Handsomely built with modern comfort and amenities. Meet Guests on the covered porch and welcome them into the first floor open kitchen and great room with stone fireplace. On the first floor is also the dining room, office, den, mudroom and breezy screened porch for summer drinks. First floor primary suite with sparkling ensuite bathroom and sitting room with fireplace is its own hideaway. Upstairs, three more large ensuite bedrooms for the crew. One-car garage located off the first floor for easy access to the kitchen, two oversized garages below. Located at the end of a shared private drive with similar homes, and maybe some new friends, this retreat will be home base for all of your Berkshire adventures.

Privacy, expansiveness & spectacular views into CT! This contemporary cedar home is an idyllic, private sanctuary in a dream location featuring a hilltop swimming pool w/ stone patio, horse barn & room for horses, koi pond w/ bridge, mature landscaping, and beautiful stonework throughout. The spacious interior of this light-filled home with soothing earth tones & warm woods includes 3 BRs, 2.5 bathrooms, open concept floor plan, office space, central A/C, jetted tub, screened porch, fireplace, skylights, and incredible views both inside & out. Gather year-round with friends & family at this spectacular retreat!

Nestled three miles from the heart of downtown Great Barrington, this contemporary oasis offers a designer details and breathtaking 360-degree views. A wood burning stove invites warmth and comfort, beamed ceilings, designer lighting, and wide plank wood floors add a touch of elegance. Chefs kitchen and soaking tub beckon for indulgence, while the main floor primary bedroom with a wraparound deck offers a private retreat. A second primary bedroom on the second floor provides additional luxury.

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

Exceptional custom-built contemporary home with magnificent views. Featuring multi-level living including a beautiful great room/living room with floor-to-ceiling stone wood burning fireplace, expansive well-appointed kitchen with large breakfast area and walk-in pantry, and a formal dining room. The first floor also offers a primary suite with walk-in closets, an office with laundry room, a mudroom, and a half bath. The second floor has two bedrooms, one bathroom and an office overlooking the great room. The lower level offers a large family room, bedroom (currently used as an exercise room) a bath, and a two-room workshop. There is a separate screened porch on the wraparound porch and a hot tub to take in all the amazing views.

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.

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

UNDERMOUNTAIN HOUSE. Nestled beneath majestic views of Mt. Everett, this stunning modern barn-style home floats above the landscape. A boulder strewn rain garden creates a covered bridge effect. Clad in ebony stained cypress and stone with a standing seam metal roof, this award winning house has wonderful privacy with views of a wildlife pond and a fruit orchard. The house has an open living/dining area with a wood-burning fireplace adjacent to a three season porch with its own wood-burning fireplace. The architects designed a pierced wood screen to separate the dining area from an intimate banquette in the kitchen, and to create the most marvelous lighting effect at night. An office, powder room, and a primary suite complete the first floor.

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.

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.

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.

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.

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 &

EIGHT BUILDING ESTATE COMPOUND for discriminating buyers on quiet country road. THREE PARCELS COMBINED. created exclusively with custom, high-end designer elements & imported materials in 2021-22. #71: MAIN HOUSE features 3 BRs, 2 1/2 baths, tiled fireplace, first floor primary BR, Club House/Guest House w/kitchen (no stove), living room, loft office or BR, extensive landscaping, heated gunite pool, pickleball court. Pink House: office/playhouse. #67: UNDER CONSTRUCTION: 6,000+/- POST & BEAM luxury 3-level, 3-BR home with inground pool & 2-BR Guest House. UNIQUE SANCTUARY w/Indonesian tub, fountain, antique fireplace, jeweled floor, koi pond.#73 GUEST HOUSE: Custom 3-BR 1 bath retreat over 3 bay garage. CLOSING PREFERRED IN OCTOBER. SEPTEMBER 27 WEDDING CONFIRMED.

Set on 36 acres in the Berkshires' most coveted town, this stunning 8600 sq ft home is completely turnkey, tastefully designed, and a mere 12 years old. Turning off of bucolic West Rd, a gently winding driveway brings you past two beautiful ponds, through the woods, and arrives on a sunny plateau - nicknamed ''Ebbets Field'' and the site of this spectacular retreat. Abutting 899 acre Alford Springs Reserve, this custom-built home was thoughtfully designed to host family, friends, and guests across multiple discrete living areas. Main House. A striking glass walkway leads from the three-car garage to the vaulted-ceiling kitchen, which boasts a double-oven Wolf range and plenty of space for cooking and gathering. A light-filled dining area adjoins the kitchen, along with a large living