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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
264
# of Listings
3
Avg # of Bedrooms
$482
Avg. $ / Sq.Ft.
$1,293,351
Med. List Price

Browse Annapolis Real Estate Listings

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264 Properties Found. Page 17 of 18.

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.
#MDAA2129812

ANNAPOLIS

668 N BESTGATE ROAD

None Beds

None Baths

0.65 acres

$325,000

MLS#: MDAA2129812

Welcome to effortless living in one of Annapolis' most sought-after locations. With new systems like the efficient gas furnace and hot water heater, this well-maintained 2-bedroom, 2-bathroom condominium offers 1,065 square feet of comfortable living space with one standout feature that sets it apart: main-level access. In a building with no elevator, this ground-floor location means you'll never climb a single flight of stairs—ideal for those seeking accessibility and convenience. Step outside your front door onto a charming patio where you can enjoy your morning coffee or unwind after a day exploring everything Annapolis has to offer. This private outdoor space adds a welcoming touch to everyday living. The real magic lies in what's just beyond your doorstep. You're within walking distance or a short drive to the Annapolis Historic District, where cobblestone streets lead to the Maryland State House, boutique shops, and acclaimed restaurants. Stroll down to City Dock for waterfront dining and sailing culture, or catch a game at Navy-Marine Corps Memorial Stadium. The U.S. Naval Academy is practically in your backyard—making this an exceptional opportunity for parents of midshipmen seeking a convenient pied-à-terre during their student's four years at the Academy. Daily conveniences are equally close at hand: grocery stores, houses of worship, and easy transportation connections to Washington, D.C. for work or weekend adventures are here. With modest association fees and no-frills ownership, this condo delivers exceptional value in a location where proximity to history, culture, and community commands a premium. Whether you're downsizing, investing, or establishing a local home base, this main-level gem offers the freedom to live well in one of the Mid-Atlantic's most charming cities.
#MDAA2140882

ANNAPOLIS

2001 WARNERS TERRACE N 102

2 Beds

2 Baths

1,065 Sq.Ft.

$324,500

MLS#: MDAA2140882

Serenity Meets Convenience at The Reserve in Heritage Harbour, a premier 55+ community! What sets this unit apart from every other in the building is its unique relationship with the outdoors. As the only unit featuring a private brick patio with direct walk-out access to the parking lot and sidewalks, it bridges the gap between condo living and the autonomy of a villa. For the pet owner, it means no more navigating elevators or hallways at 6:00 AM; for the traveler, it means unloading luggage is a breeze. It is the gold standard for accessibility and ease, seamlessly blending indoor comfort with the outdoors. Inside, the home shines with fresh paint and gleaming hardwood floors. The open-concept living and dining areas flow naturally to the patio, creating an expansive feel for entertaining. The kitchen features 42-inch cabinetry, Corian countertops, and a four-burner gas stove with a grill insert, plus a sun-drenched bistro breakfast nook. The primary suite is a true sanctuary, featuring brand-new plush carpeting and a unique sunroom sitting area—ideal for a home office or reading nook. The spa-like ensuite boasts a new walk-in shower, granite counters, and a vessel sink. Practicality is built-in with a spacious walk-in closet, a dedicated laundry room with a new washer/dryer, and an extra storage cage in the building’s basement. Heritage Harbour Living: Living here grants access to The Lodge, the community’s social heartbeat. Enjoy world-class amenities including: indoor and outdoor pools & fitness center, tennis, pickleball, bocce, and a community golf course, woodworking shop, arts room, and a well-stocked library, private kayak launch on the South River. 90+ clubs and a robust social calendar. Located just minutes from Downtown Annapolis with easy access to Routes 50 and 97, this home offers the perfect balance of peaceful retreat and urban accessibility. Don’t miss this rare opportunity for true single-level living in a vibrant, amenity-rich enclave.
#MDAA2135514

ANNAPOLIS

940 ASTERN WAY 102A

1 Beds

1 Baths

1,073 Sq.Ft.

$321,349

MLS#: MDAA2135514

Spring has arrived, and this beautifully updated 3-bedroom, 2-bath condo offers the perfect opportunity to enjoy the best of the Annapolis lifestyle. Located on the 3rd floor, this light-filled home combines modern upgrades, comfort, and unbeatable access to outdoor recreation and waterfront attractions. Inside, the open-concept living, dining, and kitchen area creates a warm and inviting flow, complete with a cozy fireplace—perfect for relaxing after a day on the water or exploring the city. The renovated kitchen (2022) features granite countertops, farmhouse sink, stainless steel appliances, and contemporary cabinetry designed for both everyday living and entertaining. Brand-new windows (2021) fill the home with natural light. The spacious primary suite includes a private en-suite bath and direct access to a walkout patio overlooking the community pool—an ideal spot for morning coffee, evening sunsets, or enjoying the spring breeze. Generous closet space throughout and updated bathroom finishes add to the home’s appeal. For buyers who love the outdoors, this location is exceptional. Just minutes away, enjoy scenic walking and biking trails, waterfront views, picnic areas, dog-friendly spaces, and seasonal outdoor activities at Quiet Waters Park, a local favorite with over 300 acres of trails and water access. You’re also moments from Historic Downtown Annapolis, Spa Creek, Back Creek marinas, waterfront dining, kayaking, sailing, and Chesapeake Bay attractions, making it easy to enjoy the coastal lifestyle that makes Annapolis so desirable. Community amenities include a swimming pool and convenient pet stations for easy living. Whether you're looking for a primary residence, a low-maintenance coastal retreat, or a home close to parks and the waterfront, this condo offers outstanding value and location. Now is the perfect time to make your move—schedule your private showing today and experience spring in Annapolis at its best.
#MDAA2129788

ANNAPOLIS

10 SANDSTONE COURT L

3 Beds

2 Baths

1,333 Sq.Ft.

$310,000

MLS#: MDAA2129788

Turnkey Investment Opportunity – 2 Bed, 2 Bath Condo with Tenant in Place + Rental Upside. Excellent opportunity for investors seeking immediate rental income with future growth potential. This well-maintained 2-bedroom, 2-bathroom condo is currently leased at $2,200/month, providing steady cash flow from day one, with market rents estimated around $2,600/month—offering clear upside. The unit features a bright, open layout with abundant natural light, a cozy wood-burning fireplace, and the convenience of an in-unit washer and dryer. The updated kitchen includes modern appliances, while recent upgrades such as a 2-year-old HVAC system and newer carpet (installed within the last 2 years) help minimize near-term maintenance costs. The spacious primary suite includes a private en-suite bathroom, and the second bedroom offers flexibility for tenants or future owner use. The unit also includes two assigned parking spaces, a highly desirable feature for both tenants and homeowners. Located in a well-maintained community with sought-after amenities including a pool and fitness center, this property is attractive to renters and equally appealing as a comfortable future residence—perfect for an investor today and homeowner tomorrow. Ideally situated with easy access to parks, shopping, and downtown, the location supports strong and consistent rental demand. Tenant in place—making this a true turnkey investment. Immediate income today with the potential to increase rents closer to market value.
#MDAA2142956

ANNAPOLIS

40 GREYSTONE COURT G

2 Beds

2 Baths

1,336 Sq.Ft.

$310,000

MLS#: MDAA2142956

Price reduced! 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.
#MDAA2138378

ANNAPOLIS

10 AMBERSTONE COURT B

2 Beds

2 Baths

1,138 Sq.Ft.

$309,900

MLS#: MDAA2138378

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.
#MDAA2140406

ANNAPOLIS

796 FAIRVIEW AVENUE F 796 F

1 Beds

1 Baths

756 Sq.Ft.

$308,000

MLS#: MDAA2140406

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!
#MDAA2128842

ANNAPOLIS

7101 BAY FRONT DRIVE 301

1 Beds

1 Baths

1,000 Sq.Ft.

$300,000

MLS#: MDAA2128842

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.
#MDAA2138752

ANNAPOLIS

21 SILVERWOOD CIRCLE 11

3 Beds

2 Baths

1,670 Sq.Ft.

$300,000

MLS#: MDAA2138752

Welcome to this fully renovated, single level condo on the 2nd floor of the building. One of the most recently updated 2-bedroom unit in the community, featuring brand-new flooring throughout and a gorgeous new kitchen with granite countertops, new stainless steel appliances, and other modern finishes. The open-concept living area is spacious and inviting. Community amenities include an outdoor pool, exercise room, and recreational clubroom. Reserved/assigned parking is available for two vehicles.
#MDAA2142030

ANNAPOLIS

10 SANDSTONE COURT G

2 Beds

2 Baths

1,103 Sq.Ft.

$298,500

MLS#: MDAA2142030

Welcome to this beautifully updated terrace-level condo offering the perfect blend of comfort and style. This 2-bedroom unit features fresh paint, brand-new carpet, and an upgraded kitchen complete with new countertops and stainless steel appliances. Enjoy easy single-level living with a spacious, open-concept layout that flows seamlessly to a private setting with peaceful forest views—ideal for relaxing or entertaining. Community amenities include an outdoor pool, fitness center, and clubhouse. Two reserved parking spaces convey. Move-in ready and one of the best updated units in the community—don’t miss it!
#MDAA2142750

ANNAPOLIS

10 SANDSTONE COURT K K

2 Beds

2 Baths

1,200 Sq.Ft.

$295,000

MLS#: MDAA2142750

Take advantage of the opportunity to own this beautifully maintained two-bedroom, two full bath condo in Annapolis. Offering convenient one-level living, this home combines comfort, updates, and an ideal location. The kitchen is thoughtfully appointed with granite countertops, stainless steel appliances, updated LED lighting, and additional seating space—perfect for casual dining or entertaining. Hardwood flooring and crown molding add warmth and character to the living and dining areas. Step outside to your private patio, ideally situated near the community pool and grills, creating an easy extension of your living space. The spacious primary suite features a large walk-in closet and a private bath with walk-in shower. Both bedrooms offer newly installed carpet (2026). A second full bath with tub and shower provides flexibility for guests or family. The separate laundry room includes a washer and dryer, plus valuable storage space. The monthly condo association fee adds exceptional value, covering water, sewer, oil for the hot water heater, trash and recycling, snow removal, grounds maintenance, and pool membership. The association also maintains the hot water heater and installed a new roof in 2026, offering additional peace of mind. Ideally located just minutes from downtown Annapolis and Quiet Waters Park, this home offers the perfect blend of low-maintenance living and access to everything Annapolis has to offer.
#MDAA2138190

ANNAPOLIS

300 HILLTOP LANE 300B

2 Beds

2 Baths

1,078 Sq.Ft.

$285,000

MLS#: MDAA2138190

BIG LOFT AREA**NEW PRICE-GREAT VALUE***Welcome home to this spacious two bedroom two full bath condo with a loft. Stainless appliances in the kitchen, the stove is brand new, fine cabinets and granite countertops. Hardwood flooring in the living room and dining room, and a nice balcony though the living room slider. The primary bedroom has a large walk-in closet and attached full bath. And, the second bedroom is across the hall from the second full bath. Go up the spiral staircase to a huge family room area. The bathrooms were renovated in 2024 and the washer and dryer were replaced in 2024 as well. There are two (dual) HVAC systems, one for the lower level (replaced in 2022) and one for the loft (replaced 2019). A new roof was installed 2026, and is maintained by the condo association. The community has a great outdoor pool for summertime, and across Hilltop Dr is plenty of recreational opportunity at The Pip Moyer Rec Center and Truxton Park. Great price for a great location!
#MDAA2126114

ANNAPOLIS

300 HILLTOP LANE 300I

2 Beds

2 Baths

1,321 Sq.Ft.

$280,000

MLS#: MDAA2126114

Ground Floor Living! Absolutely stunning & fully remodeled condo in Fairwinds of Annapolis. Featuring 2 bedrooms and 2 full bathrooms, this condo shows as well as any condo you will find in the entire community. The unit boasts brand new LVP flooring, beautiful white Shaker cabinets, stunning new quartz counters, new SS appliances, 2 spectacularly remodeled bathrooms, brand new lighting throughout, and entire unit freshly painted. In unit laundry with custom made "Kenneth Alexander" barn door. It will be hard to find a more finely appointed condo in the entire association!
#MDAA2139322

ANNAPOLIS

205 VICTOR PARKWAY D 205D

2 Beds

2 Baths

972 Sq.Ft.

$279,999

MLS#: MDAA2139322

NEW HVAC November 2024*** NEW LIGHTING 2024***NEW ELECTRICAL PANEL 2026 ***New shower door in master bathroom >>>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.
#MDAA2139798

ANNAPOLIS

5 SILVERWOOD CIRCLE 1

2 Beds

2 Baths

N/A

$279,900

MLS#: MDAA2139798

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