Nestled in the heart of Red Hook village, this historic grand Victorian offers the best of both worlds. Just steps from charming shops and restaurants, it also provides over an acre of backyard privacy, complete with multiple outbuildings, studio space, an in-ground pool, and ample relaxation areas. The inviting covered wraparound porch leads into a classic front foyer and parlor, suitable for business or leisure, thanks to the home's R-20 zoning, which allows for Bed & Breakfast use. The first floor features four distinct areas that can serve as living rooms, each with cozy nooks perfect for curling up by the wood-burning fireplace. The kitchen flows into a sunlit dining area and living room, creating a warm and open atmosphere. Legally a 9-bedroom home, it currently functions as a 5-bedroom, 3.5-bath residence, with potential for expansion. The home boasts spacious, bright interiors with stunning original details throughout. Updates include newly refinished parquet flooring in the upstairs floor, new vinyl lining for the pool, new furnace and oil tank from two years ago, roof approx. ten years old. The private backyard offers delightful surprises, including a large garden shed, a detached two-car garage with an attached workshop, potential in another space (formerly an art studio), and two smaller storage rooms at the far end. Built to last in 1890 and lovingly maintained for 45 years by one family, recent updates include a new pool liner, oil tank, and furnace. A short walk to Red Hook Middle & High School in the Red Hook School District, the property is across from the iconic Historic Diner, steps from numerous parks and walking trails, and just 2 hours from NYC and 15 minutes from the Rhinecliff train station. Additional Information: Heating Fuel: Oil Above Ground, Parking Features: 2-Car Detached.