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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
290
# of Listings
3
Avg # of Bedrooms
$450
Avg. $ / Sq.Ft.
$1,031,642
Med. List Price

Browse Annapolis Real Estate Listings

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290 Properties Found. Page 5 of 20.

Price just reduced by $75,000! Sellers have found home of choice!! Come take advantage of this fabulous opportunity! Discover an enchanting classic brick residence in Murray Hill— Lovingly maintained and beautifully detailed, this timeless home features solid plaster walls, hardwood floors, 8½‑foot ceilings, and graceful archways. The updated kitchen flows seamlessly into a versatile layout that can easily accommodate a first‑floor primary suite—currently styled as a family room with an office and adjoining full bath. Charming, intimate evenings come alive in the inviting living room, centered around a wood‑burning fireplace with an elegant mantel and built‑in bookcases. Step onto the tiled, screened porch for a tranquil retreat, and appreciate the practicality of a mudroom just off the kitchen. The spacious walk‑up attic offers abundant storage or future creative possibilities, while the large basement—complete with a separate entrance and workshop space—provides even more room to grow. Roof is 13 years old and HVAC units are less than 4 years old. Located just steps from Maryland Hall for the Performing Arts, home to the annual Annapolis Film Festival, the Annapols Symphony, art classes and live music. And only three blocks away, Amos Garrett Park awaits—perfect for launching your kayak or paddleboard or taking the boat taxi to City Dock! A rare opportunity to own a character‑filled home in one of Annapolis’s most beloved neighborhoods. Don’t miss it!
#MDAA2121372

ANNAPOLIS

637 CHASE STREET

3 Beds

2 Baths

4,333 Sq.Ft.

$1,219,000

MLS#: MDAA2121372

RARE FIND -- Lock & Leave! Private setting in Sailor's Quay in heart of Eastport -- tucked away off main street with lovely plantings in front and a shaded back patio surrounded by trees -- perfect retreat and/or entertaining in style! Brick front porch entry, Hardie-plank exterior, open floor-plan with four levels of flexible space. Custom touches throughout including plantation shutters, wall coverings, crown molding and wainscotting. Main level has hardwood floors, walls of windows for light -- living room with gas fireplace, dining room, powder room and kitchen with atrium door out to a fenced rear yard with circular paver patio and half-wall for extra seating and electric awning....secluded and magical! There is a pretty stone pathway amongst hydrangeas that leads to the front of the house. Upstairs is the primary suite with adjoining bath situated at rear of house and two additional bedrooms with full bath on hallway. Also on the hallway is a large laundry closet currently used for clothing but with washer/dryer hookups intact On the third floor there is a large room (30 x20) which serves as family room and 4th bedroom. The lower level is partially finished into rooms with insulation and an egress window -- workshop with upgraded electricity, storage, utility, office and a half-bath with plumbing to add shower. Additional laundry with washer and dryer is in place here. Two-zoned gas HVAC, 75-gal HWH, garden lighting and sprinkler system on timers. Sailor's Quay community has guest parking off-street on Stevens Alley as an added bonus to their HOA lawn / tree maintenance and snow removal. This is an opportunity to live in-town close to shops, restaurants and all that City Dock / DTA has to offer. Pop over to Vin 909 or Easport Kitchen, Adams Grille, Diehl's Produce, etc in Eastport Shopping Center. So many services nearby to make life easy and spontaneous!
#MDAA2119148

ANNAPOLIS

10 SAILORS WAY

4 Beds

2 Baths

2,843 Sq.Ft.

$1,195,000

MLS#: MDAA2119148

Experience luxury and light in this rare 3-bedroom, 2.5-bath condo in the highly sought-after Park Place community. This corner unit boasts incredible 180° views and is filled with natural light from expansive windows throughout. With three deeded garage parking spaces located right next to each other—an unparalleled convenience in downtown Annapolis—you’ll never have to worry about parking again. Inside, a spacious open-concept layout welcomes you with upgraded appliances, generous storage, and a stylish design that makes everyday living and entertaining effortless. The sun-drenched living and dining areas flow into a modern kitchen, ideal for both casual meals and special gatherings. The serene primary suite features an en-suite bath and a peaceful ambiance, while two additional bedrooms offer the perfect setup for guests, a home office, or both. Park Place offers a true lock-and-leave lifestyle with 24/7 front desk staff, beautifully maintained grounds, a pool, fitness center, party room, and a private outdoor patio with grills and a dog park. And for added convenience, a private shuttle picks up right from the courtyard and takes you anywhere in downtown Annapolis. Perfectly positioned to enjoy the best of in-town living, this home combines elegance, ease, and vibrant community energy. Welcome to Park Place—your next chapter starts here.
#MDAA2112582

ANNAPOLIS

5 PARK PLACE 428

3 Beds

2 Baths

1,822 Sq.Ft.

$1,195,000

MLS#: MDAA2112582

Experience the Essence of Annapolis Charm at 179 Green Street Nestled in the heart of historic downtown Annapolis, this beautifully updated home blends timeless character with modern comforts. Just steps from vibrant Main Street, the waterfront, boutique shopping, and Annapolis Elementary School, this location offers the very best of city living in one of the city's most coveted neighborhoods. Inside on the main level, you'll find wide-board pine floors, a thoughtfully updated kitchen with new cabinetry and appliances, and inviting front and side porches perfect for morning coffee or evening relaxation. Rarely found in downtown Annapolis, two oversized off parking spaces add incredible convenience. Upstairs, the home features two spacious bedrooms and a versatile third room—ideal for a home office, den, or oversized walk-in closet. The newly fenced backyard offers a private oasis for entertaining, dining al fresco, or simply enjoying the outdoors. Living at 179 Green Street means immersing yourself in a lifestyle rich with history and culture. Stroll cobblestone streets to award-winning restaurants, art galleries, and the iconic City Dock. Enjoy sailing, community events, and the vibrant energy of downtown—right outside your door. Don’t miss your chance to own a piece of Annapolis charm. Schedule your private tour today.
#MDAA2111662

ANNAPOLIS

179 GREEN STREET

2 Beds

1 Baths

2,304 Sq.Ft.

$1,175,000

MLS#: MDAA2111662

Perfectly situated just minutes from the heart of Downtown Annapolis, yet tucked away for privacy, this 4 br, 3.5 bath NEW CONSTRUCTION coastal inspired home with a 2 car garage and optional detached guest cottage by Whitehall Building & Company offers the best of both worlds—convenience and tranquility. With over 3,400 square feet of finely crafted living space across three levels, every detail has been thoughtfully designed to deliver both comfort and sophistication. Step inside and be greeted by soaring 10-foot ceilings, expansive wide-plank flooring, and an open-concept layout ideal for both everyday living and elegant entertaining. The chef’s kitchen is the centerpiece of the home, featuring a grand center island, quartz countertops with matching backsplash, premium stainless steel appliances, and abundant storage. Flowing seamlessly into the breakfast area and spacious family room, this home is designed for hosting unforgettable gatherings. A versatile flex room offers the perfect space for a formal dining room, private home office, or cozy reading retreat. Additional main-level highlights include a custom mudroom, walk-in pantry, and stylish powder room. The upper level is a true sanctuary, boasting a luxurious primary suite with a generous walk-in closet and spa-inspired bath complete with dual vanities, a frameless glass shower, and a freestanding soaking tub. Two additional bedrooms share a beautifully appointed guest bath, while a convenient second-floor laundry room adds ease to daily living. The lower level provides endless possibilities, including a spacious recreation room, full bath and optional 5th bedroom—perfect for overnight guests or extended family. For those seeking even more flexibility, an optional detached guest house is available, offering a private one-bedroom suite with full bath, living room, and kitchenette—an ideal space for visitors, multigenerational living, or an au pair. All of this in an enviable location just minutes from the U.S. Naval Academy, fine dining, boutique shopping, waterfront attractions, and major commuter routes. Don’t miss the opportunity to personalize your finishes and create the luxury home of your dreams in the heart of Annapolis.
#MDAA2123968

ANNAPOLIS

13 ELLIOTT ROAD

4 Beds

3 Baths

3,292 Sq.Ft.

$1,175,000

MLS#: MDAA2123968

Sellers are offering $25,000 to go towards siding replacement. This beautiful property offers three levels of spacious, comfortable living in the neighborhood of Epping Forest. Walking through the front door, vaulted ceilings and natural light greet you in the dining/living room area off the kitchen. A main level bedroom suite offers convenience and a second suite upstairs boasts extra privacy. The Severn River can be seen through the trees off the double level deck which is accessed through the dining room, primary suite, or basement common room. On the bottom level, two bedrooms share a full bath and a common living space. Sliding doors add more natural light and additional exits to the lower deck. The private neighborhood beach and clubhouse offer peak enjoyment in the summer months! The club house offers family and golf cart friendly community for all ages! Ample storage, parking, and living space make this home unique in the gated community! HVAC replaced in October of 2020 Both decks replaced in December of 2020 Water treatment system replaced in February of 2022 Roof replaced in November of 2023 Buyer must review and acknowledge Epping Forest Constitution and Bylaws. See Documents.
#MDAA2095698

ANNAPOLIS

319 EPPING WAY

4 Beds

3 Baths

2,372 Sq.Ft.

$1,150,000

MLS#: MDAA2095698

English Tudor featuring a stone front patio for nature lovers and bird watchers. Surrounded by large trees for tons of shade and a 45 foot rear deck for large gatherings and rear lawn for play areas. Almost 4000 square feet of living space plus an oversized garage 24x25 with a floored attic space above for expansion or storage. The great room has cathedral ceilings, wood beams and wide plank redwood siding, wood burning fireplace. and sliders to rear deck. The community has water privileges with fishing pier and canoe storage and sidewalks for dog walking or strolling the neighborhood. Convenient location for commuting to Baltimore or D.C. and 20 minutes to BWI Airport. Six miles to Downtown Annapolis for great shopping and restaurants.
#MDAA2117832

ANNAPOLIS

553 CHOPTANK COVE COURT

5 Beds

4 Baths

3,569 Sq.Ft.

$1,100,000

MLS#: MDAA2117832

Tucked away on a quiet cul-de-sac in the Sought-After Harness Creek Overlook community, this classic colonial home offers a seamless blend of timeless style and modern updates. Situated on a beautifully landscaped lot, the residence features 4 bedrooms and 3½ baths, thoughtfully designed for comfort and functionality. Inside, you'll find hardwood floors throughout the main level, fresh paint, and new carpet—making this home truly move-in ready. The spacious, updated kitchen with SS appliance and quartz counters is perfect for entertaining. A custom-built screened porch overlooks the woods, offering a private retreat just steps from your living spaces. The split staircase adds architectural charm, and the unfinished basement with rough-in for a bath and high ceilings provides plenty of room to expand. Beyond the home, enjoy easy access to the best of Annapolis living—walk the trails to Quiet Waters Park to tastings at Great Frogs Winery. Short drive to local boating marinas and the vibrant shops and restaurants of downtown Annapolis. Easy commuting access to 50 and 97 and BWI.
#MDAA2121364

ANNAPOLIS

22 POTTERS LANE

4 Beds

3 Baths

3,652 Sq.Ft.

$1,098,000

MLS#: MDAA2121364

Exuding grace at the moment of entry, this expansive two-story home features an open-plan layout ideal for modern living. A fireplace anchors the Great Room, which flows into the dining area and gourmet kitchen with a versatile island. Upstairs are three bedrooms, a loft suite sitting room, and a luxurious owner’s suite with spa-style bath. Extra space abounds with a main-level study, upstairs loft, bright morning room, and finished basement with a recreation room—offering room for work, play, and everything in between.
#MDAA2118102

ANNAPOLIS

118 STILLY WAY

5 Beds

5 Baths

4,934 Sq.Ft.

$1,065,990

MLS#: MDAA2118102

This stunning home, available for delivery in April, boasts high-end upgrades throughout. It features a first-floor owner's suite, plus three additional bedrooms on the second level, along with two full bathrooms and a spacious loft. The gourmet kitchen is a chef’s dream, complete with custom cabinetry and an open-concept design. The impressive two-story family room with soaring ceilings creates a dramatic focal point, while the finished basement rec room, featuring a wet bar with a refrigerator and sink, is perfect for entertaining. Experience luxury living at its finest—schedule your tour today! Photos for illustration purposes only. Agent must attend first visit.
#MDAA2103810

ANNAPOLIS

106 STILLY WAY

4 Beds

4 Baths

4,594 Sq.Ft.

$1,047,590

MLS#: MDAA2103810

New Construction - Move In Ready March 2025! Please go to Model home to tour! Welcome to the Lynnfield model at Parkside Preserve, where luxury meets tranquility in this stunning new construction adjacent to the serene Quiet Waters Park. With over 5,017 finished square footage this meticulously designed living space across four levels, featuring 5-bedrooms, 5.5-bathrooms, 4th level loft, and finished lower level with a a true walk-out basement is a perfect fit for modern living. Step inside and be captivated by the elegance of the owner’s suite, featuring a tray ceiling and a spacious walk-in closet. Enjoy the comfort of 9' ceilings throughout, including in the finished basement, and cozy up by the gas fireplace in the expansive living area. The exterior impresses with a blend of brick and HardiePlank, complemented by a welcoming front porch and a front-entry garage. The heart of the home—the kitchen—is a chef’s dream. It boasts two 36' wall ovens (one with an air fryer), a 30' gas cooktop, a stainless steel hood, and a built-in microwave. The staggered white maple cabinetry, complete with under-cabinet lighting and display glass door cabinets, pairs beautifully with the iced white quartz countertops and tiled backsplash. All full bathrooms feature maple cabinetry, quartz countertops, and oversized ceramic tile for a touch of luxury. The finished basement is an entertainer’s paradise with an enormous rec. room, a wet bar, and the fourth full bath. This is more than just a home—it’s a lifestyle. Don’t miss the opportunity to be the first to live in this spectacular residence at Parkside Preserve. Photos are for illustration purposes only.
#MDAA2098972

ANNAPOLIS

110 STILLY WAY

5 Beds

5 Baths

5,017 Sq.Ft.

$1,039,990

MLS#: MDAA2098972

Welcome to an exquisite single-family residence—a turnkey, move-in ready home just minutes from Historic Annapolis, major commuter routes, and marinas. Thoughtfully updated and designed for both daily living and grand entertaining, this property seamlessly blends refined finishes with functional living spaces. A stunning new gourmet kitchen with custom cabinetry, upgraded appliances and a large island, perfect for entertaining family and friends. Spacious family room with a fireplace. Generously sized bedrooms with beautifully renovated bathrooms. A fully finished lower level featuring an additional kitchen, a spacious bedroom, recreation room and an additional full bath making it ideal for guests or extended family. Walkout access to the rear yard. An expansive deck and a level and well-manicured backyard that backs to serene trees. Bedroom level laundry room. Generous amounts of storage and a garage that easily fits 2 cars.
#MDAA2119720

ANNAPOLIS

210 BOWEN COURT

5 Beds

3 Baths

4,880 Sq.Ft.

$1,025,000

MLS#: MDAA2119720

Welcome to this exceptional former model home in the prestigious Monticello enclave—ideally located just moments from Annapolis’ finest dining, shopping, and commuter routes. This residence showcases endless upgrades and over 6,700 square feet of refined living across three spacious levels, blending timeless elegance with cutting-edge comfort. A dramatic two-story foyer with striking black-and-white marble flooring and designer lighting sets the tone upon entry. The formal dining room offers a sophisticated setting for entertaining and opens seamlessly to an outdoor deck, perfect for al fresco gatherings. The gourmet eat-in kitchen is a culinary dream, featuring high-end appliances, quartz countertops with a waterfall edge, and an open flow into the family and breakfast rooms—designed for effortless living. The main level includes an ensuite bedroom, ideal for guests or multigenerational living, as well as integrated smart features like electronic door locks, a whole-house sound system, and destination control thermostats. Upstairs, retreat to a luxurious Primary Suite complete with a private sitting area with fireplace, balcony, and an enviable walk-in closet with built-in storage. The spa-inspired bath offers a jetted soaking tub, new steam shower, dual vanities, and curated designer finishes. Three additional spacious bedrooms include an en-suite and a Jack-and-Jill bath—perfect for family or guests. The fully finished walk-out lower level is built for entertainment and flexibility, featuring a wet bar, recreation area, theater, and a private bonus suite for guests, hobbies, or office space. Additional features include an irrigation system, smart home technology, a 2-car garage, and access to Monticello's private amenities including a community pool and dog park—all in a tree-lined, beautifully maintained neighborhood.
#MDAA2116636

ANNAPOLIS

2000 MONTICELLO DRIVE

6 Beds

6 Baths

6,612 Sq.Ft.

$999,000

MLS#: MDAA2116636

Stunning Updated Colonial in a Water-Privileged Community! This beautifully renovated four-bedroom, two-and-a-half bath home features a custom kitchen with all-new cabinetry, Calcutta Quartz countertops, and sleek stainless-steel appliances, including dual ovens with a gas cooktop. The inviting family room is equipped with built-in surround sound speakers, perfect for entertaining. The luxurious primary suite offers a spa-like experience with a large shower featuring dual shower heads, a soaking tub, a custom border-lit mirror, and a towel warming bar for those chilly days. Convenience is key with a second-floor laundry closet. Step outside from the family room onto a spacious Trex deck that overlooks a large backyard. The property includes an attached two-car garage and a fantastic 30x50 detached two-story toy barn garage, complete with a car lift 10' doors and 13' ceilings and the potential to finish the upstairs space into a perfect in-law or teen apartment. This home also boasts a new roof, a freshly paved driveway, and all-new plumbing and insulation. Enjoy the perks of a water-privileged community with access to a sandy beach and a community dock. This home and Detached garage sits on a double lot with separate gravel road on backside for easy access for boats, RV's storage. This home truly has it all!
#MDAA2111664

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

3,078 Sq.Ft.

$950,000

MLS#: MDAA2111664

Welcome to your dream home in the exclusive Windfern Forest community—a private, water-privileged enclave of executive homes offering both tranquility and recreation. Nestled on a spacious .54-acre cul-de-sac lot, this well-maintained home offers approximately 5,100 square feet of living space. Inside, you’ll find four generously sized bedrooms and 3.5 bathrooms, including a luxurious primary bedroom suite that features an attached sitting room. The main level showcases hardwood floors adding warmth and sophistication, along with custom window treatments, cozy family room with fireplace, and a bright sunroom. A dedicated library/den/office with custom built-ins provides a productive and stylish workspace. The elegant formal dining room with its beautiful molding sets the stage for memorable entertaining. Enjoy the versatility of the lower-level recreation room plus bonus room and full bath—ideal for a guest suite, a home gym, or media space. You’ll also appreciate the abundant storage in the unfinished portion of the basement. Enjoy professionally landscaped grounds and access to kayaking, paddleboarding, and boat slips. Access to boat slips is available on a first-come, first-served basis. Conveniently located near shopping centers, restaurants, and major commuter routes, offering convenience without sacrificing peace and quiet. This home blends comfort, elegance, and lifestyle—making it a rare opportunity in a highly desirable setting.
#MDAA2114686

ANNAPOLIS

534 POST OAK ROAD

4 Beds

3 Baths

5,040 Sq.Ft.

$950,000

MLS#: MDAA2114686

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