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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
265
# of Listings
3
Avg # of Bedrooms
$481
Avg. $ / Sq.Ft.
$1,290,957
Med. List Price

Browse Annapolis Real Estate Listings

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Over $5M

108 Properties Found. Page 6 of 8.

Welcome to Heritage Harbour, Annapolis’ premier 55+ community offering resort-style living and an unmatched lifestyle. Now priced better, this spacious end-unit villa boasts over 2,500 square feet of living space and is filled with natural light thanks to its desirable end-unit location. Freshly painted throughout with brand new flooring and carpet, this home is truly move-in ready and features soaring ceilings that enhance the open, airy feel. The main level is designed for easy, one-level living and includes a generous primary bedroom with en-suite bath, along with a convenient half bath for guests. The bright and spacious kitchen offers plenty of room for a table or center island, making it a perfect gathering space. The family room features a cozy fireplace and opens directly to a private, fenced-in patio—ideal for relaxing or entertaining outdoors. A welcoming front porch provides yet another great space to unwind and enjoy the neighborhood. Upstairs, you’ll find a large second bedroom with ample closet space, a full bath, and a versatile loft area that works perfectly as a home office, guest retreat, or second family room. Additional highlights include a one-car garage with extra storage and low-maintenance living at its finest. Enjoy all the incredible amenities Heritage Harbour has to offer, including a clubhouse, indoor and outdoor pools, fitness center, golf course, tennis and pickleball courts, walking trails, community events, and more—all just minutes from downtown Annapolis. This is the one you’ve been waiting for—don’t miss it!
#MDAA2139088

ANNAPOLIS

906 PERRY LANDING COURT

2 Beds

2 Baths

2,569 Sq.Ft.

$599,900

MLS#: MDAA2139088

Before you scroll past this one, take a second look. This clean slate is the kind of home people come back to after they have missed it. ** 2 Silopanna Court ** stands out as one of the most compelling options in Annapolis within this price range and location. Tucked away on a quiet cul-de-sac just minutes from downtown Annapolis, this 2,000± square foot home offers the rare combination of privacy, meaningful upgrades, and everyday convenience. Since 2021, major improvements have already been handled for you, including a new roof, windows and sliders, vinyl siding with upgraded gutters, HVAC system, water heater, and fully updated kitchen and bathrooms... giving buyers confidence in both condition and long-term value. The layout offers 4 bedrooms and 2.5 baths with a natural flow that allows you to live comfortably day-to-day while still allowing flexibility for how you use the space. Set on a manageable, low-maintenance lot with no HOA, this is an ideal fit for buyers who want space and freedom without added restrictions. With its location just minutes to downtown Annapolis, dining, water access, and commuter routes, the home delivers both accessibility and a tucked-away feel. We’re already seeing increased activity after the repositioning. If you’ve been watching this one, now’s the time to act, this is typically where the prepared buyer steps in and it’s gone before you know it. Don't let that happen to you.
#MDAA2141372

ANNAPOLIS

2 SILOPANNA COURT

4 Beds

2 Baths

2,000 Sq.Ft.

$599,900

MLS#: MDAA2141372

Located in the water-privileged community of Cape St. Claire in Annapolis, this Dutch Colonial offers a practical layout, recent updates, and a private outdoor setting. The home features a traditional floor plan with multiple living areas, allowing for flexible use of space for everyday living, entertaining, and work-from-home needs. Recent interior improvements include fresh paint, bathroom upgrades, and newer vinyl plank flooring, providing a clean, updated feel. Major system updates include a newer roof and water heater, helping reduce the likelihood of immediate maintenance expenses. Set on a 0.21-acre shaded lot with established trees, the property offers natural privacy and a comfortable outdoor environment. An outbuilding provides additional storage or workspace. The 1-car garage and large driveway accommodate parking up to 4+/- vehicles. Cape St. Claire is a well-established, water-privileged community known for its access to the Chesapeake Bay lifestyle. Residents have access to multiple private community beaches, boat ramps, fishing piers, playgrounds, and open recreational areas. The Little Magothy River is located approximately five blocks away, providing convenient access for kayaking, boating, and fishing. The property is located within the Broadneck school district (buyer to verify), a factor many buyers consider when evaluating location. Conveniently located near Route 50, offering access to Annapolis, Baltimore, and Washington, D.C.
#MDAA2140126

ANNAPOLIS

1075 SUN VALLEY DRIVE

4 Beds

2 Baths

2,274 Sq.Ft.

$599,000

MLS#: MDAA2140126

New on site 2 days ago
Located in the popular waterfront community of Cape St. Claire in Annapolis, this lovingly renovated rancher sits on an elevated lot with fenced yard, large shed with electric, 40x14 garage with electric and ample off-street parking for guests. There is a multi-level deck with awning and paver patio in back for entertaining family and friends. Two finished levels feature 4 Bedrooms and 3 Full Baths, Recreation Room with brick wood-burning fireplace and den/office. Freshly painted and hardwood floors refinished -- the house sparkles! Recent improvements include Roof (2022), Windows (2022), HVAC (2023) and HWH (2022), Bathrooms remodeled and Kitchen updated. (2026). A wonderful opportunity to move in and immediately enjoy The Cape and all it has to offer – multiple beaches and parks, three marinas, shopping center, Broadneck High School, Cape St. Claire Elementary and Cape St. Claire Swim Club.
#MDAA2143804

ANNAPOLIS

970 HIGHPOINT DRIVE

4 Beds

3 Baths

2,062 Sq.Ft.

$595,000

MLS#: MDAA2143804

Welcome to this beautiful 2 bedroom 2 bath coveted end unit condo in the sought-after gated Chesapeake Harbour community, This home is a rare find, offering the perfect blend of privacy, natural light, and outdoor space. Inside, the additional square footage an end unit offers creates an open floor plan bathed in sunlight, thanks to windows on three sides. The living spaces are airy and inviting, with seamless flow from the cozy living room to the dining area and updated kitchen. You'll love the thoughtful details, including hardwood floors, a fireplace for those cooler evenings, and scenic views that bring the outdoors in. This home is ideally located to enjoy watching the sunrise over Chase Pond and the Bay with your morning coffee or tea. Later in the day the oversized wrap-around deck invites you to relax, entertain, or simply soak in the tranquil surroundings and watch the sunset over the Marina. Chesapeake Harbour is a vibrant, amenity-rich community with access to 2 pools, 2 tennis and pickle ball courts, kayaking, walking trails and a marina, all just minutes from downtown Annapolis. Whether you're a boating enthusiast or simply crave the coastal lifestyle, this property checks all the boxes. Don’t miss your chance to own this one-of-a-kind retreat. Schedule your tour today and experience Chesapeake Harbour living at its finest!
#MDAA2138114

ANNAPOLIS

2110 CHESAPEAKE HARBOUR DRIVE 101

2 Beds

2 Baths

1,237 Sq.Ft.

$595,000

MLS#: MDAA2138114

Elegant brick and siding split-foyer residence offering 4 bedrooms and 3 renovated full bathrooms on a beautifully sized 0.21-acre lot. The thoughtfully designed upper level features a sun-filled living room, formal dining area, well-appointed brand new kitchen with new appliances, and seamless access to the rear deck—perfect for refined indoor-outdoor living. Three bedrooms and two full baths complete the main level. The lower level is highlighted by a private primary suite with a generously renovated full bathroom, providing an ideal owner’s retreat or guest quarters, along with a spacious family/recreation room, laundry area, and mechanical room. Luxury vinyl flooring extends throughout both levels, complemented by windows in excellent condition. Major updates include the roof and HVAC system. Serviced by well and public sewer. A well-maintained home offering comfort, privacy, and timeless appeal.
#MDAA2134820

ANNAPOLIS

721 FAIRWAY DRIVE

4 Beds

3 Baths

2,080 Sq.Ft.

$585,000

MLS#: MDAA2134820

New on site 3 days ago
WELCOME HOME!This beautifully Renovated Eastport Marina Condo with Deeded 30’ Slip A 54 & Waterfront Pool.This 3-bed, 2-bath end-unit condo in sought-after Severn House Condominiums blends coastal charm with modern luxury. Nearly every detail has been refreshed or rebuilt—new electrical, premium hardwood flooring throughout, added in-unit laundry, and a fully renovated kitchen featuring butcher-block countertops, stainless-steel appliances, gas range with vent hood, built-in microwave, and designer recessed lighting throughout the home. Custom built-ins include a butler’s pantry and laundry cabinetry for smart, hidden storage.A full wall of sliding glass doors opens to a spacious deck offering peaceful seasonal views of Back Creek. The residence also includes a large deeded basement storage unit.Enjoy exclusive ownership of a deeded deep water 30+ foot boat slip—one of the few in Annapolis with direct vehicle access, allowing you to drive right to the dock for easy loading and unloading.Located in the heart of Eastport, Severn House offers a waterfront pool, beautifully maintained grounds, and the area’s most protected deep-water marina. Sidewalks lead to Downtown Annapolis, the U.S. Naval Academy, and the city’s famed restaurants and shops.This turnkey waterfront condo perfectly balances luxury, comfort, and location—schedule your private showing today.
#MDAA2144142

ANNAPOLIS

755 FAIRVIEW AVENUE 755 D

3 Beds

2 Baths

1,295 Sq.Ft.

$584,999

MLS#: MDAA2144142

***Major Price Reduction***Enjoy luxury condo living in this first-floor 2-bedroom, 2-bath home. Featuring gleaming hardwood floors, spacious and bright layout, and a stylish kitchen, this residence combines comfort and convenience. Park Place offers exceptional amenities including 24/7 concierge service, a pool, fitness center, meeting and party rooms, library, and a rear outdoor patio with a kitchen and grilling area—perfect for entertaining. The unit comes with a storage space as well as parking. Additional perks include a dog park and easy access to restaurants and shopping. A fabulous in-town location you won’t want to miss. Welcome home!
#MDAA2138356

ANNAPOLIS

5 PARK PLACE 107

2 Beds

2 Baths

1,272 Sq.Ft.

$575,000

MLS#: MDAA2138356

Welcome to Your Annapolis Dream Lifestyle! Fall in love with this sun-drenched, beautifully positioned home in the highly sought-after Southwoods community—just moments from everything that makes Annapolis so special. Imagine strolling to downtown for Navy games, enjoying waterfront dining, or taking daily walks along charming Main Street with your furry companion. This is more than a home—it’s a lifestyle. Step inside to a bright, open-concept floor plan designed for modern living and effortless entertaining. The seamless flow between living and dining spaces is anchored by a cozy fireplace—perfect for gathering with family and friends. Unwind on your screened porch with a refreshing drink, overlooking a low-maintenance yard bursting with color and fragrance—your own private retreat. Upstairs, this rare layout features two spacious primary en suites, each offering comfort and privacy. One bath is enhanced by a skylight, filling the space with beautiful natural light. The versatile lower level expands your options with a home office or third bedroom, media/lounge area, and laundry room—with a rough-in ready for a third full bath. The kitchen shines with warm wood flooring and upgraded stainless steel appliances, including a sleek smart touchscreen refrigerator—blending style and function perfectly. With timeless appeal and room to add your personal touch, this home is an incredible opportunity to create something truly special. All just minutes from downtown Annapolis, the Naval Academy, marinas, yacht clubs, shopping, dining, and easy access to Route 50. Opportunities like this don’t last—schedule your showing today and start living the Annapolis lifestyle you’ve been dreaming of! Bring Offers for Seller to Review!
#MDAA2141522

ANNAPOLIS

1561 RITCHIE LANE

3 Beds

2 Baths

2,322 Sq.Ft.

$575,000

MLS#: MDAA2141522

New on site 4 days ago
HERITAGE HARBOUR! It's the perfect size! 2 Bedrooms. 2 full Baths. Den. Sun Room Addition. Deck (2025). HVAC (2025). Architectural Shingle Roof (2021). HHCA's site touts the community as... an established community in Annapolis, offering beautiful wooded lots and featuring a wide variety of recreational, cultural, social, and educational activities for its residents. Residents can participate in over 90 activities, clubs and committees. The center of community activities is the Lodge, which features a welcoming atrium, an auditorium, indoor and outdoor pools, fitness center, library, boutique, activities room, woodwork shop, game rooms, coffee corner and meeting rooms. Behind the Lodge, residents enjoy a picnic area, horseshoes, bocce ball and kayaking on our waterfront on the South River. We also offer multiple tennis and pickleball courts, a nine-hole golf course, a pro shop, a clubhouse dining room, a pier with boat slips and RV and boat storage on a lot in the community. Residents enjoy the convenience of regular bus trips to shopping centers and special bus trips to cultural destinations, as well as volunteer drivers for medical appointments. Our pet-friendly community of active residents always welcomes newcomers!
#MDAA2143166

ANNAPOLIS

2550 GOLFERS RIDGE ROAD

2 Beds

2 Baths

1,661 Sq.Ft.

$570,000

MLS#: MDAA2143166

Beautiful 1 BR /1.5 Bath condo, penthouse level w/many extras in the most luxurious, secure building in downtown Annapolis. Great sunset views, natural light, large custom BUILT-IN walk-in closet, plus 2 additional closets. sliding glass doors with luxury electric blinds system, wood floors throughout, gourmet kitchen w/Sub Zero refrigerator, Washer/Dryer inside the guest bathroom, Asko dishwasher, stainless appliances & granite counters. Updated, beautifully remodeled shower. Many building amenities: Pool, Hot Tub, Fitness Center, large Party Room, 24/7 live Concierge/Security Person in lobby. One deeded Underground Garage Parking Space with remote door opener. Washer/Dryer inside the guest bathroom. Note; Light fixture above dining table excluded. Extra Garage Storage unit may be available separately. Luxury living in the heart of Annapolis, just blocks to Downtown City Dock attractions and restaurants.
#MDAA2143430

ANNAPOLIS

5 PARK PLACE 732

1 Beds

1 Baths

926 Sq.Ft.

$567,900

MLS#: MDAA2143430

Location Location location!! Modern rancher style home located near everything Annapolis has to offer! It's just minutes to Downtown Annapolis. The House is much bigger than it looks. A beautiful fenced in backyard with a composite decking awaits for outdoor entertaining. This house also features 5 bedrooms and two full bath. This home is almost 2,000 sf. finished. Entire home was fully renovated in 2025. The finished basement features a laundry room, family room, 2 spacious bedrooms, and one full bathroom. The whole top level features 3 bedrooms, one full bath, open concept style kitchen with island that opens to the dining space and large living room. New HVAC, plumbing and electrical system. Move-in ready, fully furnished!! This home really offers a wonderful opportunity to enjoy Annapolis living — just minutes from shopping, dining, and commuter routes.
#MDAA2130284

ANNAPOLIS

1002 TYLER AVENUE

5 Beds

2 Baths

1,920 Sq.Ft.

$565,000

MLS#: MDAA2130284

Welcome to 102 Vanguard Lane, an elegant gated community offering a home with refined finishes and comfort in the heart of Annapolis. Rich hardwood floors throughout the main level, while the kitchen impresses with granite countertops and a brand-new refrigerator. Custom plantation shutters & blinds; upgraded lighting & more! Exterior w/ Hardiplank siding & beautiful deck off kitchen that includes an amazing indoor/outdoor fireplace! This beautifully updated home showcases brand-new paint and new carpet throughout, creating a pristine, move-in-ready experience. Thoughtfully refreshed and designed for both everyday luxury and memorable gatherings, this home offers an exceptional lifestyle just minutes from Annapolis dining, shopping, and waterfront attractions. A rare opportunity to enjoy comfort, style, and location—all in one exceptional property.
#MDAA2134520

ANNAPOLIS

102 VANGUARD LANE

4 Beds

3 Baths

2,000 Sq.Ft.

$565,000

MLS#: MDAA2134520

A truly exceptional opportunity—a dream space ready for new owner.  Welcome to a design-forward showcase where every detail has been reimagined and curated to create a warm, modern aesthetic sanctuary.   With over $150,000 in custom upgrades, this one-of-a-kind residence offers a level of creativity and craftsmanship rarely seen in the community. ***Experience your best Annapolitan lifestyle in the sought-after Winters Chase section of Riva Trace—where nature, water access, and amenities are all just steps away.***Spanning three fully finished levels and backing to trees for added privacy, this home blends everyday convenience with elevated living. A one-car garage and close proximity to tennis courts the walking path and community pier with water access complete the lifestyle appeal.***The private front courtyard has been transformed into an inviting outdoor retreat—perfect for unwinding or hosting an intimate happy hour. ***Inside, the stunning, fully reimagined kitchen was designed for both entertaining and daily living:  Featuring premium Bosch Stainless appliances, custom soft-close cabinetry, and $12,000 quartz countertops with a full-height backsplash, all centered around an oversized island offering additional prep space and seating.***Upstairs, escape to a resort-inspired owner’s suite designed for total relaxation. Highlights include designer tile accents, a 70” Boyce soaking tub, and an open-concept wet-room shower, accent walls,  integrated Bluetooth speaker with mood lighting and Second Chance antique closet door for a true resort-style experience.  ****The secondary bedroom offers a walk-in closet, remote-control window shades, and access to attic storage with zoned HVAC. A beautifully remodeled $14,000 guest bath features rustic cabinetry, custom tilework, a frameless glass shower, and rain shower head. ***The finished lower level adds incredible versatility—perfect for a home office, gym, recreation room, or even a cinematic theater experience, complete with cabinetry and shelving that conveys. ***This is more than a home—it’s a lifestyle upgrade.***Schedule your private showing today and experience it for yourself.***Be sure to explore the interactive floor plan and virtual tour.
#MDAA2142612

ANNAPOLIS

2924 WINTERS CHASE WAY

2 Beds

2 Baths

2,136 Sq.Ft.

$565,000

MLS#: MDAA2142612

New on site 3 days ago
Charming cedar sided chalet style set in the wooded and beach access community of Cape St Claire. Enter into a dramatic cathedral ceiling living and dining space with skylights, looking through to a three season clerestory windowed addition where you will welcome family and friends. Sliders from the tall window surrounded sun room open onto a deck with room for feasts and relaxing. Memories are made here. An island and deep pantry in the kitchen with a plant window for your herbs to thrive provide plenty of storage. Generous bedroom and updated bath on the main level offer convenience and privacy. Upstairs two bedrooms are separated by a second full bath. Extensive landscaping with perennials lets you enjoy nature's blooms with little fuss. A fenced garden on the sunny side of the house is waiting to provide perfect tomatoes, cukes, peppers or vivid flowers for your table. Recent updates include replaced and stained cedar siding on one wall and trim throughout. Entry porch has been refreshed as well as decking replaced on deck off sunroom. A new roof, new washer and dryer, new and upgraded alarm system top off the new luxury vinyl plank on the main level.
#MDAA2144128

ANNAPOLIS

1189 HIGHVIEW DRIVE

4 Beds

2 Baths

2,500 Sq.Ft.

$565,000

MLS#: MDAA2144128

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