Baths

1,094 Sq.Ft.

$870,000

MLS#: MDAA2144296

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

New in the Market! Extensively renovated from 2022–2024, this move-in-ready, modern Colonial is a standout offering in Anchorage, an Annapolis premier water-privileged community. Set on a private, wooded half-acre lot, this 4-bedroom, 2.5-bath residence combines approximately 2,000 square feet of refined living space with a full basement. The home’s interior showcases high-end craftsmanship, including a custom kitchen with quartzite waterfall island and counter-tops, spa-inspired bathrooms, Pella windows/doors, and Spanish ceramic tiling alongside refinished hardwoods. Residents enjoy an unparalleled waterfront lifestyle with access to a 49-slip marina, boat ramp, pool, and lakeside amenities on Lake Ogleton. Perfectly positioned just minutes from Historic Downtown Annapolis, the Naval Academy, Thomas Point Preserve and Quiet Waters Park. This location provides easy commutes to Washington, DC and Baltimore. The property’s location offers a rare balance of secluded coastal living and metropolitan accessibility. Fully renovated homes in this sought-after community are rarely available at this price point—an exceptional opportunity for the discerning buyer to live the Annapolis lifestyle.

ANNAPOLIS

1126 MAINSAIL DRIVE

4 Beds

2 Baths

1,800 Sq.Ft.

$865,000

MLS#: MDAA2145432

At last, the one you've been waiting for. A beautiful home in a waterfront community. Move right in and start enjoying the Annapolis lifestyle. Anchorage is an amenity filled waterfront community in which the yearly HOA fee includes the use of a boat slip, community pool and more.
This characterful 5 bedroom 2 1/2 bath home has approximately 2,354SF of living space and has been renovated within the last 4 years. Upgrades that include HVAC, tankless hot water heater, well pump, sewer line, roof, downspouts, gutters, soffit and windows make this home a low maintenance joy. A bespoke new sunroom addition off of the kitchen includes a wood burning stove. Simply delightful!
The sparkling kitchen with a new double oven and stainless appliances has an easy flow with classically beautiful cabinetry and quartz counters. Wood floors continue through the living room and down the hall to 3 bedrooms which include the primary with ensuite bath and an additional half bath.
Downstairs there are 2 bedrooms, a full bath, laundry room, storage room and family room with a fully lined fireplace and wood stove. Garage access is through this room. In the 2 car garage you'll find 2 EV chargers. The harmonious floor plan guides you from room to room with ease.
Sitting on nearly 1/2 acre, the outdoor space won't disappoint. Entertaining is a breeze here, enjoy the spacious deck which is adjacent to the sunroom and overlooks the level, lightly treed and fenced backyard. Landscaping which has matured with the years adds to the natural charm of the property.
Two storage sheds provide plenty of storage with one facing the driveway for easy bike storage access.
The community waterfront on Lake Ogleton includes 49 deep water slips in the marina, community pool, kayak storage, boat ramp and basketball court. The Chesapeake Bay is a quick motor away and historic downtown Annapolis is minutes by car underscoring the desirability of this home's locale.
Filled with amenities and coupled with location, Anchorage is a community that truly has it all.

ANNAPOLIS

1106 MAINSAIL DRIVE

5 Beds

2 Baths

2,059 Sq.Ft.

$849,000

MLS#: MDAA2139090

Positioned as one of the best values in Kingsport, this beautifully maintained 5-bedroom, 4.5-bath home offers nearly 5,000 sq ft of finished living space and a layout ideal for both everyday living and entertaining. With comparable homes in the community trending in the mid-high $800s to $900,000 range, the current pricing presents a compelling opportunity for buyers seeking space, location, and long-term value. Ideally located just minutes from Downtown Annapolis and directly across from the community pool, clubhouse, playgrounds, dog walking area, and walking trails, this home offers both convenience and lifestyle. Inside, you’ll find hardwood flooring, a soaring two-story family room with fireplace, a gourmet kitchen with stainless steel appliances and Jenn-Air cooktop, and a private main-level office. The upper level features a spacious primary suite with two walk-in closets and a spa-style bath, along with generously sized additional bedrooms. The lower level includes a finished recreation room, a fifth bedroom or office with egress, a full bath, and additional unfinished space with potential for a media room, gym, or extended living area. The home has been well maintained, is fully functional, and offers a strong foundation for a buyer to personalize over time. Seller is offering a $10,000 concession, which may be applied toward buyer’s allowable closing costs or other permitted expenses, subject to lender guidelines. Seller is seeking clean, competitive offers aligned with current list price, and any requests for concessions should be incorporated into the overall offer terms. Property is being sold as-is. Seller requires 15–30 days to secure home of choice.

ANNAPOLIS

712 COYBAY DRIVE

5 Beds

4 Baths

4,230 Sq.Ft.

$844,995

MLS#: MDAA2143208

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.

$835,000

MLS#: MDAA2140978

Welcome to this beautifully maintained, newer Colonial (built in 2021) offering the perfect blend of modern design and peaceful privacy in Annapolis. Featuring 5 bedrooms and 3.5 baths, this home delivers the feel of new construction—without the wait.

Step inside to discover 9-foot ceilings and a bright, open-concept layout ideal for both everyday living and entertaining. The gourmet eat-in kitchen boasts a spacious island, seamlessly connecting to the inviting family room highlighted by a cozy gas fireplace. A convenient main-level bedroom adds flexibility for guests or multigenerational living.

Upstairs, you’ll find a generously sized laundry room and a luxurious primary suite complete with a private ensuite bath. The fully finished basement expands your living space with a large recreation area, den, and full bath—perfect for work, play, or relaxation.

Enjoy the outdoors from the newly built 18x18 deck overlooking a flat, half-acre lot that offers exceptional privacy. The backyard is thoughtfully designed with an above-ground pool and a dedicated fire pit area—ideal for gatherings year-round.

A newly completed walk and bike path nearby provides easy access to Sandy Point, downtown Cape St. Claire, and Anne Arundel Community College—an incredible amenity for an active lifestyle. Tucked just around the corner from Cape St. Claire, this property offers added space and seclusion while remaining close to everything Annapolis has to offer.

Schedule your private showing today and experience all this exceptional home has to offer!

ANNAPOLIS

1402 INSEY RD

5 Beds

3 Baths

3,148 Sq.Ft.

$830,000

MLS#: MDAA2145384

#MDAA2137260

ANNAPOLIS

76 OLD MILL BOTTOM ROAD N 205

3 Beds

3 Baths

1,729 Sq.Ft.

$825,665

MLS#: MDAA2137260

JUST REDUCED! RENOVATED EASTPORT GEM With MODERN COASTAL FINISHES! ABOUT THE HOME: 3 levels of luxury living featuring 4 Bedrooms and 3.5 Bathrooms. Open-concept main level with New Hickory hardwood floors and designer lighting throughout. THE GOURMET KITCHEN: Custom white Shaker cabinetry, modern black hardware, Quartz countertops, oversized center island, and premium stainless appliances with gas cooking. THE PRIMARY SUITE: A rare main-level primary retreat with walk-in closet and spa-like bath featuring custom tile work and glass-enclosed shower. THE FLEXIBLE LOWER LEVEL: Fully finished walk-up basement with a 4th bedroom/office, family room with wood accent wall, and a custom full bath—perfect for a guest or in-law suite. THE EXTERIOR: Iconic white picket fence in front, with cozy front porch, and a private rear yard with beautiful wood privacy fence is expanded by an additional 736 SF (included in sale). New Andersen 100 series windows, Hardie Plank siding, and new hardscaped paths. PARKING: Private driveway with 2 off-street parking spaces. LOCATION: Unbeatable walkability to Downtown Annapolis, Maritime activities, and local favorites. See Annapolis City site for details on the Eastport Choice Neighborhood Initiative! Enjoy all that Eastport has to Offer! Don't Let This One Get Away! Make your Appointment Today!
Active Ring Camera on Property.

ANNAPOLIS

152 JEFFERSON STREET

4 Beds

3 Baths

2,282 Sq.Ft.

$825,000

MLS#: MDAA2142230

Discover the perfect blend of Annapolis charm and contemporary luxury at 1107 Brashears Street in desirable Eastport. Meticulously transformed and fully remodeled, this truly turn-key home presents 5 bedrooms and 2 full baths. Upon arrival, an inviting screened-in front porch welcomes you into a residence created for comfort. The main level is designed for modern living and entertaining, featuring an open floor plan anchored by a gourmet kitchen boasting a large center island and quality, stylish finishes that ensure a fresh, modern aesthetic. The layout offers maximum convenience with a valuable main-level bedroom and full bath. The comprehensive renovation inside and out showcasing stylish design and quality finishes throughout.

The property is further enhanced by an expansive backyard, creating an outdoor retreat for the whole family to enjoy. The large paver-patio with fire pit, is ideal for entertaining, and family dinners. This Eastport gem perfectly balances premium convenience with exceptional comfort. This is your opportunity to own a like-new home in a prime location.

ANNAPOLIS

1107 BRASHEARS STREET

5 Beds

2 Baths

1,800 Sq.Ft.

$825,000

MLS#: MDAA2142894

Welcome home to this beautifully maintained transitional Craftsman in sought-after Clifford Estates, NO HOA! From the moment you arrive, you’re greeted by a spacious Trex front porch, the perfect place to sip your morning coffee, unwind after a long day, and wave to neighbors passing by. Step inside to discover an inviting, light filled interior featuring Brazilian cherry hardwood flooring, neutral tones, and a traditional, flowing layout designed for both everyday living and entertaining. The bright and airy living room offers abundant natural light, while the chef’s kitchen truly shines with granite countertops, updated backsplash, stainless steel appliances, a large island with additional storage, ample cabinetry, a pantry, and space for a breakfast table. A formal dining room provides the perfect setting for holiday gatherings or casual dinners, and a convenient main level powder room completes the space. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite featuring extra windows, a large walk-in closet, and an ensuite bath with dual vanities. An additional full hallway bath and bonus storage area add even more functionality.
The lower level offers incredible flexibility currently set up as a home gym, it’s ready for your vision. Finish it for additional living space, create guest quarters, or simply enjoy the storage. A cozy pellet stove adds warmth and charm as an additional heat source. Situated on a large corner lot, this home provides plenty of room to spread out. The rear Trex deck creates an ideal outdoor living space for entertaining or relaxing. With a detached garage, storage shed, attached three car garage, and a two car driveway, parking and storage are effortless. Additional highlights include a new roof (2025) for peace of mind. Enjoy a prime location just minutes from shopping, dining, and entertainment, including Annapolis Mall and the Maryland Renaissance Festival, with easy access to USNA, Fort Meade, Baltimore, Washington, DC, and BWI Airport.
This is the one you’ve been waiting for, schedule your private tour today.

ANNAPOLIS

92 CLIFFORD BOULEVARD

4 Beds

2 Baths

2,252 Sq.Ft.

$820,000

MLS#: MDAA2139188

1 ... 7 8 9 10 11 ... 19

Buyers resources

7 Reasons to Work with a Realtor

7 Principles For Home Buying Success

Getting a Mortgage To Buy a Home

Home Hazards Awareness

Key Items For Home Inspection

Questions When Buying a Condo

Questions When Choosing a Realtor

Sellers resources

8 reasons to work with a realtor

Calculating Capital Gains

Checklist for Better Showing

Cleaning Home For Sale

Improving Odds Of an Offer

Preparing Home for photoshoot

Selling Your Home for More $$

Buyers resources

BUYERS RESOURCES

Sellers resources

SELLERS RESOURCES

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

First Name

Last Name

Email

Phone

MLS Property Number

Your message

What is 3 + 4 ?

Reason for contacting?

Buying a home

Selling a home

Other

I agree to receive email communication and understand I can unsubscribe at any time.

I agree to be contacted by Maryland Sandbox via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. Privacy Policy

Update Your Temporary Password

Accessibility Menu

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Email address (Must be valid)

Already have an account ? Login here

Continue your home search

Email address

First name First Name

Last name Last Name

Phone number (Optional)

Password

I agree to receive communications and understand I can unsubscribe at any time.

I agree to be contacted by Maryland Sandbox via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. Privacy Policy

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service