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Homes for sale in Chester, MD

Figures for Chester, MD, week ending November 1, 2026.

Paige

watching Chester · 92 homes for sale

Paige

New activity picked up in Chester this week, with 7 homes coming on the market after a week of 0 new additions. Right now, there are 92 homes for sale overall, and I can take you to see a few of them today. At 232 Evelyne Street, there is a 4 bedroom residential home that has been listed for 163 days, now asking $799,900. If you prefer something listed yesterday, 55 Queen Caroline Court is a 3 bedroom residential home asking $320,000. There is also 231 Dominion Road, a 5 bedroom residential income property listed for 38 days at $599,000. Sellers are making moves, with 3 asking prices reduced in the last 7 days at a median reduction of 4.1 percent. While listed homes carry a median of 28 days on market, the 31 homes sold in the last 30 days had a median of 49 days on market before selling at a median sold price of $675,000. It shows how properties are shifting as fresh options come online. Are you looking to buy or sell a home in Chester right now?

232 EVELYNE STREET

For SaleBright MLS

232 EVELYNE STREET, Chester

4 bd · 4 ba · House · 163 DOM

MDQA2017378, TTR Sotheby's International Realty

231 DOMINION ROAD

For SaleBright MLS

231 DOMINION ROAD, Chester

5 bd · Multi-family · 38 DOM

MDQA2018864, Long & Foster Real Estate, Inc.

121 SWITCHGRASS WAY Unit 42

For SaleBright MLS

121 SWITCHGRASS WAY Unit 42, Chester

2 bd · 2.5 ba · Condo · 3 DOM

MDQA2019122, Engel & Volkers Annapolis

406 DOMINION ROAD

For SaleBright MLS

406 DOMINION ROAD, Chester

3 bd · 2 ba · House · 4 DOM

MDQA2019164, Sell Your Home Services

1905-1907 KEISTER DRIVE

For SaleBright MLS

1905-1907 KEISTER DRIVE, Chester

3 bd · 1 ba · House · 5 DOM

MDQA2019150, Five Star Real Estate

411 MERGANSER COURT

For SaleBright MLS

411 MERGANSER COURT, Chester

2 bd · 2 ba · Condo · 6 DOM

MDQA2019168, Chesapeake Real Estate Associates, LLC

For SaleBright MLS

1837 HARBOR DR, Chester

3 bd · 2 ba · House · 6 DOM

MDQA2019130, Benson & Mangold, LLC

2627 CECIL DRIVE

For SaleBright MLS

2627 CECIL DRIVE, Chester

3 bd · 2 ba · House · 6 DOM

MDQA2019148, Long & Foster Real Estate, Inc.

227 GIBSON CIRCLE

For SaleBright MLS

227 GIBSON CIRCLE, Chester

3 bd · 3 ba · Townhouse · 10 DOM

MDQA2019154, RE/MAX Executive

107 WIDGEON WAY

For SaleBright MLS

107 WIDGEON WAY, Chester

3 bd · 3 ba · Townhouse · 18 DOM

MDQA2019058, RE/MAX Leading Edge

101 BUFFLEHEAD COURT

For SaleBright MLS

101 BUFFLEHEAD COURT, Chester

2 bd · 2 ba · Condo · 25 DOM

MDQA2019010, The KW Collective

2703 SHERMAN DRIVE

For SaleBright MLS

2703 SHERMAN DRIVE, Chester

3 bd · 3 ba · House · 26 DOM

MDQA2018980, Rosendale Realty

100 SCHOONER WAY

For SaleBright MLS

100 SCHOONER WAY, Chester

3 bd · 3 ba · Townhouse · 28 DOM

MDQA2018964, LPT Realty, LLC

1 QUEEN VICTORIA COURT

For SaleBright MLS

1 QUEEN VICTORIA COURT, Chester

2 bd · 2 ba · Townhouse · 28 DOM

MDQA2018958, Douglas Realty LLC

For SaleBright MLS

107 LEE ROAD, Chester

3 bd · 1 ba · House · 31 DOM

MDQA2018842, Open Door Brokerage, LLC

830 WARBLER WAY Unit 2843

For SaleBright MLS

830 WARBLER WAY Unit 2843, Chester

2 bd · 3 ba · Condo · 31 DOM

MDQA2018944, Berkshire Hathaway HomeServices PenFed Realty - OP

1509 CALVERT ROAD

For SaleBright MLS

1509 CALVERT ROAD, Chester

4 bd · 3 ba · House · 33 DOM

MDQA2018902, Long & Foster Real Estate, Inc.

205 DOMINION LANE

For SaleBright MLS

205 DOMINION LANE, Chester

3 bd · 2 ba · House · 33 DOM

MDQA2018906, EXP Realty, LLC

8-E PINEY NARROWS ROAD

For SaleBright MLS

8-E PINEY NARROWS ROAD, Chester

0 bd · 0 ba · House · 34 DOM

MDQA2018904, Benson & Mangold, LLC

168 REDSTART DRIVE

For SaleBright MLS

168 REDSTART DRIVE, Chester

2 bd · 3 ba · House · 37 DOM

MDQA2018874, RE/MAX Leading Edge

111 MARSHGRASS WAY Unit 43

For SaleBright MLS

111 MARSHGRASS WAY Unit 43, Chester

2 bd · 3 ba · Condo · 38 DOM

MDQA2018854, Long & Foster Real Estate, Inc.

117 WRIGHT ROAD

For SaleBright MLS

117 WRIGHT ROAD, Chester

3 bd · 2 ba · House · 39 DOM

MDQA2018892, Douglas Realty LLC

Tap a home and I'll open it here — we can keep talking about it.

More in Chester

Under $600K (51)

Nearby in DMV

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