Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a warm and inviting escape. Two additional en-suite guest bedrooms occupy the second floor with sitting area between. Residents enjoy exclusive access to a resort-inspired amenity suite—pool, fitness center, clubhouse, and tennis—all just minutes from the cultural and culinary heart of Lenox. A rare blend of privacy, comfort, and sophistication. This is a truly outstanding home, must see.

Beautifully renovated New England Farmhouse with thoughtful modern updates! The home retains original character with wood floors, some exposed timber framing, and a cozy fireplace. Chef's kitchen with high end appliances for serious cooking and easy entertaining. Four comfortable bedrooms, one a primary ensuite, with two additional flex spaces that work for offices, guests , den or creative studios. The screened porch is a three season favorite! EV charger and efficient systems. Set in a prime Berkshire location close to skiing, and minutes to Main Streets of Great Barrington & Stockbridge. Authentic, soulful and elevated, whether full-time or as a vacation home..

Set on 60+ acres of manicured Berkshire grounds, this four-bedroom, five-and-a-half-bath single-owner home is a rare find. Cedar shingle roof, wide-pine floors and walls, natural stone finishes, and wood-burning and gas fireplaces speak to the craftsmanship throughout. The kitchen flows into an open living space with den and sitting room, creating cozy nooks perfect for gathering. A welcoming second-floor primary suite with en-suite bath wakes up to sweeping mountain views every morning. A fully appointed in-law suite with private entrance, kitchen, and bath offers exceptional accommodations for family or guests. Breathtaking views of the Berkshire Hills, with Jiminy Peak and Bousquet visible from the expansive deck. Close to Tanglewood, Jacob's Pillow, Lenox and Lee.

Timeless Craftsmanship Meets Modern Living-Built in 2004, this exquisitely crafted historic reproduction home seamlessly blends old-world charm with contemporary comfort. Set on 1.82 acres with sweeping mountain views, this 3-bedroom, 2.5-bathroom home features meticulous hand-crafted details throughout-honoring traditional design while offering the conveniences of modern construction. The welcoming gourmet eat-in kitchen is perfect for everyday living & entertaining. Step out to the inviting covered porch-an ideal spot to savor morning coffee & evening sunsets with mountain vistas. The primary suite captures stunning views, while the expansive yard provides additional room to roam. 2-car oversized garage. Secluded setting just minutes to downtown Great Barrington & Berkshire attractions.

If you dream of having a beautiful, elegant property on a tranquil waterfront, this home could make it a reality. Light, bright and perfectly appointed describes this lakeside getaway. Whether it's a swim, a paddle, a cool drink on your private deck, or a formal gathering with friends and family, this home has no compromise. Minutes to the amenities of the Berkshires like Jacobs Pillow, Tanglewood, hiking, biking, skiing and more! Come and make your dream a reality.

Uncommonly Superb View -- A Vermont Meadow Retreat Tucked quietly into a broad meadow and surrounded by lush Vermont landscape, this property enjoys one of those rare, completely unspoiled western vistas: a full, harmonious sweep of the Taconic Mountain ridgeline, framed perfectly within human scale. The almost 40 acre setting--meadow bordered by deep woodland--creates a sense of arrival, privacy, and permanence that is difficult to replicate. The architect designed home blends natural materials inside and out, offering a calming, organic environment that feels inseparable from the land around it. One of the sellers' guiding goals the architect skillfully interpreted, was harmony with the landscape, expressed most beautifully in the roofline: ... (see more)

Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the 2-car garage is a sunny space for all of your seasonal gear. Upstairs, the large primary bedroom includes a 2nd wood-burning fireplace and en suite bath, while two additional bedrooms share a full bath. Main floor office and a finished lower level currently serves as guest accommodations, media room, fitness, laundry, and a variety of additional uses. New landscaping! 4 bed Title V, completed 4/26.

Beautifully maintained 4-bedroom, 4.5 bath home located in one of Lenox's most desirable neighborhoods. Thoughtfully designed floor plan featuring a spacious living room with vaulted ceiling and abundant natural light. The well-appointed kitchen offers granite countertops, stainless steel appliances, and comfortable dining area overlooking the private backyard. Generous first-floor primary suite provides convenience and privacy, while three additional bedrooms and well-appointed baths offer ample space for family and guests. A versatile den/home office and finished lower-level family room add flexibility for today's lifestyle. Enjoy outdoor living from the screened porch and stone patio surrounded by mature landscaping. Conveniently located just minutes from downtown Lenox and Tanglewood.

Discover this breathtaking timber-frame home sited on a peaceful and private 10-acre park-like setting central to the Berkshires. Redesigned by architect Pam Sandler, who added a vaulted great room ceiling, a welcoming front porch, a spacious screened porch, and a 3-car garage. Featuring a first-floor en-suite primary bedroom, a generous living & dining area anchored by a commanding fieldstone fireplace, and a well-planned kitchen with all stainless appliances. Three upstairs bedrooms have ample closet space, and the basement family room with a wood-burning stove offers a cozy winter retreat. This eco-friendly home features a newly built barn, solar panels, and heat-pump climate control. There is so much to experience in this beautifully updated home, just 10 minutes from Tanglewood.

Dreaming of your own private sanctuary? 30+ acres await exploration! Enter between two stone pillars and the long winding driveway will take you past woodland glades, open spaces, mature tree stands, manicured lawns and a magnificent spring-fed swimming quarry! Acres of open cleared land afford additional usage options. Cedar log home, one-owner custom built. Large wrap-around deck and long covered porch; great for summer entertaining! Inside you'll enjoy over 2000 sf of relaxed country living. Great room with vaulted ceiling, massive stone fireplace. Open kitchen w. granite counters and island w seating. Two first floor bedrooms and full bath. Upper level with spacious primary suite and an open loft with fireplace. Finished walk-out lower level w. 2 car garage. Truly one-of-a-kind!

Set in the heart of the Berkshires of Lee, Mass, this beautifully maintained 4-bedroom home captures the essence of Berkshire living with panoramic, elevated views for all 4 seasons that will leave you speechless; particularly in Autumn, when views in the Berkshires explode with color. A 4th oversized garage below the house is the perfect place for all of your toys. Inside, the home offers 3 finished levels of flexible living space designed with an open concept. The 1st floor primary suite provides the ease of one-level living and features a newly renovated bathroom with walk-in shower, creating a spa-like retreat with tasteful tile finishes.

Own a piece of Williamstown history with this beautifully preserved Greek Revival modern farmhouse, set along the Green River on just under 20 picturesque acres. This exceptional property offers a rare combination of historic charm and modern comfort, with ample acreage for farming or livestock, ponds, barns, an in-ground pool, and more. The main residence features 5 bedrooms and 4 bathrooms, while the attached guest house offers 2 bedrooms and 2 bathrooms, providing flexibility for extended family, guests, or multi-generational living. Step inside this timeless home to discover thoughtful modern upgrades designed for everyday living. A spacious mudroom at the rear entrance keeps daily life organized, while the stunning kitchen—complete with stainless steel appliances, granite countertops

Special Berkshire retreat on 25 private acres in Harrington Woods with beautiful views. Offering 5,400 sq ft, this 4-bedroom, 4-bath home features oversized rooms and high ceilings. The main level includes a recently renovated chef's kitchen, expansive primary suite with walk-in closets, guest room/office, library with built-ins, dramatic living room and a 400 sq ft screened porch. The walkout lower level offers two additional bedrooms, exercise room, family room, professional pool table, sauna and steam shower. Additional highlights include an oversized 2-car garage with Level 2 EV charger, 12x24 storage shed, and a 30-panel solar array with a transferable utility credit. HOA amenities include tennis, pickleball and a heated seasonal pool. Minutes to Otis Ridge and Great Barrington.

Great Barrington A masterful rebuild with reverence for Great Barrington's past and a bold reimagining for modern living. This 5-bedroom, 4-1/2 bath colonial sits in-town and blends historic charm with contemporary luxury for effortless, years-long comfort. Property Highlights 5 Bedrooms | 4 Full Baths + 1 Half Bath** Complex rebuild from the ground up** - preserved nod to the town's heritage with a fresh, modern interior Chef's Kitchen** - high-end appliances, ample prep space, and thoughtful layout for entertaining Radiant Floor Heating** - in entry Dual Fuel Heat throughout High Velocity Central Air Conditioning** - efficient, quiet climate control Solid Heavy Doors with Emtek Hardware** - substantial, timeless feel with premium finishes 4-Season Porch**

Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The heart of the home is a dramatic, light-filled great room anchored by soaring cathedral ceilings and a brick fireplace paired with charming built-ins. The main level is designed for entertainment and ease, featuring a lavish first-floor primary suite with walk-in closets and a spacious ensuite bath. Upstairs, three additional guest bedrooms are complemented by a private, separate bonus studio

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.

Perfectly positioned on the border of Hancock and Williamstown, this striking Post & Beam contemporary estate offers a rare blend of architectural sophistication and rustic elegance. Spanning approximately 27 acres of meadows and woodlands, this property serves as a secluded sanctuary with views of countryside, mountains, and it is 3.5 miles to Jiminy Peak Ski Resort. The home's interior unfolds across three expansive levels defined by windows, views, soaring ceilings, and rich hardwood flooring. The main living areas include a cozy living room with a Mansfield model wood-burning stove, media/music areas, and a 3-season sunroom that flows seamlessly onto a spacious trex deck. The chef's kitchen is a masterpiece of function and style, complete with a walk-in pantry and dining area.

MOTIVATED SELLER; WILLING TO NEGOTIATE ON UPGRADES AND IMPROVEMENTS. Indulge in refined Berkshire living on an exclusive cul-de-sac, where effortless HOA services complement this exquisite new construction. Offering 4,200 sq ft of thoughtfully designed, environmentally conscious living less than a mile from downtown Great Barrington, this home is the perfect modern retreat. Enter through a covered portico into a soaring cathedral-ceiling great room filled with natural light and serene woodland views. A wonderful screened porch expands the living space for peaceful mornings or easy entertaining. The open layout seamlessly connects the living, dining, and chef's kitchen, featuring premium appliances, quartz countertops, and a spacious island. A sophisticated split-bedroom design.

Located in a ''hidden'' neighborhood behind a stonewall entrance, this newly built home offers tranquil living just 5 minutes from the heart of Great Barrington. The spacious farmhouse front porch is the perfect spot to enjoy quiet mornings or gather in evenings with family and friends. Light-filled and open, the main level features an elegant living and dining area framed by French doors, a gas fireplace, and a chef's kitchen designed for effortless entertaining. Also on the 1st floor, a guest bedroom suite enjoys a private bath with shower and soaking tub. On the 2nd floor the generous primary suite offers dual walk-in closets as well as an luxuriously oversized shower and soaking tub.

Classic eyebrow colonial along the Roeliff Jansen Kill w/ renovated barn and large tillable field across the road. The home has been completely redone from the studs out. Exposed beams, vaulted ceilings, radiant heat, central air, new plumbing, new electrical yet so many original details were preserved. Kitchen is open to dining with wood stove and seating area making this the center of the home. Off the entry is the den (with laundry closet) and the living room with french doors to a patio. Upstairs there are three bedrooms, two with en suite baths. The barn is three stories of finished space with central air and heat. Lower level presently a wood shop, main floor is separated into two large studios; high ceilings, natural light. 2nd floor is a large space with full bath and kitchenette.