Set on a plateau with panoramic, protected views, West Wind Hill is a masterfully crafted estate spanning 391 acres that straddles the Connecticut and New York border. Reached by a private, gated drive that winds past old stonewalls, open meadow, and a serene pond, the property offers a level of privacy rarely found within two hours of New York City. The stone-and-shingle residence was built with singular attention to craft: the architect camped on site before construction began to orient the home for the finest light and views in every season, and the estate's stonework, including a 20-foot great room fireplace, was quarried directly from the hilltop on which the house sits. Reclaimed chestnut floors, hand-detailed millwork, and banks of French doors and windows run throughout the roughly 8,919-square-foot residence, which includes six bedrooms, a paneled library, a chef's kitchen with its own massive stone hearth, a billiard room, a media room, and a wine cellar with tasting room. The primary suite occupies a private wing of the main level. A stone-and-gunite pool and pool house with full kitchen, plus two stone barns, complete the grounds, which also include hiking trails, open meadows, and a pond. The offering includes five additional unencumbered parcels in Connecticut and further unrestricted acreage across the state line in New York, a significant and rare landholding that opens the door to a multi-generational compound, a conservation legacy, or possible future development. Few properties in the region combine this scale of craftsmanship, privacy, and flexibility in a single offering.