Welcome to this winery and tasting room located in the beautiful southern Berkshires! This business/farm is located right on Rt 7 which is considered the ultimate New England road trip. Capture tourists year round with nearby Tanglewood, the botanical gardens, Butternut ski resort and so much more! This spacious post and beam building consists mainly of two large rooms both with lofts. One, currently a tasting room with a wrap around loft, floor to ceiling windows for abundant light, a dramatic center staircase and french doors leading to the patio and outdoor space. The second room is currently an event center with loft. The tiled lobby has access to storage and a handicapped bathroom. The opportunity exists to live on site with the attached apartment; kitchen, full bath, small

Clover Hill Farm......The Lenox home you've been waiting for!! Located in a most unexpected enclave on a dead end cul-de-sac is this hidden gem........a Post & Beam Contemporary surrounded by almost twelve aces of privacy, meadows and mature landscaping with the bonus of a fabulous barn. With three levels of living space, this home has wonderful common living spaces with open kitchen/dining/family open to the beamed double volume Great Room with soaring fireplace, four season sunroom, main level primary bedroom en suite, three guest bedrooms, lower level family/game room with fireplace and generous outdoor decking to relax and enjoy the view of terraced stone walls, meadows and the serene Berkshire woods. A must see!

A true diamond in the rough and priced to sell ! One of the most requested towns in the Berkshires and the lowest tax rate in South County all on 31 private acres. Live in your own guest cottage while you complete the build out on a custom and gorgeous timber frame home ! Enjoy the beautiful views of Tom Ball mountain and the relaxing sounds of a babbling brook in the front of the property. There are also apple trees, grape vines, hiking trails and a small pond adding to its appeal. The cottage has a recent renovation that's 95% completed. It has vaulted ceilings, soapstone counter tops, butcher block island and stainless appliances just waiting for your finishing touch. Don't let this unbelievable opportunity pass you by !

This Alford property has it all.....a stunning contemporary Colonial with separate guest quarters, high speed fiber optic, a free standing heated barn with finished workspace & storage, a beautiful orchard all surrounded by 3+ acres on a country road minutes from Great Barrington, around the corner from scenic hiking trails, just over the hill from Catamount Skiing & zip lining, a 20 minute drive to Tanglewood & Alford's low property tax rate. This impeccably maintained home welcomes you with a stylish kitchen, open common spaces washed with natural light, 3 bedrooms and a separate fully equipped guest quarter with bedroom, bath, living room & kitchen...a must see property!

At the end of a long tree lined driveway, you'll find a fabulous 4 bedroom, 5 bath Dutch Gambrel with detached garage only minutes to Great Barrington. This spacious home is set on almost 5 sunny acres, which include a possible abutting building lot. This place has it all - great entertaining spaces, perfect cook's kitchen, fireplaces and private and peaceful outdoor gardens, along with a lovely screened-in porch to take in the gorgeous landscaping. Home built in 1989 with 2004 and 2019 renovations. A luscious hi-beamed master suite is on the first floor. Meticulously maintained so you can move right in!

Pristine, custom-built home in a lovely Lenox neighborhood. Close to downtown, this beautiful one-owner home on a corner lot has plenty of space to relax and enjoy the peaceful setting. Three beautifully appointed levels, with high-end finishes throughout, are thoughtfully laid out to include five bedrooms and four full baths. A true primary suite, with a luxurious soaking tub and expansive walk-in closet add to the comfort and convenience of the home, while the soaring ceilings and light-flooded rooms provide the wow factor. This home makes quite an impression the moment you walk in. A chef's kitchen overlooks a beautiful family room, with a gas fireplace and picture windows framing the view of the partially wooded lot. The dining room is also open to the kitchen, giving

High Mowing, is a magical Williamstown estate spread over fifteen glorious acres, and nestled in the hills less than 5 minutes from Williams College. This exquisitely welcoming home is different from any other property in the Berkshires, and it seamlessly integrates beautiful nature and sophisticated culture in an incomparable and eclectic way. The property has been meticulously developed with an artist's eye and a craftsman's hand to blend perfectly with its environment, complementing the colors and textures of surrounding fields, woods, and mountains, exposed under the huge open sky of day and starry nights.

Perched high on the hill and surrounded by more than 30 acres of land, this custom Timberpeg home overlooks breathtaking, wide-ranging vistas, and sunset views to the Catskills. The heart of the home is an open-floor plan kitchen and living area, flooded with natural light, creating a warm and inviting space. An impressive 31-foot stone fireplace, equipped with a wood stove insert adds a touch of rustic elegance and warmth.Three bedrooms, each featuring its own private ensuite bathroom ensures the utmost comfort and privacy for family or guests. Additionally, the convenience of an elevator provides effortless access to every floor.Conveniently located only 5 minutes to Chatham, 20 minutes to Hudson, and 30 minutes to Great Barrington. This extraordinary property not only offers a

An unusual and wonderful early barn conversion, originally built in the 1700s and converted to a house around 1910. The current owner has renovated and added onto it thoughtfully and completely. A large open space with lots of windows, a huge stone fireplace and a cathedral ceiling define the living a dining rooms. The kitchen was enlarged and remodeled in 2012 with Wolf and SubZero appliances, and Cherry cabinets. With five bedrooms and four and a half baths on two levels, all but one of the bedrooms are ensuite. The very creative and bright primary bedroom, up a few steps from the second floor, also has a cathedral ceiling and gorgeous built-ins. This romantic property contains a large field, lawns, woodland and huge ponds; a virtual national geographic display of bird and animal life.

A peaceful waterfront home situated on the pristine Highland Lake; this beautiful family compound offers a rare opportunity to enjoy lakefront living on a private waterfront lot. The 4000 sq ft renovated home offers lake views from most rooms, including the primary suite that opens to a screened-in porch. There is plenty of room to stretch out with 5 bedrooms and several large open rooms. Complete with an oversized workspace and ample parking. Included in the home are 3 fully furnished cottages and a walkout basement apartment for your guests or extra income throughout the year. There is a recently installed solar array, a Tesla charging station, and a backup generator. Paradise found! 20 min. to Northampton, less than 1 hour to the Berkshires. 3 1/2 hrs. from NYC and 2 hrs. from Boston.

A unique opportunity to own two amazing residential units affording 2 bedrooms and full bath each with gourmet kitchens and soaring vaulted ceilings in walking distance to all things central to Lenox. Just 2 miles from Tanglewood, rentals would be the obvious choice in an already difficult rental market, or take advantage of an owner/operator dream living and working at the same location with an iconic, upscale Italian Steakhouse below you. Mixed use and turnkey ready to go, the current family owners are retiring after 35 years and are ready for a new start. Its Location is in the robust central part of Lenox with an extremely large outdoor dining patio and walking distance to most shopping attractions. 3 hours to NYC, 2.5 Hours to Boston; 30-60 minutes to most Berkshire attractions!

This custom built home is situated on a hilltop, offering a private and peaceful setting with scenic views. 4 bedrooms, 2.5 baths and a fully finished basement with a separate exterior entrance. A spacious living room boasts cathedral ceilings with a walk out patio for entertaining and taking in the views. In the kitchen, a butcher block island is surrounded by granite counters, with a cozy and quaint breakfast nook. Cathedral ceilings continue into the first floor primary suite featuring 2 walk in closets, a propane fireplace and large ensuitewith a soaking tub. Upstairs, 3 additional bedrooms share a hall bath. This home includes central air conditioning, propane heating, underground electric and a full house generator for added convenience and comfort. The property spans over 35 acres,

The Garden Gables Inn is ideally located in the center of Lenox on over 4+ private park-like acres with gardens, patios, mature trees and a heated 70' pool. Beautifully furnished and tastefully decorated, the inn consists of 15 unique rooms all with updated private baths, several with fireplaces and all fully air conditioned. The historic 1780 main building and attached Cottage includes 9 guest rooms and 2 spacious suites. The separate Orchard Cottage includes 4 ensuite rooms with separate entrances, cathedral ceilings and fireplaces. There are 2 charming dining areas in the main building in addition to the library/music room and cozy ''sherry room'' both with fireplaces. The kitchen is well equipped with updated appliances and adjoins the private innkeeper's quarters.

Set on 20 private acres of pasture & woods, w/riding trails & pond, this fully equipped equestrian farm consists of a 4 bedroom residence, stable with apartment, indoor arena & bucolic grounds. This stunning contemporary home features a gorgeous, well-outfitted chefs kitchen w/walk-in pantry, towering ceilings & wall of glass. Formal dining room is accessed through butler's pantry. Bright & inviting den w/cathedral ceiling. Anchored by stone fireplace, the living room opens to wood deck w/stone walls & hot tub overlooking the pastoral scene. A custom built office, half bath & small den w/door to outside complete the first floor. Upstairs, a dramatic primary suite w/fireplace, balcony, skylights, cathedral ceiling, 2 walk-in closets & bathroom w/soaking tub. Also on this floor is a 2nd

Custom-built five-bedroom Timbercraft home on 8+ acres. Private tennis/basketball court, in-ground Gunite heated pool. Pennsylvania Stone and cedar shake exterior, three-sided fireplace and Timberframe truss ceiling in great room. Large state-of-the-art kitchen and breakfast nook tower. Plenty of deck areas to enjoy the outdoors. Lower level equipped with workout room, sauna and plenty of room for games. First-floor bedroom suite with full bath and gas fireplace. High-speed internet allows you to work remotely, and a large studio space above the garage make it perfect for private office or guest quarters. Don't miss out on this opportunity to have your own retreat in the Berkshires.

NOW UNDER $3M! Calling all creative minds - artists, musicians, recording artists, producers, makers, and lovers of historic mill building restorations! STUNNING, ONE-OF-A-KIND, modern and historic mill building in the dynamic village of Housatonic, MA is THE PLACE for you to Make Art | Make Music | Live Life in the heart of the Berkshires. Seize the moment to make this extraordinary property yours! Utterly unique in the Berkshires. Light-filled, three stories of open space. 1st FLR includes studio, recording studio, kitchen and bath w adjoining private, walled gardens at each side. 2nd FLR comprises gallery space, living room, primary bedroom suite and guest bedroom with private bath. 3rd FLR is fully open loft space. Finished basement. Central AC. Residential and comm possible.

HISTORIC BERKSHIRE FARM 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.

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.

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 40 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.

ALMOST NEW! Finished 2017. Occupied by 1st/current owners in 2020. Nestled on 5.4 acres, surrounded by woodlands, this custom designed estate home is over 6,800 sq. ft. of luxury. 6 bedrooms/6.5 impeccably renovated bathrooms- an entertainer's dream. As you enter through the front door, you'll be awed by the lustrous mahogany/cherry hardwood floors, gorgeous chef's Kitchen & huge Main Floor Primary Bedroom Suite. On the 2nd Level are 4 generous Bedrooms INCL. 800+ sq. ft. of living space w/private entrance, full bathroom, kitchenette. Addt'l: Lower level bed/bath, 2 laundry rooms, 500 bottle wine cellar, 5 zone HVAC, organic garden, heated pool w/electric cover. OVER $1MM in reno. Owner building new home. Serene, private, walk to Tanglewood/Downtown Lenox. Fall 2024 occ. POF req'd.