Effortless One-Floor Living in Chestertown – 204 Rolling Rd Comfort, Convenience, and Chestertown Charm

Located just minutes from downtown Chestertown, 204 Rolling Rd is a beautiful example of how modern comfort can blend seamlessly with Eastern Shore lifestyle. This three-bedroom, two-bath ranch-style home offers nearly 2,300 sq ft of thoughtfully designed living space — all on one level — making it perfect for anyone seeking low-maintenance living without sacrificing style or space. Spacious Living, Inside and Out From the moment you walk in, you’ll notice how bright and welcoming this home feels. The open flow between the living, dining, and kitchen areas creates a warm, connected atmosphere that’s perfect for entertaining or relaxing with family.

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First Floor

A Landmark Home in the Heart of Chestertown’s Historic District

Few homes capture the spirit of Chestertown quite like this. Built in 1863, the residence at 105 High Street stands as a rare opportunity to own a piece of Eastern Shore history — thoughtfully restored for modern living. This five-bedroom, four-and-a-half-bath Victorian combines 19th-century craftsmanship with 21st-century comfort. From the moment you step inside, you’re greeted by soaring ceilings, intricate millwork, and a grand three-story staircase that defines the home’s timeless character.

A Blend of History and Modern Comfort

Every detail tells a story. The chef’s kitchen has been fully updated with stainless appliances and elegant finishes, offering the perfect…

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