835 High St, Chestertown, MD 21620

2-unit investment in Chestertown. Excellent opportunity for college parents to house their students. Possibly live in one side and rent the other. Backs up to Rails and Trails for easy stroll to downtown Chestertown.

109 N Water St, Chestertown MD 21620

Welcome to the Esau Watkins House (circa 1739), believed to be the earliest remaining dwelling on the Chester River in Historic Chestertown, the capitol of Kent County, Maryland. Rarely does a home of this significance become available in the heart of Chestertown’s famed Water Street district.

This five-bedroom, three-and-one-half-bath historic gem offers captivating, unobstructed views of the unspoiled Chester River. Notable features of this home include extensive random width wood plank flooring, proportionally balanced trim work, gorgeous scalloped built-in corner cupboards, a sun-filled riverside enclosed porch, a living room with wood burning fireplace, spacious second-floor primary suite, adequate “step-in” closets, and storage, walk out full basement, lush waterside garden, and sea-walled frontage with pier deck for water access.

This highly sought-after location is within a short, pet-friendly, walking distance to several well-reviewed restaurants, two delicious bakeries, intriguing boutique shops/galleries, and the highly acclaimed Downtown Chestertown Farmer’s Market. The Chester River offers endless watersports, world-class crabbing, fishing, kayaking, and undisturbed shoreline exploration. Chestertown is home to Washington College, the Chestertown Tea Party, and the sailing ship “Sultana.” Come Enjoy!

Lot 142 & 143 Clarissa Rd. Chestertown, MD 21620

Lot 142 & 142 - .34 +/- acre lot in Chesapeake Landing. Perc Approved, See documents for perc information. We suggest seeing Kent County Environmental Health for perc verification and further information. Perfect place to build your home or spec house! Located near public boat ramp and marina.

Brices Mill Road

Rarely do properties like this come on the market in Kent County! Located just two +/- miles to Downtown Chestertown, this 23.5 +/- acre small farm offers everything one could want, 10.4 +/- tillable acres, 7.5 +/- wooded acres with stream, 45x60 Mortan pole building, and 2400 sq. ft. 3-4 bedroom, 2.5 bath one level home with marvelous unobstructed views of open field and woods. Enjoy watching or hunting deer, turkeys, or geese on your own property! The home was built in 1990 by the same family who presently reside there now. Features include a large primary suite, eat-in kitchen, spacious living room with fireplace and cathedral ceiling opening to a covered patio overlooking the property, 2 car attached garage, and a deep concrete floored crawl space. The condition and location of their property is exceptional!

Fairlee Road

Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Lots of wildlife in the area. Perfect location to build your new home back off the road in a convenient location. Maybe even have your own deer stand! Plat is filed in Kent County Land Records in Plat Book MLM liber1, Folio 391 dated 6/19/1995.