$425,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 3,165sqft
Single family home for sale
Douglas Realty Llc
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$425,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 3,165sqft
Single family home for sale
Douglas Realty Llc
$419,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,216sqft
Sale Pending
Taylor Properties
$419,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,676sqft
Sale Pending
Coldwell Banker Chesapeake Real Estate Company
$400,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,000sqft
Single family home for sale
Doug Ashley Realtors, Llc
$399,900
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 1,936sqft
Single family home for sale
Save 6, Incorporated
$399,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,904sqft
Single family home for sale
Doug Ashley Realtors, Llc
$395,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 3,664sqft
Townhouse for sale
Coldwell Banker Chesapeake Real Estate Company
$385,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,630sqft
Single family home for sale
Rock Hall Properties Real Estate
$384,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,512sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
$375,000
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 787sqft
Condo for sale
Ttr Sotheby'S International Realty
$375,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 1,790sqft
Single family home for sale
Benson & Mangold, Llc
$372,000
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,277sqft
Sale Pending
Doug Ashley Realtors, Llc
$370,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,504sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
$369,999
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,271sqft
Sale Pending
Coldwell Banker Waterman Realty
$366,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,432sqft
Single family home for sale
Northrop Realty
$364,000
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,625sqft
Sale Pending
Coldwell Banker Chesapeake Real Estate Company
$359,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,036sqft
Single family home for sale
Doug Ashley Realtors, Llc
$350,000
Bedrooms: 1Bd
Bathrooms: 1Ba
Area: 850sqft
Condo for sale
Ttr Sotheby'S International Realty
$350,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,034sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
$350,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,942sqft
Sale Pending
Long & Foster Real Estate, Inc.
$349,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,304sqft
Single family home for sale
Re/Max Executive
$340,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 1,972sqft
Single family home for sale
Cross Street Realtors Llc
$339,900
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 1,294sqft
Sale Pending
Doug Ashley Realtors, Llc
$339,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,724sqft
Sale Pending
American Premier Realty, Llc
$339,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,250sqft
Single family home for sale
Clark & Co Realty, Llc
$339,000
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 3,371sqft
Single family home for sale
Doug Ashley Realtors, Llc
$334,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,900sqft
Sale Pending
Chesapeake Real Estate Associates, Llc
$330,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,628sqft
Sale Pending
Benson & Mangold, Llc
$329,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,896sqft
Single family home for sale
Long & Foster Real Estate, Inc.
$329,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,499sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
$325,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,404sqft
Sale Pending
Ttr Sotheby'S International Realty
$325,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,427sqft
Sale Pending
Ttr Sotheby'S International Realty
$325,000
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 2,198sqft
Single family home for sale
Ttr Sotheby'S International Realty
$325,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,404sqft
Single family home for sale
Serhant
$320,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,096sqft
Single family home for sale
Gunther-Mcclary Real Estate
$319,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: --sqft
Sale Pending
Real Broker, Llc - Chester
$319,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,650sqft
Single family home for sale
Real Broker, Llc - Chester
$315,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,440sqft
Single family home for sale
Benson & Mangold, Llc
$314,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,232sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
$313,500
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,216sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
$305,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,008sqft
Single family home for sale
Re/Max Chesapeake
$304,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,232sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
Showing 1 - 42 of 117 homes for sale in Chestertown, MD
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Based on information from Bright MLS through Nov 2, 2026, 2:00 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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Homes Available
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Median List Price
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