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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

274

# of Listings

3

Avg # of Bedrooms

$510

Avg. $ / Sq.Ft.

$1,357,507

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

117 Properties Found. Page 3 of 8.

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

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

#MDAA2142262

ANNAPOLIS

520 HARBOR DRIVE

4 Beds

3 Baths

2,600 Sq.Ft.

$800,000

MLS#: MDAA2142262

Welcome to this beautifully maintained custom built Tudor Style home! With a primary suite and full bath on the main level and another primary suite with full bath on the upper level, this home is perfect for multi-generational living! The upper level features 3 spacious bedrooms and 2 full baths; the main level has 1 bedroom and 1.5 bath; and the lower level has another full bath and several areas to make 2-3 additional bedrooms. The huge 1,100 sqft finished lower level has multiple rooms including a large rec room that can fit a pool table, games and a bar area; plus a family room or theatre room and private entrance! There is even space for a kitchenette! There are so many possibilities with this extra space including an apartment or in-law suite! The laundry is located on the main level in the mudroom off of the garage so you don't need to go to the basement to do laundry. Situated on almost a half of acre and only 2 blocks to the Chesapeake Bay! The backyard is fully fenced in and ready for summertime entertaining! The lot next to the home is a preserved wooded lot that offers privacy and attracts wildlife. This home is nestled between Oyster Creek, Fishing Creek, and the Chesapeake Bay. Oyster Harbor offers the best of Coastal Maryland living—just minutes from historic downtown Annapolis, top-rated restaurants, shopping, and commuter routes. Quiet Waters Park is only minutes away with walking trails, dog park/beach, concerts, ice skating, and so much more! The home has been well cared for and maintained. Recent updates include: HVAC, water heater, main level LVP floors that are very durable, trex deck and renovated front porch with tile, custom plantation shutters, renovated primary suite and luxury full bath, front load w/d, freshly painted epoxy floor in basement, professionally cleaned, professionally landscaped...and more! Sellers are motivated and ready for another family to make this their home! MOVE-IN READY AND A MUST-SEE! You won't find many homes with this lot size and location for this price. The lot offers extra space for parking a boat, RV..and more. Schedule your showing today! OPEN HOUSE SUN 5/17 1-3PM!

ANNAPOLIS

3280 ARUNDEL ON THE BAY ROAD

5 Beds

4 Baths

3,144 Sq.Ft.

$799,900

MLS#: MDAA2144206

MAJOR PRICE REDUCTION. Total living square footage is approximately 2,020. Property offers two spaces for off street parking, with a separate concrete pad for a boat. Eastport living is all about energy and convenience, this charming coastal home has it in abundance. Enjoy a rare double lot complete with new wood fencing creating a private outdoor space, new roof, windows, interior upgrades and thoughtful finishes. Additional upgrades include a tankless water heater, for an endless supply. You'll find a light filled space and recently refinished gleaming hardwood floors throughout.
Outside and you're across form Annapolis Athletic Club and less than a mile to local pubs, Historic Annapolis and The Naval Academy. Where character and comfort come together. Easy commute to Washington DC and major airports.

*Four bedroom, with the fourth being a flex space office/guest room*

ANNAPOLIS

1100 BAY RIDGE AVENUE

4 Beds

2 Baths

1,720 Sq.Ft.

$799,000

MLS#: MDAA2141488

Experience upscale urban living in this stunning 3rd-floor Everest model at Grandview, ideally located on the retail boulevard side of Annapolis Town Center. This residence offers a true city feel with unbeatable walkability to premier shopping and dining.
The open-concept living and dining area features bamboo flooring, a dramatic tray ceiling, and floor-to-ceiling glass doors leading to a private balcony filled with natural light. Elegant French doors open to a versatile bonus room, ideal as a home office or third bedroom.
The kitchen is designed for both entertaining and everyday living, showcasing stone and granite countertops, a professional-grade double oven, and a peninsula breakfast bar. A spacious laundry room and additional storage cage add convenience.
Two luxury bedroom suites each feature custom closet organizers. The primary suite includes a spa-inspired bath with a soaking tub and walk-in shower, while the second suite offers a double-sink vanity and walk-in shower—perfect for guests or flexible living.
Enjoy resort-style amenities including concierge services, fitness center, and a rooftop pool with social lounges, plus two assigned garage parking spaces. Walk to Whole Foods, Target, and top restaurants like True Food Kitchen and Cooper’s Hawk. Minutes from Historic Downtown Annapolis, Anne Arundel Medical Center, Annapolis Mall, with easy access to Route 50 and I-97.
A must-see for those seeking a luxury, maintenance-free lifestyle.

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 309

2 Beds

2 Baths

1,681 Sq.Ft.

$755,000

MLS#: MDAA2135756

#MDAA2137262

ANNAPOLIS

76 OLD MILL BOTTOM ROAD N 102

3 Beds

2 Baths

1,853 Sq.Ft.

$742,425

MLS#: MDAA2137262

New on site 4 days ago

Life at Chesapeake Harbour feels like being on vacation every single day. Mornings begin with coffee on the balcony as the sun rises over the marina and the Chesapeake Bay. Even simple moments feel special here, whether it’s curling up with a book by the fireplace on a rainy afternoon, taking an evening stroll along the shoreline, or enjoying dinner on the deck as the sky changes colors over the water. This meticulously maintained two-level condo offers approximately 1,600 square feet of light-filled living space, perfectly designed to capture the beauty of its waterfront setting. From the moment you walk inside, the home feels bright and open, with marina and bay views from the living room, primary suite, and loft creating a true retreat. Fresh paint throughout, refreshed bathrooms, a new HVAC system and new water heater in 2024 add comfort and peace of mind, making the home truly move-in ready. The main living area is warm and inviting with vaulted ceilings, skylights, a cozy wood-burning fireplace, and walls of glass framing the incredible views. Sliding doors open to a private balcony overlooking the water, the perfect place to unwind after a day on the boat, enjoy a glass of wine at sunset, or simply watch the activity at the marina below. The remodeled gourmet kitchen blends thoughtful design with everyday function, featuring stainless steel appliances, soft-close cabinetry, and pull-out drawers that make the space as practical as it is beautiful. The primary suite offers a peaceful escape with bay views, direct access to the deck, and a spa-like bath that feels calm and relaxing after a day on the water. A spacious second bedroom and additional full bath provide comfortable accommodations for guests. Upstairs, the finished loft offers wonderful flexibility for a home office, reading lounge, or additional living space, complete with skylights and panoramic views. Beyond the home itself, Chesapeake Harbour offers one of Annapolis’ most sought-after waterfront lifestyles. Residents enjoy a private beach, fishing and crabbing piers, two pools, tennis courts, kayak storage, walking paths, and 24-hour gated security. Meet friends for dinner at The Beacon, spend the afternoon by the pool overlooking the water, or hop on your boat for a sunset cruise. Just minutes from historic downtown Annapolis, yet tucked away in a peaceful waterfront setting, this is the kind of home where life naturally slows down and every day feels like a getaway. Welcome home!

ANNAPOLIS

2118 CHESAPEAKE HARBOUR DRIVE E 202

2 Beds

2 Baths

1,618 Sq.Ft.

$739,000

MLS#: MDAA2145492

Price Reduced! Modern and “like-new” townhome ideally located just minutes to Downtown Annapolis and Eastport, offering easy access to waterfront dining, marinas, and shopping! This nearly new construction home at 118 Treblis Way showcases modern style, thoughtful enhancements, and effortless living in a prime Annapolis location. This home (Largest Model / 4 Levels) has been meticulously improved by the current owners, featuring hardwood flooring on every level (excluding bedrooms) for a seamless and elevated look throughout. Freshly repainted from top to bottom, the interior feels bright, clean, and completely move-in ready. Designer wallpaper accents on three of the four levels add a custom, upscale touch that sets this home apart, with each space carefully curated to blend comfort and contemporary style. Ideally situated near Quiet Waters Park, enjoy easy access to scenic walking trails, dog parks, and outdoor recreation, all while being just minutes from the best of Annapolis living. With its like-new condition, stylish upgrades, and unbeatable location, this home is a standout opportunity you won’t want to miss.

ANNAPOLIS

118 TREBLIS WAY

3 Beds

3 Baths

2,348 Sq.Ft.

$739,000

MLS#: MDAA2141836

#MDAA2144284

ANNAPOLIS

1022 HARBOR DRIVE

5 Beds

3 Baths

2,600 Sq.Ft.

$735,000

MLS#: MDAA2144284

Now priced at $729,900—reduced from $749,900—and including a $5,000 seller credit toward closing costs, this stunning Bridgeport model condo offers unmatched value in the Grandview community.
Experience breathtaking views from this stunning Bridgeport model condo in the highly sought-after Grandview community! This beautifully designed home features an open-concept floor plan with gleaming hardwood floors and abundant natural light throughout.
The spacious gourmet kitchen is a chef’s dream, complete with granite countertops, stainless steel appliances, and ample cabinetry, perfect for both everyday living and entertaining. The primary suite offers elegant tray ceilings, private access to the deck, and a luxurious ensuite bath with a soaking tub and dual vanities.
Step outside to your expansive private deck and take in panoramic views—ideal for morning coffee or evening relaxation.
Residents of Grandview enjoy resort-style amenities, including a rooftop pool, bar and lounge, library, meeting room, state-of-the-art fitness center, concierge service, secure entry, and 2 garage parking with an assigned space.
Conveniently located within walking distance to shopping, dining, and everyday essentials, this home offers both luxury and lifestyle in one exceptional package.

Schedule your private tour today!

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 915

2 Beds

2 Baths

1,616 Sq.Ft.

$729,900

MLS#: MDAA2141622

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