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.

A rare and captivating Berkshire offering, this architect-designed home is filled with spectacular natural light, where expansive windows frame protected views of rolling meadows and hills, seamlessly bringing the outdoors in. Located across from conservation land and less than half a mile from Tanglewood, this pristine property offers the perfect balance of sophisticated country living and exceptional convenience. Beautifully designed for both entertaining and privacy, the spacious interiors feature vaulted ceilings with open beams, skylights, and light-filled rooms throughout. The dining room overlooks exquisite gardens through a wall of glass. 5 bedrooms and baths include a serene primary suite with three exposures, spa-like bath & generous closets. IT DOESN'T GET ANY BETTER THAN THIS:

Perched high on one of Egremont's most desirable country roads, this exceptional estate offers breathtaking panoramic views stretching more than 30 miles across rolling meadows, mountain ranges and Prospect Lake. Facing south and surrounded by approximately 15 private acres, the property combines natural beauty, privacy and convenience just minutes from downtown Great Barrington and major Berkshire attractions. This contemporary residence was thoughtfully designed to capture the spectacular scenery from nearly every room. Soaring ceilings and sun filled living spaces create a warm and inviting atmosphere throughout the home.The residence features:5 bedrooms,5 full and 1 half bathrooms,A dramatic great room flooded with natural light,Three fireplaces, A charming three-season screened porch

A rare opportunity to own a masterfully reimagined circa-1861 post-and-beam barn, transformed into a one-of-a-kind luxury estate set on 89 pristine acres in the heart of Columbia County. Surrounded by sweeping pastoral views, open fields, and tranquil natural beauty, this exceptional property offers privacy, scale, and timeless craftsmanship. The residence spans approximately 6,000 square feet across two levels, seamlessly blending historic character with modern sophistication. Soaring ceilings, exposed beams, and wide-plank wood floors milled from trees harvested directly from the property*create an authentic connection to the land and the home's heritage. At the heart of the home is a dramatic great room, ideal for entertaining or quiet evenings

A house that stops people mid-sentence! At the Lenox/Stockbridge line on the western shore of Lily Pond, discover this one-of-a-kind home. A rare architectural sanctuary where nature, privacy, and imagination quietly redefine Berkshire living. Embraced by woods and water, this 4br, 4ba contemporary is bathed in extraordinary light. Enter and you'll find over 5000 sf. living space. Bedrooms are spaced apart for maximum privacy; the open living area takes center stage for entertaining. Post-and-beam great-room/atrium w stone floor. Open kitchen w custom cherry cabinetry. First floor primary suite. Outside, enjoy over 4 acres of privacy: lawn, gardens and your own nature trails! Deeded rights to the White Pines beach on Stockbridge Bowl. Walking distance to Tanglewood! Must see!

Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living experience unlike anything else on the market.The first floor features an impressive great room with soaring timber beams, an elevated Malm fireplace, and floor-to-ceiling glass that captures the surrounding vistas. A gourmet kitchen imported in its entirety from Germany anchors the main living space with exceptional craftsmanship and modern sophistication. Radiant heat throughout the main

Hawks Nest Ridge. Quiet privacy on 8.6 acres. Decks, patio, screened porch and pool all enjoy the view and the natural setting. Dramatic open floor plan with walls of windows to the views, soaring stone wood burning fireplace spanning three stories. Cook's kitchen with walk-in pantry. First floor primary suite with gas fireplace and dressing room all abutting library and office. 4 private bedroom suites in total each with their own sitting areas (additional sleeping options possible). Family room with wet bar and gas fireplace. Exercise room with steam shower. 3-bay garage. A very special retreat with plenty of room for guests and entertaining. Just a short jaunt to dining, shopping, recreational and cultural venues in West Stockbridge, Lenox, Stockbridge and Great Barrington.

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.

Stunning Views! Exquisite Tudor-style stucco estate set on more than 18 breathtaking acres with panoramic views and a winding approach that creates an extraordinary sense of arrival. Bright, airy, and thoughtfully designed, this 5-bedroom, 5-bath residence blends timeless architecture with modern comfort and exceptional indoor-outdoor living. The heart of the home is a stunning great room featuring soaring ceilings, abundant natural light, and hardwood floors throughout. An open-concept layout flows seamlessly into the generous chef's kitchen, complete with a professional-grade gas range, spacious dining area, and direct access to the expansive deck overlooking the rolling landscape. The main-level primary suite offers privacy and convenience with a spacious bath and ....

Welcome to an extraordinary lakefront estate on the shores of Pontoosuc Lake, an offering that sets a new benchmark for luxury living in the Berkshires. With over 7,494 square feet of total space, including exceptional garage capacity ideal for car collectors or hobbyists, this remarkable property offers unparalleled scale, versatility, and setting.The main living area showcases a thoughtfully designed open floor plan that flows seamlessly toward the water, ensuring the views are always front and center. Enjoy sweeping northern-facing vistas of Pontoosuc Lake, Mount Greylock, and the surrounding Berkshire hills. Whether relaxing on the expansive deck, swimming in the in-ground pool, or departing from your private dock, the connection to nature and water is ever-present.

Beautifully sited to capture light and long-range views, this architect-designed residence offers timeless elegance within a serene natural setting. Bright, sophisticated interiors open seamlessly to a screened porch and stone terraces overlooking the pool and manicured grounds. Generous proportions and refined architectural details define the living spaces, complemented by a beautifully reimagined library/office, dining, living media/den and kitchen. First-floor primary suite serves as a private retreat, while additional en-suite bedrooms provide comfort and discretion for guests. An upper-level loft (w/ elevator)offers space for gym, studio, or media. A rare offering of privacy, design, and distinction in the Berkshires.

East Hill Farm offers 227 acres of protected quiet, anchored by the elegant 1798 Thomas Shepard House. A private hilltop world. Main house: Georgian-Federal; 5 BR, 5.5 BA, ~5,000 SF; 5 fireplaces; unusually high ceilings, wide-board floors, antique glass, rooms that hold the light, views that connect. Graceful, welcoming. A complete estate that also can be a working-farm or equine property: barns + outbuildings, pastures, private trails + roads, 4+ acre pond, gardens + orchard, pool, pool house, greenhouse, tennis. A vast former Arabian horse barn, now guest compound, or for you to reimagine. Preserved with rigor, lived in with joy, and rooted in the land and history that defines the Berkshires. Read the whole story. Read the whole story - Click!

Come relax amid sweeping pastoral and mountain views in this exceptional retreat designed for both entertaining and everyday comfort. The impressive great room, anchored by a massive stone fireplace, offers a welcoming focal point and flows into a spacious well-designed kitchen/dining area. A screened porch with fireplace overlooks the pool and rolling landscape, creating a seamless indoor-outdoor experience. The first-floor primary suite features a luxurious bath and tranquil views. An exceptional cinema room includes theater-style reclining seats and a half bath. Generous guest accommodations throughout. A private office suite with full bath. Outdoors, enjoy an infinity pool, bluestone patios, lush gardens, a charming pool house -- all just three miles from downtown Great Barrington.

The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental.The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a strong performer for weddings, corporate retreats, and multi-generational stays.The grounds feature open lawns, established gardens, and west-facing views. Fully ADA compliant and walkable to Lenox's restaurants, shops, and cultural venues.A rare opportunity to own a large-scale, income-producing property in one of the Berkshires' most established locations.

The Definition of Ultimate Privacy! A masterpiece of a home invites the most fastidious prospect. Built with the utmost dedication to detail that no item too small was overlooked. The ability to expand and build to your heart's desire is here. Perhaps a pool, tennis court, even a football field is within your reach. This property consists of 200+ acres, a 6,700 sq. ft home, Primary En-Suite on the first level, 2 bay garage, Extra Large Enclosed Barn capable of sheltering a bulldozer with a private space up above. Nestled in the foothills of the Berkshires on beautiful winding country roads. A lovely vineyard just around the corner, a short 25 minute drive to BDL International airport and just under 3 hours to NYC and 2 to hours to Boston. Come make this your dream get-away!

A Home like no other in the Berkshires. You will simply not find a Property like PIERCE PEAK, anywhere. Award Winning Architectural Design by Burr & McCallum, crested upon the summit of Cunningham Hill. Cleared for HELIPAD . Open plan living with Indoor and Outdoor Living Rooms. Gourmet Kitchen, 2 Primary and 2 connected Loft spaces. 2 Bedroom Guest Quarters. Gym. Infinity Pool w/Bar, Fireplace and Outdoor Shower. 360 Degree views of NY and Mass. 6 Acre Equestrian / Hobby Farm included with this 31 acre Estate. State-of-the-art Mechanicals include the efficiency of Geo-Thermal Heating & Cooling. On-site Generator, Security Gate and Privacy galore. On the NY and Massachusetts border. Close to all Berkshire and Hudson Valley attractions. For those who seek the extraordinary... (see Video)

Majestic Tudor Berkshire Estate on 71 Acres atop Tom Ball Mountain in the hamlet of Alford, MA. Privacy and Breathtaking views from nearly every room. Formal Entry and Foyer. Stately Living Room and Dining Room. Comfortable Great Room with Gourmet Kitchen. Den, Family Room, Gym and Massage Room. 5 en-suite Bedrooms in the Main House. Separate 2 Bedroom Guest House w beamed ceilings and full amenities. Manicured grounds boast an infinity Pool and Hot Tub, Pool House with full Bath, Tennis Court and Pickleball Court. 7 Garages and additional Barn. Exquisite architectural touches, state-of-the-art home technology and security, in the most peaceful of surroundings. Easy access by road, rail and private Airport. Close to Tanglewood and Berkshire attractions. *Fully Furnished and ready to enjoy!