"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!"

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This open concept Vivaldi model in Centreville’s premier 55+ community of Symphony Village combines quality and style in one exceptionally desirable home.

Welcome to Fairgale, a tasteful waterfront community located minutes from Historic Chestertown and Rock Hall. This 36.66 total acre property with 1250+/- feet of stable shoreline and 21+/- fertile tillable acres is ideally elevated and positioned to take advantage of the panoramic water views and sunsets across Fairlee Creek. The thoughtfully designed residence has the perfect balance to host both casual or formal gatherings, either indoors or outdoors. The exterior of the residence includes a wonderful slate patio, brick sidewalks, a beautiful gunite swimming pool, a storage building for small watercraft and lawn equipment, and a winding asphalt driveway. The interior includes a chef’s eat-in kitchen with a cozy gathering area, a formal living room with double patio doors, a formal dining room, an office, and a private first-floor primary bedroom suite with two spacious walk-in closets and a large walk-in shower. Upstairs, you will find three additional bedrooms with two spacious full ceramic tiled baths. The finished basement is a grandchild's dream with a marvelous game room area, built-in bunk beds, a separate bedroom, a full bath and a separate outside entrance. Other notable interior features include beautiful wood floors (Oak and Heart Pine), designer tile in bathrooms and laundry room, a gourmet kitchen featuring professional grade appliances, an expansive butcher block center island, granite counters, and exposed ceiling beams. A large sliding glass door opens onto the lovely, screened porch overlooking the pool and patio. This home is loaded with numerous other tasteful finishes and features for which you must see to appreciate. Water access is available from the gently sloping lawn to the water's edge or also a short golf cart ride away from the community waterfront area where you will find the property's own deep water boat slip with a new 5-ton electric boat lift and community boat ramp. This property offers the epitome of true Eastern Shore living, with timeless style and endless possibilities! www.22600fairgalefarmlane.com

Prime storefront/office space.

Celebrating the water on Langford Creek! This rare offering is conveniently situated in a highly sought-after location within a short country drive to Historic Downtown Chestertown or a several minute ride to Rock Hall. The property offers breathtaking southwestern unobstructed views of Langford Bay and the Chester River. The property comes complete with a multi slip, deep water dock (6+ feet depth) with one slip covered and two slips with lifts. The cozy cottage has 3 full bedrooms and a sleeping loft along with two full baths. Notable features include a first-floor primary suite with sliding doors leading to water's edge, a waterside shaded screened porch, living room with wood-burning fireplace, separate dining room, upgraded eat-in kitchen, and separate laundry room. The home is situated with gorgeous views, across the rarely utilized adjoining community open space, of Horner Cove. Also included is a shaded waterside elevated patio, an emergency generator, a partial basement, a state-of-the-art Advantax Septic Treatment System and waterside bulkheading.

Phenomenal hunting property with 30+ acres tillable, mature woods, and waterfowl impoundment with 10' high tinsel fencing.

Located at the end of the cul-de-sac in the heart of Queenstown, this ranch home has three bedrooms and two full bathrooms. Low maintenance hardwood and tile floors throughout. The kitchen has sliding glass doors that leads out onto the patio and backyard. Rear access to the mudroom with utility sink and washer and dryer. Detached garage in back for motorcycles or play toys. Quick access to Route 50 for an easy commute to Kent Island and Annapolis, close to Queenstown outlets, boat ramps, and Queenstown Golf Course. Tenant has moved out and the home is vacant.

Sold in 2023

This wonderful home is ideally located just outside of Chestertown on a corner lot in the desirable neighborhood known as Kent Acres. The home has been lovingly cared for by the same owner since 1978. Location, location, location being only 2 miles to Chestertown, 10 miles to Rock Hall, and only several miles to Chester River and Langford Creek public landings. Highlights of this manageable home include true oak hardwood flooring, wood burning fireplace, tiled baths, a separate den/office, a screen porch with vaulted ceiling, a partially finished dry basement, 3 bedrooms, 2 tiled baths, and a lovely front yard with attractive landscaping. Other notable features to mention are a one-car attached garage with storage cabinets, an emergency generator, and a completely new roof system in 2019. There is an adjoining half-acre lot in the rear that is also available for an additional $59,000 that was perc approved in 1985.

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!

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.