Set on 21.5 acres at the end of a long, winding private drive, this extraordinary residence is a true architectural gem--where art, landscape, and modern living converge. Originally designed by Robert McMahon and built by Lou Boxer and later reimagined through a contemporary project by Deborah Reiser of the award-winning RUR Architecture with Hird Design and Construction as the builder, the home reflects a sophisticated, transitional approach to residential architecture and interior design. With five bedrooms and four baths, the home is defined by its dramatic walls of glass, seamlessly framing bucolic country views, a classic red barn, and thoughtfully designed gardens. Natural light pours into every space, creating an ever-changing connection to the surrounding landscape. The kitchen is

WHISPERING PINES. This tranquil property will call to you as you wind your way through the tall pine-lined driveway. It is a very private setting and just minutes to Butternut, town, and everything else the Berkshires have to offer. Beautiful mature gardens, Gunite Pool, screen porch, and 3600 sq ft of living space to dwell. This 4 bedroom home has 2-Primary en-suite, a large den over the 2-car attached garage. First floor office space or overflow room for guests. A newer first floor Primary Suite wing added in 2017 boasts a very large walk-in closet, steam shower and an ample-sized bedroom. The expansive screen porch looks out on the yard, pool, yard and gardens. Partially finished will easily help you expand upon this magnificent home. A second 2-car garage for enhanced storage space.

Just a half mile beyond New Marlborough village, this architectural gem offers 5,653 square feet of superior craftsmanship in an enchanting private setting along the Umpachene River. Distinctive circular towers, flowing curved walls, and graceful arched windows are in perfect harmony with the surrounding natural landscape. Custom millwork and premium natural finishes offer a balance of warmth and luxury in this elegant but comfortable 5-bedroom 4.5 bath home. Enter through the grand foyer into the expansive kitchen, living & dining areas, anchored by a striking Scandinavian Soapstone wood stove and a marble wood burning fireplace. A sunny breakfast room off the kitchen leads to a greenhouse atrium and an impressive indoor pool pavilion, fully heated for year-round enjoyment.

Welcome to your ultimate country retreat, where the charm of history meets the ease of modern living. Here, timeless beauty and serenity reign--an escape where silence is broken only by the wind in the fields and the song of birds.The 1828 brick colonial, a masterpiece of its era, has been exquisitely restored to showcase spacious, light-filled rooms that draw the outdoors in, framing views of meadows, a sparkling pool, and the stately barn. The barn itself is a wonder, waiting to be reimagined--perhaps as a guest house, an artist's studio, or a setting for unforgettable gatherings.Surrounded by farms and opening to distant hills, the landscape feels both boundless and intimate. The pool, perfectly placed, invites leisurely afternoons and is graced with its own elegant pool house.

PRISTINE LAKEFRONT SANCTUARY: Perfectly sited with generous frontage on the shores of Lake Windemere, this sprawling post and beam residence offers lakefront views from every room, with four bedrooms and three and a half baths, blending rustic elegance with timeless comfort. Windmere Lake is a privately owned lake flanked by homes tucked away along the waterfront. Designed for gathering and gracious living, the home provides expansive spaces for family and friends to come together while embracing the natural beauty that surrounds it. Whether enjoying peaceful mornings by the water or hosting memorable evenings in the warm, inviting interiors, this is country living at Enjoy four of the best restaurants the Berkshires has to offer just minutes away.

OFFERED FULLY FURNISHED AND TURNKEY. Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views. The main home, a modernist design collaboration between Bauhaus designer George Giusti and architect Crane De Camp, is a two-bedroom, three-and-a-half-bath masterpiece that features a gym, sauna, and gardens designed by a local landscape architect. For guests, they can choose between the three-bedroom, two-bath Cottage or the one-bedroom Cabin, both of which are intimate and offer plenty of privacy for family and friends. Whether it's poolside by day, trails in the afternoon, or hanging by the fire pit at night, there is something for everyone at this mid-century getaway set in the Berkshire hills and only minutes to Litchfield County

As seen in Architectural Digest, this meticulously reimagined 1875 farmhouse compound unfolds across 11.5 lush acres on a quiet, bucolic dead-end country road, with protected views. Brought to life in collaboration with AD100 design firm Sachs Lindores and landscape design by Judy Murphy, the property is full of historic character with refined modern comfort. The compound includes a four-bedroom, four-bath main house, a one-bedroom, one-bath guest house and a large barn relocated from New York State. Outdoors, a private heated in-ground pool, gas-fired pizza oven and fire pit, orchard, fenced vegetable garden, and poolside outdoor shower create an idyllic country retreat. All systems were replaced in 2019, with high-speed internet and central A/C, just minutes from Great Barrington.

NODIN FARM. A spectacular 130 acre property, rich in history, and lovingly maintained by only four owners during the past 225 years. Perhaps the word ''Farm'' understates the true magnificent character and charm of this outstanding home that has been carefully expanded and preserved and updated with premium appliances, the highest quality cabinetry, and with state-of-the art heating and AC equipment. True to its history the ''farm'' encompasses a large barn complex with one wooden and one main gambrel roof brick barn. There is a separate brick ''bull barn'' with architectural plans for a guest house. Did I mention the 7 bay brick car garage with an office and a gym? The entire barn complex was repaired and shingled with premium asphalt shingles in 2024! This is a must see property.

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 - Click!