$359,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,036sqft
Single family home for sale
Doug Ashley Realtors, Llc
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101 S College Ave, CHESTERTOWN, MD 21620 
8999 Orchard Dr, CHESTERTOWN, MD 21620
201 River Rd, CHESTERTOWN, MD 21620
3D Tour
956 Washington Ave, CHESTERTOWN, MD 216203D 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
202 Valley Rd, 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 216203D Tour
9816 Fairlee Rd, CHESTERTOWN, MD 21620 
423 Calvert St, CHESTERTOWN, MD 216203D Tour
25475 Turnberry Ct, CHESTERTOWN, MD 21620 
21217 Texas Ave, CHESTERTOWN, MD 216203D Tour
7844 Chester Ct, CHESTERTOWN, MD 21620 3D Tour
108 Oak Leaf Dr, CHESTERTOWN, MD 21620 3D Tour
301 Lincoln Dr, Chestertown, MD 21620 
611 Cannon St, CHESTERTOWN, MD 216203D Tour
311 Devon Dr, CHESTERTOWN, MD 21620 3D Tour
126 Char Nor Manor Blvd, Chestertown, MD 21620 
10594 Millbrook Dr, CHESTERTOWN, MD 21620
217 Philosophers Ter, CHESTERTOWN, MD 21620
136 Hilltop Dr, CHESTERTOWN, MD 21620
New Construction
107 Metcalf Rd, CHESTERTOWN, MD 21620
132 Prospect St, CHESTERTOWN, MD 21620
118 Little Harbor Way #202, CHESTERTOWN, MD 216203D Tour
231 Richard Dr, CHESTERTOWN, MD 21620 3D Tour
107 Longfellow Dr, CHESTERTOWN, MD 21620 
103 Flying Cloud Dr, Chestertown, MD 21620
23055 Old Fairlee Rd, CHESTERTOWN, MD 21620
8750 Georgetown Rd, CHESTERTOWN, MD 21620
23069 Raleigh Rd, CHESTERTOWN, MD 21620
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Homes for Sale with AC in 21620, MD
106 Homes for Sale
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$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$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
$325,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,427sqft
Sale Pending
Ttr Sotheby'S International Realty
$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
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
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
3D Tour$299,500
Bedrooms: 2Bds
Bathrooms: 3Ba
Area: 1,867sqft
Sale Pending
Doug Ashley Realtors, Llc
3D Tour$299,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,152sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
$275,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 920sqft
Single family home for sale
Select Land & Homes, Llc
3D Tour$499,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 3,504sqft
Single family home for sale
Doug Ashley Realtors, Llc
3D Tour$349,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,304sqft
Single family home for sale
Re/Max Executive
$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
$366,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,432sqft
Single family home for sale
Northrop Realty
New Construction$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
3D Tour$1,279,000
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 2,956sqft
Single family home for sale
Ttr Sotheby'S International Realty
3D Tour$295,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: --sqft
Single family home for sale
Doug Ashley Realtors, Llc
$339,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,724sqft
Sale Pending
American Premier Realty, Llc
$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
Showing 43 - 84 of 106 homes for sale in MD 21620
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Based on information from Bright MLS through Nov 4, 2026, 1:30 AM. 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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