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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
320
# of Listings
3
Avg # of Bedrooms
$464
Avg. $ / Sq.Ft.
$1,069,545
Med. List Price

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320 Properties Found. Page 8 of 22.

OFFER DEADLINE WEDNESDAY AT 10PM OCTOBER 22nd. Welcome to this stunning California-style elevated rancher nestled on a 1.11-acre professionally landscaped lot in the highly desirable Downs on the Severn. Offering a perfect blend of luxury, comfort, and thoughtful upgrades, this home is a peaceful retreat surrounded by nature. This special, well cared for home features 3 Bedrooms and 4 Bathrooms. There is also an additional half bath in the entrance of the home. All bedrooms are located on the main level of the home. Come see this Luxurious, Modern ,Primary Suite with two expansive walk-in closets and a beautifully updated ensuite bath. The two additional main-level bedrooms share a fully renovated hall bath.. There are recently installed Birdseye Maple hardwood floors that flow seamlessly throughout the entire home, adding warmth and elegance. Interior Upgrades & Layout feature a Gourmet Kitchen Renovation with custom cabinetry, granite countertops, stainless steel appliances, and open-concept flow to the dining and family rooms. This home is perfect for entertaining all year round. Bright and airy layout enhanced by 4 new skylights, bringing natural light into the heart of the home. As you walk to the back you are greeted by a Sunroom/Screened Porch with a cozy gas fireplace, perfect for year-round enjoyment! In the summertime open up all the full length windows and doors to enjoy outdoor living inside! There is a side facing, 2 car garage with plenty of room. You will absolutely feel like you are on vacation when you venture up the private, landscaped driveway. There is always plenty of room for parking on this private lot. Mature and newly enhanced landscaping will make you feel as if you are in Homestead Gardens! There is also 7 Sprinkler Zones on the property for easy care. The Downs On Severn features 2 marinas, a community pool with swim team, tennis courts with pickle ball, clubhouse with year round socials, and tot lot with little library. The new Clements Creek floating dock Marina with community tables with fire pits where just put in 2024 . There are all boat size slips and we would check what is currently available. There are also boat lifts available for an extra fee. You will feel like you are always on vacation at 1676 Saint Albans Square! Come make an appointment to view this home today as this home will not be on the market very long on the market!
#MDAA2128692

ANNAPOLIS

1676 SAINT ALBANS SQUARE

3 Beds

3 Baths

3,959 Sq.Ft.

$969,000

MLS#: MDAA2128692

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.

$965,000

MLS#: MDAA2128442

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

New on site 2 days ago
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

Welcome to Kingsport , a water privileged community packed with beautiful homes and all the modern conveniences. This stunning 5BR/4.5BA luxury home is ready for new beginnings. Grand residence featuring hardwood foyer, formal oval dining room, living room, and main-level office. Gourmet kitchen with custom island cooktop, dual wall ovens, granite counters, and abundant cabinetry opens to the family room with vaulted ceilings, plantation shutters, and gas fireplace. The additional room off the foyer is perfect for the home office. The upper level includes a primary suite with spa bath and dual walk-in closets, en-suite second bedroom, plus two additional bedrooms with shared bath. The finished lower level offers a rec room with a wet bar, guest suite, playroom and an abundance of storage. Fully fenced yard with paver patio and raised garden bed. Property backs up to woods and walking paths. The community offers a pool, multiple playgrounds, hiking and biking trail, kayak launch and storage. The community pier situated at the end of Crab Creek is the perfect place to unwind, go fishing or have a picnic. Close proximity to all commuter routes and minutes from downtown Annapolis
#MDAA2120506

ANNAPOLIS

730 CRISFIELD WAY

5 Beds

4 Baths

5,151 Sq.Ft.

$865,000

MLS#: MDAA2120506

Ameri-Star Homes is pleased to offer this incredible opportunity for a to-be-built, craftsman-style home situated on a beautiful almost half acre lot with walkout basement condition in the well-established neighborhood of Rolling Knolls, in Annapolis. *Builder is paying $5,000 TOWARDS CLOSING COSTS with use of builders approved lender and title company. Our exciting Taft model is appointed with an abundance of features that you deserve, 9-foot ceilings main level, engineered hardwood floors on the entire first floor, granite or quartz countertops in the kitchen, upgraded cabinets with soft close doors and drawers, ceramic-clad baths and laundry room floor, stainless appliances, washer and dryer package, stone accents on the exterior, architectural roof shingles, upgraded craftsman style moldings, craftsman newel posts with oak rails with black iron pickets, a garage door opener with wifi, a sodded lawn and generous landscaping package and so much more. ALL STANDARD! A home that you certainly will be proud to drive up to. There is 2,580 square feet of above grade living space to enjoy and plenty of room for expansion including adding an optional finished rec room, an optional basement bedroom and optional full bathroom in the basement at an additional cost. This location is a convenient commute to Baltimore and Washington DC and just minutes to historic Annapolis, Maryland. This is a rare opportunity for new construction in the Annapolis area. The images illustrated in this listing may be representative of the builder’s work in likeness and quality and may show optional features that are available. Prices, terms, conditions, and availability are subject to change without prior written notice. Other plans are available for this lot, including a rancher plan.
#MDAA2123152

ANNAPOLIS

2175 GLENCREST CIRCLE - TAFT MODEL

4 Beds

2 Baths

3,480 Sq.Ft.

$849,990

MLS#: MDAA2123152

Experience over 5,000 square feet of refined comfort in this beautifully appointed 4-bedroom, 2.5-bath Colonial, nestled at the end of a quiet cul-de-sac in the highly desirable Bowen Manor community of Annapolis. From the moment you step inside, you’ll appreciate the soaring ceilings, abundant natural light, and seamless flow that make this home perfect for grand entertaining and effortless everyday living. The main level is anchored by a expansive kitchen featuring a large center island, double ovens, and a sunny eat-in area that opens to the spacious family room with a cozy gas fireplace. A bright, window-lined sunroom just off the kitchen provides a welcoming spot for morning coffee or quiet afternoon reading. You’ll also find a private home office tucked behind French doors, along with elegant formal living and dining rooms enhanced by custom moldings and thoughtful details throughout. Upstairs, the expansive primary suite offers a true retreat, complete with a lighted tray ceiling, a massive walk-in closet, and a spa-like en-suite bath. Three additional generously sized bedrooms share a stylish full bath, and the convenient upstairs laundry room adds modern functionality. The walk-out lower level provides a second family room—ideal for movie nights, game days, or play space—with plenty of room left over to finish as a rec room, gym, media center, or guest suite. Outside, enjoy the fully fenced backyard and spacious deck—perfect for summer barbecues or peaceful evenings at home. Located just minutes from commuter routes, shopping, dining, and historic downtown Annapolis, this home offers space, style, and location—plus the rare bonus of an assumable 4.625% mortgage. Don’t miss your chance to make this exceptional home your own!
#MDAA2127918

ANNAPOLIS

229 BOWEN COURT

4 Beds

2 Baths

5,112 Sq.Ft.

$849,900

MLS#: MDAA2127918

Rare Opportunity to Build Your Dream Home Near Historic Downtown Annapolis 3268 Kitty Duvall Drive | Offered at $875,000 | Includes Lot, Site Work Budget & Customizable Chestnut Model by Timberlake Homes Embrace the chance to create your dream home on a peaceful, build-ready .62-acre wooded lot just minutes from the charm and energy of downtown Annapolis. Nestled off a quiet, private gravel lane, this flat homesite offers public sewer access and the benefit of preliminary engineering already completed—making it easier and faster to build. This exclusive opportunity includes Timberlake Homes’ highly flexible and elegant Chestnut floorplan, thoughtfully designed to combine comfort, functionality, and style. Enjoy the tranquility of a secluded setting with convenient access to vibrant shops, waterfront dining, cultural landmarks, and historic marinas. Highlights of the “To Be Built” Chestnut Model: 2,251–2,498 sq. ft. | 4 Bedrooms | 2.5+ Bathrooms Welcoming open foyer with tucked staircase and central powder room Spacious family room with optional 4' extension and fireplace Gourmet eat-in kitchen with 42” maple cabinetry, granite countertops, walk-in pantry, breakfast island, and Samsung appliances (including a double wall oven) Mudroom entry from a 2-car garage Elegant oak stairs from main to upper level Hardwood, LVP, or laminate flooring throughout main level 9’ ceilings on main level with 9’ foundation walls for added volume Ceramic tile in all bathrooms Stylish brushed nickel hardware and Moen® fixtures throughout Optional features: deluxe primary bath, third full bath, sunroom, and lower-level recreation room Chestnut Floorplan Overview: The Chestnut offers timeless appeal with a flexible layout. A bright foyer opens to a versatile flex room, while the central staircase leads to four generously sized bedrooms upstairs, a full hall bath, and a convenient second-floor laundry room. Enhance your living space with thoughtful options like a sunroom, extended family room, or finished basement recreation area. Additional Notes: Timberlake Homes makes no representations regarding the lot or its sale. Please contact the listing agent to connect directly with the builder. Photos and floor plans may show upgraded features not included in the base price. Final pricing may vary depending on selected options and builder allowances.
#MDAA2117802

ANNAPOLIS

3268 KITTY DUVALL DRIVE

None Beds

None Baths

N/A

$849,000

MLS#: MDAA2117802

Welcome to 42 City Gate Lane in the desirable City Gate neighborhood of Annapolis. This move-in ready residence offers 3 bedrooms, 2 full baths, and 2 half baths, thoughtfully updated for modern living. The showpiece main level features a complete open-concept renovation: upgraded cabinetry, a generous center island, sleek quartz counters, and stainless steel appliances—all seamlessly connected to bright living and dining spaces with flowing hardwood floors. Step outside to a private patio that’s ideal for entertaining or a quiet morning coffee. Recent improvements provide peace of mind and curb appeal, including a new roof and gutters installed in 2024, along with a new front door and rear sliding door. With a walkable location just moments to Downtown Annapolis and the Waterfront—as well as the State House, the U.S. Naval Academy, shops, dining, parks, and commuter routes—this home blends style, convenience, and comfort in one exceptional package. Convenient overflow parking at both ends of the street.
#MDAA2124168

ANNAPOLIS

42 CITY GATE LANE

3 Beds

2 Baths

2,100 Sq.Ft.

$824,900

MLS#: MDAA2124168

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