$115,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 910sqft
Single family home for sale
Real Broker, Llc
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108 Pine St, CHESTERTOWN, MD 21620 
3D Tour
108 Oak Leaf Dr, CHESTERTOWN, MD 216203D 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
112 Elm St, CHESTERTOWN, MD 21620
23055 Old Fairlee Rd, CHESTERTOWN, MD 21620
8750 Georgetown Rd, CHESTERTOWN, MD 21620
23069 Raleigh Rd, CHESTERTOWN, MD 216203D Tour
10751 Millbrook Dr, CHESTERTOWN, MD 21620 
119 Darden Rd, CHESTERTOWN, MD 21620New Construction
#35 Landing Ln, CHESTERTOWN, MD 21620 New Construction
#25 Landing Ln, CHESTERTOWN, MD 21620 New Construction
104 Landing Ln, CHESTERTOWN, MD 21620 New Construction
#36 Landing Ln, CHESTERTOWN, MD 21620 New Construction
#37 Landing Ln, CHESTERTOWN, MD 21620 New Construction
104 Little Harbor Way, CHESTERTOWN, MD 21620 New Construction
102 Little Harbor Way, CHESTERTOWN, MD 21620 New Construction
106 Landing Ln, CHESTERTOWN, MD 21620 3D TourNew Construction
216 Blakefield Dr, CHESTERTOWN, MD 21620 3D Tour
10800 Cliff Rd, CHESTERTOWN, MD 21620 
121 Primrose Rd, CHESTERTOWN, MD 216203D Tour
24339 Chestertown Rd, CHESTERTOWN, MD 21620 
8833 Georgetown Rd, CHESTERTOWN, MD 21620
213 Central Dr, CHESTERTOWN, MD 21620
134 Char Nor Manor Blvd, CHESTERTOWN, MD 21620
100 Metcalf Rd, CHESTERTOWN, MD 21620
26933 Mallard Rd, CHESTERTOWN, MD 21620
300 Hickory Ln, CHESTERTOWN, MD 21620
349 & 351 High St, CHESTERTOWN, MD 216203D Tour
411 Greenwood Ave, CHESTERTOWN, MD 21620 3D Tour
7653 Broad Neck Rd, CHESTERTOWN, MD 21620 
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21620, MD Homes For Sale & Real Estate
168 Homes for Sale
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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
$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
3D Tour$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
New Construction$786,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,964sqft
Condo for sale
Gunther-Mcclary Real Estate
New Construction$1,099,900
Bedrooms: 4Bds
Bathrooms: 4Ba
Area: 2,784sqft
Condo for sale
Gunther-Mcclary Real Estate
New Construction$813,900
Bedrooms: 3Bds
Bathrooms: 4Ba
Area: 2,192sqft
Condo for sale
Gunther-Mcclary Real Estate
New Construction$753,500
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,964sqft
Condo for sale
Gunther-Mcclary Real Estate
New Construction$765,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,964sqft
Condo for sale
Gunther-Mcclary Real Estate
New Construction$849,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,980sqft
Condo for sale
Gunther-Mcclary Real Estate
New Construction$839,500
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,964sqft
Condo for sale
Gunther-Mcclary Real Estate
New Construction$799,900
Bedrooms: 3Bds
Bathrooms: 4Ba
Area: 2,092sqft
Condo for sale
Gunther-Mcclary Real Estate
3D TourNew Construction$559,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,400sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
3D Tour$1,495,000
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 5,241sqft
Sale Pending
Taylor Properties
$350,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,034sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
3D Tour$269,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 960sqft
Single family home for sale
Doug Ashley Realtors, Llc
$364,000
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,625sqft
Sale Pending
Coldwell Banker Chesapeake Real Estate Company
$314,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,232sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
$279,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,128sqft
Single family home for sale
Meredith Fine Properties
$245,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,140sqft
Townhouse for sale
Bayside Realty
$625,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,600sqft
Sale Pending
Coldwell Banker Chesapeake Real Estate Company
$1,198,000
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 3,640sqft
Sale Pending
Gunther-Mcclary Real Estate
$395,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 3,664sqft
Townhouse for sale
Coldwell Banker Chesapeake Real Estate Company
3D Tour$419,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,676sqft
Sale Pending
Coldwell Banker Chesapeake Real Estate Company
3D Tour$375,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 1,790sqft
Single family home for sale
Benson & Mangold, Llc
Showing 85 - 126 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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