CLASSIC ARCHITECTURE WITH CONTEMPORARY ELEGANCE! A beautifully maintained home set back from the road. Exceptional landscaping embraces the property, offering a private sanctuary. A front porch welcomes you to the first floor. A light-filled,capacious living room, dining room with a fireplace opened to both main rooms, a primary suite with two walk-in closets, a 1/2 bath, and study open to a large kitchen and laundry room with access to the two-car garage. The second floor has a loft, three bedrooms, two full baths, generous closets, and storage spaces. A spacious deck with screened-in gazebo are at the rear of the house. Walk to Lake Mansfield, 5 minutes to vibrant downtown Great Barrington, Mahaiwe Theater, Triplex Cinema!

Loft 402 is one of Greylock WORKS' most sought-after residences: a large, south-facing 2BR | 2BA + Study Berkshires loft with soaring 16-foot ceilings, luminous all-day light, and sweeping views of the hills. Set within the region's most celebrated mill conversion, this exceptional home blends architectural authenticity with contemporary design in a way that defines modern Berkshire living.The expansive living and dining area features regionally sourced schist countertops, gorgeously restored original hardwood floors, and hand-burnished structural elements that anchor the home in its mill history. South-facing windows flood the space with natural light and frame tranquil hill views that shift with each season.

Custom modern home with open plan living area, high ceilings and oversized windows everywhere bringing in tremendous natural light. One level living with large gorgeous marble kitchen, great working island and wall pantry. Guest wing off entry with two bedrooms and a hall bath. Entry hall has a powder room, hooks for coats and closet. The primary suite, on the south side, has french doors to private backyard with saltwater pool, walk-in closet, soaking tub and separate shower. Sited at the back of the 1.5 acres the house sits nicely above the front yard and allows for a more private backyard area to enjoy the pool, patio and fire pit. Large full basement and custom shed are just a few more of the perks of this thoughtful home.

THEY DON'T BUILD HOUSES LIKE THIS ANYMORE.They don't build love at first sight anymore, either. But Sky Hill Farm - a genuine 1798 Federal colonial in Tyringham Valley - has been creating that exact feeling for over two centuries.In 1912, Adele LeBourgeois Chapin wrote about first arriving here at dusk, walking through high grass to the old front door with its worn stone steps and feeling the homely welcome as she went in. ''This old house was beautiful,'' she wrote, ''the rooms perfectly proportioned, the mantlepieces charming old Colonial ones... I felt as if I was at home at last.''That feeling hasn't changed. Views of Tyringham's Shaker Fields65+ acres3,443 sq ft3 bedrooms2 1/2 baths2 barnsPasture & Hay fieldsFor the whole story click MORE -or reach out

Easy living Ranch home on beautiful Onota Lake. Fantastic views of the Lake and Distant Berkshire Hills. Enjoy westerly sunset views from your expansive, manicured lawn and almost every room in the house. A quiet setting with comparable homes and easy access to all the Berkshires has to offer. Needs a little TLC, but well worth it for this sought after location and lifestyle. Hardwood floors refinished and interior recently painted.

This beautiful home was built in 2006, and updated in 2022. The house is situated on just shy of 5 Acres in the town of Egremont. The home is flooded with sun all day, rarely needing a light on in the house. Direct access to the Green River at the edge of property to cool off on those hot summer days. A new central AC system was installed throughout home and apt A New backup generator, rain gutters, new lighting inside and out, full painting inside and out in 2025. First floor primary suite with jet tub and separate shower. The oversized rear screened in porch is divine, you will never want to leave. A Giant lawn for entertaining and a separate in law apartment for your guests. The garage with radiant heat is perfect for your classic cars or boat. Low Taxes and 5 minutes to GB town.

The Woodlands -- A Private 74-Acre Retreat in Great Barrington!A rare opportunity to own a private and picturesque Berkshire retreat in the heart of Great Barrington. Set on seventy-four acres of meadow, orchard, and forest, The Woodlands offers a refuge of uncommon scale and serenity--just two minutes from Ski Butternut and five minutes to downtown Great Barrington's restaurants, shops, and cultural life. The property abuts the Thomas & Palmer Brook Reserve, a Berkshire Natural Resources Council preserve spanning more than 300 acres of protected woodland and scenic trails, extending your own land into a vast network of wild beauty.

A total 41 acres includes a 2nd building lot of 26 acres allowing one to build ones own home with mountain views. A 36x52 work shop. One full time residence and a separate summer studio. Some land does go into New Marlborough. Surrounded by conservation land. Passive solar views facing South and West. Property has been a sculpture park for many years. Trails throughout. Views to Connecticut.

A master stoneworker and his family spent a year walking 11 acres to find the one perfect spot. Then they built their dream around it - every fieldstone placed by hand from rocks cleared by 150 years of farming, hand-hewn cherry beams harvested from the land soaring above the stone-clad Great room. This rustic modern farmhouse embodies the truth that in simplicity lives beauty. The timber-framed screened porch catches every breeze, while the spa-like steam shower opens directly to an outdoor shower enclosed by artful ''lace walls.'' Closed-cell insulation, owned solar array, and rich oak floors throughout create effortless comfort. Now, as the ocean calls them back, this net-zero sanctuary awaits those who will write its next chapter. Read the full journey of this modern farmhouse!

Welcome to Cannondale Compound. Set on 20 private acres with far-reaching mountain views, this 7,300-square-foot architectural retreat is ideally suited for large gatherings. Designed with soaring modernist lines and exceptional craftsmanship, the home offers multiple living and dining areas, seven bedrooms across two connected wings, expansive porches and balconies, and both indoor and outdoor pools. Outdoor highlights include a hot tub, pool house with bathroom, pavilion, garden, and a fully enclosed treehouse for summer overnights, along with deeded Queechy Lake rights for swimming and kayaking.The main wing of the home features a dramatic triple-height great room with a fieldstone fireplace, flanked by a wraparound deck.

A beautiful Contemporary on 11 private acres, 6 miles to downtown Great Barrington. Soaring ceiling great room. The open-plan, gourmet kitchen feature's a Viking range, stone countertops, and a large pantry leading to a delightful four-season porch, perfect for enjoying the western views. The large living room in centered by a striking floor-to-ceiling chiseled stone fireplace, cathedral ceilings, and glass doors leading to the rear deck, lovely first floor en-suite primary with a new beautiful bath. Flexibility and comfort, the home includes two additional ensuite bedrooms and a nursery room on the second floor, plus a third floor dorm room ensuite. A beautiful front porch an attached two-car garage and a classic barn complete this special property. Minutes to downtown Great Barrington.

Step into a piece of history with the once Iconic Card Lake Inn Tavern, now transformed into a stunning residential haven in the heart of downtown West Stockbridge. This property offers not only a prime location but also an exceptional living experience, combining modern amenities with charming historic character. The building houses six completely renovated high-end apartments, each thoughtfully designed to meet the needs of modern living. These units feature elegant wood floors and come equipped with all necessary appliances, including dishwashers and in-unit laundry facilities. Central air conditioning ensures comfort year-round, while tiled double-sink bathrooms add a touch of luxury. Ample storage space is available in each unit, allowing residents to keep their living areas tidy.

Stunning Post and Beam Home with Log Facade. Nestled in a park-like setting with views of Mount Washington. Outdoor Amenities Galore. Extensive patios and wraparound decks provide the perfect venues for outdoor gatherings including a private bocce ball court, outdoor hot tub, and private dog park. The first floor offers generous entertaining spaces, including two to three bedrooms that provide flexibility for guests or additional family members. The open kitchen/dining area is perfectly positioned to capture southeast-facing views. The primary suite includes a luxurious bath and expansive walk-in closets. On the lower level there is a private walkout suite, full bath, gym, and kitchenette. 3 car oversized garage/shop and generator.

The Ephraim Chapin House, a.k.a the ''Landlord Abel House'' was built in Chicopee c. 1725. In 1979 this handsome home & tavern was dismantled and relocated to Southfield. There it was re-erected upon a new foundation atop a hill, where it now resides on a 51-acre estate straddling the banks of Konkapot River. Once the beloved retreat of an artist and a serious collector of early American art and antiques this 3-story 4-bedroom home has been painstakingly rebuilt and restored.Original wainscoting in the ''keeping room'' is a rare example of interior decorative painting by the Scroll Painter, a documented but unnamed American decorative artist active the 1790's. Other details include original floorboards & exposed chestnut beams, center chimney with 6 brick fireplaces... (See ''More''.)

Located on one of Egremont's most picturesque roads, this beautifully designed contemporary home offers panoramic views from nearly every room. Set in a low-tax town just minutes from Great Barrington, this home is private, comfortable and versatile. The main house has perfect flow, great scale rooms, tons of light, a beautiful stone fireplace, custom Kitchen, and the prettiest of outdoor spaces. The connected ADU/Guest suite has a private entry, ideal for guests, caretaker, or rental income. Perfect for primary residence, vacation retreat, or income producing property. A tranquil setting with easy access to area amenities. Come enjoy the view!

HISTORIC BERKSHIRE FARM Best bargain in the Berkshires! 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 in a secluded, serene setting and surrounded by lush gardens, fruit trees, wildlife and Nature Conservancy on 3 sides, custom-built home offers extraordinary privacy and tranquility. Crafted using wood milled directly from the property, this rustic yet contemporary home boasts a wealth of unique details that highlight exceptional craftsmanship. Moose, deer, bear, turtles, fox and more visit mature grounds tended by master gardener. Incorporates a native stone fireplace, ash sapling banister, antique leaded glass accents, & reclaimed 18th-century tavern doors from historic Egremont Tavern. These elements blend seamlessly with the open-concept floor plan, highlighted by soaring vaulted ceilings and oversized windows. 5 Brs, 5BA w/ attached separate apartment w/ balcony.

Nestled beside 900 acres of Alford Springs Nature Preserve, this contemporary colonial is sited on 5.8 acres. Built in 2005 and fully renovated in 2021, it boasts high-efficiency HVAC and hot water, 14GW of seller-owned solar, an open main floor plan, gorgeous kitchen with top-of-the-line appliances, front porch, screened porch, large 2-car garage, and generously-sized rooms throughout. Two spacious additional rooms adjacent to the primary and a guest suite are currently used as a gym and office/studio. Move-in ready with incredible privacy yet 15min to the center of Great Barrington.

A completely transformed barn renovated into a chic home with every modern convenience. Located in the desirable town of Egremont and just minutes from Great Barrington, this delightful property offers long-range pasture views with the Green River just beyond.Thoughtful living spaces for every walk of life featuring a roomy primary suite on the first floor, an additional primary suite that occupies the entire third floor, and inviting spaces for guests and gatherings. Key features include top brands like Waterworks, Wolf, Schluter, Graff, Bertazzoni, and Kohler, along with Danby marble, Italian stone, and oak floors. Every window offers views of the expansive 13.5 acres with lush meadows, fully fenced, which offer endless possibilities for nature lovers, hobby farmers, or equestrians.

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 brings in 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, screened porch with fireplace and beautiful perennial gardens. Hidden off the drive is a guest cottage with open living area, bedroom and full bath.