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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
270
# of Listings
3
Avg # of Bedrooms
$425
Avg. $ / Sq.Ft.
$922,557
Med. List Price

Browse Annapolis Real Estate Listings

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$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

91 Properties Found. Page 1 of 7.

Development opportunity in an established boutique shopping & business district. Value is in the land (approximately 15,000 sq. ft.). Being offered "as is - where is". Former location of Tara's Gifts at the gateway to West Annapolis. B1 zoning permits retail, office & residential use. Easy access to/from Rt. 50. Walkable to offices, restaurants, shopping, downtown Annapolis, USNA & Navy/Marine Corp. Memorial Stadium. Assemblage possible with adjacent buildings at 2 & 4 Annapolis Street grossing rent from 6 retail & 2 residential tenants totaling $20,700/Mo.
#MDAA2127368

ANNAPOLIS

10 ANNAPOLIS STREET

None Beds

None Baths

2,064 Sq.Ft.

$975,000

MLS#: MDAA2127368

Redevelopment opportunity in an established boutique shopping & business district. Value is in the land (approximately 15,000 sq. ft.) Being offered "as is - where is". Former location of Tara's Gifts at the gateway to West Annapolis. B1 zoning permits retail, office & residential use. Easy access to/from Rt. 50. Walkable to offices, restaurants, shopping, downtown Annapolis, USNA & Navy/Marine Corp. Memorial Stadium. Possible assemblage with adjacent 2 buildings at 2-4 Annapolis Street...gross rents totaling $20,700/Mo. from 6 retail & 2 residential tenants. Total land area for 2, 4 & 10 Annapolis Street is approximately 37,500 sq. ft. (0.86 acres).
#MDAA2127370

ANNAPOLIS

10 ANNAPOLIS STREET

None Beds

None Baths

0.34 acres

$975,000

MLS#: MDAA2127370

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

Nestled in the serene Dellwood community, this contemporary gem offers an exclusive lifestyle defined by luxury and comfort. Perfect location leaves you minutes from downtown Annapolis, Luminus Health Hospital as well as all the charm Annapolis proper (Parole) has to offer. Step inside to discover an inviting open floor plan adorned with rich hardwood and ceramic tile flooring, seamlessly blending elegance with warmth. The heart of the home features a country-style kitchen equipped with stainless steel appliances, including a six-burner stove and double ovens, perfect for culinary enthusiasts. Main level bedroom if needed with full bath attached. Currently being used as the office. Unwind in the spacious living area, complete with a cozy wood stove or wood burning fireplace and built-in sound system, or retreat to the inviting screened in porch to take in the natural setting of this large corner lot. Enjoy outdoor living with multiple decks and porches, a personal lap pool, ideal for exercise or relaxation. The property also includes water access to the Severn River with boat slip included if that fits your needs , enhancing your lifestyle with boating and fishing opportunities. With an attached garage and additional storage, this home is designed for effortless living.
#MDAA2131896

ANNAPOLIS

1800 SEVERN GROVE ROAD

3 Beds

3 Baths

2,281 Sq.Ft.

$967,000

MLS#: MDAA2131896

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.

$950,000

MLS#: MDAA2127206

Just across the street from the water in Southaven, this Annapolis home offers the kind of space and flexibility that’s increasingly hard to find. Recently updated, the main level includes a renovated kitchen with quartz countertops, dual ovens, gas cooking, stainless steel appliances, and modern cabinetry. The main level also features a living room with built-in speakers, a dining room, an optional sitting room, a half bath, garage access, and a coat closet at the front entry. Upstairs are four well-sized bedrooms, two thoughtfully updated full baths designed with a clean, timeless aesthetic, and a laundry room. The walkout lower level remains unfinished and offers excellent storage, along with a bathroom rough-in for those who may wish to explore future expansion. Exterior updates include a newer roof and a recently paved driveway. The attached two-car garage supports everyday needs, while the detached three-car garage offers access to an unfinished upper-level space that provides additional room to tailor to personal needs. A back deck extends off the main level, with a second deck accessible from the unfinished space above the three-car garage. Community water access is located across the street. The Southaven community also offers a community pier and a kayak/paddleboard launch area. Set on a generous lot with ample storage and water access, 2942 Southaven Drive combines usability with the relaxed coastal character that makes this part of Annapolis so appealing.
#MDAA2131620

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

3,078 Sq.Ft.

$949,900

MLS#: MDAA2131620

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.
#MDAA2132158

ANNAPOLIS

52 PRIMROSE HILL LANE

5 Beds

4 Baths

4,226 Sq.Ft.

$949,000

MLS#: MDAA2132158

• 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

New on site 1 day ago
Welcome to your dream home in the St Margaret's Landing! This exquisite 5-bedroom, 4.5-bathroom residence offers three expansive levels of living. Originally a Ryland home model, this property features two primary suites—one on the main level and another on the upper level—ideal for multi-generational living or hosting guests. Inside, you'll find custom closets, elegant plantation shutters, and gleaming hardwood floors throughout. Modern lighting fixtures add a touch of sophistication to every room. The gourmet kitchen, with its inviting island, is perfect for casual breakfasts or entertaining guests, while the fully screened deck offers a serene spot for morning coffee or evening happy hours as you watch the sunset. Enjoy the privacy of a tree-lined backyard, providing a peaceful retreat. Cozy up by the fireplace in the inviting family room or host memorable holiday dinners in the formal dining room. The versatile lower level is designed for entertainment and relaxation, featuring a movie area, workout space, and room for game nights, complete with two bars, a pool table, and a full bathroom. This meticulously maintained home is a rare find in one of the area's most sought-after neighborhoods. Don’t miss the opportunity to make it yours!
#MDAA2132320

ANNAPOLIS

1612 TRAWLER LANE

5 Beds

4 Baths

4,986 Sq.Ft.

$929,000

MLS#: MDAA2132320

The perfect blend of 1950s charm and modern Annapolis living, situated steps from the water and an easy walk or bike ride across the Naval Academy Bridge to West Annapolis and the historic downtown area. This classic Pendennis Mount ranch-style home, built in 1959, has been beautifully updated. Step inside to find the home's original character with hardwood floors, now opened up into a generous main living and dining area. The real showstopper is the expansive rear kitchen addition featuring vaulted ceilings, huge windows overlooking the backyard, and a chef's setup: granite countertops, stainless steel appliances, a gas cooktop, and a large walk-in pantry. The main level hosts 3 bedrooms and a full bath, while the finished lower level provides excellent flexibility with a large den, 2 additional bedrooms, a kitchenette, and bonus room with french doors that open to a patio—perfect for a guest suite or entertaining space. You’ll also appreciate the two-car attached garage with extra storage space for a workshop or whatever your needs may be. The driveway was freshly paved last year. Situated on a spacious, fully fenced 0.34-acre lot with mature trees, this property offers rare privacy and two patios. Enjoy the quiet, safe streets of the highly desirable Pendennis Mount community featuring a newly renovated community playground. You are minutes away from Jonas Green Park. Commuting is convenient with swift access to routes toward Baltimore and Washington D.C.
#MDAA2131196

ANNAPOLIS

1913 DULANEY PLACE

5 Beds

2 Baths

3,287 Sq.Ft.

$925,000

MLS#: MDAA2131196

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.

$925,000

MLS#: MDAA2112582

New on site 3 days ago
This is an estate sale and being sold "As Is." A rancher that has been in this family for years, it does require updating--the value of this property is in the land and located in Pendennis Mount as many individuals would love to build a larger home in this community or rehab an existing home. This property is located in the well-desired subdivision of Pendennis Mount with properties selling for up to $9M on the water.. This property in not located in the "city" of Anapolis so no city property tax assessed. There is a private community access to the waters of the Severn River that has a pier and boat slips.... If one wants to join the Boat Club, one can join--agent is verifying fees and will update this info. There is also a public county park, Jonas Green Park, just outside of Pendennis Mount (next to the Naval Academy Bridge off Rt. 450) that offers a sandy beach for cartop boat launching, 288-foot fishing pier, picnic tables and restrooms for public use, but no swimming--(per their website). One can access downtown Annapolis, the Naval Academy within minutes. Easy access to Rtes 2, 50 and I-97. Easy driving to DC, Baltimore, or the Eastern Shore.
#MDAA2130856

ANNAPOLIS

16 BRICE ROAD

3 Beds

1 Baths

3,872 Sq.Ft.

$900,000

MLS#: MDAA2130856

This is the one you've been waiting for! First open house scheduled for Sunday, November 23, 2025 from 2-4pm. Come visit this well maintained, 5 bedroom, 3 and 1/2 bath gorgeous home located on 1.43 acres in the sought after community of The Ridges! This lovely home is situated in a wooded wonderland while still being close to all that Annapolis has to offer! As you enter, you'll immediately note the beauty and warmth of the gleaming hardwood floors throughout the main level. The floor plan provides for a spacious formal dining room and separate living room which has a charming bay window that overlooks the backyard. You'll next discover the bright and inviting kitchen with plenty of room for preparing a gourmet meal! The center island is a great place for hanging out, while the breakfast table area is fantastic for casual dining. Your attention is then drawn to the huge family room with soaring ceilings and a lovely wood burning fireplace that's perfect for those cozy winter nights. Sliding glass doors are to your left, and what a treat they reveal! An amazing screened in porch awaits you and is sure to be a favorite spot for enjoying the pleasures of the outdoor world. Back inside, a bonus room presents options to be a guest room, office, or library- you choose! Rounding out the main level is a cute half bath for convenience. Ascending the stairs, you'll turn to the left to enter your spacious primary bedroom suite! Vaulted ceilings with hardwood floors will impress you upon entering this room. You'll next be drawn into the spectacular primary bath, remodeled just weeks ago! Featuring a show stopping soaking tub, double sink vanity, new LVP flooring, paint, toilet, and lighting - this room wows! Back into the hallway, you'll find three additional bedrooms with a full hall bath to service them. Going further, you'll enter an oversized loft that overlooks the family room making it a great space for a TV room, playroom, or another option for an office! Next, you'll head back downstairs to explore the lower level. You'll first enter an enormous recreation room with endless options for use! Make it a game room with space for a pool table, bar, or movie theatre. You'll also find a 5th bedroom with an ensuite full bath on this level, as well as two large storage rooms for seasonal items. An attached two car garage with space for shelving, along with parking pads for additional guests, rounds out all this house has to offer. 2025 updates include refreshing the deck and screened in porch, as well as remodeling the primary bathroom. Roof replaced 2015, water heater 2017, Goodman HVAC unit 2017, well pump replaced 2018, kitchen remodeled 2018, driveway replaced 2019. Minutes to restaurants, shopping, and downtown Annapolis, this is a perfect location for all your needs. *All inforamtion deemed reliable but should be independantly verified for accuracy.
#MDAA2128064

ANNAPOLIS

621 WOOD LOT TRAIL ROAD

5 Beds

3 Baths

4,325 Sq.Ft.

$894,900

MLS#: MDAA2128064

PRICE ADJUSTED on this wonderful 4-bedroom home! 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.

$890,000

MLS#: MDAA2128894

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