Perfetto. A pebbled, willow-shaded drive welcomes you to a classical villa elegantly and privately set in a coveted location minutes from Great Barrington. Taking design cues from ancient Rome and built to exacting standards, its light filled interiors yield fully protected views of fields, meadows and mountains. Sophisticated details and quality craftsmanship are everywhere evident--19 sets of French doors for ideal indoor-outdoor flow, varied ceiling heights, living room with custom mantel, serene primary suite, guest wing, central courtyard with formal gardens and reflecting pool, pergola and lap pool, and chef-ready kitchen, central AC, and generator. Privacy, ease, and expansive views, all in a 2,716-square-foot sanctuary on Baldwin Hill.

This exquisite single-family home spans an impressive 4,300 square feet, offering an unmatched blend of elegance and modern comfort. With 5 spacious bedrooms and 4.5 beautifully renovated bathrooms, every detail has been meticulously crafted to perfection. Walking distance to downtown Great Barrington's shops and restaurants, the house is in one of the quietest areas of ''The Hill''. 12 rooms including a formal dining room, a sophisticated library/den, and a versatile media/recreation room. The chef's kitchen, featuring premium counters, a WOLF range, a Sub Zero refrigerator, a wine cooler, and a butler's pantry for seamless entertaining. The home is filled with natural light. Comfort is ensured year-round with air conditioning and central heating on every floor.

Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it offers plenty of room to entertain and relax. The large cook's kitchen is perfect for preparing meals for large gatherings, while the heated sun room provides a cozy spot to enjoy your morning coffee and take in the stunning views of the surrounding fields. This home also features 5 spacious bedrooms (primary with en-suite, four jack-and-jill), each with their own unique charm and character.

Seize this rare opportunity to complete a 55-unit expansion within an existing condo association. With a majority of infrastructure in place and high demand in the area, this semi-completed development offers exceptional return potential. Originally approved in 2002 as a 40B development, this project is ready to be picked back up where it left off. All current permits, site plans, and engineering documents on hand shall be transferred as part of sale, providing a streamlined path for completion. Don't miss the chance to capitalize on this ready-to-go project in desirable Great barrington.

Extraordinary and expansive estate property near the top of the hill on prestigious and desirable Bulkley Street. Consisting of three separate parcels over 11+ acres, this offering provides a rare opportunity to acquire an expanse of gorgeous acreage within minutes of Williamstown center, Williams College, the Clark Art Institute, the new Williams College Museum of Art, and close by the 2600 acres ecological reserve, Hopkins Memorial Forest. The four bedroom, three and one half bath main house, sitting atop the hill, has been beautifully updated while maintaining its gracious character and features an array of public spaces both intimate and open, with an especially appealing four season sunporch overlooking the lovely gardens, graceful and sweeping grounds, and the distant ridgeline.

Truly, a one of a kind, stunning property both inside and out with scenic views of the sprawling land down to Long Pond. This thoughtfully crafted and designed home was curated to incorporate the natural serene outdoors into gracious open common spaces allowing warm natural light and comfortable flow. The first floor boasts the great room with wood burning fireplace open to the chefs kitchen with a large pantry and dining with built ins, unique sunroom with walls of glass and screened porch that extends the indoor outdoor living space while overlooking the pergola, play house and down to the water. The first floor primary en suite and office/den sitting area offer privacy in its own separate wing. The second level has ample guest space with three bedrooms, two en suite full baths and

Set in the heart of Old Chatham, this classic Colonial rests on an exceptional 101-acre landscape of rolling pasture, woodland, and wide-open country views. From its elevated vantage point, the home looks out over a 2.5-acre swimmable pond, open fields, and a stretch of Hudson Valley scenery that changes beautifully with the seasons. Flooded with natural light, the seven-bedroom home offers generous space to gather and unwind with family and friends. At its center, the kitchen and living areas are designed for connection. The open kitchen and dining space flows easily into the main living room, where a stone fireplace anchors the room and creates a natural place to come together after a day outdoors. Stainless steel appliances and ample workspace make the kitchen as functional as it is

A rare offering of 118 acres in the highly sought-after Tyringham Valley. Sage Hill Farm encompasses an exceptional landscape of rolling meadows and woodlands, mature landscaping, exquisite gardens, beautifully crafted hardscape and handsome barns. Dating to 1817, the main house retains many of its original architectural details and is complemented by a partially renovated 1970s addition and separate 1941 guest house. The grounds are impressive, with a beautiful setting for the heated in-ground pool and ample areas to enjoy the property's extraordinary acreage. The original house and addition offer generous accommodations for family and guests, including six bedrooms and four bathrooms, two of which are roughed for plumbing. . . .

A UNIQUE NEW HOME UNDER CONSTRUCTION IN THE HEART OF STOCKBRIDGE, MASSACHUSETTS Historic Living: In an era of increasingly homogenized architecture, this extraordinary timber frame Dutch house replica offers something rare: a true sense of place. Rooted in the early traditions of the surrounding Housatonic Valley, the home is a thoughtful homage to the region's European heritage--crafted with authenticity, integrity, and many locally sourced materials designed to age gracefully. Inspired by early 18th-century Dutch design, the residence features massive anchor beam construction, a steeply pitched roof, thick plank floors and richly textured materials that develop warmth and patina over time. Traditional casement windows with deep sills, exposed timber framing, and masonry fireplaces

Welcome to 19 Buckingham Lane, a completely turnkey, beautifully curated waterfront retreat designed by internationally acclaimed interior designer Jess Cooney of Jess Cooney Interiors. Offered fully furnished, this newly renovated home sits directly on the shores of Lake Garfield and features four bedrooms and three baths across three levels. Soft earth tones, richly textured wood finishes on floors, walls and ceilings, and elegant stone surfaces create a relaxed yet sophisticated atmosphere for lakefront living. Tucked into a private cove, it offers exceptional peace and seclusion while the expansive deck provides the perfect setting for entertaining with sweeping water views. And if you don't own a boat, you're in luck--one is included with the sale.

Now offered at a new compelling price! Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living experience unlike anything else on the market. The first floor features an impressive great room with soaring timber beams, an elevated Malm fireplace, and floor-to-ceiling glass that captures the surrounding vistas. A gourmet kitchen imported in its entirety from Germany anchors the main living space with exceptional craftsmanship and modern sophistication.

Fabulous Property with ponds, rushing streams, huge acreage & a gem of a house. The 220 acres abuts state forest and beautiful Walker & Spark Brooks both run through the property. The 2BR/2.5B home has lovely views of the pond & hills beyond, and was totally renovated to the highest standards in 2023 & 2024. Native stone fireplace, heart pine floors, new kitchen, baths, heating, mahogany decks, outdoor shower, windows & insulation. There is a large post & beam barn plus stone foundations from an earlier barn. The fishing is great and trails have been cleared for hiking and horseback riding. Conveniently located near Tanglewood, Jacobs Pillow and most other Berkshire cultural attractions as well as state forests and wildlife management areas. Under 3 hrs. to NYC, 2.5 hrs. to Boston

A Landmark Berkshire Estate of Extraordinary Provenance, the Oliver Wendell Holmes summer cottage. Set on 15 private acres in the heart of the Berkshires, a rare American legacy estate commissioned in 1847 as the summer residence of renowned physician, poet, & author Oliver Wendell Holmes Sr. Two centuries later, this extraordinary property remains a testament to architectural elegance, literary heritage, & timeless craftsmanship. The offering preserves original hardwood floors, intricate millwork, & the grandeur of a distinguished era. Its storied halls welcomed literary icons including Longfellow, Melville, & Hawthorne. Surrounded by exceptional privacy, Holmesdale is more than a residence, it is an irreplaceable American landmark

Rare opportunity to acquire a four-building industrial complex totaling approximately 193,037 SF in a centrally located Pittsfield industrial corridor. The property consists of Building A (57,755 SF), Building B (18,125 SF), Building C (59,313 SF), and Building D (57,844 SF), offering a variety of configurations suitable for manufacturing, warehousing, distribution, and industrial users. The main building has 32 offices and conference spaces, plus at least 15 additional spaces throughout the warehouse. Buildings are fully sprinklered and feature clear heights ranging from 8'-30'. The site benefits from two truck-access entrances, providing efficient circulation and logistics capabilities. Building D offers potential for a separate parking area.

Prime retail development on a high-traffic stretch of Stockbridge Road in Great Barrington, MA - Established tenants in place providing immediate income - Excellent opportunity for value-add through lease restructures, unit-mix optimization, or signage/branding enhancements - Diversified income across four buildings and five rental spaces -Ample on-site parking - Proximity to dining, tourism, and regional services Accessibility & Local Market - Easy access to I-90 and regional routes - Located in Great Barrington, a growing Berkshire County hub for shopping and tourism - Complementary retail and service anchors nearby Inclusions

OFFERED FULLY FURNISHED AND TURNKEY. Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views. The main home, a modernist design collaboration between Bauhaus designer George Giusti and architect Crane De Camp, is a two-bedroom, three-and-a-half-bath masterpiece that features a gym, sauna, and gardens designed by a local landscape architect. For guests, they can choose between the three-bedroom, two-bath Cottage or the one-bedroom Cabin, both of which are intimate and offer plenty of privacy for family and friends. Whether it's poolside by day, trails in the afternoon, or hanging by the fire pit at night, there is something for everyone at this mid-century getaway set in the Berkshire hills and only minutes to Litchfield County

Set on private acreage with breathtaking views of the Berkshire Hills and majestic Mount Greylock, this exceptional custom-built estate offers a rare combination of timeless craftsmanship, luxury, and natural beauty. Built in 2007 and thoughtfully designed to embrace its picturesque surroundings, nearly every window captures stunning panoramic views, filling the home with natural light and creating a seamless connection to the landscape.

EXPANDED CONTEMPORARY CAPE Appointed with elegant detail, masterfully crafted, this stunning home is nestled on over 9 private acres offering 9 rooms, 4 bedrooms, 3 full and 2 half baths. An open floor plan flows seamlessly from the generous living room, featuring a striking coffered ceiling and a fireplace surrounded by natural raw granite, into a large kitchen and dining area perfect for entertaining. A stunning wrought iron detail by Ivan Bailey enhances the staircase.. A media room with glass-paned sliders and built-in bookcases completes the exceptional living space. The first floor primary ensuite is a true retreat, boasting a soaring vaulted ceiling and two large walk-in closets. The second floor offers three additional bed rooms, and two full baths.

At the Lenox/Stockbridge town line on the shore of Lily Pond, sits this architectural gem! Offering a rare combination of privacy artfully aligned with nature and a premier location. Set on six acres within the grounds of the original historic Wheatleigh estate, the property is within walking distance of Tanglewood, the Linde Center, Kripalu and Lenox village. Designed by Berkshire architect David Rothstein, the house is ideally positioned to engage its landscape. Large bay windows invite natural light and frame views of water, trees, and gardens. Custom cherry woodwork adds warmth and craftsmanship. The layout is both flexible and refined. First floor primary suite supports single level living, while 3 additional bedrooms and a library occupy the upper level. Lofts, towers and