Here are the Top Newest Listings of Chestertown MD Waterfront and Water Access Homes for Sale as of October 7, 2015. All Chestertown Waterfront properties are on the Chester River and there are many wonderful Water Access Communities with many full time homes as well as River Front Homes and Vacation Homes.

Founded in 1706, Chestertown rose in stature when it was named one of the English colony of Maryland's six Royal Ports of Entry. The shipping boom that followed this designation made the town at the navigable head of the Chester River wealthy. In the mid-eighteenth century, Chestertown trailed only Annapolis and was considered Maryland's second leading port.

A burgeoning merchant class infused riches into the town, reflected in the many brick mansions and townhouses that sprung up along the waterfront. Another area in which Chestertown is second only to Annapolis is in its number of existing eighteenth century homes.

As of the 1790 census, Chestertown was the geographical center of population of the United States.

Chestertown was incorporated in 1805, and was named for the Chester River.

Inventories are very low, the lowest in over 5 Years. If you are considering Selling Your Chestertown Waterfront or Water Access Home, please call us for a property evaluation or simply sign up for out Free Market Analysis

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 1
$899,000NEW FOR SALE
117 Water Street
ChestertownMD 21620
7 beds7 baths | Single Family Home 
0.33 acre lot
Courtesy of Long & Foster Real Estate, Inc.
#KE8765080
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 13
$450,000NEW FOR SALE
26909 Mallard Road
ChestertownMD 21620
4 beds3 baths | Single Family Home 
0.67 acre lot
Courtesy of Doug Ashley Realtors, LLC
#KE8585171
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 29
$429,900NEW FOR SALE
10788 Mallard Point Road
ChestertownMD 21620
4 beds3 baths | Single Family Home 
0.57 acre lot
Courtesy of Long & Foster Real Estate, Inc.
#KE8564511
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 30
$699,000NEW FOR SALE
300 N Water Street
ChestertownMD 21620
4 units | Multi Family Home 
0.36 acre lot
Courtesy of Coldwell Banker Chesapeake Real Estate Co
#KE8764566
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 30
$699,000NEW FOR SALE
300 Water Street
ChestertownMD 21620
6 beds5 full, 1 partial baths | Single Family Home 
0.36 acre lot
Courtesy of Coldwell Banker Chesapeake Real Estate Co
#KE8756013
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 15
$699,000NEW FOR SALE
217 Water Street #2
ChestertownMD 21620
4 beds3 full, 1 partial baths | Duplex 
2,800 sq ft
Courtesy of Coldwell Banker Chesapeake Real Estate Co
#KE8122012

Steve Hubbell REALTOR® - of the The "Bay Property Team", Selling Cecil County Waterfront -  - The "Bay Property Team" was formed in 2006 by Susan and Steve Hubbell to specialize in helping Buyers and Sellers invest in Waterfront and Water Access Properties in Chesapeake City, Elkton, Earleville, and Warwick in Cecil County MD and local Rivers and Creeks including the Sassafras River and Chester River. We also serve, Georgetown, Galena, and Kennedyville in Kent County MD, including Chestertown, and surrounding areas. (800)-890-0381 (Equal Housing Opportunity (O)-1-(410)-398-9000)