Just 3 miles from Tanglewood and moments from the heart of Lenox, this 36+ acre estate offers rare scale, privacy, and flexibility in one of the Berkshires' most sought-after settings. A long, tree-lined driveway creates a strong sense of arrival, unfolding into two separate residences surrounded by woods, open land, and long-range possibility. The acreage offers both seclusion and the ability to selectively open views toward October Mountain State Forest. The main residence is thoughtfully configured for multi-generational living. The first floor centers around a large living and dining room anchored by an oversized stone fireplace, an eat-in kitchen with oak cabinetry and granite counters, and multiple access points to the outdoors.

This striking modern retreat was designed by internationally recognized architect Alfredo Brillembourg to feel completely at home in its Berkshire setting. Clean contemporary lines, warm natural materials, and expansive walls of glass create a seamless connection between the house and the surrounding landscape. Seasonal views and changing natural light bring a different feel to the home throughout the day. Inside, soaring ceilings and open gathering spaces make the home feel impressive without being formal. The sleek modern kitchen flows easily into the main living and entertaining areas, while private bedroom suites on both the first and second floors offer comfortable places to get away.

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.

A lovely, winding approach to this gorgeous 21-acre estate ensuring serenity, privacy, and the beauty of living in the country. There's an impressive architect-designed guest house with 2 ensuite bedrooms, balconies, dramatic exposed beams and vaulted ceilings. The guest house is an extraordinary place for rentals, or hosting family and friends both winter and summer.The main house is 3-4 bed, 2 1/2 bath, views of Tom Ball mountain, the 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 this Berkshire Waterfront Paradise! With amazing lake and sunset views this home has it all. Five bedrooms all with lake views. Your family and friends will find the total relaxation the Berkshires can offer. Whether it's a swim, paddle, fishing or a water ski on the lake it's all just steps out the door. The beautiful stone fireplace sores to compliment this open space and provides a warm cozy touch. Come and start to relax as you enter into paradise.

Welcome home to 56 private, mountain top acres in Berkshire County. This 4-bedroom, 2.5-bathroom home offers perhaps the highest elevation in the Berkshires and timeless panoramic views facing Goose Pond to the east and Mt Greylock to the north and beyond. The main house features a gorgeous 1st floor primary suite. Outside, you will find a garden barn and a large, 1500 Sq ft workshop for any hobby or project. Take a short walk past the house to discover a second stunning vista overlooking the scenic Tyringham / Lee Valley. With room to expand the current home or add an Accessory Dwelling Unit (ADU), this secluded property is the ultimate private retreat.

Located on one of Columbia County's finest roads in the town of Spencertown, this impeccably-maintained private 2922 sq ft. colonial home on 7.4 acres has all of the modern amenities! A fabulous setting with stunning distant views, the home features an open chef's kitchen and great room plan, which was expanded and redesigned in 2021, with Sub Zero refrigerator, Wolf gas oven and Miele dishwasher stainless steel appliances, subway tile backsplash and separate island. The home features a central hallway with an elegant living room and working fireplace, dining room, home office/den, washer/dryer units on both the first floor and basement, central AC and full-house generator. In addition, there is a second driveway entrance with RV/EV electric, which leads to a park-like meadow with walking

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.

Spectacular Homestead! Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns and maintenance building. 161 pristine acres with stunning views, mountain paths, and 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.

Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side captures the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere you look you stop to take in the view, large bath with walk-in closet and laundry. The inner courtyard has a heated pool, sunken jacuzzi, outdoor shower, screen porch with fireplace and beautiful perennial gardens. Hidden off the drive is a guest cottage with open living area, bedroom and full bath.

Multi generational Possibilities & Income potential! 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, Pickle Ball, 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!

Some homes offer extraordinary settings. Others offer exceptional living. Rarely does one offer both. Embracing its extraordinary setting, this classic center hall Colonial is all about the way it lives. The heart of the home is an inviting open kitchen with a breakfast nook and a beautiful sitting area where walls of glass and French doors open to a stunning stone patio, tranquil waterfall, and exquisitely landscaped gardens. The adjoining dining room and front-to-back living room with a soaring cathedral ceiling and charming fireplace create warm, inviting spaces for family gatherings and entertaining. A magnificent 1800 sf post & beam barn with cathedral ceilings offers endless possibilities as an artist's studio, yoga retreat, office, media room, wellness space, guest house.

Luxurious, fully-modernized 1850s Victorian in the heart of Great Barrington. Elegant, four-story 3600 sq. ft. newly renovated clapboard and shingle house with covered porch. Meticulous renovation features chef's kitchen, four+ bedrooms, 4.5 bath, second floor and basement laundry, walk-out finished basement with private entrance and bathroom, perfect for guest suite or professional office. High-end appliances, including 6-burner Wolf stove and Bosch French door refrigerator with two freezer drawers, Bosch dishwasher, wine cooler and microwave in the island. Full-size prep sink in the kitchen island, 36'' farmhouse sink in the main counter. Cabinets are all-wood with soft-close drawers and doors; vented whole-house A/C and heat pump with propane back-up; primary bath with heated floor

COMMANDING VIEWS OVER LAKE GARFIELD WITH A STUNNING MOUNTAIN BACKDROP, this beautifully updated home offers charm with modern refinement. Original architectural character has been thoughtfully preserved, while expansive windows fill the home with light and frame the breathtaking scenery. Recently renovated chef's kitchen, first floor primary bedroom, and loads of closet space address today's needs. And could there be any better spot to watch sunsets than the expansive front porch? What's more, a well-appointed suite in the separate carriage house offers flexible space for guests, a home office, or artist's studio. Features include eight private acres, high speed internet, low Monterey taxes, and proximity to the Monterey bathing beach and the incomparable tomatoes at Anna's farm stand.

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

Tucked at the end of a long, winding drive, where nearly twenty acres of woodland create an exceptional sense of privacy, this expansive contemporary residence feels quietly removed from everything--yet remains just minutes from the cultural and recreational treasures that define the Berkshires. The house reveals itself gradually. Cathedral ceilings lend a grand sense of arrival to the entry and living room, where expansive windows fill the home with natural light and frame changing views of the surrounding landscape. From there, the home's scale shifts naturally to spaces that feel warm, comfortable, and inviting.

Welcome to Treetops. A long private driveway passing a large pond sets the scene for this impressive hilltop retreat with 6,000 square feet across three levels and seasonal views of the Taconic Hills. Built with wood hewn from trees on the property, including the distinctive stairway, the home offers a huge open-plan main level ideal for gatherings, along with an indoor pool, hot tub, sauna and a dramatic two-story primary suite. Five bedrooms and five baths provide ample space for guests, with additional bedrooms on the upper and lower levels plus a family room downstairs. A second home may be built on a conserved, included, second parcel. Expansive decks, a three-car garage, sold fully furnished, and abutting the Appalachian Trail conservation lands complete the offering.

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.

Extraordinary and expansive estate property near the top of the hill on prestigious and desirable Bulkley Street. Consisting of three separate parcels over 11+ acres, this offering provides a rare opportunity to acquire an expanse of gorgeous acreage within minutes of Williamstown center, Williams College, the Clark Art Institute, the new Williams College Museum of Art, and close by the 2600 acres ecological reserve, Hopkins Memorial Forest. The four bedroom, three and one half bath main house, sitting atop the hill, has been beautifully updated while maintaining its gracious character and features an array of public spaces both intimate and open, with an especially appealing four season sunporch overlooking the lovely gardens, graceful and sweeping grounds, and the distant ridgeline.

Truly, a one of a kind, stunning property both inside and out with scenic views of the sprawling land down to Long Pond. This thoughtfully crafted and designed home was curated to incorporate the natural serene outdoors into gracious open common spaces allowing warm natural light and comfortable flow. The first floor boasts the great room with wood burning fireplace open to the chefs kitchen with a large pantry and dining with built ins, unique sunroom with walls of glass and screened porch that extends the indoor outdoor living space while overlooking the pergola, play house and down to the water. The first floor primary en suite and office/den sitting area offer privacy in its own separate wing. The second level has ample guest space with three bedrooms, two en suite full baths and