Chester, MD homes for sale & real estate

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OPEN SAT, 12PM TO 3PM

ABOUT THIS HOME
Chester, MD Homes for Sale
OPEN SATURDAY 12-3PM. Kent Island Living at Its Best! Welcome to this stunning colonial-style home nestled in the desirable Clayborne Woods community in Chester. Offering 2,332 square feet of thoughtfully designed living space, this beautifully maintained residence blends elegance with modern updates and everyday comfort. From the inviting covered front porch with newly replaced fiberglass columns (2025) to the upgraded interior, every detail has been carefully considered. Step inside to a welcoming two-story foyer leading to a formal living room and separate dining area. The interior features LVP flooring (2020), ceramic tile, plush new carpet throughout the stairs/upper level (2026) and

$569,900

4 beds2.5 baths2,332 sq ft

233 Cross Creek Ct, Chester, MD 21619

Covered front porch • Plush new carpet • Fiberglass columns

(301) 340-8700

COMING SOON

$439,000

3 beds3 baths1,750 sq ft

41-D Queen Catherine Ct, Chester, MD 21619

$635 HOA • Garage • Community pool

(410) 465-1770

FLOOR PLAN

$345,000

3 beds1.5 baths1,080 sq ft

1609 Crab Alley Dr, Chester, MD 21619

0.46 acre lot • 2 garage spots • Pool

(703) 570-7307

OPEN SAT, 11AM TO 1PMFLOOR PLAN

ABOUT THIS HOME
Chester, MD Homes for Sale
Waterfront homes are common on Kent Island. Waterfront acreage is not. The difference is the land -- and at 1.65 acres with 205 feet of protected shoreline, this property belongs in a conversation with the finest waterfront offerings on Kent Island, not the most common. Waterfront properties with this combination of acreage, waterfront footage, and finishes are rare at this price point. The locals called it Keister's Folly. In the mid-1940s, Dr. Keister built a cinder block barn on Kent Island overlooking Cox Creek, hoping to raise Black Angus cattle on 25 acres. The acreage was too small for the endeavor -- but the barn he built was extraordinary. In the early 1960s, the developer of the H

$1,290,000

5 beds2 baths2,700 sq ft

2513 Cecil Dr, Chester, MD 21619

Shoreline reinforced • Protected shoreline • Private pier

(855) 450-0442

OPEN SUN, 12:30PM TO 2:30PM3D WALKTHROUGH

ABOUT THIS HOME
Chester, MD Homes for Sale
Welcome to 148 Elinor Street, where timeless coastal style meets a beautifully reimagined interior in the sought-after waterfront community of Gibson’s Grant. This 3-bedroom, 2.5-bath Hartley model by Koch Homes underwent an extensive renovation in 2025, creating a truly turnkey home filled with thoughtful upgrades, designer finishes, and exceptional attention to detail. Step inside to refinished and newly stained hardwood floors, fresh designer paint, upgraded lighting, new interior doors with Emtek hardware, and a beautifully updated staircase. The dining room was opened to create a more connected, airy flow, while upgraded recessed lighting and Lutron Caséta switches add mod

$899,000

3 beds2.5 baths2,464 sq ft

148 Elinor St, Chester, MD 21619

Updated staircase • Extensive renovation • Upgraded lighting

(703) 378-8810

Property at 43-A Queen Neva Ct, Chester, MD 21619, 3 beds, 2.5 baths

$459,000

3 beds2.5 baths2,008 sq ft

43-A Queen Neva Ct, Chester, MD 21619

(410) 224-3600

Property at 2702 Sherman Dr, Chester, MD 21619, 5 beds, 3 baths

$989,000

5 beds3 baths2,752 sq ft

2702 Sherman Dr, Chester, MD 21619

(703) 378-8810

Property at 207 Thomas White Blvd, Chester, MD 21619, 3 beds, 2.5 baths

$819,900

3 beds2.5 baths2,479 sq ft

207 Thomas White Blvd, Chester, MD 21619

(443) 353-5281

Property at 209 Harrier Way, Chester, MD 21619, 4 beds, 3 baths

$747,900

4 beds3 baths3,142 sq ft

209 Harrier Way, Chester, MD 21619

(410) 643-2244

Property at 320 Bayberry Dr, Chester, MD 21619, 3 beds, 2 baths

$897,750

3 beds2 baths2,331 sq ft

320 Bayberry Dr, Chester, MD 21619

(410) 486-4504

Property at 313 Thomas White Blvd, Chester, MD 21619, 4 beds, 2.5 baths

$825,000

4 beds2.5 baths3,291 sq ft

313 Thomas White Blvd, Chester, MD 21619

(443) 906-3848

Property at 214 Bayberry Dr, Chester, MD 21619, 3 beds, 3 baths

$924,000

3 beds3 baths2,745 sq ft

214 Bayberry Dr, Chester, MD 21619

(410) 822-6665

Property at 134 Richard Ingle Way, Chester, MD 21619, 4 beds, 3.5 baths

$749,000

4 beds3.5 baths2,185 sq ft

134 Richard Ingle Way, Chester, MD 21619

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

$989,800

5 beds3.5 baths3,036 sq ft

203 Riverside Dr, Chester, MD 21619

(301) 945-9010

Property at 108 Blenny Ln, Chester, MD 21619, 3 beds, 2.5 baths

$389,900

3 beds2.5 baths1,899 sq ft

108 Blenny Ln, Chester, MD 21619

(410) 224-3200

Property at 113 Bentons Pleasure Rd, Chester, MD 21619, 4 beds, 2.5 baths

$868,000

4 beds2.5 baths3,168 sq ft

113 Bentons Pleasure Rd, Chester, MD 21619

(410) 823-0033

Property at 205 Riverside Dr, Chester, MD 21619, 3 beds, 2 baths

$699,000

3 beds2 baths1,524 sq ft

205 Riverside Dr, Chester, MD 21619

(443) 292-6767

Property at 201 Switchgrass Way #34, Chester, MD 21619, 3 beds, 2.5 baths

$859,500

3 beds2.5 baths2,602 sq ft

201 Switchgrass Way #34, Chester, MD 21619

(410) 280-5600

Property at 205 Anchor Ln, Chester, MD 21619, 5 beds, 3 baths

$525,000

5 beds3 baths3,000 sq ft

205 Anchor Ln, Chester, MD 21619

(703) 378-8810

Property at 2004 Bridgepointe Dr, Chester, MD 21619, 3 beds, 2 baths

$374,900

3 beds2 baths1,524 sq ft

2004 Bridgepointe Dr, Chester, MD 21619

(443) 274-1900

Property at 6010 Bridgepointe Dr, Chester, MD 21619, 3 beds, 2 baths

$380,000

3 beds2 baths1,885 sq ft

6010 Bridgepointe Dr, Chester, MD 21619

(410) 758-0333

Property at 111 Flycatcher Way, Chester, MD 21619, 5 beds, 4.5 baths

$1,200,000

5 beds4.5 baths3,225 sq ft

111 Flycatcher Way, Chester, MD 21619

(410) 208-3500

Property at 315 Bentons Pleasure Rd, Chester, MD 21619, 3 beds, 2 baths

$629,900

3 beds2 baths1,688 sq ft

315 Bentons Pleasure Rd, Chester, MD 21619

(866) 987-3937

Property at 117 Flycatcher Way, Chester, MD 21619, 3 beds, 3.5 baths

$1,200,000

3 beds3.5 baths2,930 sq ft

117 Flycatcher Way, Chester, MD 21619

(410) 208-3500

Property at 536 Warbler Way, Chester, MD 21619, 2 beds, 2.5 baths

$789,990

2 beds2.5 baths2,010 sq ft

536 Warbler Way, Chester, MD 21619

(410) 208-3500

Property at 1012 Auckland Way, Chester, MD 21619, 3 beds, 3.5 baths

$599,900

3 beds3.5 baths2,076 sq ft

1012 Auckland Way, Chester, MD 21619

Property at 230 Switchgrass Way #12, Chester, MD 21619, 2 beds, 2.5 baths

$525,000

2 beds2.5 baths2,003 sq ft

230 Switchgrass Way #12, Chester, MD 21619

(855) 450-0442

Property at 121 Merlin Dr, Chester, MD 21619, 2 beds, 2 baths

$697,900

2 beds2 baths2,118 sq ft

121 Merlin Dr, Chester, MD 21619

(410) 263-8686

Property at 233 Peregrine Dr, Chester, MD 21619, 4 beds, 3 baths

$724,999

4 beds3 baths3,151 sq ft

233 Peregrine Dr, Chester, MD 21619

(410) 758-0333

Property at 2855 Cox Neck Rd, Chester, MD 21619, 4 beds, 4.5 baths

$1,195,000

4 beds4.5 baths4,413 sq ft

2855 Cox Neck Rd, Chester, MD 21619

(410) 304-2250

Property at 108 Price Rd, Chester, MD 21619, 3 beds, 2 baths

$216,000

3 beds2 baths1,160 sq ft

108 Price Rd, Chester, MD 21619

(410) 320-6785

Property at 330 Serenity Ln, Chester, MD 21619, 7 beds, 8 baths

$5,400,000

7 beds8 baths10,667 sq ft

330 Serenity Ln, Chester, MD 21619

(410) 280-5600

Property at 123 Flycatcher Way, Chester, MD 21619, 3 beds, 3 baths

$1,100,000

3 beds3 baths2,789 sq ft

123 Flycatcher Way, Chester, MD 21619

(410) 208-3500

Property at 106 Bodys Neck Rd, Chester, MD 21619, 3 beds, 2.5 baths

$435,000

3 beds2.5 baths1,595 sq ft

106 Bodys Neck Rd, Chester, MD 21619

(410) 643-3404

Property at 111 Marshgrass Way #41, Chester, MD 21619, 3 beds, 2.5 baths

$998,000

3 beds2.5 baths— sq ft

111 Marshgrass Way #41, Chester, MD 21619

(410) 770-3600

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

$515,000

2 beds2.5 baths1,586 sq ft

34-E Queen Anne Way, Chester, MD 21619

(301) 970-2447

Property at 232 Evelyne St, Chester, MD 21619, 4 beds, 3.5 baths

$840,000

4 beds3.5 baths3,312 sq ft

232 Evelyne St, Chester, MD 21619

(410) 673-3344

Property at 114 Merganser Ct, Chester, MD 21619, 2 beds, 2 baths

$287,500

2 beds2 baths1,069 sq ft

114 Merganser Ct, Chester, MD 21619

(443) 988-0483

Property at 807 Auckland Way, Chester, MD 21619, 3 beds, 3.5 baths

$425,500

3 beds3.5 baths2,100 sq ft

807 Auckland Way, Chester, MD 21619

(855) 450-0442

Property at 5011 Bridgepointe Dr, Chester, MD 21619, 3 beds, 2.5 baths

$354,900

3 beds2.5 baths1,302 sq ft

5011 Bridgepointe Dr, Chester, MD 21619

(410) 312-0000

Property at 54-D Queen Caroline Ct, Chester, MD 21619, 3 beds, 2.5 baths

$309,900

3 beds2.5 baths1,440 sq ft

54-D Queen Caroline Ct, Chester, MD 21619

(410) 643-4131

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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)

$442,259

-29.2% YoY | Jun 2026

1 year
3 year
5 year

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

Location

Data

Jun 2026

Growth

% YoY

Chester, MD

$442,259

-29.2%

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