Chester, MD homes for sale & real estate

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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
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

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

OPEN SAT, 2PM TO 4PM

ABOUT THIS HOME
Chester, MD Homes for Sale
Beautiful Home in Gibson’s Grant with Elevator, Open Floor Plan & Two-Car Garage Welcome to this beautifully appointed home in the sought-after waterfront community of Gibson’s Grant on Kent Island. This residence offers a perfect blend of comfort, style, and convenience — featuring a spacious open floor plan and an attached two-car garage. No need to worry about stairs — a full elevator effortlessly transports you to the grand second-floor primary suite, complete with a cozy sitting area and private porch. Throughout the home, you’ll find thoughtful upgrades, including a gourmet kitchen with granite countertops, hardwood floors, custom trim, and elegant

$875,000

3 beds2.5 baths2,520 sq ft

202 Mchenny Ct, Chester, MD 21619

5,550 sq ft lot • 2 garage spots • Community pool

(410) 224-2200

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 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 302 Teal Ct Unit A, Chester, MD 21619, 2 beds, 1.5 baths

$305,000

2 beds1.5 baths1,073 sq ft

302 Teal Ct Unit A, Chester, MD 21619

(410) 451-3300

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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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

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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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