227 ACRES. 227 YEARS. AND ONE EXTRAORDINARY HILLTOP FARM-ESTATE: EAST HILL FARM, THE BERKSHIRES

East Hill Farm offers 227+ acres of protected quiet, anchored by 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 panes, long views and light.

Preservation integrity; 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, gunite pool + pool house, tennis, deep wells, generator, and modern connectivity.

Plus a former Arabian horse barn now a 4-residence compound with remarkable flexibility, whether kept as living spaces or reimagined. Ask for the full story.

For those who love historically significant properties, lavish gardens, and expansive land. Safeguarded with rigor and lived in with joy.

East Hill Farm sits high on a Southern Berkshire hilltop where the air quiets and the horizon opens. At its center stands the 1798 Thomas Shepard House, a Georgian–Federal home built for a prominent local citizen — composed symmetry, dentil cornice, unusually high ceilings, hand-blown glass windows that lend its rooms a magical light. Elegant, but not precious. It has the patina and ease of a farmhouse lived in across centuries.

The house was meticulously restored with preservation-level commitment: the historic core carefully disassembled and reassembled in the 1980s, compromised elements replaced, original materials reinstated wherever possible. Seamlessly integrated additions — a current kitchen, cathedral-ceilinged library, separate office, three-car garage — support easy modern daily life without disturbing what matters. Five bedrooms, five and a half baths, five fireplaces, approximately 5,000 SF.

The 227+ acres are not theoretical. Already organized into pastures, woodlands, a 4+ acre pond, established gardens, orchard, and internal trails and private roads, the land feels complete — because it is complete. The property abuts protected conservation and state forest, securing its privacy and quiet long into the future.

The estate’s supporting buildings are equally serious: a substantial late-18th century barn, additional agricultural and equipment structures, a gunite pool with pool house, and a tennis court. Originally a dramatic Arabian horse barn, the guest compound now offers four self-contained residences with cathedral ceilings and individual kitchens — approximately 6,668 SF, 10 bedrooms, 9 baths — suited for multi-generational living, staff, rental income, or creative repurposing.

What you cannot recreate is the whole of it. Assembling 227+ acres with this level of infrastructure, established plantings, pond, barns, and a mature setting in the Berkshires would take decades and many millions of dollars — and still be unlikely to be this coherent.

Five to ten minutes from Southern Berkshire restaurants. Close enough to the Berkshires’ world-class cultural venues. Far enough, when you turn back up the hill, to feel like you’ve left it all behind.

227 acres. 227 years. Come experience the extraordinary.

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