On the crest of Woodruff Mountain, moments from The Southfield Store, York Lake, and area amenities, a classic country estate awaits. Its centerpiece is a stately 5BR, 5000sf, c. 1798, Georgian-Federal home, set on a 232-acre property encompassing a 3,550sf historic barn, smaller barns & run-ins, gardens & green house, Gunite pool & pool house, tennis court, fields, pastures, stream, mile-long trail abutting Sandisfield State Forest, and 5-acre spring-fed pond, all arranged for maximum livability and delight. You'll be pleased with the elevator, generator, & other mod cons, and charmed by historic details, stunning vistas, & untrammeled view of the star-studded night sky. Not enough? A 6,000sf guest house with four apartments suggests myriad uses for guests or income. Perfectly beautiful.

The origins of East Hill Farm date to the 1740s, when New Marlborough was first settled, and Thomas Shepard came from Cambridge, Massachusetts, to establishe a home in Southfield. In 1798, he built a grander residence signifying his prosperity and stature in the community. Shepard's new home boasted a facade and interior details in the latest neoclassical style, eight rooms including four bedrooms, five fireplaces, and expansive views across pasture and fields to the south. Now on the market for the first time in 55 years, East Hill Farm awaits a new steward to write a new chapter in its rich history. Throughout its 226-years, the now 232-acre property has been enhanced and adapted to meet the needs and wishes of many generations. The property's new owner will benefit from a classic vision of what a gracious country home should be, with tennis court, Gunite swimming pool, pool house, green house, spring-fed pond and streams, historic three-story barn, two smaller barns, woodlands and trails, perennial gardens, pastures, run-in sheds, and an expansive guest house with four apartments and totaling nine bedrooms. A three-bedroom caretaker's house, set on five acres, though not part of this listing, is being offered separately to the buyer of East Hill Farm. Classic, too, is the landscape design: gardens near the house lead the eye to pasture, hedgerow, and pond, and, beyond that, to a distant west view. Sight lines are punctuated by towering sugar maples, stone walls. The property abuts both Sandisfield State Forest and New Marlborough Land Trust acreage, connecting the two. About 2.5 hours drive from New York and Boston and 60 minutes from Bradley International Airport, East Hill Farm offers privacy as well as unparalleled access to culinary, recreational, and cultural amenities, including Sandisfield State Forest, York Lake, 1,000-acre Pond, Southfield Store, Old Inn on the Green, Butternut ski resort, and Great Barrington's shops, restaurants, and performance venues. Tanglewood, five Equity theaters, Jacob's Pillow Dance Festival, and amenities in northwest Connecticut are within easy reach. New Marlborough is a low-tax town of artists, writers, craftspeople, and second-home owners, attracted by its laid-back, sophisticated rural atmosphere. Its meeting house is the venue for the Music & More series and exhibits by painters, sculptors, ceramicists, and photographers, while its village green is the setting for a vibrant Saturday morning farmers' market.

The Thomas Shepard House

Listed in the National Register of Historic Places, the Thomas Shepard House was built by Connecticut housewright John Collar who did many homes in the southern Berkshires; one of his design trademarks was the creation of passages and closets next to the chimneys between rooms. In 1798, the Georgian architectural style was transitioning into the lighter, brighter Federal fashion; for instance, the home's fireplace surrounds feature both Georgian bolection moldings and Federal mantels. One unique detail is its enclosed staircase, which is thought to be original and reflect an early use of the house as a meeting place for a progressive Christian community. Subsequent owners have honored the home's original features: millwork and chair rails, chimney cupboards, hardware, wide-board flooring with original T-nails, the dining room's cooking fireplace with oversized beehive oven, and 12-over-12 window sash crafted of dense, durable first-growth wood, containing hand-blown 18th-century glass, and fitted with storms for maximum R-value. Subsequent owners have also added features for comfortable modern living. In the 1930s, a rear ell was added. The sellers enlarged this, bringing the home's size to an estimated 5,000sf and allowing for radiant heat, modernized kitchen, five bathrooms, large mudroom with laundry, family room with kitchenette and full bath, four-car garage, plus a second-floor sunroom, library, and additional bedroom. An elevator connects the library to the family room, a generator keeps things running whatever the weather, and the basement incorporates a wine cellar. The home's cedar shake roof was put on in 2021, there is high-speed Internet, a security system, a drilled well, and the heating fuel is oil. The National Register report is available upon request.

Lifestyle Amenities

On the north side of East Hill Road, the current owners created a tennis court, 20'x40' Gunite swimming pool, pool house, greenhouse, and 1,960sf barn. Behind it, a mile-long woodland loop road connects the main compound with the guest house to the east and pond to the west. Just west of the home's roofed flagstone patio and ancient apple tree, parterre gardens brim with perennials, annuals, and herbs, blueberry bushes, irises, peonies, and heritage roses. A picturesque 280sf garden shed provides a sweet focal point there, while a broad, mowed path leads to a stone wall and rustic gate, pasture, large spring-fed pond, estimated to be five acres in size for boating, fishing, and swimming. On the road's south side are pastures and woodlands, a stream with charming footbridge, and two barns. The current owners brought in a three-story, 3,550sf, 18th-century barn, dismantled in Vermont and reconstructed on site; this contains a number of large bays and two work rooms. They also built a smaller barn near the stream. Each of the pastures has a water source. In addition, there are two run-in sheds with electricity and running water, and three utility sheds. A portion of the property is in Massachusetts Chapter 61A, which provides for reduced taxes on agricultural properties.

The Guest House

The guest house is a 6,000sf structure, built in the 1930s as a barn for Arabian horses. Reimagined circa 1990, it contains four duplex apartments, each with radiant heat, independent exterior entrance, living/dining room with fireplace and cathedral ceiling, workable kitchen, first- and second-floor baths, generous closet space, and garage and storage space. It has a new oil/wood furnace, a fire security system, and a shared laundry room off the hallway that connects the apartments to the garage.

Apartment 1: Spacious first-floor living/dining room with fireplace and French doors opening to a large, private terrace, den with built-ins, full bath; kitchen, and gracious good-morning staircase leading to the upper floor, which has three bedrooms with one en suite and one shared bath.

Apartment 2: Spacious first-floor living/dining room with fireplace and doors onto a large, private terrace, den with built-ins, half bath, and kitchen, and staircase leading to two bedrooms with shared bath.

Apartment 3: Spacious first-floor living/dining room with fireplace and French doors to the lawn, den with built-ins, kitchen, half bath, and staircase leading to the two bedrooms and shared bath on the second floor.

Apartment 4: Spacious first-floor living/dining room with fireplace and built-ins, den with built in shelving, full bath with claw-foot tub, kitchen, and staircase to two bedrooms and shared bath on the second floor.