3D Tour
$350,000
Bedrooms: 1Bd
Bathrooms: 1Ba
Area: 850sqft
Condo for sale
Ttr Sotheby'S International Realty
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3D Tour117 Water St N #2B, CHESTERTOWN, MD 21620 3D Tour117 Water St N #1A, CHESTERTOWN, MD 21620 3D Tour117 Water St N #1A, 1B, 2A, & 2B, CHESTERTOWN, MD 21620 3D Tour
200 Manor Ave, CHESTERTOWN, MD 21620 3D Tour117 Water St N #2A, CHESTERTOWN, MD 21620 3D Tour117 Water St N #1B, CHESTERTOWN, MD 21620 
7482 Poplar Ave, CHESTERTOWN, MD 21620
104 Conley Dr, 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
956 Washington Ave, CHESTERTOWN, MD 21620 3D Tour
8620 Park Dr, CHESTERTOWN, MD 21620 3D Tour
25440 Learman Rd, CHESTERTOWN, MD 21620 
129 Trafford Dr, CHESTERTOWN, MD 21620
Preston Ln, Chestertown, MD 21620
23043 Bay Shore Spur, CHESTERTOWN, MD 21620
1904 Pondtown Rd, CHESTERTOWN, MD 21620
102 Flying Cloud Dr, CHESTERTOWN, MD 216203D Tour
7989 Quaker Neck Rd, CHESTERTOWN, MD 21620 
139 Prospect St, CHESTERTOWN, MD 21620
New Construction
10584 Klamath Rd, CHESTERTOWN, MD 21620
202 Valley Rd, CHESTERTOWN, MD 21620
10572 Watonga Rd, CHESTERTOWN, MD 21620
100 Prospect St, CHESTERTOWN, MD 21620
109 S College Ave, CHESTERTOWN, MD 21620
214 Silver Heel Rd, CHESTERTOWN, MD 21620
102 Pine St, Chestertown, MD 21620
720 Deep Landing Rd, CHESTERTOWN, MD 216203D Tour
118 Grant Ct, CHESTERTOWN, MD 21620 3D Tour
21125 Iowa Ave, CHESTERTOWN, MD 21620 
22360 Great Oak Landing Rd, CHESTERTOWN, MD 21620
113 Pear Tree Point Rd, CHESTERTOWN, MD 216203D Tour
9816 Fairlee Rd, CHESTERTOWN, MD 21620 
423 Calvert St, CHESTERTOWN, MD 21620
23416 Cloquet Rd, CHESTERTOWN, MD 216203D Tour
25475 Turnberry Ct, CHESTERTOWN, MD 21620 
21217 Texas Ave, CHESTERTOWN, MD 216203D Tour
7844 Chester Ct, CHESTERTOWN, MD 21620 
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21620, MD Homes For Sale & Real Estate
168 Homes for Sale
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3D Tour3D Tour$685,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 3,000sqft
Condo for sale
Ttr Sotheby'S International Realty
3D Tour$1,500,000
Bedrooms: 7Bds
Bathrooms: 5Ba
Area: 5,400sqft
Luxury condo for sale
Ttr Sotheby'S International Realty
3D Tour$325,000
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 2,198sqft
Single family home for sale
Ttr Sotheby'S International Realty
3D Tour$375,000
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 787sqft
Condo for sale
Ttr Sotheby'S International Realty
3D Tour$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
$239,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,280sqft
Townhouse for sale
Cummings & Co. Realtors
$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$275,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,248sqft
Manufactured home for sale
Doug Ashley Realtors, Llc
3D Tour$499,900
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,524sqft
Single family home for sale
Doug Ashley Realtors, Llc
3D Tour$3,000,000
Bedrooms: 3Bds
Bathrooms: 4Ba
Area: 3,142sqft
Sale Pending
Ttr Sotheby'S International Realty
$480,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 3,176sqft
Single family home for sale
Elevated Real Estate Solutions
$525,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,824sqft
Sale Pending
Shoreline Realty
$385,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,630sqft
Single family home for sale
Rock Hall Properties Real Estate
$265,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,967sqft
Sale Pending
Keller Williams Flagship
$329,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,896sqft
Single family home for sale
Long & Foster Real Estate, Inc.
3D Tour$2,200,000
Bedrooms: 5Bds
Bathrooms: 5Ba
Area: 4,305sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
$198,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,200sqft
Single family home for sale
Redfin Corp
New Construction$319,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: --sqft
Sale Pending
Real Broker, Llc - Chester
$325,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,427sqft
Sale Pending
Ttr Sotheby'S International Realty
$325,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,404sqft
Single family home for sale
Serhant
$215,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,373sqft
Single family home for sale
Real Broker, Llc - Chester
$419,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,216sqft
Sale Pending
Taylor Properties
$340,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 1,972sqft
Single family home for sale
Cross Street Realtors Llc
$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
3D Tour$457,500
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,664sqft
Single family home for sale
Re/Max Executive
3D Tour$339,900
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 1,294sqft
Sale Pending
Doug Ashley Realtors, Llc
$525,000
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 2,688sqft
Sale Pending
Doug Ashley Realtors, Llc
$250,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,296sqft
Sale Pending
Doug Ashley Realtors, Llc
3D Tour$535,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,624sqft
Sale Pending
Long & Foster Real Estate, Inc.
$185,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,136sqft
Townhouse for sale
Compass
$384,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,512sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
3D Tour$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
3D Tour$670,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 3,248sqft
Single family home for sale
Doug Ashley Realtors, Llc
Showing 43 - 84 of 168 homes for sale in MD 21620
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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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