MLS Listings for Sale in Chester, MD

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ABOUT THIS HOME
MLS Listings for Sale in Chester, MD
Step inside and see this meticulously cared for home! This home features a first floor primary bedroom with an ensuite full bath. Just 5 minutes from the Chesapeake Bay Bridge and all the beaches, parks, boat ramps, and waterfront venues you love to visit. .. right in your own neighborhood! This " Home Sweet Home" in Chester, Queen Anne's County, MD has been thoughtfully improved throughout, with luxury vinyl plank floors, kitchen with updated appliances & counter tops as well as a breakfast nook. The kitchen opens to a large family room with a cozy gas fireplace. The dining area overlooks the rear patio, where the owners have thoughtfully added a retractable awning. Th

$519,900

3 beds2.5 baths2,066 sq ft

112 Chessie Ct, Chester, MD 21619

7,598 sq ft lot • Garage • Built 2000

(443) 249-7653

COMING SOONVIDEO TOUR

ABOUT THIS HOME
MLS Listings for Sale in Chester, MD
Set within Southwind, one of Kent Island’s most sought-after waterfront communities, this exceptional residence offers an elegant blend of craftsmanship and comfort with 10 foot ceilings and beautiful crown molding. Perfectly sited on an acre overlooking Crab Alley Bay and Eastern Bay, the home’s peaceful setting is enhanced by sweeping water views, mature landscaping, and a private waterside pool that invites year-round enjoyment. Inside, timeless design meets modern refinement. The first-floor primary suite provides a serene retreat, joined by two additional guest suites on the main level—each with its own ensuite bath for privacy and comfort. Upstairs, a fourth bedroom

$1,899,000

4 beds5 baths3,460 sq ft

2907 Cox Neck Rd E, Chester, MD 21619

1 acre lot • $146 HOA • 2 garage spots

(410) 280-5600

NEW 8 HRS AGO

ABOUT THIS HOME
MLS Listings for Sale in Chester, MD
Beautifully maintained first-floor condominium offering an open, inviting floor plan. This residence features two spacious bedrooms and one and a half bathrooms. The light-filled living and dining areas provide direct access to a patio, with storage closet. All kitchen appliances, stainless steel, only 1 year old, and counter tops updated. Both bathrooms remodeled in 2021. Washer & dryer brand new. Located in a highly desirable community of Bayside, offering exceptional amenities including scenic walking trails, a clubhouse with a party room, fitness center, swimming pool, and tennis courts. Conveniently situated near shopping, dining, and major commuter routes, this home offers the

$305,000

2 beds1.5 baths1,073 sq ft

302 Teal Ct Unit A, Chester, MD 21619

Kitchen appliances • Stainless steel • Storage closet

(410) 451-3300

COMING SOON

ABOUT THIS HOME
MLS Listings for Sale in Chester, MD
Professional photos coming soon. Discover this beautifully updated 3-bedroom, 2.5-bath home located on a scenic 0.35-acre corner lot in the highly desirable Harbor View community, just two miles east of the Chesapeake Bay Bridge. Inside, enjoy a modern kitchen with new countertops and backsplash, engineered hardwood floors on the main level, and a spacious lower-level family room plus a versatile bonus room. Recent upgrades include a new roof (2019) with 50-year shingles, new windows, and a new vinyl pool liner with warranty. Step outside to your fully fenced back yard and private in-ground pool and deck, perfect for summer entertaining and relaxing. The commun

$495,000

3 beds2 baths1,728 sq ft

1916 Stevens Dr, Chester, MD 21619

0.35 acre lot • $3 HOA • Pool

(410) 224-2200

COMING SOON

ABOUT THIS HOME
MLS Listings for Sale in Chester, MD
Inviting 3-bedroom, 1.5-bath brick rancher set on a half-acre lot that backs up to beautiful open farmland—offering peace, privacy, and picturesque views. Inside, you’ll find a spacious living room plus a cozy family room, providing plenty of space for both relaxation and entertaining. Enjoy the seasons year-round in the fantastic three-season room overlooking the backyard—perfect for morning coffee or evening gatherings. Located in the sought-after Marling Farms community, residents enjoy multiple beach areas, a boat launch, and a playground, making it ideal for outdoor enthusiasts and families alike. Don’t miss this wonderful opportunity to enjoy the best of Easter

$409,900

3 beds1.5 baths1,693 sq ft

1407 Calvert Rd, Chester, MD 21619

0.52 acre lot • $8 HOA • Car-dependent

(410) 758-0333

Property at 162 Kirwans Landing Ln, Chester, MD 21619, 4 beds, 2.5 baths

$949,000

4 beds2.5 baths2,404 sq ft

162 Kirwans Landing Ln, Chester, MD 21619

(410) 263-8686

Property at 202 Mchenny Ct, Chester, MD 21619, 3 beds, 2.5 baths

$875,000

3 beds2.5 baths2,520 sq ft

202 Mchenny Ct, Chester, MD 21619

(410) 224-2200

Property at 104 Golden Eye Ct, Chester, MD 21619, 2 beds, 2 baths

$300,000

2 beds2 baths1,073 sq ft

104 Golden Eye Ct, Chester, MD 21619

(443) 274-1900

Property at 1870 Harbor Dr, Chester, MD 21619, 2 beds, 1 bath

$324,900

2 beds1 bath832 sq ft

1870 Harbor Dr, Chester, MD 21619

(443) 274-1900

Property at 1839 Harbor Dr, Chester, MD 21619, 4 beds, 2 baths

$384,999

4 beds2 baths2,035 sq ft

1839 Harbor Dr, Chester, MD 21619

(301) 970-2447

Property at 906 Auckland Way, Chester, MD 21619, 3 beds, 3.5 baths

$530,000

3 beds3.5 baths2,076 sq ft

906 Auckland Way, Chester, MD 21619

(410) 673-3344

Property at 3000 Herons Nest Way #11, Chester, MD 21619, 2 beds, 2.5 baths

$555,900

2 beds2.5 baths2,003 sq ft

3000 Herons Nest Way #11, Chester, MD 21619

(410) 263-8686

Property at 1221 Cox Nck, Chester, MD 21619, 4 beds, 2.5 baths

$529,900

4 beds2.5 baths1,482 sq ft

1221 Cox Nck, Chester, MD 21619

(855) 550-0528

Property at 201 Golden Eye Ct, Chester, MD 21619, 2 beds, 2 baths

$285,000

2 beds2 baths1,073 sq ft

201 Golden Eye Ct, Chester, MD 21619

(410) 673-3344

Property at 1401 Calvert Rd, Chester, MD 21619, 2 beds, 2 baths

$454,900

2 beds2 baths1,444 sq ft

1401 Calvert Rd, Chester, MD 21619

(410) 643-5005

Property at 2865 Cox Neck Rd, Chester, MD 21619, 4 beds, 3.5 baths

$2,259,000

4 beds3.5 baths5,122 sq ft

2865 Cox Neck Rd, Chester, MD 21619

(410) 721-1500

Property at 245 Peregrine Dr, Chester, MD 21619, 4 beds, 3 baths

$700,000

4 beds3 baths3,151 sq ft

245 Peregrine Dr, Chester, MD 21619

(410) 972-4000

Property at 1405 Little Creek Rd, Chester, MD 21619, 2 beds, 1 bath

$19,500

2 beds1 bath764 sq ft

1405 Little Creek Rd, Chester, MD 21619

(302) 217-6692

Property at 135 Nauset Ln, Chester, MD 21619, 3 beds, 3 baths

$814,900

3 beds3 baths2,399 sq ft

135 Nauset Ln, Chester, MD 21619

(855) 450-0442

Property at 132 Claiborne St, Chester, MD 21619, 3 beds, 3.5 baths

$660,000

3 beds3.5 baths2,400 sq ft

132 Claiborne St, Chester, MD 21619

(301) 490-5400

Property at 312 Teal Ct Unit F, Chester, MD 21619, 2 beds, 2 baths

$305,000

2 beds2 baths1,073 sq ft

312 Teal Ct Unit F, Chester, MD 21619

(443) 292-6767

Property at 132 Kestrel Ln, Chester, MD 21619, 4 beds, 3.5 baths

$995,000

4 beds3.5 baths3,634 sq ft

132 Kestrel Ln, Chester, MD 21619

(410) 280-5600

Property at 9-B Queen Victoria Way, Chester, MD 21619, 3 beds, 2.5 baths

$399,000

3 beds2.5 baths1,680 sq ft

9-B Queen Victoria Way, Chester, MD 21619

(301) 490-5400

Property at 141 Switchgrass Way #34, Chester, MD 21619, 3 beds, 2.5 baths

$684,950

3 beds2.5 baths2,600 sq ft

141 Switchgrass Way #34, Chester, MD 21619

(443) 274-1900

Property at 108 Bodys Neck Rd, Chester, MD 21619, 3 beds, 2.5 baths

$499,900

3 beds2.5 baths1,791 sq ft

108 Bodys Neck Rd, Chester, MD 21619

(410) 643-3404

Property at 205 Anchor Ln, Chester, MD 21619, 6 beds, 3 baths

$550,000

6 beds3 baths3,500 sq ft

205 Anchor Ln, Chester, MD 21619

(443) 274-1900

Property at 200 Harrier Way #21, Chester, MD 21619, 3 beds, 2.5 baths

$679,900

3 beds2.5 baths2,600 sq ft

200 Harrier Way #21, Chester, MD 21619

(410) 546-3211

Property at 34-E Queen Anne Way, Chester, MD 21619, 2 beds, 2.5 baths

$469,000

2 beds2.5 baths1,104 sq ft

34-E Queen Anne Way, Chester, MD 21619

(301) 970-2447

Property at 114 Addison Ct, Chester, MD 21619, 3 beds, 2.5 baths

$549,900

3 beds2.5 baths2,342 sq ft

114 Addison Ct, Chester, MD 21619

(410) 643-5005

Property at 5-H Piney Narrows Rd, Chester, MD 21619

$49,000

— beds— baths960 sq ft

5-H Piney Narrows Rd, Chester, MD 21619

(410) 643-3033

Property at 170 Harrier Way #34, Chester, MD 21619, 3 beds, 2.5 baths

$740,000

3 beds2.5 baths2,602 sq ft

170 Harrier Way #34, Chester, MD 21619

(410) 263-3400

Property at 1340 Queen Anne Dr, Chester, MD 21619, 3 beds, 2 baths

$464,900

3 beds2 baths1,248 sq ft

1340 Queen Anne Dr, Chester, MD 21619

(443) 274-1900

Property at 1000 Herons Nest Way #22, Chester, MD 21619, 2 beds, 2.5 baths

$488,000

2 beds2.5 baths1,900 sq ft

1000 Herons Nest Way #22, Chester, MD 21619

(443) 274-1900

Property at 154 Harrier Way, Chester, MD 21619, 2 beds, 2 baths

$639,545

2 beds2 baths1,900 sq ft

154 Harrier Way, Chester, MD 21619

(443) 274-1900

Property at 170 Harrier Way #11, Chester, MD 21619, 2 beds, 2.5 baths

$499,000

2 beds2.5 baths2,003 sq ft

170 Harrier Way #11, Chester, MD 21619

Property at 1000 Herons Nest Way #32, Chester, MD 21619, 2 beds, 2 baths

$499,000

2 beds2 baths1,900 sq ft

1000 Herons Nest Way #32, Chester, MD 21619

(443) 274-1900

Property at 312 Blenny Ln, Chester, MD 21619, 3 beds, 3 baths

$479,000

3 beds3 baths1,899 sq ft

312 Blenny Ln, Chester, MD 21619

(301) 850-0255

Property at 190 Harrier Way #11, Chester, MD 21619, 2 beds, 2.5 baths

$540,000

2 beds2.5 baths2,003 sq ft

190 Harrier Way #11, Chester, MD 21619

(443) 274-1900

Property at 170 Harrier Way #22, Chester, MD 21619, 2 beds, 2.5 baths

$510,000

2 beds2.5 baths1,900 sq ft

170 Harrier Way #22, Chester, MD 21619

(410) 972-4000

$349,000

2 beds2 baths1,280 sq ft

54-H Queen Caroline Ct, Chester, MD 21619

(410) 643-2244

Property at 600 Old Point Rd, Chester, MD 21619

$349,900

— beds— baths— sq ft

600 Old Point Rd, Chester, MD 21619

(410) 729-7700

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MLS Listings for Sale in Chester

There are currently 42 mls listings for sale in Chester at a median listing price of $550K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chester stay on the market for 75 days and receive 1 offers. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 14 homes have been sold in Chester. In addition to houses in Chester, there were also 16 condos, 12 townhouses, and 0 multi-family units for sale in Chester last month. Find your dream home in Chester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chester. Our Chester real estate stats and trends will give you more information about home buying and selling trends in Chester. If you're looking to sell your home in the Chester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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