Perched high on a hilltop and approached by a winding drive framed by natural rock outcroppings, this newly constructed home was thoughtfully designed to blend modern efficiency with warmth, character, and a strong connection to its surroundings. Far-reaching views and exceptional natural light define the experience throughout the home, with oversized Marvin windows and soaring cathedral ceilings creating a bright and airy atmosphere in every season. The interior combines clean lines with organic materials, including exposed wood beams, radiant heated tile floors throughout the main level, and a stunning oak-topped island that anchors the kitchen and gathering spaces. Bluestone patios extend the living areas outdoors, creating an ideal setting for entertaining or simply enjoying the

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...

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

A remarkable offering of this restored 18th century Georgian home built in 1764 on almost 4 acres with the possibiilty of an additional building site as part of the listing price; with an early barn and shed opposite the Clark Art Institute. Once located on Main St where the College President's house now sits, it was moved by oxen to its current location in 1800. (RRBrooks.)Restoration efforts follow the Deerfield tradition of interior feather-edged sheathing and paneling, wide pine board flooring and a large colonial cooking fireplace with adjacent beehive oven in the keeping room. 4-5 bedrooms/3.5 baths.

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.

Sun Filled Historic Reproduction Home Built in 2004 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 Gt Barrington & Berkshire attractions.

Fabulous historic church. Located in the Stockbridge hamlet of Interlaken. Quiet and exclusive neighborhood just off Rt.183. Stylishly decorated by a renowned architect and designer. High ceilings, huge windows, and mahogany fittings. Beautifully restored kitchen with many original details. Marble topped sink/counter. Walk through to the magnificent living area to step back in time to an earlier era. Then on to the nave to enjoy soaring ceilings, oversized windows and room for entertaining. Enjoy this 'party space.' Or use for an artist studio, recording studio or any pastime that needs space. Minutes to Berkshire Botanical Garden, Tanglewood and the center of Historic Stockbridge.

Discover this sleek 2022 contemporary set on a beautifully landscaped parcel of just over 2 acres. Thoughtfully designed for low-maintenance, efficient living, this home offers 3 bedrooms, 3 bathrooms, and approximately 2,400 square feet, with every detail crafted for both beauty and everyday convenience.

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

Originally a gift from Williams College President Harry A. Garfield, the son of United States President James Garfield, to his daughter, this elegant and gracious South Street home is available for the first time in over thirty years. Fine architectural details abound with beautiful crown moldings and woodwork, six panel doors, gleaming oak flooring, abundant built-in shelving and cabinetry, and large, light-filled floor-to-ceiling windows. The spacious entrance hall opens on your left to a stunning wood-paneled library lined with ample book-shelving and warmed by a corner fireplace with wood mantel and slate hearth. Ahead, the lovely living room, with another handsome fireplace with decorative mantel, side pilasters and marble hearth, provides access to a covered slate side terrace.

Exceptional Federal style reproduction farmhouse located in a peaceful setting on a scenic country road. Offering 3-4 bedrooms, 3.5 bathrooms, beautiful hardwood and marble floors. The kitchen with Viking range, custom cherry cabinets, granite countertops and walk-in pantry opens to a family room with a brick Rumford fireplace. The formal dining room opens into the living room. There are French doors to a heated sunroom that connects to a barn/garage with 2nd floor great room and full bathroom. The grounds include a bluestone patio and Goshen steps to the home. Property setting has mature landscaping and perennial gardens. Adjacent undeveloped 2.5 acre lot included.

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.

Attention Investors! Excellent 6-unit investment opportunity in Lee with strong existing income and flexible rental potential. Five of the six units have been renovated with premium finishes, complemented by a newer roof, updated electrical and newer heating systems--helping reduce near-term maintenance and capital needs. Currently operated with a mix of long-term and seasonal rentals, the property offers flexibility for traditional leasing, short-term rental use, or a combination of both. The spacious 4BR/2BA unit also provides an attractive owner-occupancy option while generating income from the remaining units. Public water and sewer, separate utilities, ample parking and convenient access to the Mass Pike, Lee Outlets and Berkshire attractions. Easy to show- come see for yourself!

Cross the charming historic-style covered bridge and enter a world of privacy, nature, and endless possibilities. This remarkable 94-acre sportsman's estate offers river frontage on the Farmington River, expansive woods, trails, and room to roam. At the heart of it all is a spacious split-level home with 3 bedrooms and 2.5 baths, featuring fresh paint, new flooring, and a new roof. A 5-bay barn/garage provides incredible space for vehicles, equipment, hobbies, and toys. A separate mobile home offers flexible additional space for a studio, guest quarters, office, or creative retreat. Whether you're seeking a private Berkshire escape, outdoor adventure, or simply a place where the woods are truly your own, 132 North Main Road is a rare opportunity to own your very own Hundred Acre Wood!

Set on a desirable tree-lined dead-end street in the heart of Lenox, this beautifully restored 1937 Cape blends timeless character with exceptional craftsmanship. Featured in Berkshire Magazine, the 3,740 sq. ft. home offers original heart pine floors, a wood-burning fireplace, and extensive updates including new plumbing, electrical, Pella windows, roof, and central AC. The three-level layout features 3 bedrooms, 4 full baths, two upper-level suites, and a finished lower level with a guest suite, office, and workshop. French doors open to a wraparound veranda overlooking Goshen stone terraces, fruit trees, and a fire pit. Walk to downtown Lenox with convenient sidewalk access, while Tanglewood is just minutes away.

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.

Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes -one a four bedroom home and a 1000 sq ft guest house-both 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. Spacious garage allows room for cars, hobbies and workshop, perfect pool site, and privacy ensured by abutting protected land. Generator for both houses.Access to town beach. A generous seller credit opportunity toward buyer's preferred improvements upon acceptable offer. Online psf is in error. Actual is $469 psf

Tucked away on a peaceful private drive, this custom Craftsman home (built 2022) combines timeless architectural character with effortless modern living. Designed with accessibility and everyday ease in mind, the main level features zero-step entry and true single-level functionality. At the heart of the home is a bright, spacious cook's kitchen that flows seamlessly into welcoming living spaces. Outdoor living shines with both a classic front porch to take in quiet sunsets and a stunning screened porch designed for bug-free Berkshire evenings. The versatile 4-bedroom layout features a private primary suite alongside an attached in-law apartment-ideal for multigenerational living, long-term guests, or rental potential. A dedicated home office makes remote work a breeze,

Custom built contemporary home on over 2 acres, 5 minutes to Great Barrington center. Large open first floor with vaulted ceilings and lovely gathering space. Kitchen is dreamy w/large island, coffee bar, ample storage and tons of working space. Open to dining area as well as the living room with propane fireplace. Large screened in porch flanks the east side of the home expanding the footprint 3 seasons a year. A mud room entry off the garage with laundry, two offices and a powder room complete this floor. Upstairs there are two guest rooms with en suite baths and a primary suite with fireplace and large bathroom. The LL offers an add'l 1900 sq ft (not included) with a game room, gym, guest bedroom, media and full bath. Truly turn key w/ sunset views over the neighboring private airport.

TO BE BUILT: Gorgeous neighborhood setting with lush landscaping and Indulge in refined Berkshire living on an exclusive cul-de-sac, where effortless HOA services complement this exquisite new construction. Offering 3,808 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.