Chestertown Homes with Circular Driveway Parking desc

Welcome to Chestertown, Maryland—a charming riverside town that perfectly blends history, culture, and natural beauty. Nestled in Kent County along the picturesque banks of the Chester River, Chestertown is renowned for its vibrant arts scene, quaint shops, and rich colonial heritage. Stroll through the historic downtown area, where you’ll find beautifully preserved 18th-century buildings, delightful cafes, and local galleries showcasing the work of talented artisans. The town also hosts a variety of events throughout the year, including the popular Chestertown Tea Party Festival, celebrating its storied past.

For those considering a home in this idyllic setting, you'll find a selection of properties featuring circular driveways—an elegant touch that enhances both convenience and curb appeal. Homes with circular driveway parking not only provide ample space for multiple vehicles but also offer a graceful entrance that welcomes guests with open arms. Imagine driving up to your dream home, surrounded by lush greenery and the charm of Chestertown’s historic charm.

Living in Chestertown means enjoying a close-knit community with access to scenic parks, recreational activities, and a variety of outdoor adventures. Whether you’re kayaking on the river, exploring the nearby Eastern Shore, or simply savoring the local cuisine, life in Chestertown is both peaceful and fulfilling. With its unique blend of history, culture, and stunning homes, including those with circular driveways, Chestertown is truly a gem waiting to be discovered. Come and experience the magic of this enchanting town!

Newest Chestertown Homes with Circular Driveway Parking desc

$1,375,000

4 Beds ⋅ 5 Baths

Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away. The home features 4 bedrooms and 5 full bathrooms, plus a large loft that could be used as an additional bedroom. The large eat-in kitchen has expansive windows that perfectly frame the water view. A great spot for entertaining! Doors in the kitchen lead to the waterfront deck, spanning the front of the home. A new roof was installed in June, 2026. In both sitting rooms, you’ll find fireplaces that have been conveniently updated to propane. The first-floor primary bedroom opens up to the waterfront deck and offers a fantastic water view, as well as a large bathroom that was recently updated. Upstairs you’ll find two waterfront bedrooms, one with an updated attached bath. There's a second full bathroom and ample closet space in the hallway. Downstairs, there are two additional full bathrooms and a large bedroom. Above the kitchen sits the light-filled loft, a great office, studio, or extra bedroom. The exterior has a generous front porch, outdoor shower, circular drive, 2-car garage, fenced dog run, and additional garage space connected to the basement. This light-filled waterfront property is located 15 minutes away from the waterfront community of Rock Hall and historic Chestertown.

22470 Fairgale Farm Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

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