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
323
# of Listings
3
Avg # of Bedrooms
$461
Avg. $ / Sq.Ft.
$1,054,467
Med. List Price

Browse Annapolis Real Estate Listings

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$250,000 - $500,000

$500,000 - $1M

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$3M - $5M

Over $5M

102 Properties Found. Page 1 of 7.

Ready for Quick Move-in! This expansive two-story home showcases a gracious design with abundant room to grow and entertain. Off the foyer is a formal dining room that complements the casual nook and breakfast room, plus a gourmet kitchen and a Great Room with a charming fireplace. On the second floor is a loft surrounded by three secondary bedrooms and a luxurious owner’s suite with a spa-style bathroom. A lower-level recreation room presents endless possibilities. Home is on smart rent lock for your viewing pleasure.
#MDAA2118098

ANNAPOLIS

120 STILLY WAY

6 Beds

5 Baths

4,934 Sq.Ft.

$999,990

MLS#: MDAA2118098

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.

$985,000

MLS#: MDAA2112582

Welcome to 1909 Eleanor Ct, a stunning colonial featuring five bedrooms and three and a half bathrooms. You’ll fall in love the moment you walk in! Highlights include a large eat-in kitchen that opens to the family room, perfect for gatherings, plus a mudroom with ample storage. There’s even a cozy area off the kitchen ideal for a home office or homework station. The oversized owner’s suite boasts a custom walk-in closet and a spacious bathroom for the ultimate retreat. The fully finished basement includes a full bathroom, and the three-car garage provides plenty of space for vehicles and storage. All of this sits on a flat lot in a quiet cul-de-sac, offering both privacy and convenience.
#MDAA2127206

ANNAPOLIS

1909 ELEANOR COURT

5 Beds

3 Baths

5,124 Sq.Ft.

$975,000

MLS#: MDAA2127206

Fantastic brick front Cape Cod, quality built by KOCH Homes! First time offered for sale! This lovely 1/2+ acre property backs to Quiet Water’s Park with Harness Creek water access. Enjoy three finished levels! Step into a welcoming two-story foyer and a soaring two-story family room with a propane gas fireplace that opens to the spacious kitchen with eating area and large center island! A very large laundry room/mud room with additional storage is conveniently located off both the garage and kitchen. The large first floor owner suite features a walk-in closet, spacious owner bath, and a separate office/sitting room with additional closet space and an atrium door leading to the deck! Separate living room and dining room with hardwood floors! Hardwood floors extend throughout the first level! Upstairs offers three generous sized bedrooms and a large full bath! The lower level provides an enormous finished recreational room and plenty of unfinished space for all your storage needs. With a little cosmetic updating this home will be your dream!
#MDAA2111626

ANNAPOLIS

795 HARNESS CREEK VIEW DRIVE

4 Beds

2 Baths

4,549 Sq.Ft.

$975,000

MLS#: MDAA2111626

Time to Make a Lifestyle Change – Stunning & Fabulous at The GrandView! Welcome to The Flagship, a unique and highly sought-after corner unit in the premier GrandView community. Perfectly positioned for the best location, views, and luxury, this residence offers an unmatched lifestyle in the heart of Annapolis Town Center. Step inside and be captivated by the wall of windows that flood the space with natural light and showcase panoramic views of Annapolis Town Center’s vibrant activity. Enjoy morning coffee or evening cocktails from your private, covered corner balcony. This 2-bedroom, 2-bath home is beautifully appointed with granite countertops, 10-foot coffered ceilings, hardwood floors, and custom window treatments. Recent upgrades include: New HVAC system, New stainless steel appliances, New bedroom carpeting, Updated lighting and black hardware through out. Additional features include an assigned storage unit and two reserved garage parking spaces. Residents of The GrandView enjoy luxury amenities such as: Concierge services, Fitness center, and Rooftop pool with stunning city views. Live the walkable lifestyle! Stroll to Whole Foods Market, Target, fine dining, cafés, banking, and boutique shopping—all just steps from your door. You’re minutes from Historic Downtown Annapolis, Annapolis Mall, Anne Arundel Medical Center, and with easy access to Route 50 and I-97 for effortless commuting. This is truly a must-see residence—a perfect blend of comfort, convenience, and modern elegance in one of Annapolis’ most desirable addresses.
#MDAA2127946

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 1004

2 Beds

2 Baths

1,794 Sq.Ft.

$975,000

MLS#: MDAA2127946

This stunning home is move-in ready and 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.
#MDAA2125928

ANNAPOLIS

106 STILLY WAY

4 Beds

4 Baths

4,594 Sq.Ft.

$974,990

MLS#: MDAA2125928

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 605 Yawl Court, a sophisticated residence nestled in sought-after St Margarets Landing, offering a unique blend of modern elegance and timeless charm. This stunning home features 4 spacious bedrooms and 3.5 luxurious bathrooms, sprawling over 4,000 square feet of exquisitely designed living space. Step inside to discover updated interiors boasting gorgeous new flooring, graceful wrought-iron banisters, and plantation shutters. The open kitchen is equipped with newer, stainless appliances, perfectly catering to your culinary endeavors. Abundant natural light floods the home, highlighting a neutral decor palette that complements any style. The main level hosts a serene primary suite, providing a tranquil escape with its own private en-suite bath with updated vanity and lighting. Venture to the upper level to find two bedrooms and a full bath, and a versatile space, ideal for a den, home office, or a relaxing reading nook. The lower level is a haven for entertainment and fitness, featuring built-ins, a stacked stone wall, electric fireplace, a dedicated home gym, and fourth bedroom and full bathroom. Outdoors, a private backyard and deck offer an idyllic setting for entertaining or enjoying quiet evenings under the stars. The property's expansive lot ensures privacy and ample space for leisurely pursuits. Experience the perfect blend of luxury and comfort in this extraordinary Annapolis home, where every detail is thoughtfully curated for the discerning homeowner. Welcome Home!
#MDAA2127742

ANNAPOLIS

605 YAWL COURT

4 Beds

3 Baths

4,436 Sq.Ft.

$949,900

MLS#: MDAA2127742

Welcome to 52 Primrose Hill Lane - the original model home in Craftmark’s Primrose Hill community, where timeless design meets modern, low-maintenance living in the heart of Annapolis. Thoughtfully designed with style and sustainability in mind, this home offers nearly 4,000 sq ft of refined living space that allows you to spend more time doing what you love - on the water, at your beach house, or on the golf course. Inside, open and airy living spaces flow seamlessly from a gourmet kitchen with quartz counters and an oversized island to light-filled dining and lounging areas. The layout blends sophistication with practicality — offering two en-suites ideal for guests or multigenerational living and a finished lower level perfect for work, wellness, or entertainment. As the former model, the home showcases elevated Craftmark details: custom built-ins, a marble-surround gas fireplace, designer lighting, and fine millwork. Step outside to a private patio or enjoy the community’s green space and walking trail — all maintained by the HOA for effortless living. Primrose Hill is a well-managed, energy-efficient enclave that makes smart use of space inside and out. With easy access to downtown Annapolis, Eastport, and commuter routes to D.C. and Baltimore, 52 Primrose Hill Lane offers an elegant, eco-conscious lifestyle where convenience, design, and balance come together beautifully.
#MDAA2124872

ANNAPOLIS

52 PRIMROSE HILL LANE

5 Beds

4 Baths

4,226 Sq.Ft.

$949,000

MLS#: MDAA2124872

• Eclectic downtown location with 8 on-site parking spaces • Unit has a reception/bullpen area, 5 offices, a kitchen that seats 4, copy/fax room and 2 restrooms (one with shower) • Upgraded finishes and systems throughout • Close proximity to Maryland State House, Circuit Court, State Office Buildings, United States Naval Academy, Annapolis City Dock, and St. John’s College • Walking distance to Rams Head Bar & Grill, El Toro Bravo, Level, Tsunami, and various retail shops and services • Taxes for the unit are $10,040 annually • MX zoning, permitting uses of office, retail, restaurants, galleries, and laboratories.
#MDAA2110468

ANNAPOLIS

79 WEST STREET 1

None Beds

None Baths

1,971 Sq.Ft.

$940,000

MLS#: MDAA2110468

This stunning log home on 2.48 scenic acres (with the potential to subdivide) offers the perfect blend of rustic elegance and thoughtful upgrades. Surrounded by lush landscaping, the property provides treetop views and a glimpse of the water during the winter months. The impressive two-story living room showcases a dramatic wood-burning fireplace and flows effortlessly into the dining area and the gourmet kitchen, which features granite countertops, a breakfast bar, ample cabinet space, and all major appliances. Three generously sized bedrooms are located on the main level, each with gleaming hardwood floors. The primary suite includes a ceiling fan, walk-in closet, a spa-like bathroom with a soaking tub and separate shower, and private access to the deck. Upstairs, a sunlit loft with oversized skylights offers flexible space for a home office, family room, or den and includes a full bathroom. The finished basement adds even more living space, with a spacious recreation room featuring wall-to-wall carpeting and recessed lighting, a fourth bedroom, a laundry area, and plenty of storage. Outdoor living is just as inviting, with a large rear deck that backs to wooded privacy and a welcoming front paver walkway and deck. The driveway provides ample parking, and the home is just a short walk from community beach access. Ideally located near major highways and downtown Annapolis, this home offers tranquil surroundings with convenient access to shopping, dining, and everyday necessities.
#MDAA2113476

ANNAPOLIS

2977 SOUTHAVEN DRIVE

4 Beds

4 Baths

3,200 Sq.Ft.

$925,000

MLS#: MDAA2113476

Welcome to this charming modern Craftsman-style home, offering 5 bedrooms and 3.5 bathrooms across three beautifully finished levels. Built in 2022, this home showcases timeless curb appeal and over 2,900 square feet of inviting living space filled with natural light. Step inside to an open and welcoming floor plan where the heart of the home is the stunning kitchen — featuring gorgeous countertops, a large center island, and stainless steel appliances. The kitchen opens to a cozy family room centered around a gas fireplace with a marble mantel, creating the perfect space for gatherings and relaxation. Upstairs, the spacious and airy primary suite offers abundant natural light, an ensuite bathroom with an oversized shower and soaking tub, and a generous walk-in closet. Three additional bedrooms, a full hall bathroom, and convenient upper-level laundry complete this floor, along with easy-access attic storage. The finished lower level expands your living and entertaining space with a large recreation room — ideal for a game room, home theater, or gym — plus a fifth bedroom, full bathroom, and walkout access to the backyard. A stylish bar area and additional storage complete this level. Outside, enjoy a serene retreat backing to trees. The deck invites you to unwind and take in the peaceful surroundings, complemented by a custom bluestone patio below, a fully fenced backyard, and all-new landscaping. Additional highlights include ADT security system, two-car garage, shed, and recently added gutter guards. Located in the Cape St. Claire community, residents enjoy easy access to the neighborhood playground, community beach, kayak racks, boat ramp, and clubhouse — bringing outdoor adventure and coastal charm right to your doorstep. All within the sought-after Broadneck school district and minutes from major commuter routes. Don’t miss the opportunity to make this home yours – schedule your private tour today!
#MDAA2128798

ANNAPOLIS

1214 RAMBLEWOOD DRIVE

5 Beds

3 Baths

3,438 Sq.Ft.

$925,000

MLS#: MDAA2128798

Welcome to one of Annapolis’ most sought-after waterfront communities, where residents enjoy a waterfront pool, and a private marina and boat ramp that’s just minutes to the Chesapeake Bay by boat. This beautifully updated four-bedroom home at 1141 Mainsail Drive in Anchorage is situated just down the block from all these amazing amenities and sits on a spacious one-third acre lot framed by mature trees and manicured landscaping. Inside, the home features a bright open floor plan with gorgeous hardwood floors, crown & chair-rail moldings, and large windows that fill the space with natural light. The chef’s kitchen boasts stainless steel appliances, quartz countertops, and an inviting breakfast area that opens to a cozy family room with a double-sided brick fireplace. The sliding glass doors that open to the back deck make grilling and al fresco dining a breeze. A formal living and dining room offer flexibility for entertaining, and the main level also includes a powder room and access to the oversized two car garage. Upstairs, the primary suite includes a private bath with a renovated walk-in shower and updated fixtures. Three additional bedrooms are ample in size and there’s a second renovated bathroom. There is a wonderful office nook overlooking the front yard. The finished lower level, with Pergo flooring, provides a spacious recreation and/or office space with room for storage and a workshop area. Outdoors, the circular driveway provides a gracious entry and leads to an attached two-car garage. The beautifully landscaped backyard is private and offers plenty of space for enjoyment in addition to the brick patio. Residents of Anchorage enjoy an unparalleled lifestyle centered around the community’s marina, pool, and social events, all while being just minutes from downtown Annapolis, Quiet Waters Park, and top-rated schools. Whether boating on Lake Ogleton, gathering at the waterfront picnic area, or simply enjoying evening walks around the neighborhood, life in Anchorage feels like a year-round retreat.
#MDAA2128894

ANNAPOLIS

1141 MAINSAIL DRIVE

4 Beds

2 Baths

3,264 Sq.Ft.

$910,000

MLS#: MDAA2128894

Welcome Home to spectacular 722 Coybay Drive! This elegant brick-front Colonial is located in the amenity-rich Kingsport community, offering both luxury and convenience. Featuring 5 bedrooms, 3 full baths, and 2 half baths, this home provides abundant space for family, guests, and entertaining. Inside, enjoy a well-designed layout with spacious living areas, a gourmet kitchen, and refined finishes throughout. The primary suite is a true retreat with a luxurious bath, while additional bedrooms offer flexibility for home offices, hobbies, or guest rooms. Outside, the property boasts a beautifully maintained exterior and access to the community’s top-notch amenities, including a pool, trails, and recreational areas. Located close to shopping, dining, and commuter routes, this home perfectly blends elegance with everyday convenience. Don't miss your chance to tour, schedule your showing today and experience the charm and sophistication of 722 Coybay Drive!
#MDAA2128170

ANNAPOLIS

722 COYBAY DRIVE

5 Beds

3 Baths

5,387 Sq.Ft.

$899,999

MLS#: MDAA2128170

Nestled into the tree tops off a private drive in highly sought after Winchester on the Severn, this mid century raised rancher will check all your boxes. From the moment you pull up the private drive to the home, you are immediately at ease. Step out of the car to the sounds of birds and the rustle of the trees. You will feel as though you have escaped it all, yet you are right in the heart of Winchester, a quick drive from Historic Downtown Annapolis and a stones throw to the famed B&A trail. As you enter the front walk, you will be immediately struck by the quality of craftsmanship and materials on the exterior of the home. Once inside, the rich wood beams, wood trim and floors strike a dramatic combination with the soaring ceilings. The abundant windows and doors leading out to the sunroom will ensure that the beauty of the natural surroundings take center stage. The chef's kitchen is equipped with granite countertops, a deep sink, lovely picture window over the sink, double wall ovens and high end fixtures. The sunroom serves as an additional dining space and relaxing sitting room with full views of the surroundings. You will feel as though you have escaped to a mountain retreat! The main level offers a full hall bath and three comfortable bedrooms including an owner's suite with ensuite bath and double closets. The fully finished lower level is a lovely living space on its own with a cozy den, office and flexible bonus space that could be a 4th bedroom with its own ensuite bath. The lower sunroom is the perfect spot to partake in your morning yoga and meander out to the hot tub for a leisurely soak. Entertaining is a breeze with the expansive, multi-level decks and putting green for fun. After a day on the water, use the outdoor shower to rinse away the salt and sand. Winchester offers two beaches (one is referred to as Dog Beach for obvious reasons) and two marinas. The beauty of a water access community on the Severn River is easy access into Annapolis by boat without going out into the choppy Bay. You can hop on a small tender and dock in town at the dinghy dock for dinner any time you please. Walk or bike up the B&A trail for coffee, ice cream or grab must haves at the gourmet cheese shop. Brunch at the Severn Inn overlooking the River or pop over to Garten Beer Garden for a lovely supper with friends. This is not merely a beautiful home, this is a highly sought after lifestyle.
#MDAA2128442

ANNAPOLIS

1534 CIRCLE DRIVE

4 Beds

3 Baths

3,470 Sq.Ft.

$899,000

MLS#: MDAA2128442

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