Located just steps from the Appalachian Trail and the New York state line, this historic 1820 Colonial and guest cottage offer a unique blend of historic craftsmanship, character, and charm. Set on 8.38 acres in northwest Sherman, the property showcases many period details - from original stone fireplaces and custom built-ins to handsome stone walls, patios, steps, and terracing. The main residence features 10 spacious rooms, including four bedrooms, two full baths, a generous living room, a formal dining room, and a west wing library with a beautiful stone floor. A sun-filled, eat-in kitchen and two flexible home offices-one on each level-offer flexibility for today's lifestyle. Polished red doors from the kitchen and library lead to south-facing stone patios, perfect for entertaining or quiet moments in the sun. Additional highlights include a detached two-story pole barn/two-car garage, and a charming guest cottage thought to have been the original barn or stable. Set at the opposite end of the semi-circular drive, the cottage offers private guest quarters, studio space, or rental income potential. Known as "The Willis Sherwood House" and featured in Sherman Sentinel Houses & Barns, this residence has evolved from a simple four-room cottage into a treasured family home, lovingly improved and expanded across generations. Ideally located just minutes from Metro-North trains, with easy access to NYC and beyond, this is a unique opportunity to own a piece of Sherman's history.