Here are the Top Chestertown MD Waterfront and Water Access Homes for Sale as of August 9, 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

39 Results Price (high to low)
View Details
 30
$3,900,000FOR SALE
22607 Handy Point Road
ChestertownMD 21620
7 beds5 full, 2 partial baths | Farm 
21.02 acre lot
Courtesy of Long & Foster Real Estate, Inc.
#KE8367394
View Details
 29
$3,900,000FOR SALE
6349 Broad Neck Road
ChestertownMD 21620
4 beds3 full, 1 partial baths | Farm 
6,448 sq ft143.4 acre lot
Courtesy of Cross Street Realtors LLC
#KE8668481
View Details
 29
$3,150,000FOR SALE
24091 Providence Plantation Lane
ChestertownMD 21620
6 beds5 full, 1 partial baths | Farm 
76.07 acre lot
Courtesy of Brandywine Fine Properties Sothebys INTL Realty
#KE7969481
View Details
 30
$2,975,000NEW FOR SALE
5793 Quaker Neck Landing Road
ChestertownMD 21620
4 beds4 full, 1 partial baths | Farm 
4,314 sq ft65.13 acre lot
Courtesy of Long & Foster Real Estate, Inc.
#KE7943447
View Details
 29
$2,385,000FOR SALE
5268 Quaker Neck Road
ChestertownMD 21620
5 beds4 full, 1 partial baths | Farm 
4,748 sq ft42.07 acre lot
Courtesy of Coldwell Banker Chesapeake Real Estate Co
#KE8635536

 

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)