$549,900
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,464sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
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$549,900
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,464sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
$799,900
Bedrooms: 3Bds
Bathrooms: 4Ba
Area: 2,472sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
$399,900
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 1,936sqft
Single family home for sale
Save 6, Incorporated
$519,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,475sqft
Single family home for sale
Re/Max Advantage Realty
$898,000
Bedrooms: 3Bds
Bathrooms: 4Ba
Area: 2,172sqft
Townhouse for sale
Gunther-Mcclary Real Estate
$679,900
Bedrooms: 3Bds
Bathrooms: 4Ba
Area: 3,228sqft
Single family home for sale
Benson & Mangold, Llc
$1,195,000
Bedrooms: 5Bds
Bathrooms: 5Ba
Area: 3,243sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
$730,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,176sqft
Single family home for sale
Ttr Sotheby'S International Realty
$825,000
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 2,639sqft
Single family home for sale
Gunther-Mcclary Real Estate
$305,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,008sqft
Single family home for sale
Re/Max Chesapeake
$320,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,096sqft
Single family home for sale
Gunther-Mcclary Real Estate
$372,000
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,277sqft
Sale Pending
Doug Ashley Realtors, Llc
$799,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,857sqft
Sale Pending
Cross Street Realtors Llc
$350,000
Bedrooms: 1Bd
Bathrooms: 1Ba
Area: 850sqft
Condo for sale
Ttr Sotheby'S International Realty
$685,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 3,000sqft
Condo for sale
Ttr Sotheby'S International Realty
$1,500,000
Bedrooms: 7Bds
Bathrooms: 5Ba
Area: 5,400sqft
Luxury condo for sale
Ttr Sotheby'S International Realty
$375,000
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 787sqft
Condo for sale
Ttr Sotheby'S International Realty
$200,000
Bedrooms: 1Bd
Bathrooms: 1Ba
Area: 700sqft
Condo for sale
Ttr Sotheby'S International Realty
$275,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 975sqft
Single family home for sale
Taylor Properties
$824,900
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 4,353sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
$1,495,000
Bedrooms: 9Bds
Bathrooms: 7Ba
Area: 4,776sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
$275,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,248sqft
Manufactured home for sale
Doug Ashley Realtors, Llc
$499,900
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,524sqft
Single family home for sale
Doug Ashley Realtors, Llc
$2,200,000
Bedrooms: 5Bds
Bathrooms: 5Ba
Area: 4,305sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
$319,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: --sqft
Sale Pending
Real Broker, Llc - Chester
$419,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,216sqft
Sale Pending
Taylor Properties
$339,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,250sqft
Single family home for sale
Clark & Co Realty, Llc
$525,000
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 2,688sqft
Sale Pending
Doug Ashley Realtors, Llc
$867,000
Bedrooms: 4Bds
Bathrooms: 4Ba
Area: 4,145sqft
Sale Pending
Taylor Properties
$244,500
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 912sqft
Single family home for sale
Re/Max Leading Edge
$115,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 910sqft
Single family home for sale
Real Broker, Llc
$499,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 3,504sqft
Single family home for sale
Doug Ashley Realtors, Llc
$259,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,200sqft
Townhouse for sale
Real Broker, Llc
$157,400
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 910sqft
Single family home for sale
Anr Realty, Llc
$675,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,600sqft
Condo for sale
Benson & Mangold, Llc
$1,279,000
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 2,956sqft
Single family home for sale
Ttr Sotheby'S International Realty
$786,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,964sqft
Condo for sale
Gunther-Mcclary Real Estate
$1,099,900
Bedrooms: 4Bds
Bathrooms: 4Ba
Area: 2,784sqft
Condo for sale
Gunther-Mcclary Real Estate
$813,900
Bedrooms: 3Bds
Bathrooms: 4Ba
Area: 2,192sqft
Condo for sale
Gunther-Mcclary Real Estate
$753,500
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,964sqft
Condo for sale
Gunther-Mcclary Real Estate
$765,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,964sqft
Condo for sale
Gunther-Mcclary Real Estate
$849,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,980sqft
Condo for sale
Gunther-Mcclary Real Estate
Showing 1 - 42 of 49 homes for sale in Chestertown, MD
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Based on information from Bright MLS through Nov 4, 2026, 6:45 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
49
Homes Available
$ NaN
Median List Price
- Days
Avg on Market