Lovely Carriage House in splendid location. Just minutes from prestigious Clark Art Institute with its world-renowned collection of French Impressionist and American Art, and the numerous trails wandering through the meadows and woodlands of its 140 acre campus, and a stone's throw from the outstanding Taconic Golf Club, this charming residence, once part of the Cluett Estate, affords privacy with its 1.4 acres as well as proximity to all Williamstown has to offer. The four bedroom, three and one half bath home features a stellar and spacious living room with large woodburning fireplace, a formal dining room opening to a screened porch overlooking the pleasing grounds, a warm bookcase-lined den with another fireplace, a kitchen with breakfast nook. and stone terraces. With ample room

Just up the road from the world-renowned Jacob's Pillow Dance Center, this stunning architect-designed sanctuary sits on 14 sprawling acres with panoramic views of Greenwater Pond and the rolling valley beyond. At the heart of this masterfully crafted 1998 home is the great room with soaring vaulted ceilings centered on a magnificent oversized stone fireplace. This spectacular space is banked by a wall of glass windows and doors leading to an impressive 60-foot deck for a front row seat to dazzling sunsets. The great room flows seamlessly into a sleek and thoughtfully appointed kitchen, and a spacious dining room perfect for entertaining a crowd. The primary suite serves as a personal haven, featuring its own stunning vistas, dual primary baths, and a small office. The lower level...

Completed in 2022 and set atop one of North Berkshire County's most scenic country roads, this architecturally striking contemporary residence was thoughtfully designed to embrace natural light, energy efficiency, exceptional indoor-outdoor living, and panoramic views of the Mount Greylock Reservation. Positioned along sought-after Bailey Road in Lanesborough, the property offers a rare combination of modern design, privacy, and breathtaking Berkshire mountain scenery just minutes from Williamstown, Jiminy Peak, Mass MoCA, and the region's renowned cultural destinations.

A custom built home set on 16 private acres, offering 5-bedrooms, 5 full baths, 1 half bath with over 4,000 square feet of living space. Surrounded by natural beauty and peaceful scenery, the property provides the perfect balance of privacy, space, and comfort. Inside, you'll find generously sized rooms, multiple living and entertaining areas, and a flexible floor plan ideal for both full-time living and weekend retreat use. The spacious primary suite, ample guest accommodations, and thoughtfully designed layout make this home well-suited for hosting family and friends. An unfinished area in the basement allows for an additional room made to your liking. A short drive to Otis ridge and the Otis Reservoir, making outdoor activities right in your backyard!

Welcome to 221 Bailey Road in Lanesboro, MA., an exquisite ranch-style home offering approximately 4,200 sqft of luxurious living space. Nestled on 87 acres atop a mountain, this property provides unparalleled privacy and breathtaking views that enhance its serene atmosphere. The open-concept living area is perfect for entertaining, featuring abundant natural light and seamless flow between spaces. Energy efficiency is a hallmark of this home, ensuring comfort year-round while minimizing utility costs. Ample room for family and guests, this stunning residence combines modern amenities with the tranquility of nature. Some of the amenities this home offers a three car garage, heated in ground pool, owned solar and a cozy wood stove for those chilly Berkshire nights.

Welcome to Serenity Hill.This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road. Less than a mile from Wyantenuck Country Club and just five minutes from downtown Great Barrington. This home offers a peaceful sense of seclusion without ever feeling far from the heart of the Berkshires.Inside, you'll find an airy, open layout with natural flow from room to room, designed with both comfort and connection in mind.

Single level Berkshire retreat tucked away on 5.91 peaceful acres just minutes from downtown Great Barrington. Abutting the Tom Ball Mountain Trail & land reserve, this custom-built ranch offers the perfect blend of privacy, comfort, and versatility. Built in 2005, the home features over 2,400 square feet of living space with 3 bedrooms, 2.5 baths, abundant natural light, and an easy-flowing floor plan ideal for everyday living or entertaining. The expansive lower level and dual-garage configuration provide exceptional flexibility for a workshop, studio, recreation space, guest quarters, or future expansion. Enjoy wooded surroundings, open sunny spaces, solar panels, and a serene country setting just moments from the Berkshires' renowned dining, culture, and outdoor recreation.

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

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.

Designed in 1929 by noted architect Henry Seaver (Berkshire Museum, Lenox Town Hall), this distinguished Georgian Colonial was once the centerpiece of Pittsfield's social scene. The home preserves exquisite 18th-century details - mantels, wainscoting, and finely crafted woodwork salvaged from two of the city's earliest residences, making it a living piece of Berkshire history. Set back on 2.5 private acres along prestigious Crofut Street, the estate offers 5 bedrooms and 5 baths, including twin primary suites ideal for hosting friends and family year-round. Gracious living and dining rooms, a peaceful sunroom, a cozy study, and a large eat-in kitchen with Viking range and butler's pantry combine period elegance with modern comfort. This turn-key estate is offered fully furnished and

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.

MOTIVATED SELLER. 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.

Tucked at the end of a quiet cul-de-sac just minutes from Tanglewood, this light-filled country contemporary is designed for easy Berkshire living, with bright open spaces, a convenient first-floor primary suite, and seamless indoor-outdoor flow. Mornings begin in a sunlit kitchen that opens effortlessly to the main living areas, while a vaulted great room with gas fireplace creates a natural gathering space year-round. In warmer months, doors open to a wraparound deck, screened porch, and stone patio overlooking landscaped grounds--ideal for long evenings outdoors and relaxed entertaining.The spacious first-floor primary suite features a sitting area, double vanity, soaking tub, and two walk-in closets. Additional spaces include a four-season sunroom and home office or den. Upstairs,

Welcome to elegant single-level living in one of Lenox's most coveted locations. Ideally positioned on prestigious Saint Andrews Drive, this exceptional home offers privacy, comfort, and stunning views--just minutes from the heart of the Berkshires.This expansive 3,379-square-foot residence features four bedrooms and four full baths, thoughtfully designed for both everyday living and entertaining. Each bedroom includes its own private bath, ensuring comfort and privacy for family and guests alike.A grand living room with soaring ceilings and a double wood-burning fireplace flows seamlessly into a cozy den, separate office, and formal dining room. The gourmet eat-in kitchen is beautifully appointed and enhanced by custom woodwork and artistic tile details throughout.

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.

One of the most exceptional homes to come to market, this remarkable property blends timeless elegance with resort-style living. Featuring 5 bedrooms, 3.5 baths, including private guest quarters with bath and secondary staircase, this home offers both sophistication and versatility. The luxurious primary bedroom suite is a true retreat, complete with a spacious en-suite bath designed for comfort and relaxation. A stunning new kitchen serves as the heart of the home, thoughtfully designed for both everyday living and refined entertaining. Impeccably curated interiors extend seamlessly to breathtaking outdoor spaces highlighted by a spectacular heated in-ground pool, extraordinary landscaping, and meticulously maintained grounds. A true masterpiece of design and luxury living.

''Best of Berkshire Living: Gardens, Grand Trees & Income-Ready Guest Cottage''Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming 1BR guest cottage, with large living room and mini-splits, is ideal for rental income or private guests. Garages for 5+ cars, perfect pool site, and privacy ensured by abutting protected land.

Set on 22 private acres, this Monterey retreat offers a peaceful escape from city and suburban life. Freshly painted this spring, it's near Lake Garfield and Monterey Town Beach, and across from Beartown State Forest. The bright, expansive home features four ensuite bedrooms, including a spacious primary suite, large entertaining areas, and cathedral & vaulted ceilings. Outdoors, enjoy a 16' x 40' heated gunite pool, an outdoor enclosed shower, a large stone patio, and the year-round Loom Brook flowing through the woods. The lower level includes a sauna, exercise pool, and utilities. A two-car garage connects to a mudroom with laundry, half bath, and outdoor shower, plus a large bonus room above. A rare opportunity at this price in scenic, convenient Monterey, with fiber internet.

Discover a rare lakefront opportunity on Otis Reservoir with amenities seldom found in one property. Combined with the lower lot, enjoy 62 feet of direct waterfront, a grandfathered boathouse with electricity and electric lift, waterfront bathhouse with living room, heated garage, dedicated hot tub room with fireplace, and lake views from nearly every room. Perfect for entertaining with an updated kitchen, multiple living areas, separate driveways, ample parking, and two storage sheds. Remodeled in 2021 with new heating and cooling, on-demand hot water, quartz island, stacked cabinetry, stainless appliances, and gas range. Walk-out basement. Sold fully furnished and ready to enjoy.

Views, privacy, and frontage on Mill Pond. This custom built classic Gilligan house is the perfect home for hosting family and friends with plenty of space both inside, and out. There are 4 plus bedrooms and 5 baths, including a generous primary suite on the first floor, a large den, and a bonus room above the 2 car garage. The property includes a fenced, in- ground pool, extensive flat lawn, perfect for soccer or croquet, and a private dock for paddle boats, fishing and watching out for the resident Bald Eagle! The house sits on 4.49 acres and also includes 4 additional lots for a total of almost 13 acres.