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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

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$250,000 - $500,000

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Over $5M

274 Properties Found. Page 10 of 19.

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.
#MDAA2142690

ANNAPOLIS

19 BOUCHER PLACE

3 Beds

3 Baths

1,800 Sq.Ft.

$819,000

MLS#: MDAA2142690

520 Harbor Drive isn’t simply another home hitting the market — it’s the opportunity buyers spend months waiting to find in Hillsmere and rarely secure. Perfectly positioned in the heart of one of Annapolis’ most loved waterfront communities, this home delivers the lifestyle that keeps people here for years: private beaches, marina access, boat ramps, a community pool, playgrounds, and effortless access to the South River and Chesapeake Bay. From the moment you arrive, the home feels polished, intentional, and completely move-in ready. This isn’t a cosmetic refresh — this home has been extensively renovated with permits and thoughtfully updated throughout, delivering the confidence and peace of mind buyers want. The work is already done with updated systems, quality finishes, and a level of care that is difficult to replicate. Inside, light-filled spaces and a flowing layout create the kind of everyday comfort buyers are searching for, anchored by a beautifully designed kitchen that opens seamlessly into generous living and gathering spaces built for both entertaining and real life. Step outside and the experience only gets better with a brand-new paver patio creating the perfect setting for summer gatherings, morning coffee, or evenings under the stars. The huge fully fenced backyard offers exceptional space and privacy, while the detached shed adds valuable storage and flexibility. And then there is Hillsmere itself — where life truly revolves around the water. Residents enjoy neighborhood traditions and waterfront gatherings throughout the year, from the annual Fourth of July bike parade to beach picnics and community events that bring neighbors together. The community beach features a playground overlooking the water, and many consider Hillsmere to offer one of the most desirable beach and pool lifestyles in Annapolis. This is more than a move-in ready home — it is a chance to become part of a community people fall in love with and rarely want to leave.
#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!
#MDAA2144206

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*
#MDAA2141488

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.
#MDAA2135756

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 309

2 Beds

2 Baths

1,681 Sq.Ft.

$755,000

MLS#: MDAA2135756

Welcome to brand-new luxury living at Element at Mill Creek, a new construction community of modern condominiums designed for style, comfort, and convenience. This spacious, light-filled home offers southern exposure and a private balcony with serene views of lush forest retention—perfect for relaxing or entertaining. Inside, enjoy a chef-inspired kitchen with quartz countertops, upgraded cabinetry, stainless steel appliances, and a large center island. The open-concept living and dining areas create a warm, inviting atmosphere ideal for gatherings or quiet evenings. The primary suite features a generous walk-in closet and a spa-style bath with high-end finishes. Additional features include a full-size washer and dryer, included window treatments, ample storage, and reserved parking. As part of the new Element at Mill Creek community, you’ll enjoy low condo fees, resort-style amenities, and the ease of low-maintenance living in a brand-new home. Inquire today about available floor plans and pricing—your perfect new home is waiting!
#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!
#MDAA2145492

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.
#MDAA2141836

ANNAPOLIS

118 TREBLIS WAY

3 Beds

3 Baths

2,348 Sq.Ft.

$739,000

MLS#: MDAA2141836

Discover a truly one-of-a-kind property in the highly sought-after Annapolis Roads community. This exceptional 5-bedroom, 3-bathroom single-family home sits on 0.4 acres and includes a detached, oversized two-car garage with a newly renovated one-bedroom, one-bathroom apartment above—perfect for guests or extended family. The main residence, apartment, and garage have all been freshly painted. The upper level features newly refinished hardwood floors, while the lower level boasts durable, waterproof luxury plank flooring. The apartment is equipped with a new water heater and mini-split system, and the main house includes a brand- new washer and dryer for added convenience. Enjoy stunning views of the Chesapeake Bay along with access to an array of community amenities, including Lake Ogleton, a private beach, pavilion with playground and fire pit, boat ramp, stand-up paddleboard and kayak launch, and a community pier—all with no HOA fees. Please note that there is an easement on the property. It’s runs against the right side of the fence line.
#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!
#MDAA2141622

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 915

2 Beds

2 Baths

1,616 Sq.Ft.

$729,900

MLS#: MDAA2141622

Welcome to the highly sought-after “Davenport” corner unit in the prestigious GrandView community — perfectly positioned in one of the most desirable locations in the Annapolis Town Center. This exceptional residence is filled with natural light thanks to a stunning wall of windows, offering breathtaking sunset views each evening. Step outside to your private covered corner balcony and enjoy the outdoor. Inside, you’ll find a thoughtfully designed floor plan featuring: 2 bedrooms, 2 baths, den/home office, hardwood floors throughout (no carpet!), granite countertops, 10-foot coffered ceilings and custom window treatments. Additional highlights include two assigned garage parking spaces and access to luxury amenities such as concierge services, a fully equipped fitness center, and a rooftop pool. Live just steps from everything the Annapolis Town Center has to offer — including Whole Foods Market, Target, banking, and some of Annapolis’ best restaurants and nightlife. You’re also just minutes from Historic Downtown Annapolis, Annapolis Mall, Anne Arundel Medical Center, and have easy access to Route 50 and I-97 — making commuting a breeze. MUST SEE UNIT! All showings scheduled through ShowingTime.
#MDAA2137884

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 503

2 Beds

2 Baths

1,602 Sq.Ft.

$725,000

MLS#: MDAA2137884

Stylish Street-Level Condo in the Heart of Annapolis. Welcome to this spacious 1-bedroom, 1.5-bath residence in the highly desirable Acton’s Landing community. Ideally located on the street level for easy access, this condo blends everyday convenience with upscale living. The open-concept design offers a bright, expansive living area and a well-appointed kitchen featuring a center island, breakfast bar, and ample storage—perfect for both weekend escapes and full-time living. A separate den provides flexible space for a home office or a cozy retreat. The primary suite serves as a private sanctuary, complete with a spa-like bath that includes a soaking tub, walk-in shower, and generous closet space. Enjoy the convenience of the building’s parking garage just steps from your door. Residents also have access to a range of amenities, including a fitness center, gathering rooms, library, and more. Just a short walk to the water taxi, park and the shops, restaurants, Naval Academy and the historic charm of downtown Annapolis. Experience the perfect blend of comfort, convenience, and coastal charm in the heart of Annapolis.
#MDAA2142366

ANNAPOLIS

66 FRANKLIN STREET 20

1 Beds

1 Baths

1,342 Sq.Ft.

$725,000

MLS#: MDAA2142366

A very special custom built home in a wonderful water privileged community! Located in Arundel On The Bay community, which provides a sense of neighborhood, as well as many scenic opportunities. Enjoy a short walk to the beach and numerous parks. Views of the Bay can be enjoyed at the cross streets or the end of Cohasset. The setting is well landscaped, private, and tranquil. The outdoor area in the rear of the house works as a quiet retreat or a fabulous entertaining area. Enjoy this bright and open home with the many unique special architectural features. Enjoy the bamboo recessed ceiling in the open kitchen, the mahogany front door, refinished cypress wood floors, and patio fireplace and cooking area to name a few. The main level of the home features a two car garage (with half currently used for storage) and mud room just inside. Enter the front and there is a large foyer with powder room, and private den. Enjoy the open gourmet kitchen with granite counters and gorgeous wood cabinets which all open to living room with stone fireplace and dining area. The upper level features a generous primary bedroom suite with a large walk in closet (complete with expander storage) and an attractive spa like bath. There are two other bedrooms on this level, as well as a full hallway bath. The laundry room is off this hallway bathroom. Don't miss the oversized window flooding the stairs with bright light. The floored attic with high ceilings is accessed by a pull down stairway. There is also an outdoor shed for garden equipment. The totally fenced rear yard has been hardscaped and landscaped as a perfect spot for outdoor dining or quiet enjoyment. The side yard looks out to a treed area and walking path. There is a community pier where an owner can lease a boat slip as well as a rack for kayaks or canoes. There is also a community boat ramp with slips for rent and an additional crabbing ramp. The neighborhood enjoys many community events throughout the year which are advertised on the brick pillars as you enter the neighborhood. A delightful place to call home!
#MDAA2143110

ANNAPOLIS

3420 COHASSET AVENUE

3 Beds

2 Baths

2,416 Sq.Ft.

$725,000

MLS#: MDAA2143110

An absolute must see! Stunning 4 bed 3 1/2 bath updated home in sought after Hillsmere Shores. This home just had cosmetic upgrades including but not limited to fresh paint throughout, new carpet, new fixtures, new appliances more. Home features two bedrooms upstairs to include a primary with his and hers walk in closets and a spa like primary bath. The second floor boasts two additional bedrooms. One being a second primary with an en suite and fireplace. The home includes a large deck outback and completely fenced back yard. This property is available for immediate occupancy. Come check it out. Seller will provide home warranty with full price offer.
#MDAA2144216

ANNAPOLIS

110 KUETHE DRIVE

4 Beds

3 Baths

1,809 Sq.Ft.

$715,000

MLS#: MDAA2144216

Beautifully maintained and filled with natural light, this inviting home offers an open floor plan with vaulted ceilings, hardwood floors, and comfortable living spaces designed for both relaxing and entertaining. The spacious primary suite features a private sitting area and en-suite bath, while the cozy fireplace and rear deck create the perfect setting for everyday living. A fenced backyard backing to trees provides added privacy and a peaceful outdoor retreat. Located in the sought-after water-privileged Bay Highlands community with beaches, marina, boat ramp, playgrounds, and easy access to Downtown Annapolis.
#MDAA2142452

ANNAPOLIS

1180 BAY HIGHLANDS DRIVE

3 Beds

2 Baths

1,758 Sq.Ft.

$710,000

MLS#: MDAA2142452

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Sellers resources
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