350 Tory Hill Farm Road, Hillsdale

Peace and seclusion on a private road.
Pass through a stone gate and travel a long, winding driveway to reach this exceptional property, quietly nestled into the mountainside. The setting is serene, with only the sounds of birds and the breeze in the air. From its elevated position, the home offers uninterrupted, layered views of the Berkshire mountains stretching far beyond to distant peaks.
At over 6,400 square feet, the main house is built from the hand-hewn beams of two large historic barns, relocated and reimagined to create expansive interior volumes that feel both grounded and light. The main level centers around a great room with open kitchen, dining, and living areas that connect to a more intimate library alcove, corner screened porch, and open-air deck. A grand primary suite with a spa-like bath—including a large steam shower and soaking tub for two—is connected by a glass gallery.
Hovering above the main living space is a comfortably sized loft/den with a quiet reading nook oriented toward the eastern sunrise. The full-footprint lower level has tall ceilings and includes a generous recreation and media room, two bedrooms, two full bathrooms, a gym, climate controlled wine cellar, a generous laundry room, and a kitchenette/bar that services the outdoor pool terrace.
Separate from the main house, a one-bedroom guest cottage sits elevated among the trees. It includes a sitting area, kitchenette, full bath, and a private deck with filtered mountain views. The two car garage has room for additional recreational vehicles and is fully heated and cooled.
Outdoors, a 35-foot 'pebblecrete' pool with retractable cover and a summer shower sit on the edge of the hillside, surrounded by lush vegetable and cut flower gardens, an outdoor kitchen, and a substantial garden shed. Forged walking trails traverse the property, leading to peaceful spots and a hidden orchard.
Located on private Tory Hill—home to several notable properties—this is a retreat with uncommon privacy, thoughtfully designed spaces, and a deep connection to the surrounding landscape. Set in the heart of the Roe Jan region, just moments from the Berkshires, this is a property where quiet comfort and natural beauty live in happiness.

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