$269,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 960sqft
Single family home for sale
Doug Ashley Realtors, Llc
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$269,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 960sqft
Single family home for sale
Doug Ashley Realtors, Llc
$267,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,404sqft
Manufactured home for sale
Doug Ashley Realtors, Llc
$265,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,967sqft
Sale Pending
Keller Williams Flagship
$264,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: --sqft
Townhouse for sale
Real Broker, Llc - Chester
$259,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,200sqft
Townhouse for sale
Real Broker, Llc
$259,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,280sqft
Townhouse for sale
Real Broker, Llc - Chester
$259,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,280sqft
Townhouse for sale
Real Broker, Llc - Chester
$259,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,140sqft
Single family home for sale
Samson Properties
$250,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 37,026sqft lot
Land for sale
Select Land & Homes, Llc
$250,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,296sqft
Sale Pending
Doug Ashley Realtors, Llc
$245,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,140sqft
Townhouse for sale
Bayside Realty
$244,500
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 912sqft
Single family home for sale
Re/Max Leading Edge
$239,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,280sqft
Townhouse for sale
Cummings & Co. Realtors
$238,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,008sqft
Sale Pending
Lpt Realty, Llc
$229,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 2,344sqft
Single family home for sale
Select Land & Homes, Llc
$225,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 37,897.2sqft lot
Land for sale
Select Land & Homes, Llc
$222,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 936sqft
Single family home for sale
Doug Ashley Realtors, Llc
$215,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,373sqft
Single family home for sale
Real Broker, Llc - Chester
$200,000
Bedrooms: 1Bd
Bathrooms: 1Ba
Area: 700sqft
Condo for sale
Ttr Sotheby'S International Realty
$200,000
Bedrooms: 4Bds
Bathrooms: 1Ba
Area: 1,816sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
$200,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 5.81acres lot
Land for sale
Coldwell Banker Chesapeake Real Estate Company
$198,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,200sqft
Single family home for sale
Redfin Corp
$185,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,136sqft
Townhouse for sale
Compass
$175,000
Bedrooms: 2Bds
Bathrooms: --Ba
Area: 1,160sqft
Sale Pending
Keller Williams Select Realtors Of Annapolis
$175,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,360sqft
Single family home for sale
Thurston Wyatt Real Estate, Llc
$157,400
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 910sqft
Single family home for sale
Anr Realty, Llc
$125,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 1.8acres lot
Land for sale
Cross Street Realtors Llc
$115,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 910sqft
Single family home for sale
Real Broker, Llc
$110,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 1.93acres lot
Land for sale
Keller Williams Flagship
$109,999
Bedrooms: --Bds
Bathrooms: --Ba
Area: 7,945sqft lot
Sale Pending
Select Land & Homes, Llc
$88,900
Bedrooms: --Bds
Bathrooms: --Ba
Area: 21,060sqft lot
Sale Pending
Select Land & Homes, Llc
$85,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 3,096sqft lot
Land for sale
Taylor Properties
$79,000
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 1,296sqft
Single family home for sale
Cummings & Co Realtors
$75,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 2.2acres lot
Land for sale
Re/Max Chesapeake
$69,900
Bedrooms: --Bds
Bathrooms: --Ba
Area: 4.03acres lot
Land for sale
Samson Properties
$60,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 21,780sqft lot
Land for sale
Long & Foster Real Estate, Inc.
$59,999
Bedrooms: --Bds
Bathrooms: --Ba
Area: 22,000sqft lot
Sale Pending
Benson & Mangold, Llc
$59,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 1.37acres lot
Land for sale
Coldwell Banker Chesapeake Real Estate Company
$55,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 3acres lot
Land for sale
Doug Ashley Realtors, Llc
$55,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 30,448sqft lot
Land for sale
Doug Ashley Realtors, Llc
$55,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 22,500sqft lot
Land for sale
Coldwell Banker Chesapeake Real Estate Company
$49,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 1.95acres lot
Land for sale
Village Real Estate Company Llc
Showing 43 - 84 of 101 homes for sale in Chestertown, MD
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Based on information from Bright MLS through Nov 4, 2026, 12:45 PM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information
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$ NaN
Median List Price
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Avg on Market