Custom built salt box home situated on 32 subdividable acres at the end of dirt town maintained road.. Beartown State forest abuts this property. Amenities include: PRIVACY, heated inground Gunite pool, stunning views of Monument Mnt., established gardens include apple orchard, Lilies and Peonies. Main House inc. living room, kitchen, dining room and library all with fireplaces. 4 bedrooms, 2 full baths, expansive ensuite primary with views. 3rd floor with two bedrooms and full bath. Finished lower level with gym, screening room, pool table space. New oil fired boiler and HWH Free standing 3 bedroom caretakers house with additional 2 bedroom apartment. A LITTEL PIECE OF HEAVEN! Minutes to Great Barrington and Stockbridge. If you seek privacy .....we have it here!

Perched at the top of the hill sits a curated, modern home overlooking the valley with stunning views of the Catskills and breath-taking sunsets. Next to the 1,000 acre Rhinestrom Hill Audubon Society wildlife sanctuary in Hillsdale, this perfect getaway is private yet minutes to everything. Grand room with fireplace, wet/coffee bar, and a wall of glass. Fully-equipped chef's kitchen. Wideboard, rift-sawn White Oak flooring. 3 ensuite bedrooms on main level. 5.5 baths. Primary suite with spa bath - double showers, dual vanities, soaking tub. Custom millwork throughout. Lower level playroom, movie theater, and sauna. Home office with separate entrance that could be used as an additional bedroom with full bath. Screened porch with infrared heaters and outdoor television. Heated pool.

In 2021, The Freeman was transformed utilizing high-quality materials from an aging nineteenth-century estate to a clean and modern getaway and top-performing rental property. The main house, renovated to be 100% carbon-neutral, features six fireplaces, two dining rooms, a library, 1500sqft bluestone deck and more. The Freeman sits atop 57 acres of greenery to explore, containing a tennis court, four-acre vineyard, mountain views and a dock to access Harman Marsh Pond. Individuals, wedding parties, and corporate retreats alike have come to The Freeman to enjoy its secluded feel while being close to key Berkshire attractions like Catamount Ski Area, Bash Bish Falls, and downtown Great Barrington. This property is just over 100 miles from both Boston and New York City.

Welcome to a truly unique opportunity to own a magnificent waterfront property on Prospect Lake. Roughly 500' of Lakefront Spanning an impressive 59 acres, this expansive estate offers unparalleled privacy and endless potential for those with a vision. Whether you're looking to create a private retreat, subdivide for development, or renovate the existing home, this property provides a canvas limited only by your imagination. Spend your days swimming, kayaking, or fishing right from your doorstep. The surrounding land is perfect for hiking, horseback riding, or simply exploring the great outdoors. With ample room for gardens, orchards, or even equestrian facilities, the estate can be transformed into a self-sustaining sanctuary.

Custom Built Craftsman Contemporary Home nestled in a beautifully landscaped property with an orchard, gardens and path to a seasonal brook. Inside this well appointed home you will find large rooms, radiant floor heat throughout & forced air, Vaulted ceilings, whimsical lighting, Fireplaces, Indoor pool, hot tub and sauna. Two primary suites on main floor and 2/3 more bedrooms in the lower walkout portion of the home. Large Timber Frame screen porch and deck overlooking rear of the property. Media room and recreation room with more space for added entertainment. A 4+ car plus heated garage with an ample unfinished area above for storage or a creative mind. Bonus Option (not included in listed price)to this property is a brand new 2 bedroom contemporary guest house for an expanded fami

A stunning compound located in the picturesque New England town of Richmond. A one-of-a-kind combination of a legendary and historic c1776 home integrated with the Berkshires premiere full-service equestrian facility, including indoor and outdoor rings. This Compound has rich history. With 27 pastoral acres views are abundant. The home offers 7 bedrooms, 7.5 baths, three cottages, a gorgeous barn for events, 5 paddocks, 6000 square foot heated arena with an owners luxury apartment and viewing area, an outdoor arena, a jump field, 3 barns with 26 stalls, 2 tack rooms. Equidistant from New York City and Boston, easy access to International airports or take advantage of private flights from the Pittsfield airport.

225 Acre 18 hole Golf Course / Horse Ranch in the heart of the Berkshires. Former Egremont Country Club. Build your dream home with seclusion and privacy assured. Enjoy mountain views, spring fed ponds, endless pastures, and serene forested trails. An escape from the world and yet only minutes to town and a little over 2 hours to NY City & Boston. (* Additional Acreage may be available.)

225 Acre 18 hole Golf Course / Horse Ranch in the heart of the Berkshires. Former Egremont Country Club. Build your dream home with seclusion and privacy assured. Enjoy mountain views, spring fed ponds, endless pastures, and serene forested trails. An escape from the world and yet only minutes to town and a little over 2 hours to NY City & Boston. (* Additional Acreage may be available.)

The Birches....welcome to your new oasis in the Berkshires where every season is memorable. This magical compound has been architecturally redesigned & renovated using the finest materials offering all the modern amenities a buyer wants to live, play, relax and work from, surrounded by 20+ acres of privacy & far reaching protected views in all directions. This stunning contemporary has big open common areas for gathering, first floor primary en suite, guest bedrooms en suite and a private two bedroom guest quarters w/kitchenette, custom crafted wine room, and an exercise room all offering plenty of space for a large crowd or intimacy for a few. Just arrive with your suitcase and enjoy all this impeccably maintained estate has to offer; a beautiful gunite heated pool w/waterfall &

''A Perfect Place Farm'' - a Berkshires Masterpiece on 17+ AcresThe one you've been waiting for...a preeminent build in a premier location. 37 Main Rd checks off the wish list: sweeping views, modern comforts, privacy, location, and colonial era character, but in an immaculately kept turnkey 2002 home.Located in Tyringham valley, one of the Berkshires' most majestic locations, 37 Main Rd is idyllically sited on the northern slope of Tyringham valley, and faces to the southwest. The expansive front porch, sunroom, and living and sleeping quarters all are positioned to track the sun's daily arc across this picturesque east-west valley.

Significantly restored in 2024! Sellers have masterfully updated this legacy home w/ a cool & fresh aesthetic that preserves the integrity of its Mid-century Modern design. Updates to the 1st floor primary suite, kit, entertainment kit, bathrooms & freshly painted interiors are just a few of the improvements. The airy main living spaces w/ their expansive sliding glass doors offer sublime views of the resort-like grounds complete w/ manicured lawns, patios, in-ground pool, playground, newly resurfaced tennis/pickle ball court, gardens curated by a Master Gardener & distant mountain views. The 7 bedroom, 7 bathroom estate w/ 8200 sq ft of versatile living space prominently sited on 57+ acres is 3 hours to NYC and 2 Hours to Boston!

The beauty of nature surrounds on a sleepy winding country road, this New and Truly one-of-a-kind single level home-blends modern & rustic seamlessly inside and out. 66 Magical acres w/views in every direction. Beautiful inside and outdoor spaces include a Gunite pool, sauna, outdoor shower, and patio with firepit, 4 beds plus office, 5 baths an open concept filled with natural light. 3 stunning living rooms, pool house/guest wing plus a 3 car garage, all with metal roofing. Plenty of spaces for work or meditation to meet everyones needs. Live in paradise, amazing setting, gently sloping meadow, beautiful flower beds, quiet, peaceful, private with abundant wildlife. A nature lover's dream abutting the Williams River. Build a family compound or guest home on the extra lot.

Elegant Berkshire Stone Estate with 125 acres of Canyon Ranch Serenity. Thoughtful design combined with masterful craftsmanship in this exquisite turnkey home, a rare offering in the Pinecroft compound of Canyon Ranch. The split floor plan boasts 300 year old reclaimed timber floors, crown moldings throughout. A sumptuous primary wing with stone fireplace and dual walk-in closets and bathrooms. The great room is anchored by a floor to ceiling stone fireplace with incredible iron work and an artisanal custom designed wet bar. Nano doors bring the outdoors in during the warmer months. The heart of the home is the eat-in chef's kitchen with Sub Zero/ Thermador appliances, oversized island with dual dishwashers with pocket doors to the formal dining room. Rounding out the main floor

CROW HOUSE - An Enchanting Private Stone-and-Timber Compound in Monterey.One of Berkshire County's most atmospheric and luxurious properties, this stone-and-timber 52-acre compound, which abuts thirteen thousand acres of protected State Forest, is a magical world unto itself. A winding driveway through horse pastures leads under a Porte cochere to a European-style courtyard, where a pergola draped in wisteria links the entrances to the five-bedroom, five-bath main house, the three-bedroom, two-bath guest house and a terrace with an outdoor dining pavilion.

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.

Atwater Pond is a remarkable 321-acre retreat in southern Berkshire County. An immaculately renovated mid-century house and 1920's guest cottage sit on the edge of a 32-acre, spring-fed pond, surrounded by hundreds of acres of pristine forest. Year-round recreational opportunities abound and a 4+ mile trail system winds through the property. Additional features include multiple docks, historic boathouse, deep water swimming hole, paddock with run-in shed, and 23' Airstream trailer. Truly the best of both worlds, the property is supremely private, yet conveniently located to take full advantage of everything the Berkshires offer. Boston and New York City can be reached in 2.5 hours or less, Bradley International Airport is only 45 min away. Offered turnkey.

Welcome to Meadow WoodThis elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lily pond, terraces, pastoral views, and privacy. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/ potting room and a studio space. The Gunite pool is surrounded by an espaliered apple tree fence & generous stone terrace. The large screened pool house includes 1/2 bath, outdoor shower, kitchenette & massive fireplace. Further from the house is the barn complex consisting of a 2 bedroom apartment with yard & patio, separate studio apartment and 4 garage bays, a barn, and cutting gardens.

One of the Berkshires' finest residences, basking in the idyllic mountain scenery. Designed and crafted to meticulous standards, this distinguished 6.2 acre compound is surrounded by captivating, protected vistas far and wide. In the enduring tradition of the regions iconic estates, this extraordinary residence is a place for life to the fullest, providing an endless source of enjoyment in exquisite indoor /outdoor spaces. Fine millwork and 9 fireplaces underscore the comfortably elegant environment. Lower-level entertainment (media)room, wine cellar, fitness studio. elevator, computerized systems. 9,339 SF with 5 bedrooms,6 full/3half baths. Wraparound tiered terraces feature pool with pool house. Glorious terraced gardens and formal gardens with fountain. Separate 3 bedroom guest house