Price Drop: $25K
$300,000
Bedrooms: 5Bds
Bathrooms: 2Ba
Area: 1,802sqft
Single family home for sale
Ttr Sotheby'S International Realty
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Price Drop: $25K234 N Kent St, CHESTERTOWN, MD 21620 
223 Mount Vernon Ave, CHESTERTOWN, MD 21620Price Drop: $500
9126 Fairlee Rd, CHESTERTOWN, MD 21620 
7545 Quaker Neck Rd, CHESTERTOWN, MD 21620Price Drop: $19K
329 Union Church Rd, CHESTERTOWN, MD 21620 
3D Tour
8820 Cumberland St, CHESTERTOWN, MD 21620
10484 Cogar Rd, CHESTERTOWN, MD 21620
106 Queen St S, CHESTERTOWN, MD 21620
6324 Quaker Neck Rd, CHESTERTOWN, MD 21620
Hot
8630 Elm Rd, CHESTERTOWN, MD 216203D Tour
7655 James Ln, CHESTERTOWN, MD 21620 3D Tour
8986 Orchard Dr, CHESTERTOWN, MD 21620 3D Tour
105 High St, CHESTERTOWN, MD 21620 
234 N College Ave, CHESTERTOWN, MD 216203D Tour
106 Harlan Loop, CHESTERTOWN, MD 21620 
10 Cedar Chase Ct, CHESTERTOWN, MD 216203D Tour
216 Birch Run Rd, CHESTERTOWN, MD 21620 
New Construction
23208 Buck Neck Rd, CHESTERTOWN, MD 216203D Tour
22974 Bay Shore Rd, CHESTERTOWN, MD 21620 
7680 Country Clb Ln, CHESTERTOWN, MD 21620
24775 Langford Rd, CHESTERTOWN, MD 216203D Tour
104 Lincoln Dr, CHESTERTOWN, MD 21620 
203 Manor Ave, CHESTERTOWN, MD 21620Hot
212 Washington Ave, CHESTERTOWN, MD 21620 
123 Trafford Dr, CHESTERTOWN, MD 216203D Tour
7415 Wilkins Ln, CHESTERTOWN, MD 21620 3D Tour
124 Wilton Rd, CHESTERTOWN, MD 21620 
222 Dutchess Rd, CHESTERTOWN, MD 21620
115 Chester Arms Dr, CHESTERTOWN, MD 216203D Tour
213 Byford Dr, CHESTERTOWN, MD 21620 3D Tour
7982 Radcliffe Rd, CHESTERTOWN, MD 21620 
7828 Country Club Ln, CHESTERTOWN, MD 21620
8732 Elm Rd, CHESTERTOWN, MD 216203D Tour
200 Manor Ave, CHESTERTOWN, MD 21620 
7482 Poplar Ave, CHESTERTOWN, MD 21620
101 S College Ave, CHESTERTOWN, MD 21620
6746 Quaker Neck Rd, CHESTERTOWN, MD 21620
8999 Orchard Dr, CHESTERTOWN, MD 21620
201 River Rd, CHESTERTOWN, MD 216203D Tour
7464 Shortall St, CHESTERTOWN, MD 21620 3D Tour
8796 Maryland Pkwy, CHESTERTOWN, MD 21620 3D Tour
8620 Park Dr, CHESTERTOWN, MD 21620 
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Single Family Homes for Sale in Chestertown, MD
95 Homes for Sale
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Price Drop: $25K$200,000
Bedrooms: 4Bds
Bathrooms: 1Ba
Area: 1,816sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
Price Drop: $500$313,500
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,216sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
$175,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,360sqft
Single family home for sale
Thurston Wyatt Real Estate, Llc
Price Drop: $19K$549,900
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,464sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
3D Tour$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
$799,900
Bedrooms: 3Bds
Bathrooms: 4Ba
Area: 2,472sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
$2,895,000
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 5,938sqft
Mansion for sale
Cross Street Realtors Llc
Hot$399,900
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 1,936sqft
Single family home for sale
Save 6, Incorporated
3D Tour$519,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,475sqft
Single family home for sale
Re/Max Advantage Realty
3D Tour$679,900
Bedrooms: 3Bds
Bathrooms: 4Ba
Area: 3,228sqft
Single family home for sale
Benson & Mangold, Llc
3D Tour$1,195,000
Bedrooms: 5Bds
Bathrooms: 5Ba
Area: 3,243sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
$79,000
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 1,296sqft
Single family home for sale
Cummings & Co Realtors
3D Tour$425,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 3,165sqft
Single family home for sale
Douglas Realty Llc
$495,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,656sqft
Single family home for sale
Cross Street Realtors Llc
3D Tour$730,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,176sqft
Single family home for sale
Ttr Sotheby'S International Realty
New Construction$319,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,650sqft
Single family home for sale
Real Broker, Llc - Chester
3D Tour$315,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,440sqft
Single family home for sale
Benson & Mangold, Llc
$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
3D Tour$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
Hot$675,000
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 2,838sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
$370,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,504sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
3D Tour$222,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 936sqft
Single family home for sale
Doug Ashley Realtors, Llc
3D Tour$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
$259,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,140sqft
Single family home for sale
Samson Properties
3D Tour$372,000
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,277sqft
Sale Pending
Doug Ashley Realtors, Llc
3D Tour$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
3D Tour$325,000
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 2,198sqft
Single family home for sale
Ttr Sotheby'S International Realty
$275,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 975sqft
Single family home for sale
Taylor Properties
$359,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,036sqft
Single family home for sale
Doug Ashley Realtors, Llc
$339,000
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 3,371sqft
Single family home for sale
Doug Ashley Realtors, Llc
$824,900
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 4,353sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
$629,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 2,430sqft
Sale Pending
Coldwell Banker Chesapeake Real Estate Company
3D Tour$304,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,232sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
3D Tour$1,495,000
Bedrooms: 9Bds
Bathrooms: 7Ba
Area: 4,776sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
3D Tour$499,900
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,524sqft
Single family home for sale
Doug Ashley Realtors, Llc
Showing 1 - 42 of 95 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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