48 Oak Rd

Built circa 1750, the historic Tobias Wynkoop House stands as a quiet testament to the early heritage of the Hudson Valley. Constructed in the region's traditional Dutch stone style, the residence reflects the enduring craftsmanship and architectural character of the area's earliest settlements.The property rests upon seven acres across the alluvial fields of the great Kaaterskill Basin, at the foot of Kaaterskill Clove--a dramatic glacier-carved gorge within the eastern Catskill Mountains. Celebrated for its sublime scenery, this remarkable valley inspired many of the Hudson River School painters, including Thomas Cole, whose landscapes first introduced the grandeur of the Catskills to a wider audience.Today the residence has been thoughtfully restored with careful respect for its historic character. Wide king board plank floors, recessed windows set within thick stone walls, and generous ceiling heights on the upper levels remain hallmarks of the home's early construction. A Vermont wood-burning stove lends warmth and atmosphere, while the kitchen and bathrooms have been tastefully renovated to balance historic integrity with modern comfort.Across the interiors, curated furnishings create an atmosphere of privacy, calm, and understated elegance--an ideal setting for extended stays in the Hudson Valley countryside.The grounds reveal the property's most enchanting qualities. Rolling meadow, mature trees, and seasonal mountain views surround the residence, while a private in-ground pool, fire-pit gathering area, and open lawn invite long stays. Close to the ski slopes and close to Woodstock, Hudson, and the Catskills. Amazing fall landscaping views for unwinding.A rare historic residence offering pastoral beauty, architectural heritage, and refined country living in the heart of the Hudson Valley.This is a seasonal rental- available from October 1, 2026 - January 1, 2027.