High on a hilltop in the Southern Berkshires stands East Hill Farm. 227 cultivated acres encompassing pristine forest, a spring-fed pond, a striking barn, verdant pastures, formal and vegetable gardens, a pool, and a tennis court. The centerpiece: a 1798 Georgian home, 5,000 SF with 5 bedrooms. Ready for private living, entertaining, horses, farming, a bespoke destination, or simply: tranquility. Includes a reimagined 6,000+ SF guest house, once an Arabian horse barn. 2½ hours to both NYC & Boston, yet a world apart. East Hill Farm offers what money rarely can buy: authenticity at scale. A 227 year-old house expanded, refined for 21st century life. Land, privacy, history, and a place of peace, which has endured through every chapter of American history. The next chapter begins with you. Reach out! Where The World Falls Away--227 acres. 227 years. One extraordinary hilltop farm. Drive up East Hill Road through Southfield village, past the store, climbing toward the top of Woodruff Mountain. The dirt road is well-maintained and lightly traveled. Sugar maples line your approach--massive, ancient trees that have watched over this land since before the house was built. Behind them, set back from the road, stands the kind of barn that makes photographers stop their cars. Three and a half stories of hand-hewn timber, painted proper New England red, moved here piece by piece from Amherst, Massachusetts, because the sellers understood that a farm needs a real barn. Not a replica. The real thing. The House Stops Your Heart--Federal period, 1798, when John Adams was president. This wasn’t just another farmhouse. When Thomas Shepard commissioned John Collar to build this, he was making a statement. 8 rooms. 5 fireplaces. Ceilings higher than any farmer needed. Those distinctive 12-over-12 windows with hand-blown glass that turns the morning light liquid. A facade with sidelight windows and dentil cornice that announced to every traveler: here lives a person of substance. Walk through that front door and the wide center hall opens before you. Original wide-plank floors--King’s boards, they called them, because timber this wide was supposed to be reserved for the Royal Navy’s masts. Twin parlors flank the entrance, flooded with southern light. To your left, the original keeping room, now the dining room, where that massive cooking fireplace with its beehive oven still works perfectly after 227 years. The draft in these fireplaces is extraordinary. The woodwork throughout is original or crafted by hand precisely to match. Chair rails, wainscoting, built-in china cabinets with their original hardware. Those small cupboards tucked around the chimneys--John Collar’s signature touch. Five Families in 227 Years--Jesse Hartwell married Thomas Shepard’s niece and turned the house into a meeting place for progressive thinkers, and through the 19th century, the Hartwell family made this their home. Then came the Arabian horse breeders in the 1930s who added the newer rear ell and built what’s now the guest house. The current sellers bought the house and five acres in 1969, then spent the next five decades not just restoring but thoughtfully expanding it. You’ll be only the fifth resident to call East Hill Farm home--and despite its National Register status, free to shape its future as you see fit. That newer section? Radiant heat underfoot, a proper mudroom with laundry, a family room or perfect home office with its own kitchen, and an elevator up to a sun-filled library with built-in shelves and an ensuite bedroom and bath. A luminous sunroom framing year-round sunsets, with sweeping views across the formal gardens, horse pastures, and the shimmering pond below. Upstairs in the original part of the house, an additional four bedrooms, each with its own character. The canopy bedroom with its blue and white toile--that’s not staging, that’s how the family lives. Wide hallways, deep closets, and in that large upstairs hall above the front door, a perfect spot to sit and read while gazing out the neoclassical window over your barn, fields and forest, mountains in the distance. 5 full and 1 half baths in all--some original 1930s with their good bones, others from the 1980s restoration. The kitchen? Also 1980s, completely functional with good counter space, and a working wood-fired stove alongside modern appliances. Morning light streams in from the east, and sunset views are to the west, opening onto fieldstone patios on either side. Everything works: oil heat from a Viessman German boiler, cedar shake roof (much replaced in 2021), private well water so good they’ve bottled it up for guests, backup generator, fiber internet. The bones are so good and the mechanicals so solid that you can move in tomorrow or update to your taste--the house won’t fight you either way. 227 Acres: A Complete World--East Hill Farm is more than the sum of its parts. From the original five-acre homestead, the current owners lovingly reunited land to create the breathtaking 227-acre estate it is today. 154 acres stretching across the north side of East Hill Road, and 73 tranquil acres to the south. To the north, a substantial portion of the property borders Sandisfield State Forest and thousands of acres of protected land. To the south, you have a section along Hotchkiss Road that is part of the New Marlborough Land Trust. Each acre is part of a dream fulfilled, a landscape that invites endless exploration and inspiration. Walk west from the kitchen patio between the formal gardens. Brick paths wind through perennial beds: heritage roses, peonies, iris. A long row of prolific blueberry bushes. In the vegetable garden, established asparagus and rhubarb come back stronger every year. Passing that perfect garden shed with its slate roof, as mist rises off the pond, becomes part of your morning coffee stroll. The pond--almost four acres, brook-fed, crystal clear. The family created it, and for decades it’s been their private swimming hole, sailing spot, fishing paradise. Circle the pond and you’ll find the big fishing rock on the west side, the perfect swimming spot on the east. Or head into the forest. Miles of trails, including a loop road that connects to Sandisfield State Forest. In spring, Lee Brook, the largest of several on the farm, roars with snowmelt. Up where the brook crosses the trail, it forms a waterfall after a hard rain. These are the headwaters of the Whiting River, and you own it. This isn’t just acreage it