3D Tour
New Construction
$559,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,400sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
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3D TourNew Construction216 Blakefield Dr, CHESTERTOWN, MD 21620 
Price Drop: $19K
329 Union Church Rd, CHESTERTOWN, MD 216203D Tour
9816 Fairlee Rd, CHESTERTOWN, MD 21620 
22360 Great Oak Landing Rd, CHESTERTOWN, MD 21620
Preston Ln, Chestertown, MD 216203D Tour
7655 James Ln, CHESTERTOWN, MD 21620 3D Tour
8620 Park Dr, CHESTERTOWN, MD 21620 3D Tour
311 Devon Dr, CHESTERTOWN, MD 21620 
10 Cedar Chase Ct, CHESTERTOWN, MD 21620
129 Trafford Dr, CHESTERTOWN, MD 21620Price Drop: $30K
105 N Water St #3, CHESTERTOWN, MD 21620 3D Tour
118 Grant Ct, CHESTERTOWN, MD 21620 3D Tour
106 Harlan Loop, CHESTERTOWN, MD 21620 
109 S College Ave, CHESTERTOWN, MD 216203D Tour
411 Greenwood Ave, CHESTERTOWN, MD 21620 3D Tour
21338 Virginia Ave, CHESTERTOWN, MD 21620 
Hot
8630 Elm Rd, CHESTERTOWN, MD 216203D Tour
7982 Radcliffe Rd, CHESTERTOWN, MD 21620 
349 & 351 High St, CHESTERTOWN, MD 21620
23043 Bay Shore Spur, CHESTERTOWN, MD 21620
23416 Cloquet Rd, CHESTERTOWN, MD 216203D Tour
117 Water St N #2A, CHESTERTOWN, MD 21620 3D Tour
7653 Broad Neck Rd, CHESTERTOWN, MD 21620 3D Tour
213 Byford Dr, CHESTERTOWN, MD 21620 
123 Trafford Dr, CHESTERTOWN, MD 21620
720 Deep Landing Rd, CHESTERTOWN, MD 21620
136 Hilltop Dr, CHESTERTOWN, MD 21620
8833 Georgetown Rd, CHESTERTOWN, MD 21620
101 S College Ave, CHESTERTOWN, MD 216203D Tour117 Water St N #2B, CHESTERTOWN, MD 21620 
121 Primrose Rd, CHESTERTOWN, MD 216203D Tour
10751 Millbrook Dr, CHESTERTOWN, MD 21620 3D Tour
126 Char Nor Manor Blvd, Chestertown, MD 21620 
214 Silver Heel Rd, CHESTERTOWN, MD 216203D Tour
21125 Iowa Ave, CHESTERTOWN, MD 21620 
103 Flying Cloud Dr, Chestertown, MD 21620
102 Pine St, Chestertown, MD 21620
6746 Quaker Neck Rd, CHESTERTOWN, MD 21620
8750 Georgetown Rd, CHESTERTOWN, MD 21620
23055 Old Fairlee Rd, CHESTERTOWN, MD 21620
102 Flying Cloud Dr, CHESTERTOWN, MD 21620
10594 Millbrook Dr, CHESTERTOWN, MD 21620
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Homes for Sale Under 600K in 21620, MD
130 Homes for Sale
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3D TourNew ConstructionPrice Drop: $19K$549,900
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,464sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
3D Tour$535,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,624sqft
Sale Pending
Long & Foster Real Estate, Inc.
$525,000
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 2,688sqft
Sale Pending
Doug Ashley Realtors, Llc
$525,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,824sqft
Sale Pending
Shoreline Realty
3D Tour$519,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,475sqft
Single family home for sale
Re/Max Advantage Realty
3D Tour$499,900
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,524sqft
Single family home for sale
Doug Ashley Realtors, Llc
3D Tour$499,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 3,504sqft
Single family home for sale
Doug Ashley Realtors, Llc
$495,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,656sqft
Single family home for sale
Cross Street Realtors Llc
$480,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 3,176sqft
Single family home for sale
Elevated Real Estate Solutions
Price Drop: $30K$459,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,098sqft
Condo for sale
Coldwell Banker Chesapeake Real Estate Company
3D Tour$457,500
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,664sqft
Single family home for sale
Re/Max Executive
3D Tour$425,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 3,165sqft
Single family home for sale
Douglas Realty Llc
$419,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,216sqft
Sale Pending
Taylor Properties
3D Tour$419,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,676sqft
Sale Pending
Coldwell Banker Chesapeake Real Estate Company
3D Tour$400,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,000sqft
Single family home for sale
Doug Ashley Realtors, Llc
Hot$399,900
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 1,936sqft
Single family home for sale
Save 6, Incorporated
3D Tour$399,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,904sqft
Single family home for sale
Doug Ashley Realtors, Llc
$395,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 3,664sqft
Townhouse for sale
Coldwell Banker Chesapeake Real Estate Company
$385,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,630sqft
Single family home for sale
Rock Hall Properties Real Estate
$384,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,512sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
3D Tour$375,000
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 787sqft
Condo for sale
Ttr Sotheby'S International Realty
3D Tour$375,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 1,790sqft
Single family home for sale
Benson & Mangold, Llc
3D Tour$372,000
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,277sqft
Sale Pending
Doug Ashley Realtors, Llc
$370,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,504sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
$369,999
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,271sqft
Sale Pending
Coldwell Banker Waterman Realty
$366,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,432sqft
Single family home for sale
Northrop Realty
$364,000
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,625sqft
Sale Pending
Coldwell Banker Chesapeake Real Estate Company
$359,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,036sqft
Single family home for sale
Doug Ashley Realtors, Llc
3D Tour$350,000
Bedrooms: 1Bd
Bathrooms: 1Ba
Area: 850sqft
Condo for sale
Ttr Sotheby'S International Realty
$350,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,034sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
3D Tour$350,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,942sqft
Sale Pending
Long & Foster Real Estate, Inc.
3D Tour$349,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,304sqft
Single family home for sale
Re/Max Executive
$340,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 1,972sqft
Single family home for sale
Cross Street Realtors Llc
3D Tour$339,900
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 1,294sqft
Sale Pending
Doug Ashley Realtors, Llc
$339,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,724sqft
Sale Pending
American Premier Realty, Llc
$339,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,250sqft
Single family home for sale
Clark & Co Realty, Llc
$339,000
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 3,371sqft
Single family home for sale
Doug Ashley Realtors, Llc
$334,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,900sqft
Sale Pending
Chesapeake Real Estate Associates, Llc
$330,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,628sqft
Sale Pending
Benson & Mangold, Llc
$329,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,896sqft
Single family home for sale
Long & Foster Real Estate, Inc.
$329,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,499sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
Showing 1 - 42 of 130 homes for sale in MD 21620
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Based on information from Bright MLS through Nov 4, 2026, 10:45 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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