$400,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,000sqft
Single family home for sale
Doug Ashley Realtors, Llc
Do Real Estate on the Go!
$400,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,000sqft
Single family home for sale
Doug Ashley Realtors, Llc
$313,500
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,216sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
$281,500
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,080sqft
Single family home for sale
Re/Max Advantage Realty
$238,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,008sqft
Sale Pending
Lpt Realty, Llc
$267,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,404sqft
Manufactured home for sale
Doug Ashley Realtors, Llc
$519,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,475sqft
Single family home for sale
Re/Max Advantage Realty
$679,900
Bedrooms: 3Bds
Bathrooms: 4Ba
Area: 3,228sqft
Single family home for sale
Benson & Mangold, Llc
$495,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,656sqft
Single family home for sale
Cross Street Realtors Llc
$730,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,176sqft
Single family home for sale
Ttr Sotheby'S International Realty
$305,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,008sqft
Single family home for sale
Re/Max Chesapeake
$275,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 960sqft
Single family home for sale
Re/Max Executive
$296,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,248sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
$222,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 936sqft
Single family home for sale
Doug Ashley Realtors, Llc
$294,900
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,056sqft
Single family home for sale
Doug Ashley Realtors, Llc
$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
$399,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,904sqft
Single family home for sale
Doug Ashley Realtors, Llc
$799,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,857sqft
Sale Pending
Cross Street Realtors Llc
$289,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,056sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
$275,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 975sqft
Single family home for sale
Taylor Properties
$304,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,232sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
$275,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,248sqft
Manufactured home for sale
Doug Ashley Realtors, Llc
$265,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,967sqft
Sale Pending
Keller Williams Flagship
$325,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,427sqft
Sale Pending
Ttr Sotheby'S International Realty
$215,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,373sqft
Single family home for sale
Real Broker, Llc - Chester
$339,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,250sqft
Single family home for sale
Clark & Co Realty, Llc
$369,999
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,271sqft
Sale Pending
Coldwell Banker Waterman Realty
$457,500
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,664sqft
Single family home for sale
Re/Max Executive
$250,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,296sqft
Sale Pending
Doug Ashley Realtors, Llc
$535,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,624sqft
Sale Pending
Long & Foster Real Estate, Inc.
$115,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 910sqft
Single family home for sale
Real Broker, Llc
$299,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,152sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
$349,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,304sqft
Single family home for sale
Re/Max Executive
$366,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,432sqft
Single family home for sale
Northrop Realty
$1,279,000
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 2,956sqft
Single family home for sale
Ttr Sotheby'S International Realty
$295,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: --sqft
Single family home for sale
Doug Ashley Realtors, Llc
$269,900
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,356sqft
Single family home for sale
Coldwell Banker Waterman Realty
$330,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,628sqft
Sale Pending
Benson & Mangold, Llc
$334,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,900sqft
Sale Pending
Chesapeake Real Estate Associates, Llc
$175,000
Bedrooms: 2Bds
Bathrooms: --Ba
Area: 1,160sqft
Sale Pending
Keller Williams Select Realtors Of Annapolis
$350,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,942sqft
Sale Pending
Long & Foster Real Estate, Inc.
$275,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,424sqft
Sale Pending
Compass
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, 7:30 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