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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

208

# of Listings

3

Avg # of Bedrooms

$514

Avg. $ / Sq.Ft.

$1,088,715

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

208 Properties Found. Page 13 of 14.

Welcome to this beautiful 2-bedroom, 2-bath condo in the highly sought-after Tidewater Colony community of Annapolis. Inside, you’ll find 9-foot ceilings, luxury vinyl plank floors, custom blinds, and a modern kitchen with granite countertops, gas cooking, and a built-in microwave.

The spacious primary suite features a double vanity and a luxurious bath with separate shower and soaking tub. Additional highlights include high-efficiency HVAC and a dedicated laundry room with full-size washer and dryer.

Enjoy resort-style living with access to the clubhouse, fitness center, pool, tennis courts, playground, and walking trails. Perfectly positioned just minutes from downtown Annapolis and Anne Arundel Medical Center, with easy commuter access to Route 50 and Route 97.

A prime location paired with comfort and convenience—this one checks all the boxes.

ANNAPOLIS

2006 PEGGY STEWART WAY 204

2 Beds

2 Baths

1,046 Sq.Ft.

$345,000

MLS#: MDAA2136790

Beautifully updated first floor condo! Featuring new LVP flooring, carpet, paint and appliances. Truley a must see.

ANNAPOLIS

2013 WARNERS TERRACE S 138

2 Beds

2 Baths

1,062 Sq.Ft.

$339,995

MLS#: MDAA2135668

+++ATTENTION ATTENTION+++ARE YOU LOOKING FOR A REHAB PROJECT?+++ THIS COULD BE THE ONE YOU HAVE BEEN WAITING FOR THEN!+++FULL PROJECT WAITING FOR YOU IN ANNAPOLIS+++MINUTES FROM DOWNTOWN ANNAPOLIS - KNOWN FOR IT'S MANY SELECTIONS OF RESTAURANTS , DIVERSE SHOPPING BOUTIQUES, AND NIGHTLIFE+++SHOPIING, SCHOOLS and PLACES OF WORSHIP NEARBY+++THIS 2 LEVEL SPLIT FOYER ALSO OFFERS AN INGROUND POOL+++KITCHEN ONLY HAS DATED CABINETS, NO appliances+++BATHROOMS ARE IN DISREPAIR, ALONG WITH SO MANY OTHER AREAS+++INVESTORS AND OWNER OCCUPANTS ARE WELCOME TO VIEW+++REAR DECK and DECK Steps are a HAZARD+++

ANNAPOLIS

391 HILLTOP LANE

3 Beds

1 Baths

1,717 Sq.Ft.

$338,000

MLS#: MDAA2136038

Fabulous Annapolis Condo Featuring 2 Bedrooms & 2 Full Baths! Tasteful Decor Thru-Out. Spacious Living Room Boasts a Corner Gas Fireplace. Updated Kitchen has Granite Counter Tops & a Breakfast Bar. Master Bedroom has an En-Suite Bath & Walk-In Closet. Access the Huge 20 x 8 Composite Deck w/ Attached Storage via the Living Room & Master Suite. Community Tot Lot & Walking Trail. Great Location w/ Easy Access to RT-50 & Only a Few Minute Drive to the Annapolis Mall, Navy-Marine Corp Stadium, Anne Arundel Medical Center and Downtown Historic Annapolis. Enjoy All That Living in Annapolis has to Offer - Restaurants, Historic Homes, Navy Games and the Wonderful Chesapeake Bay! Tenant Occupied until 4/30/26. Owner will Settle Prior to that Date & Prorate the Rent Accordingly.

ANNAPOLIS

2013 WARNERS TERRACE S 242

2 Beds

2 Baths

1,062 Sq.Ft.

$335,000

MLS#: MDAA2136090

Discover the charm of this inviting 2-bedroom, 2-bathroom condo in the desirable Scotts Crossing community. Built in 2001, this well-maintained unit features a warm blend of hardwood and carpet flooring, creating a cozy atmosphere throughout. The spacious dining area is perfect for gatherings, while the living room, complete with a gas fireplace, offers a serene retreat for relaxation. Enjoy the convenience of in-unit laundry facilities, making everyday chores a breeze. The bathrooms are thoughtfully designed, featuring both a tub shower and a walk-in shower for your comfort. Ceiling fans enhance the airy feel, ensuring a pleasant environment year-round. New dishwasher 11/24. HVAC 10/2024. Water Heater 1/2026. MIcrowave 4/21. Carpet in bedrooms replaced 6/2025.With common area maintenance included in the association fee, you can spend more time enjoying the beautifully landscaped grounds. This home is not just a place to live; it's a sanctuary where comfort meets convenience. Don't miss the opportunity to make this delightful space your own! Conveniently located close to downtown Annapolis, hospital and all major routes.

ANNAPOLIS

2159 SCOTTS CROSSING COURT 201

2 Beds

2 Baths

1,096 Sq.Ft.

$335,000

MLS#: MDAA2139656

0.65-acre corner lot along Bestgate Road in Annapolis with frontage on both Bestgate and Willey. Zoned R2, allowing for a single-family detached home. Public water and sewer connections are available through Anne Arundel County. Buyers will need to apply for service, obtain a connection permit, and pay the applicable capital facility charge along with any contractor installation costs.

The existing well and septic are assumed to be nonfunctional. All site engineering, utility applications, and permitting will be the responsibility of the buyer. Convenient location near Route 50, downtown Annapolis, and area shopping. Excellent opportunity for a custom home project or long-term hold in a highly accessible central corridor.

ANNAPOLIS

668 N BESTGATE ROAD

None Beds

None Baths

0.65 acres

$325,000

MLS#: MDAA2129812

Perched on the top floor of the sought-after Fairwinds of Annapolis community, this beautifully updated condo offers a quiet retreat with no neighbors above and serene courtyard views. Surrounded by mature trees and thoughtfully landscaped common areas, residents enjoy a well-maintained setting complete with a pool, tennis courts, tot lots, snow removal, picnic areas for grilling, bike and kayak storage racks.
Inside, the home has been updated throughout with stylish luxury vinyl plank flooring, creating a cohesive and modern feel. The spacious living room is filled with natural light and features a sliding glass door that opens to a private deck overlooking the courtyard. The deck is enhanced with new acacia wood decking and provides an ideal spot to relax or unwind. The living area flows seamlessly into the dining room, making everyday living and entertaining effortless.
The kitchen combines function and style with stainless steel appliances, including a gas range with a double oven, along with a comfortable breakfast area for casual dining.
Tucked at the end of the hall, the spacious primary bedroom offers a peaceful retreat with a walk-in closet, a second closet, and a private en-suite bath. Two additional generously sized bedrooms share a well-appointed hall bath, providing flexibility for guests, family, or a home office. An in-unit laundry room adds everyday convenience. Thoughtful updates enhance the home’s appeal, including new toilets, updated electrical components, and a newly installed range and microwave. Additional upgrades such as new window blinds and updated cabinet pulls add a polished finishing touch.
Parking is easy with ample unassigned spaces available, along with the option to secure a reserved parking decal for an additional fee. In addition to the community amenities, residents enjoy a vibrant mix of local Annapolis amenities including charming waterfront dining and boutique shopping in historic downtown and scenic strolls along the City Dock. Outdoor enthusiasts can take advantage of nearby parks, the Chesapeake Bay, easy access to bike trails, and a variety of community events and farmers markets. Combining thoughtful updates, a functional layout, and a quiet top-floor location, this home offers comfortable living in a vibrant and amenity-rich community.

ANNAPOLIS

21 SILVERWOOD CIRCLE 11

3 Beds

2 Baths

1,670 Sq.Ft.

$325,000

MLS#: MDAA2138752

OPEN HOUSE THIS SUNDAY MARCH 8TH 12 P.M. - 2:00 P.M.

Serenity Meets Convenience at The Reserve in Heritage Harbour: 1st-Floor Living in Prime Annapolis 55+ Community

Discover the perfect blend of peace and accessibility in this immaculately maintained first-floor condo. Tucked away amidst mature trees and set well back from the main road, this secure building offers a quiet retreat just minutes from Downtown Annapolis.

Step inside to find fresh paint throughout and a free-flowing floor plan with hardwood floors in the main living area (living room, dining room and kitchen). The seamless living and dining areas open directly onto a private brick patio—perfect for celebrating the seasons or enjoying easy walk-out access to the sidewalks and parking. SO convenient for walking our furry friends! The eat-in kitchen is a chef’s delight, featuring 42” cabinetry, Corian countertops, 4-burner gas stove with a grill insert and a charming bistro breakfast area.

Retreat to the generous primary suite where you'll be greeted by sun and new carpet. This space boasts a unique sunroom sitting area, a spacious walk-in closet, and a bonus storage closet.

Large primary suite bathroom offers ceramic flooring, a vessel sink, granite countertop and a new walk-in shower. A separate laundry/utility room adds to the ease of daily living. Here you'll find a new washer and dryer and loads of additional storage space.

This unit is part of a premier 55+ community that truly has it all. Beyond the secure entry and clubroom, residents enjoy resort-style amenities including indoor and outdoor pools, a fitness center, tennis and pickleball courts, a golf course, and even a kayak launch. With a full calendar of social events and a location moments from Routes 50, 97, and 665, this is low-maintenance living at its finest.

ANNAPOLIS

940 ASTERN WAY 102A

1 Beds

1 Baths

1,073 Sq.Ft.

$321,349

MLS#: MDAA2135514

This lovely first floor condo, conveniently located in Annapolis, has two bedrooms, a den and two full bathrooms. Open concept living room, dining area and kitchen with a nice patio overlooking the woods behind it. Ceramic floors in the front hall and kitchen. Freshly painted throughout. New carpet in the den and two bedrooms. Luxury vinyl plank flooring in the living room and dining room area. Washer and dryer were replaced in the past year. Two parking spaces. Community pool. Can settle quickly.

ANNAPOLIS

10 AMBERSTONE COURT B

2 Beds

2 Baths

1,138 Sq.Ft.

$315,000

MLS#: MDAA2138378

New on site today

Welcome to effortless waterfront living in the sought-after Severn House community! This charming 1-bedroom, 1-bath condo offers the perfect blend of tranquility and Annapolis lifestyle—whether you're paddleboarding out for your morning coffee, hopping on the water taxi for an evening in town, or enjoying sunset cruises from your own rented boat slip. Spend your days lounging by the waterfront pool, hosting crab feasts with friends, or simply soaking in the peaceful surroundings. Tucked away on the third floor and backing to woods, this unit offers rare privacy and a quiet retreat from the buzz of downtown—while still being just minutes away. The condo fee covers gas, water, sewer, and basic cable—making for easy, low-maintenance living (just pay electric). A dedicated basement storage unit adds extra convenience.
Located close to Eastport Shopping Center, restaurants, coffee shops, the gym, and the farmers market, this is your opportunity to enjoy the best of coastal Annapolis living—every single day.

ANNAPOLIS

796 FAIRVIEW AVENUE F 796 F

1 Beds

1 Baths

756 Sq.Ft.

$315,000

MLS#: MDAA2140406

#MDAA2129788

ANNAPOLIS

10 SANDSTONE COURT L

3 Beds

2 Baths

1,333 Sq.Ft.

$310,000

MLS#: MDAA2129788

Perhaps the finest Annapolis has to offer...A premiere, resort style retirement living option for those 60+ Time to let someone one else take care of the daily cooking and cleaning, you only need to relax, socialize with your friends and enjoy all Annapolis, Md has to offer! One monthly fee takes care of ALL utilities, daily meal, weekly cleaning, taxes, insurance, garage parking, maintenance/replacement of all appliances and HVAC. You've earned this!

ANNAPOLIS

7101 BAY FRONT DRIVE 301

1 Beds

1 Baths

1,000 Sq.Ft.

$300,000

MLS#: MDAA2128842

New on site 2 days ago

Welcome to this beautifully maintained 2-bedroom, 2-bath condominium in the desirable Annapolis Overlook community, offering 1,376 square feet of comfortable living space. This inviting home features warm wood flooring and a cozy wood-burning fireplace, creating the perfect setting for both everyday living and relaxing evenings.

Step outside onto your private balcony and enjoy peaceful wooded views—an ideal spot for morning coffee or unwinding at the end of the day. Residents of Annapolis Overlook also enjoy access to a community pool and work out room, adding to the convenience and lifestyle appeal.
Just a short stroll away is Quiet Waters Park featuring Hiking, Biking Trails, Canoe Rentals, a Dog Park and a great spot for Ice Skating weddings and special events!

Located just minutes from downtown Annapolis, the scenic waterfront, and the renowned United States Naval Academy, this home offers unbeatable proximity to shopping, dining, and entertainment.

Whether you’re looking for a primary residence, weekend getaway, or investment opportunity, this property checks all the boxes with its location, layout, amenities, and charm. Don’t miss your chance to own in one of Annapolis’ most sought-after areas!

2 assigned parking spaces #30 and #12. Plenty of Additional parking right down the street.

ANNAPOLIS

30 HEARTHSTONE COURT J J

2 Beds

2 Baths

1,376 Sq.Ft.

$295,000

MLS#: MDAA2139932

New on site 2 days ago

Popular Fairwinds Condo is a great place to live!! Two Bedroom Two Bath with den condominium ! Newer stainless steel appliances ! Freshly painted 2026 ! Luxury Vinyl thru living areas and carpet in bedrooms! Lots of closets and storage! Extra storage area included in basement ! Master bedroom has full bath ! Updated kitchen ! New light fixtures including eyeball lights! New glass door in shower of master bath! Granite countertops in kitchen! Stack washer/dryer nearly new. Awesome enclosed patio for private grilling! Amenities in Fairwinds include swimming pool, tennis courts and tot lot. (Agents: Day Sleeper some days; see remarks for Agen Private for good date for showings)

ANNAPOLIS

5 SILVERWOOD CIRCLE 1

2 Beds

2 Baths

N/A

$293,500

MLS#: MDAA2139798

#MDAA2126114

ANNAPOLIS

300 HILLTOP LANE 300I

2 Beds

2 Baths

1,321 Sq.Ft.

$290,000

MLS#: MDAA2126114

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