East Hill Farm offers 227 acres of protected quiet, anchored by the elegant 1798 Thomas Shepard House. A private hilltop world.Main house: Georgian-Federal; 5 BR, 5.5 BA, ~5,000 SF; 5 fireplaces; unusually high ceilings, wide-board floors, antique glass, rooms that hold the light, views that connect. Graceful, welcoming.A complete estate that also can be a working-farm or equine property: barns + outbuildings, pastures, private trails + roads, 4+ acre pond, gardens + orchard, pool, pool house, greenhouse, tennis.A vast former Arabian horse barn, now guest compound, or for you to reimagine. Preserved with rigor, lived in with joy, and rooted in the land and history that defines the Berkshires. Read the whole story. Read the whole story

The Definition of Ultimate Privacy! A masterpiece of a home invites the most fastidious prospect. Built with the utmost dedication to detail that no item too small was overlooked. The ability to expand and build to your heart's desire is here. Perhaps a pool, tennis court, even a football field is within your reach. This property consists of 200+ acres, a 6,700 sq. ft home, Primary En-Suite on the first level, 2 bay garage, Extra Large Enclosed Barn capable of sheltering a bulldozer with a private space up above. Nestled in the foothills of the Berkshires on beautiful winding country roads. A lovely vineyard just around the corner, a short 25 minute drive to BDL International airport and just under 3 hours to NYC and 2 to hours to Boston. Come make this your dream get-away!

A rare French Manor estate gracing one of South Berkshire's most scenic and sought-after country roads, this extraordinary 45+/- acre sanctuary offers unmatched privacy, panoramic mountain views, and a setting of timeless beauty. Bordering protected state forest, the property unfolds across rolling meadows, tranquil ponds, and a gently flowing brook--creating a secluded retreat that feels worlds away, yet remains moments from the cultural heart of the Berkshires. It is awaiting buyers final finishes.