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Homes for sale in Chestertown under $600K, MD

Figures for Chestertown, MD, week ending September 15, 2026.

Paige
Under $600K · Chestertown
Paige
104 homes of the 139 for sale in Chestertown are asking under $600K. The median asking price across everything for sale in Chestertown is $315,000, and what is listed has been on the market a median of 69 days. What are you looking for in Chestertown?
1003 TWIN COURTFor SaleBright MLS
$499,900
1003 TWIN COURT, Chestertown
3 bd · 3 ba · House · 28 DOM
MDKE2006974, Cross Street Realtors LLC
101 COLLEGE AVENUEFor SaleBright MLS
$359,000
101 COLLEGE AVENUE, Chestertown
2 bd · 2 ba · House · 37 DOM
MDKE2006918, Doug Ashley Realtors, LLC
223 MOUNT VERNON AVENUEFor SaleBright MLS
$200,000
223 MOUNT VERNON AVENUE, Chestertown
4 bd · 1 ba · House · 2 DOM
MDKE2007080, Chesapeake Real Estate Associates, LLC
7415 WILKINS LANEFor SaleBright MLS
$229,000
7415 WILKINS LANE, Chestertown
3 bd · 1 ba · House · 13 DOM
MDKE2007030, Doug Ashley Realtors, LLC
329 UNION CHURCH ROADFor SaleBright MLS
$568,900
329 UNION CHURCH ROAD, Chestertown
4 bd · 2.5 ba · House · 14 DOM
MDQA2018610, Chesapeake Real Estate Associates, LLC
24775 LANGFORD ROADFor SaleBright MLS
$315,000
24775 LANGFORD ROAD, Chestertown
3 bd · 1 ba · House · 15 DOM
MDKE2007012, RE/MAX Chesapeake
104 LINCOLN DRIVEFor SaleBright MLS
$300,000
104 LINCOLN DRIVE, Chestertown
3 bd · 1 ba · House · 16 DOM
MDKE2007032, RE/MAX Executive
217 EDMORE ROADFor SaleBright MLS
$345,000
217 EDMORE ROAD, Chestertown
3 bd · 2 ba · House · 23 DOM
MDQA2018386, Doug Ashley Realtors, LLC
7464 SHORTALL STREETFor SaleBright MLS
$304,000
7464 SHORTALL STREET, Chestertown
3 bd · 2 ba · House · 27 DOM
MDKE2006988, Chesapeake Real Estate Associates, LLC
23208 BUCK NECK ROADFor SaleBright MLS
$349,900
23208 BUCK NECK ROAD, Chestertown
3 bd · 3 ba · House · 27 DOM
MDKE2006980, Real Broker, LLC - Chester
123 TRAFFORD DRIVEFor SaleBright MLS
$375,000
123 TRAFFORD DRIVE, Chestertown
4 bd · 3 ba · House · 28 DOM
MDKE2006970, Chesapeake Real Estate Associates, LLC
7482 POPLAR AVENUEFor SaleBright MLS
$275,000
7482 POPLAR AVENUE, Chestertown
3 bd · 1 ba · House · 29 DOM
MDKE2007042, Taylor Properties
115 CHESTER ARMS DRIVEFor SaleBright MLS
$263,000
115 CHESTER ARMS DRIVE, Chestertown
3 bd · 2 ba · House · 33 DOM
MDKE2006958, Samson Properties
117 WATER STREET Unit 3BFor SaleBright MLS
$295,000
117 WATER STREET Unit 3B, Chestertown
1 bd · 1 ba · Condo · 33 DOM
MDKE2006968, Coldwell Banker Chesapeake Real Estate Company
7982 RADCLIFFE ROADFor SaleBright MLS
$455,000
7982 RADCLIFFE ROAD, Chestertown
2 bd · 2 ba · House · 34 DOM
MDKE2006950, Doug Ashley Realtors, LLC
124 WILTON ROADFor SaleBright MLS
$299,900
124 WILTON ROAD, Chestertown
3 bd · 1 ba · House · 36 DOM
MDQA2018272, Doug Ashley Realtors, LLC
8630 ELM ROADFor SaleBright MLS
$424,900
8630 ELM ROAD, Chestertown
5 bd · 3 ba · House · 39 DOM
MDKE2006914, Save 6, Incorporated
104 CHURCH ALLEYUnder ContractBright MLS
$440,000
104 CHURCH ALLEY, Chestertown
2 bd · 1.5 ba · Townhouse · 41 DOM
MDKE2006900, Coldwell Banker Chesapeake Real Estate Company

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