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Homes for sale in Chestertown under $600K, MD

Figures for Chestertown, MD, week ending October 25, 2026. Last week's read — this week's is still being written.

Paige
Under $600K · Chestertown
Paige
93 homes of the 122 homes for sale in Chestertown are asking under $600K. The median asking price across everything for sale in Chestertown is $314,250, and what is listed has been on the market a median of 69 days. What are you looking for in Chestertown?
24607 CHESTERTOWN ROADFor SaleBright MLSOpen today 10 AM-12 PM
$365,000
24607 CHESTERTOWN ROAD, Chestertown
3 bd · 3 ba · House · 12 DOM
MDKE2007204, Coldwell Banker Chesapeake Real Estate Company
7655 JAMES LANEFor SaleBright MLS
$519,900
7655 JAMES LANE, Chestertown
3 bd · 3 ba · House · 15 DOM
MDKE2007208, RE/MAX Advantage Realty
8901 BAYVIEW DRIVEFor SaleBright MLS
$525,000
8901 BAYVIEW DRIVE, Chestertown
3 bd · 3 ba · House · 16 DOM
MDKE2007118, Doug Ashley Realtors, LLC
21338 VIRGINIA AVENUEFor SaleBright MLS
$400,000
21338 VIRGINIA AVENUE, Chestertown
2 bd · 2 ba · House · 19 DOM
MDKE2007194, Doug Ashley Realtors, LLC
106 HARLAN LOOPFor SaleBright MLS
$425,000
106 HARLAN LOOP, Chestertown
4 bd · 3 ba · House · 20 DOM
MDKE2007190, Douglas Realty LLC
8820 CUMBERLAND STREETFor SaleBright MLS
$281,500
8820 CUMBERLAND STREET, Chestertown
3 bd · 2 ba · House · 31 DOM
MDKE2007156, RE/MAX Advantage Realty
234 KENT STREETFor SaleBright MLS
$325,000
234 KENT STREET, Chestertown
5 bd · 2 ba · House · 38 DOM
MDKE2007128, TTR Sotheby's International Realty
10 CEDAR CHASE COURTFor SaleBright MLSOpen today 11 AM-1 PM
$495,000
10 CEDAR CHASE COURT, Chestertown
3 bd · 3 ba · House · 40 DOM
MDKE2007124, Cross Street Realtors LLC
22974 BAY SHORE ROADFor SaleBright MLS
$315,000
22974 BAY SHORE ROAD, Chestertown
2 bd · 2 ba · House · 42 DOM
MDKE2007106, Benson & Mangold, LLC
8732 ELM ROADFor SaleBright MLS
$289,000
8732 ELM ROAD, Chestertown
3 bd · 2 ba · House · 48 DOM
MDKE2007082, Coldwell Banker Chesapeake Real Estate Company
103 METCALF ROADFor SaleBright MLS
$259,900
103 METCALF ROAD, Chestertown
3 bd · 3 ba · Townhouse · 53 DOM
MDKE2007148, Real Broker, LLC - Chester
7415 WILKINS LANEFor SaleBright MLS
$222,000
7415 WILKINS LANE, Chestertown
3 bd · 1 ba · House · 59 DOM
MDKE2007030, Doug Ashley Realtors, LLC
329 UNION CHURCH ROADFor SaleBright MLS
$549,900
329 UNION CHURCH ROAD, Chestertown
4 bd · 3 ba · House · 60 DOM
MDQA2018610, Chesapeake Real Estate Associates, LLC
24775 LANGFORD ROADFor SaleBright MLS
$305,000
24775 LANGFORD ROAD, Chestertown
3 bd · 1 ba · House · 61 DOM
MDKE2007012, RE/MAX Chesapeake
104 LINCOLN DRIVEFor SaleBright MLS
$275,000
104 LINCOLN DRIVE, Chestertown
3 bd · 1 ba · House · 62 DOM
MDKE2007032, RE/MAX Executive
123 TRAFFORD DRIVEFor SaleBright MLS
$370,000
123 TRAFFORD DRIVE, Chestertown
4 bd · 3 ba · House · 74 DOM
MDKE2006970, Chesapeake Real Estate Associates, LLC

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