Here are the Top 5 Chestertown MD Waterfront and Water Access Homes for Sale as of Janyary 11, 2014. 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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$4,900,000.007 beds, 6 bathsmls no. KE7315421
FarmHistorically significant home on 21 acres, 1000' on the Chesapeake Bay. Modern 4...Courtesy of Chesapeake Real Estate Associates, LLC
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$3,695,000.006 beds, 5.5 bathsmls no. KE7969481
FarmCreate a family compound with an additional home that can fit on the property....Courtesy of Brandywine Fine Properties Sothebys INTL Realty
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$3,495,000.004 beds, 4.5 baths4314 sq. ft.mls no. KE7943447
FarmKentfields is located on Quaker Neck close to Chestertown on Maryland's beautiful...Courtesy of Lacaze Meredith Real Estate
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$3,050,000.0012 beds, 12.5 baths13851 sq. ft.mls no. KE8223466
Single Family HomeEastern Shore waterfront manor on the Chesapeake Bay. Recently renovated, Great...Courtesy of Coldwell Banker Chesapeake Real Estate Co
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$2,250,000.005 beds, 4.5 baths4968 sq. ft.mls no. KE6606019
FarmWaterfront farm on the Chester River with marvelous hunting off the marsh & on 2...Courtesy of Sassafras River Realty, Ltd.
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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)