This stately 1865 Italianate offers a rare opportunity to own a piece of Kingston's architectural and agricultural history, just minutes from the hip Uptown Stockade District. Once the homestead at the center of a 200-acre farm, the property today still unfolds across 1.5 park-like acres spanning two parcels in leafy Roosevelt Park, with mature trees and open lawns creating a lush, private setting from every angle. A circular driveway, with a third gracious exit to a side street, winds past hydrangea beds toward a classic clapboard facade rich with original Italianate Farmhouse detail, including ornate eave brackets, arched and pedimented gable windows and elegant projecting bay windows, all freshly repainted this summer. Inside, the interior reveals a gracious center-hall layout that unfolds beneath soaring 11-foot ceilings and is surrounded on all elevations by floor-to-ceiling windows that flood the home with sunlight. Original crown moldings and other irreplaceable millwork are found throughout, alongside other period details that speak to nearly 160 years of continuous care. At more than 5,000 square feet, the home offers 5-6 bedrooms and 3.5 baths, plus a large eat-in kitchen made for gathering, a massive basement outfitted with a home gym, and a ballroom-scale staircased attic. The house also boasts rare flexibility: A semi-separate two-level wing, featuring two of the bedrooms and one full bath plus a living room, can serve as private guest quarters within the main house or be fully separated as an accessory dwelling unit for extended family or rental income. A gracious rear porch offers a spot for quiet retreat beneath the mature tree canopy, and there's also a discreetly sited 3-car garage that cleverly screens the property from the side-street entry. Inside and out, this property offers a unique blend of estate-scale living just minutes from the shops, restaurants, and historic charms of one of the Hudson Valley's hottest commercial districts.