291 Roaring Brook Rd Chappaqua, NY 10514

Welcome to the Jonathan Tompkins House, a true New Castle landmark dating back to 1750 where history and modern living intertwine. Ideally situated in the heart of Chappaqua and located within the award-winning Chappaqua School District, this fully furnished rental weaves centuries of New Castle’s past into its walls. Original hand-hewn beams and stained glass evoke timeless old-world charm, seamlessly blended with the modern conveniences of today. Step inside the original Dutch door into the dramatic main living area featuring soaring 17-foot ceilings, stained glass windows, and a working fireplace. The main living space transitions into the oldest area of the home, the dining room, where exposed weathered beams lead into the beautifully updated chef’s kitchen, complete with Viking and Sub-Zero stainless-steel appliances, generous storage, and a breakfast nook. Also conveniently located on the first floor are a half bath and full laundry room. The second level, accessible from both the dining room and main living area, includes four bedrooms, highlighted by a spacious primary suite with an ensuite bath and a hidden “secret” passage leading to a flexible bonus space ideal for a home office or library. Additional features include two more bathrooms, a second large living area, and a loft with balcony that can serve as a playroom or fifth bedroom.
Set across two storybook acres, the home’s timeless proportions are thoughtfully grounded in the landscape. A double portico entrance, two-car garage, and Tesla charging station enhance the stately Greek Revival façade, while discreet solar panels and an energy-efficient heat pump support comfortable, low-maintenance living. A generous flat patio and two-story fenced playground provide exceptional outdoor spaces designed for both everyday enjoyment and effortless entertaining. Conveniently located near Chappaqua Crossings, town, top-rated schools, dining, and just three miles from the Metro-North station, this beautifully fully furnished historic residence delivers privacy, charm, and modern living in one unforgettable setting.