Chester, MD homes for sale & real estate

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ABOUT THIS HOME
Chester, MD Homes for Sale
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 bright, modern kitchen with new countertops and backsplash, engineered hardwood floors on the main level and cathedral ceiling with skylights. Relax in the spacious lower-level family room plus a versatile bonus room/office/bedroom. 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 ent

$495,000

3 beds2 baths1,728 sq ft

1916 Stevens Dr, Chester, MD 21619

0.35 acre lot • 3 parking spots • Pool

(410) 224-2200

COMING SOON

ABOUT THIS HOME
Chester, MD Homes for Sale
Beautifully renovated/remodeled 3 bedroom, 2 full bath home in Chester, MD. Expected date to go active on the market is January 1st, 2026.

$499,900

3 beds2 baths1,750 sq ft

1906 Harbor Dr, Chester, MD 21619

0.28 acre lot • $3 HOA • Car-dependent

(240) 222-3200

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ABOUT THIS HOME
Chester, MD Homes for Sale
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 • 2 garage spots • Pool

(410) 280-5600

ABOUT THIS HOME
Chester, MD Homes for Sale
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

ABOUT THIS HOME
Chester, MD Homes for Sale
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

Property at 203 Riverside Dr, Chester, MD 21619, 5 beds, 3.5 baths

$1,099,900

5 beds3.5 baths3,036 sq ft

203 Riverside Dr, Chester, MD 21619

(301) 945-9010

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 Harbor Dr, Chester, MD 21619, 3 beds, 2 baths

$499,900

3 beds2 baths1,250 sq ft

Harbor Dr, Chester, MD 21619

(410) 643-5005

Property at 630 Warbler Way #33, Chester, MD 21619, 2 beds, 2.5 baths

$654,900

2 beds2.5 baths1,900 sq ft

630 Warbler Way #33, Chester, MD 21619

Listing provided by Zillow

Property at 630 Warbler Way #32, Chester, MD 21619, 2 beds, 2.5 baths

$654,900

2 beds2.5 baths1,900 sq ft

630 Warbler Way #32, Chester, MD 21619

Listing provided by Zillow

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 132 Wheelhouse Way #43, Chester, MD 21619, 2 beds, 2.5 baths

$1,350,000

2 beds2.5 baths1,900 sq ft

132 Wheelhouse Way #43, Chester, MD 21619

Listing provided by Zillow

Property at 30-C Queen Mary Ct, Chester, MD 21619, 2 beds, 2.5 baths

$339,900

2 beds2.5 baths1,440 sq ft

30-C Queen Mary Ct, Chester, MD 21619

(410) 255-3690

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

$524,900

4 beds2.5 baths1,482 sq ft

1221 Cox Nck, Chester, MD 21619

(855) 550-0528

Property at 132 Wheelhouse Way, Chester, MD 21619, 2 beds, 2.5 baths

$1,350,000

2 beds2.5 baths1,900 sq ft

132 Wheelhouse Way, Chester, MD 21619

(240) 375-5074

Property at 117 Redstart Dr, Chester, MD 21619, 2 beds, 2.5 baths

$879,900

2 beds2.5 baths2,010 sq ft

117 Redstart Dr, Chester, MD 21619

(240) 375-5074

Property at 527 Warbler Way, Chester, MD 21619, 3 beds, 3 baths

$869,900

3 beds3 baths2,789 sq ft

527 Warbler Way, Chester, MD 21619

(240) 375-5074

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 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 630 Warbler Way #24, Chester, MD 21619, 3 beds, 2.5 baths

$724,900

3 beds2.5 baths2,602 sq ft

630 Warbler Way #24, Chester, MD 21619

Listing provided by Zillow

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 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 630 Warbler Way #22, Chester, MD 21619, 2 beds, 2.5 baths

$574,900

2 beds2.5 baths1,900 sq ft

630 Warbler Way #22, Chester, MD 21619

Listing provided by Zillow

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 519 Warbler Way, Chester, MD 21619, 3 beds, 3 baths

$879,900

3 beds3 baths2,789 sq ft

519 Warbler Way, Chester, MD 21619

(240) 375-5074

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 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 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 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 1757 Harbor Dr, Chester, MD 21619, 4 beds, 3.5 baths

$1,125,000

4 beds3.5 baths— sq ft

1757 Harbor Dr, Chester, MD 21619

(410) 729-7700

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 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 Munich ESP Plan, Chester, MD 21619, 4 beds, 3.5 baths

$883,900

4 beds3.5 baths3,601 sq ft

Munich ESP Plan, Chester, MD 21619

Listing provided by Zillow

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 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 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 Magothy Plan, Chester, MD 21619, 2 beds, 2.5 baths

$474,990

2 beds2.5 baths2,003 sq ft

Magothy Plan, Chester, MD 21619

Listing provided by Zillow

Property at Chester Plan, Chester, MD 21619, 2 beds, 2.5 baths

$474,990

2 beds2.5 baths1,900 sq ft

Chester Plan, Chester, MD 21619

Listing provided by Zillow

Property at Franklin Plan, Chester, MD 21619, 3 beds, 3.5 baths

$858,900

3 beds3.5 baths2,930 sq ft

Franklin Plan, Chester, MD 21619

Listing provided by Zillow

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Average home prices near Chester, MD

Cities

Zip Codes

Chester, MD real estate trends

All Home Types trends in Chester, MD

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$603,750

-15.6% YoY | Oct 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Oct 2025

Growth

% YoY

Chester, MD

$603,750

-15.6%

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