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. Overview The origins of East Hill Farm date to the 1740s, when New Marlborough was first being settled, and Thomas Shepard came from Cambridge, Massachusetts, to establish a home in Southfield. In 1798, he built a grander residence signifying his stature in the community and his prosperity as a farmer. Crafted by house-wright John Collar, known to have built a number of homes in the southern Berkshires, 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. Since then, the now 230-acre property has variously served as a meeting place for a progressive Christian community, an Arabian horse farm, and a llama farm, as, throughout its 226-year history, it has been expanded and adapted to meet the needs and wishes of many generations. Now on the market for the first time in 55 years, East Hill Farm awaits a new steward to carry it forward and write a new chapter in its rich history. The property's new owner will benefit from a classic vision of what a gracious country home should be, replete 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, several run-in sheds, and an expansive guest house composed of 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, which offers far vistas, bucolic views of field and pasture, and intimate gardens near the house that give way and lead the eye to the pasture, hedgerow, and pond, and, beyond that, to a larger, distant view to the west. Being in New England, sight lines are punctuated by towering sugar maples, stone walls, split rail fences, all amidst a backdrop of verdant green in summer and vivid white in winter. Located in the southern Berkshires, East Hill Farm has, of course, unparalleled access to culinary, recreational, and cultural amenities. These include Sandisfield State Forest (which it abuts), York Lake, 1,000-acre Pond, the Southfield Store, the Old Inn on the Green, Cantina 229 (scheduled to reopen in 2024), Bash Bish and Umpachene falls, Butternut and Otis Ridge ski resorts, and the village of Great Barrington with its shops, restaurants, and performance venues. For additional recreation and protection, the property abuts both Sandisfield State Forest and New Marlborough Land Trust acreage, connecting the two. A bit farther afield, the new owners may enjoy Tanglewood, five Equity theaters, several film festivals, Jacob's Pillow Dance Festival, and the amenities in northwest Connecticut. New Marlborough, just 20 minutes from Great Barrington, is a low-tax town of artists, writers, and craftspeople, with its share of second-home owners, who enjoy its laid-back, sophisticated rural atmosphere; each summer and early fall, its meeting house hosts the Music & More series and exhibits the work of local painters, sculptors, ceramicists, and photographers, while its village green is the setting for a vibrant Saturday morning farmers' market. New Malborough is about 2.5 hours drive from New York and Boston and 60 minutes from Bradley International Airport. The Thomas Shepard House Listed on 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 small spaces between the chimneys and exterior walls, many of which later generations have appreciated as closets. In 1798, the neoclassical Georgian architectural style was transitioning into the lighter, brighter Federal fashion evidenced in fireplace surrounds that feature both the earlier Georgian bolection moldings and Federal mantels and details. One unique detail is the enclosed "cabinet"staircase, which is thought to be original and reflect an early use of the house as a meeting place for a progressive Christian sect. Exceptionally well-documented and well-preserved, the home's features have been honored by all of its owners; these include 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 and containing hand-blown 18th-century glass, and fitted with storms for maximum R-value. Other original energy features include the home's south-facing, light-welcoming front facade. While preserving its historic character, subsequent owners of the property have added features for comfortable modern living. In the 1930s, a rear ell was added. This was enlarged by the sellers, bringing the home's size to an estimated 5,000sf and allowing for radiant heat, a modernized kitchen, five bathrooms, a large mudroom with laundry, a family room or guest suite with a kitchenette that connects the main house with its four-car garage, and a second-floor sunroom, library, and additional bedroom. An elevator connects the library to the family room below it, while a generator assures that fireplaces, candles, and hearth cooking can be used for enjoyment and ambiance rather than of necessity. The basement, with its concrete floor, incorporates a wine cellar. The home's cedar shake roof was put on in 2021, there is a drilled well, and the heating fuel is oil. Also in place are high-speed Internet with Spectrum and a security system. The National Register report and Virtual Tour of the Guest House are available upon request. Lifestyle Amenities The current owners created a tennis court, 800sf (20'x40') Gunite swimming pool, pool house, and greenhouse, gardens to enhance one's experience of the property. These amenities, along with the house and its flagstone patios, gardens, orchard, pastures, run-ins and small barn, woodlands, recreational pond, and guest house, are set on 153 acres on the north side of East Hill Road. To the south, 73 acres of fields and pastures, contain the commodious three-level historic barn, smaller barn, stream with charming foot bridge, and additional woodlands. Just west of the home's roofed flagstone patio and ancient apple tree, parterre gardens limned by brick pathways brim with perennials and annuals, herbs, blueberry bushes, irises, peonies, and heritage roses. A 280sf garden shed, both picturesque and pragmatic, provides a sweet focal point, while a broad, mowed path leads to a stone wall and rustic gate, lovely pasture, and beyond that, a large spring-fed pond, estimated to be five acres in size, for swimming, boating, fishing, or lazing on its grassy shore. There is also a herb garden outside the kitchen's east door. To the north of the house are the tennis court, pool, pool house and attached greenhouse, and a 1,960sf barn with a 960sf loft. Behind it, a mile-long woodland loop road connects the main compound with the guest house to the east and pond to the west. The Barns and Pastures On the south side of East Hill Road, opposite the main house, the sellers, who bred and raised llamas here, brought in a three-story, 3,550sf, 18th-century post-and-beam barn from Vermont, dismantled for moving and reconstructed on site. This barn has a full stone foundation and ample space for farm equipment, animals, and hay. They also built a smaller barn back in the field near the stream. The large barn, painted the traditional red, features a number of large bays and two work rooms with tool benches. Each of the pastures has a water source. In addition, there are two run-in sheds with electricity and running water, along with three utility sheds. A portion of the property's 232 acres is in Massachusetts Chapter 61A, which provides for reduced taxes on agricultural properties, an asset even in low-tax New Marlborough. The Guest House The guest house is a 6,000sf U-shaped structure with gambrel roof, originally constructed as a barn for Arabian horses in the 1930s. Reimagined in the 1980s/1990s, it contains four duplex apartments, each with radiant heat fueled by the building's new oil/wood furnace, 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. There is a shared laundry room off the hallway that connects all of the apartments to the garage, and a fire security system. Apartment 1: On the first floor, a spacious living/dining room with fireplace and French doors opening to a large, private terrace, den with built-in shelving, full bath; kitchen, and gracious, beautifully detailed good-morning staircase leading to the upper floor, which has three bedrooms with one en suite and one shared bath. Apartment 2: On the first floor, a spacious living/dining room with fireplace and doors onto a large, private terrace, den with built-in shelving, half bath, and kitchen, and staircase leading to two bedrooms with shared bath. Apartment 3: On the first floor, a living/dining room with fireplace and French doors to the lawn, den with built-in shelves, kitchen, half bath, and staircase leading to the two bedrooms and shared bath on the second floor. Apartment 4: On the first floor, a living/dining room with fireplace and built-in shelving, den with built in shelving, full bath with claw-foot tub, kitchen, and staircase to two bedrooms and shared bath on the second floor. GM 7.10.24