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 home with land, multiple fireplaces, all electric service, and close to everything the Berkshires has to offer! You'll be minutes to historic downtown Stockbridge, Tanglewood, and all the entertainment venues that you love, in a quiet country setting. All the comforts of home, available to you right now! 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)

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.

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

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

A tranquil oasis in the sought after Beachwood community with its private beach and kayak launch on Stockbridge Bowl. This ranch-style cottage with hardwood floors has a spacious living/dining area with double volume wood ceilings and a gas stove for added warmth in cooler weather. The renovated kitchen boasts stone counter tops and flows onto the private, shaded screened-in porch for effortless entertaining. A bonus deck with grill is accessed off the porch. There are three comfortable bedrooms (2 with king size beds) and two small refurbished bathrooms one with a tub and one with a walk-in shower. A large laundry closet is fitted with a washer and dryer. This 3-season home has a newer roof and primary bedroom en-suite addition. Ideally located between Stockbridge, Lenox and Tanglewood.

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.

Brilliantly located very close to the Beachwood community private beach and kayak launch on Stockbridge Bowl is this atmospheric cottage replete with the charm of a bygone era. Entrance foyer into a beamed cathedral ceiling living/dining room with original stone fireplace. Living room opens onto a charming, private, screened-in porch. Completing the 1st floor is a generous kitchen, 2 BRs and 1 BA and washer/dryer. The 2nd floor has 2 BRs and 1 BA. A path at the back of the property leads directly to the community beach + kayak launch at the Grove. There are 2 split system air conditioning/heating units in the kitchen and living/dining. This is a 3 season cottage that has not been on the market in 20 years. An exceptional opportunity to update and put your stamp on a uniquely charming home.

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.

Move in ready with frontage on the Williams River. This beautifully updated and and well maintained contemporary home is the perfect landing spot for easy Berkshire living. The airy living room flows seamlessly into the spacious dining room and efficiently renovated kitchen which is also accessible through the 2 car attached garage. The large en suite primary bedroom is also on the first floor as well as a half bath and laundry area. Upstairs are 2 more bedrooms that share a bath; perfect for guests and/or office or den, as well as a huge storage closet. The property is perfectly located with 3.5 acres on the end of a quiet cul de sac, with frontage on the bucolic and clean Williams River for swimming, floating, and nature watching. Just minutes to downtown GB, Guido's, and Taft Farm's.

Set on 2.01 private acres with sweeping western views extending to Ashmere Lake and the mountains beyond, this exceptional residence offers over 4,194 square feet of thoughtfully designed living space where comfort, elegance, and natural beauty come together. Expansive windows, gracious proportions, and multiple outdoor living spaces embrace the remarkable setting, creating an ideal backdrop for spectacular sunsets and year-round enjoyment.

Welcome home to Silver Maple Farm. Stand-alone condo in established community of 59 homes. Here you'll meet new friends and neighbors at the clubhouse with fitness center, out on the tennis/pickle-ball courts or around the pool. This Cider Lane beauty has been lovingly maintained by the original owner. Privately sited at the end of the cul-de-sac, you'll enjoy the convenience of one-level living. Main level with primary suite, guest bedroom/full bath, den w pocket door. The great room features built-ins, gas fireplace and opens to spacious screened porch and open deck to savor sights and sounds of nature. Lower level is fully finished and walk-out with two additional bedrooms, full bath and large family room. Just in time to enjoy the Berkshire fall colors as the seasons change.

A UNIQUE OPPORTUNITY TO OWN A SPACIOUS LENOX HOME IN A PRIVATE, COUNTRY SETTING AT A REASONABLE PRICE. 4BR, 2.5 BATHS, WITH HARDWOOD FLOORS, OPEN KITCHEN/DINING AREA, LARGE OPEN DECK, PELLET STOVE AND AN IN-GROUND POOL. LOVELY LANDSCAPING WITH STONE WALLS, GARDENS AND OPEN LAWN AREA FOR ATHLETICS OR JUST RELAXING. GREAT CENTRAL LOCATION, A SHORT DISTANCE TO TANGLEWOOD, TOWN AND YOUR FAVORITE BERKSHIRE ATTRACTIONS AND CULTURAL EVENTS.

Don't miss this Lenox beauty tucked away on a quiet side street. Main level w hardwood flooring, living room with crown molding, formal dining w. large bay window, updated kitchen w extensive cabinetry. Family room w gas fireplace opens to large screened porch / patio. First floor laundry and 1/2 bath. Three bedrooms on the upper level; primary suite w adjoining dressing room/ primary bath with soaking tub and separate shower. Two additional bedrooms and full bath; all w hardwood flooring. Central a/c; natural gas heat/hot water; attached two-car garage. Easy maintenance perennial gardens with a focus on native and specimen plantings -over 100 species carefully planned to bloom continuously wowing sight and scent! Abutting preserved land with year-round brook-your own magical retreat!

This well-loved antique home offers a rare combination of history, thoughtful updates, and natural beauty. Set on 14+ acres with sweeping westerly mountain views, Carefully maintained over the years, the property has benefited from significant improvements, including an updated foundation, electrical and plumbing systems, heating system, windows, and roof. The home offers four bedrooms, two full baths, and a full basement, providing comfortable living space with the character and charm of an earlier era. Outside, the property unfolds across fields, gardens, mature fruit trees, and open land, with direct abutting state land and access to the Appalachian Trail nearby. An oversized detached garage with a second floor offers ample room for vehicles, equipment, storage, or a workshop.