Escape to your own island retreat where each day is a peaceful, waterfront sojourn. Nestled on an island in Big Pond, this tranquil waterfront property offers extraordinary privacy, natural beauty and modern comfort. Thoughtfully updated, the home features a masterfully renovated kitchen and bath, a first-floor bedroom and distinctive architectural details including cedar shakes, that create warmth and character throughout. All furnishings to stay. Mornings of seasonal birdsong and the delicate beauty of the new day invite ease and comfort both on the screened, full-windowed porch or on the two outdoor decks. Breathtaking views of the lake encourage leisurely relaxation while winding garden paths and natural stone walls enhance the property's timeless appeal

There is something wonderfully easy about Loft 209. Soft north light, restored wood floors, exposed brick and original mill columns give this 1,345 SF one-bedroom + study residence its character, while a thoughtful layout makes it exceptionally comfortable to actually live in. Conceived by celebrated architects LATENT Productions, Greylock WORKS reflects an uncommon respect for the historic mill, its architecture and its Berkshire setting. Original materials and industrial details have been preserved and celebrated, while highly custom modern interventions bring a quiet timelessness to the spaces. The result has a genuine sense of place--architecture that could only belong here.

El Refugio, ''The Refuge'', a hidden gem minutes from downtown Great Barrington. A 2-bedroom, 2-bath, wood burning fireplace home - with a 46' heated pool and 2-car detached garage. Set back from the road on 7+ private acres with extensive shoreline on the Williams River.

Step into an inviting, beautifully updated 3 bedroom, 3 full bath home in one of Jiminy Peak's most desirable neighborhoods. Offering an exceptional combination of comfort, style, and location, this Mountainside property places you just moments from the slopes, Marketplace, restaurants, pool, and tennis courts; an ideal setting for year-round enjoyment and an especially terrific ski opportunity. The main level features two bedrooms and two full baths, along with a light filled open-concept living space framed by floor-to-ceiling windows. Beautiful ¾'' wood flooring, crafted by the Amish from Homer wood in Pennsylvania, adds warmth and character throughout, while a wood burning fireplace creates a welcoming focal point for cozy evenings.

The driveway winds through mature woods before opening to an expansive setting that includes the 7.5-acre house parcel plus an adjacent 2.8-acre lot. Approximately one acre of lawn and mowed field surrounds the two-story home, providing sunlight and ample space for gardening, recreation, animals, or simply enjoying open land. Built in 1950, the home features an open floor plan connecting the living, dining, and kitchen areas--an arrangement that can be easily re-imagined or updated to suit a buyer's vision. The great room showcases natural wood finishes, a cathedral ceiling, and a fireplace. A sunken sunspace captures the southeastern light beautifully, especially in the winter months and a 3-season porch for warm summer days.

Reintroducing 56 Victoria Lane, with a new roof, freshly painted rooms, areas with new landscaping and more! Set on a hilltop, the end of a cul-de-sac in desirable Lanesborough, offering the perfect blend of privacy, space & functionality. This 3-bedroom, 2-bath home features over 2,600 square feet of living space & a versatile layout designed to fit a variety of lifestyles. The first floor offers 2 bedrooms & a full bath, ideal for guests, one-level living, or a convenient home office. The main living areas are filled with natural light & offer a comfortable flow for entertaining. Upstairs offers a spacious primary en-suite complete with a walk-in closet and a jetted tub.

Discover the ultimate blend of privacy, natural beauty, and waterfront living with this exceptional offering of three lots totaling over 60 acres. Included is an 11-acre waterfront parcel on the serene shores of Ashmere Lake—perfect for boating, fishing, or simply soaking in the views. Whether you're envisioning a private estate, family compound, or future development, this expansive property offers endless possibilities. All three lots are being sold together as one parcel, ensuring unmatched scale and potential in a coveted location. There is a deeded right of way through Lot #14. There is a sewer betterment fee for Lot#15.

Enchanting Egremont! Set atop a private drive on 5.3 acres in Egremont, this thoughtfully designed residence offers a rare balance of seclusion and accessibility. Surrounded by nature and positioned for easy access to the Taconic State Parkway, the property captures the essence of Berkshire living. At the heart of the home is a dramatic living and dining room defined by a soaring two story ceiling, skylights, an interior balcony, and a wood-burning fireplace. Filled with natural light, the space creates a striking setting for both everyday living and entertaining.

Come see this Stockbridge 1970's style home with land, multiple fireplaces, all electric service, and less than 1.5 miles from the Red Lion Inn! You'll be close to Berkshire attractions like Berkshire Theater Festival, Tanglewood, and all the other entertainment venues you love. Come be a part of the Berkshires lifestyle, you'll be glad you did!

Outdoor Living Meets In-Town Convenience! Rarely does a property offer such an exceptional balance of outdoor living and in-town accessibility. Located at the end of Elm Street, this home provides a peaceful retreat while remaining just minutes from downtown Williamstown, Williams College, and local amenities. Set on approximately 1.3 acres and bordering protected conservation land and the Green River Linear Park trail network, the property enjoys a rare sense of privacy and connection to nature, with direct trail access from the rear yard, all just moments from downtown Williamstown. At the heart of the home is a stunning cathedral-screened porch featuring exposed timber framing and mahogany flooring, creating an inviting three-season great room and a natural extension (click on more)

Just over the hill from Tanglewood, down a quiet country road, this year-round Richmond retreat blends privacy, rustic character, and expert craftsmanship. The heart of the home is the vaulted great room, where exposed beams, a loft balcony, and a wood stove create a warm gathering space that flows seamlessly into a beautifully crafted three-season porch with interchangeable glass and screen panels overlooking the woodland. Thoughtfully designed to preserve the home's original rustic charm, the spacious primary suite is a private retreat featuring vaulted ceilings, a sitting area with a gas stove, an ensuite bath with a soaking tub, and laundry. Wraparound decks further extend the living space outdoors, embracing the natural landscape. The walk-out lower level provides excellent storage

A compelling multi-family opportunity in move-in condition, offering comfortable living space with the added flexibility of rental income or accommodations for extended family. The property also features a barn and access to a nearby pond for fishing and kayaking. Sheffield Center is approximately two miles away, offering local restaurants, the Bushnell-Sage Library, the Sheffield Historical Society, and other village amenities. Great Barrington, with its excellent restaurants, shopping, and everyday conveniences, is only 15 minutes away, while Canaan, Connecticut, is approximately 10 minutes away.

Enjoy comfortable, move-in-ready living at this inviting Sheffield property, complete with a barn and access to a nearby pond for fishing and kayaking. The versatile layout is ideal for extended family, guests, a home office, or supplemental rental income. Sheffield Center is approximately two miles away, offering restaurants, the Bushnell-Sage Library, the Sheffield Historical Society, and the welcoming character of this historic Berkshire village. Great Barrington's restaurants, shopping, and everyday conveniences are just 15 minutes away, while Canaan, Connecticut, is approximately 10 minutes away.

This approximately 155-acre Berkshire nature preserve has enough frontage on Johnnycake Hill Road to accommodate four building lots. Nestled in the beautiful corner of the world where the Pioneer Valley meets the Berkshire Hills, the property is ideal for a myriad of outdoor uses including horseback riding and cross-country skiing. The land contains well over a mile of logging trails and old roads, past old house and school foundations, wells, and stone walls enclosing abandoned sheep pastures. The property is up the hill from the Chester Theatre, and within easy reach of many cultural venues including Jacob's Pillow, the Mahaiwe, Tanglewood, Mass MoCA, and the vibrant four college community. This peaceful hardwood forest offers a natural wildlife habitat,and significant timber value

Dramatic Price Reduction creates opportunity for updates and remodel. Gracefully situated on a gentle sloping hillside street this distinctively designed, quality built, multi-level home offers distant neighborhood mountain views. Abutting the rolling meadows of Arrowhead, Melville's historic home to embrace privacy, natural beauty much like the famed author. Surrounded by artfully designed gardens, this architecturally refined residence is a private enclave offering 4-5 bedrooms, 3 full bath, masterfully landscaped set on 1.5 acres with unique tree selection, blooming shrubs and pollinator flowering perrenials. Just 10 minutes to the culture, cuisine and art offerings of Lenox especially the sounds of Tanglewood. Minutes to all that is Berkshire while being immersed in renowned peaceful

Start showing: 9/18! Berkshire Hills at Leisure Lee! Welcome to this contemporary four-bedroom, two-bath home in this sought-after Goose Pond lake community. Bathed in natural light w large windows and slider to the wraparound deck, the living room features a vaulted ceiling, fireplace and hardwood flooring. Off the open kitchen/dining area, enjoy a spacious screened porch. The main floor includes two bedrooms, a full bath and laundry, making one-level living a reality. The second floor includes two more bedrooms, including one with a walk-in closet, and a full bath with a jet tub, shower and double sinks. Bonus: The unfinished walk-out lower level offers room to add more living space. Short walk to the swimming beach and boat launch. Amenities include canoe/kayak storage and tennis court

Set in a desirable southeast location, this spacious 4-bedroom home offers over an acre of beautifully landscaped grounds, generous outdoor entertaining areas, and an oversized garage. An abundance of natural light fills the home, highlighting the inviting living room with fireplace, built-in bookcases, and beautiful Berkshire views. The first-floor primary suite provides convenient one-level living, while a den with sliders opens to a private covered side patio. The kitchen features an indoor grill, peninsula seating, and ample storage. Conveniently located close to shopping, dining, entertainment, and the Berkshires' many outdoor venues.

A rare c.1780 estate poised for a spectacular second chapter. Perched above the village of Monterey, Ledgehurst offers a canvas for the ultimate Berkshires compound: a main house with room to create the private, en-suite retreat of your imagining, an indoor pool and sauna complex ready to be reborn as a true wellness escape, plus two barns that open the door to possibilities few properties can match. A guest house, a creative studio, a multi-generational haven; the vision is yours to shape. With over an acre of grounds, a short stroll to Lake Garfield's sandy beach, and downtown Great Barrington just 15 minutes away, this is a once-in-a-generation opportunity to bring true Berkshires living to life. Sold as-is; buyers encouraged to perform due diligence on scope and permitting.

Nestled in the heart of the Berkshires, this exceptional Williamstown residence offers more than 4,000 square feet of thoughtfully designed living space, featuring 4 spacious bedrooms and 3 bathrooms. Enjoy breathtaking mountain views from the expansive wrap-around deck--an ideal setting for morning coffee, outdoor entertaining, or simply taking in the beauty of every season. Inside, generous living spaces provide the perfect balance of comfort and elegance, making this home equally suited for everyday living or hosting family and friends. Ideally located just minutes from the cultural and recreational attractions that make Williamstown one of New England's most desirable destinations.

Loft 309 at Greylock WORKS is a distinctive north-facing 1BR | 1.5BA Berkshires residence with a generously scaled study, offering approximately 1,340 SF of thoughtfully designed living space. Set on the third floor of the region's most celebrated mill conversion, this home is defined by its warm wood ceilings, varied ceiling heights, and refined blend of historic character and modern finishes. The open living, dining, and kitchen area creates an inviting central gathering space, grounded by restored materials and an easy, functional flow for everyday living and entertaining. Energy Star appliances, Kohler and Grohe fixtures, energy-efficient windows, and an in-unit washer and dryer support both comfort and sustainability.