The equestrian elegance of this 55 acre property starts at the gated driveway. Perched on the hilltop is a fully equipped custom build multi use barn entirely heated by radiant floor heat and includes 8 14x14 stalls w/ autowaterers perfect for the breeder or veterinarian. Includes kitchenette, office, laundry and bathroom. Also included is a heated equipment shed and workshop, a heated drive through aisle for large trucks, washstalls and more! The grounds include 8 paddocks with waterers, an exercise track, 3 large pastures. A second barn offers 12 additional stalls. The meticulously kept grounds is professionally landscaped and a covered wrap around porch greets guests into the home. Kitchen has quartz counters, GE profile appliances and a slider out to a large patio

HISTORIC BERKSHIRE FARM Best bargain in the Berkshires! Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns and maintenance building. 161 acres with stunning views, mountain paths, and Jim Kelly's stunning giant stonewalls throughout. Gorgeous New England marble stone farmhouse built in 1780, with modern addition featuring vaulted ceiling and massive windows which flood the dining and kitchen area with light. Enormous custom built hearth and fireplace, mahogany full bar, artisan-made bookcases, wrap-around deck. Close to Williams College and Jiminy Peak. The property offers swimming in two private ponds, 6 bay carriage barn with second floor for offices, studios., or storage.

A lovely, winding approach to this gorgeous 21-acre estate ensuring serenity, privacy, and the beauty of living in the country. The main house includes 3-4 bed, 2 1/2 bath. An impressive architect-designed guest house has 2 ensuite bedrooms with balconies, dramatic exposed beams and vaulted ceilings. The guest house is an extraordinary place to host family and friends both winter and summer. With views of Tom Ball mountain, this property is a combination of gardens, fields, forest, and offers several outdoor living spaces, including a stone patio off the kitchen. A short jaunt to No. Six Depot, The Foundry performing arts, and Tanglewood. Central to Gt. Barrington, Lenox and Stockbridge for theatres, boutiques, skiing, golfing, museums and so much more at your fingertips!

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.

Surrounded on three sides by Nature Conservancy-protected land, 173 Hillsdale Road is one of the most private and extraordinary estates in the Berkshires -- a handcrafted sanctuary where the wilderness is literally your backyard. Moose, deer, bear, fox, and turtles roam master-gardened grounds tended with rare care; fruit trees, a garden pond, mature perennial beds, and lush native plantings make every season a revelation. Custom-built in 2000 from timber milled directly on the property, this 4,842 sq ft home carries an irreplaceable provenance that announces itself at every turn. A native stone fireplace anchors the soaring vaulted great room. An ash sapling banister curves to the interior balcony above. Antique leaded glass casts dappled light across wide-plank floors.

A RARE BEAUTY ON HISTORIC YALE HILL! Discover an historically significant gem in this perfectly renovated home! Peacefully tucked away from it all, yet close enough to enjoy a stroll to town, tennis, Library, golf & restaurants.Chef's Kitchen, large flexible living spaces, 4 Bedrooms, 4 Baths, tall ceilings and charm galore. The Mill House, transformed into a cozy Guest quarters, with 3 Bedrooms,, 3 Baths, has a lovely brookside courtyard w/Pergola, rustic charm maintained. Quiet your mind and embody perfect country living. Overlook the Kampoosa Brook, with private swimming area from your backyard! Cultural & recreational activities nearby. Great income potential. Solar powers Main house, car charger & Mill House. A MUST SEE!

A rare Berkshire offering w/ space, privacy, & exceptional versatility. Fabulous home & separate studio minutes from Tanglewood & Stockbridge Bowl. Charming 3 BR, 2.5 BA, 2,952 sq ft home - complemented by a beautifully renovated 1,800 sq ft studio barn w/ loft & full BA - rests on 8 picturesque acres with beautiful western views. Perfect for outdoor enthusiasts, culture lovers, or anyone seeking a peaceful Berkshire retreat. This location offers easy access to hiking, yoga & wellness centers, boating, skiing, & excellent dining & shopping. Inside, bright & inviting spaces include a living room w/ cathedral ceiling, fireplace, & abundant natural light. A renovated kitchen opens to a cozy den & breakfast nook, pantry, laundry, mudroom & garage.

Own a Living Masterpiece. Meticulously curated by the current stewards since 2006. This Colonial Revival offers rare fusion of 18th-century authenticity and cutting-edge modern comfort. Designed for both grand-scale entertaining and intimate family life, this c1930, 7,894 sq. ft., Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately fireplaces anchor the formal living spaces. Enjoy panoramic views and privacy from the grand porch overlooking 4 pristine acres. a state-of-the-art kitchen featuring Wolf and Sub-Zero, and no expense spared Geo-Thermal heating/cooling.

Originally built in the 1700s, this historic post-and-beam barn has been thoughtfully renovated over time while maintaining its unique character and charm. A recently installed solar energy system allows for highly efficient living with the potential for an off-grid lifestyle.The home features an open floor plan filled with natural light from numerous oversized windows. A chef's kitchen adjoins the dining area, creating an ideal space for entertaining. With three full floors of living space, the home offers four ensuite bedrooms plus an additional bedroom, providing comfort and privacy for family and guests. Enjoy seamless indoor-outdoor living with a screened porch off the main level leading to spacious decks and a hot tub. The lower level includes a media room and sauna for relaxation

Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it offers plenty of room to entertain and relax. The large cook's kitchen is perfect for preparing meals for large gatherings, while the heated sun room provides a cozy spot to enjoy your morning coffee and take in the stunning views of the surrounding fields. This home also features 5 spacious bedrooms (primary with en-suite, four jack-and-jill), each with their own unique charm and character.

This exquisite single-family home spans an impressive 4,300 square feet, offering an unmatched blend of elegance and modern comfort. With 5 spacious bedrooms and 4.5 beautifully renovated bathrooms, every detail has been meticulously crafted to perfection. Walking distance to downtown Great Barrington's shops and restaurants, the house is in one of the quietest areas of ''The Hill''.12 rooms including a formal dining room, a sophisticated library/den, and a versatile media/recreation room. The chef's kitchen, featuring premium counters, a WOLF range, a Sub Zero refrigerator, a wine cooler, and a butler's pantry for seamless entertaining.The home is filled with natural light. Comfort is ensured year-round with air conditioning and central heating on every floor.

Welcome to Camp Mohawk, a pristine lakefront property in the heart of the Berkshires. Set on Cheshire Reservoir--a serene, largely uninhabited lake--the property offers both privacy and convenient access just off Berkshire County's main north-south route.Once a summer camp, the estate features an existing main house and barns listed on the National Register of Historic Places, dating back to the late 1700s. There are also numerous sleeping cabins that could be restored.Ideal as a private family compound or for development as a spa or resort, corporate or wellness retreat, or condominium, single-family, or retirement community--the possibilities are truly endless. Can be subdivided.

Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views to the northern Connecticut hills. 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.

Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure.Inside, the home is thoughtfully designed to host both family and guests in complete comfort, offering five well-appointed bedrooms, six full bathrooms, and a half bath, providing privacy and ease for all. The first-floor primary suite serves as a true sanctuary, complete with two separate full bathrooms for an elevated sense of luxury.

The thoughtfully renovated and expanded 1940s Main House is full of exceptional spaces--elegant formal dining and living rooms in front, informal sitting area and spacious eat-in kitchen at the back, stunning central stairwell, cozy den/bar, and media room. Five comfortable bedrooms, including two luxurious primary suites. Every material, sightline, and design element has been curated with care and sensitivity. Delightful outdoor spaces abound--front and rear goshen stone patios, rolling lawns, balconies and roof spaces. Cozy historic sunroom off the living room. Above the oversized two-car garage, is a stunning light-filled studio with intricate ceiling details, exterior balcony and bathroom. The in-ground pool is surrounded by a huge patio area, gardens and pastoral views.

The Lakehouse enjoys a spectacular setting on a westerly facing cliff overlooking pristine Laurel Lake in the heart of The Berkshires. The Lakehouse is a classic three-story, shingle style mansion with 530' of lake frontage including its own dock. Built in 1903, the architecture denotes the unpretentious, timeless elegance of a turn-of-the-century lakeside cottage. There are 15 bedrooms and suites all with stunning, private bathrooms. The Lakehouse is exquisitely appointed and furnished with an eye toward showcasing the clean, graceful architectural details of the original lake cottage while adding modern ''creature comforts'' and ''cutting edge'' bathroom design. The Lakehouse is perfect for large families to gather for long weekends or extended vacations year 'round.

Blue Hill Farm: an 1820 Center Hall Colonial farm and farmhouse in excellent condition on 249 high acres with organic hay meadows and pastureland, an apple orchard, woodlands, gardens, tennis court, a 1970's caretaker/farmer's house and multiple barns. The main house has 6/7 bedrooms and three baths, along with a three-car attached garage. The property consists of seven parcels of contiguous land surrounded by the Umpachene River on three sides. There are long views to the west of the Taconic Range from inside and outside of the home, and a grouping of supportive barns to the south across a very rarely traveled, narrow dirt road. Offered for the first time since 1967, this is truly an unusual and rare offering with development possibilities featuring extraordinary views.

Welcome home to NEWGRANGE. 1920's era Manor House with lake frontage on Lake Garfield. Over 10,000 square feet of living on 7.7 Acres. Complete the restoration and enjoy original Stone Fireplaces, comfortable Living spaces, formal Dining and 10 Bedrooms. Write that novel in the paneled Office, Library or Sunroom, create delicacies in the Country Kitchen, or shoot a round of pool in the Billiard Room. When you are done, meander to your private Dock on 165 feet of glorious private lakefront. Guest House, Pond, and Gardens originally designed by Frederick Law Olmstead. Close to town, Skiing, Shopping, Dining and Tanglewood. Low, low Monterey taxes. This one-of-a-kind property is meant for enjoying all that the Berkshires has to offer.

Iconic only begins to describe this rare union of sophistication & natural splendor. Spanning 40+ secluded acres of rolling meadows, forested trails, & sweeping mountain views, this remarkable estate has welcomed world-renowned artists & hosted unforgettable gatherings, from summer soirees to intimate retreats.At its heart is the Great House--a 6,000 sq. ft. architectural masterpiece by renowned sustainable architect Allan Shope. Thoughtfully placed within the landscape, the residence reveals itself at the end of a winding, art-lined drive. Inside, soaring ceilings, an open & airy floor plan, & an indoor pool create an atmosphere of timeless elegance. With 5 bdrms, 7 bths, & separate guest or staff quarters, the home is designed for both hospitality & privacy.

Brooke Astor's COBBLE HOUSEWhere Land, Light, and Legacy ConvergeTYRINGHAM VALLEY BERKSHIRE COUNTY MASSACHUSETTS$4,300,0005,885 square feet7 bedrooms8.5 bathrooms27.9 private acres1909 Harrie T. Lindeberg design2,321 +/- feet road frontageThe Valley That Time ForgotThe drive through Tyringham Valley never fails to quiet the soul. Past stone walls that have marked these fields for centuries, through meadows where The Shakers once pastured their sheep, toward the ancient drama of the Cobble--206 acres of exposed bedrock thrust skyward by tectonic forces that shifted the very bones of the earth millions of years ago. Here you find what Tyringham Valley has always offered--that profound quiet that restores and renews.MORE OF THE STORY BELOW