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53 Photos
LANCE VERMEULEN RE, INC
$795,000

Commercial

Presenting a rare opportunity to acquire a premier commercial property strategically located in Sheffield, Massachusetts. This expansive 8,500 sq. ft. facility is ideally situated on a generous 3-acre lot with ample parking, offering a versatile foundation for a new venture to launch or an existing enterprise to expand. As the celebrated former home of a popular local brewery, this property provides a unique turn-key solution for an ambitious owner-occupier. Its location is a stone's throw from Route 7, offering outstanding accessibility and just a short, scenic drive to vibrant downtown Great Barrington and the beautiful towns of Northwest Connecticut. The building's design is a masterclass in operational efficiency, focusing on a seamless flow between production, logistics, and retail.


17 Photos
ELYSE HARNEY REAL ESTATE
$795,000
3 BD | 3 BA
Residential - Single Family

Classic 3-Bedroom Cape with Pool - Perfectly positioned between NW Connecticut and Sheffield, MA in the Berkshires. Sheffield is the oldest Town in Berkshire County - the township was purchased in 1724 from Chief Konkapot and other Stockbridge Native Americans. This bright, lovely 3-Bedroom Cape features a beautiful, heated pool, a Bedroom and Full Bath on the Main Floor, 2 Bedrooms and another Full Bath on the Second Floor, a light and bright Living Room with stone fireplace, Kitchen with large island, Dining Room, and a 2-bay Garage with a loft. Tall lilac trees frame the pool on this 1-acre parcel. Close to private schools, skiing, the Appalachian Trail, and Twin Lakes. A sweet spot to make your home, whether for year-round living or part-time relaxation.


35 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$799,000
3 BD | 3 BA
Residential - Single Family

Stunning contemporary sanctuary in Ashley Falls offering perfect blend of modern design & natural surroundings. 3BR/2.5BA residence bathed in natural light. The first floor features a comfortable den, eat-in kitchen and gracious living room with marble wood burning fireplace. A thoughtfully designed floor plan flows seamlessly to outdoor spaces including large deck for al fresco dining & expansive screened room extending living into every season. Attached oversized 2-car garage and 2 finished rooms on the lower level. Meticulously maintained gardens, beautiful heated pool, multi-zone central A/C in an incredibly private setting. Perfect retreat minutes to Salisbury/Lakeville CT & Columbia County NY, close proximity to all Berkshire cultural & outdoor attractions.


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ALDEN COUNTRY REAL ESTATE SERVICES

An exceptional commercial opportunity on busy Route 7 at the Sheffield-Great Barrington line, this 7.29-acre property offers over 1,000 feet of frontage and unmatched visibility. Formerly a GMC dealership and auto repair shop, the site includes a 5,540 sq ft garage with five oversized service bays and heavy-duty power--ideal for automotive, fleet, or light industrial use. An additional storage building on-site expands functionality.The expansive paved lot can accommodate over 100 vehicles, making it ideal for dealerships, rentals, or display. The location benefits from steady traffic, close proximity to tri-state area schools & businesses, and easy access to downtown Great Barrington's shops, restaurants, and cultural venues.


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LANCE VERMEULEN RE, INC
$995,000
5 BD | 5 BA
Residential - Single Family

Nestled at the end of a quiet country cul-de-sac, this newly built 5-bedroom, 4.5-bath home embodies refined country living. A dramatic primary suite offers dual walk-in closets and a spa-inspired bath with soaking tub, while a first-floor ensuite bedroom enhances comfort and flexibility. The gas fireplace living room and chef's kitchen create a seamless flow for entertaining, extending to a private rear patio and deck. A welcoming cedar-decked front porch, French doors, and a heated two-car garage highlight thoughtful design. Basement level with High ceilings, and plenty of windows could be easily finished. Built with foam insulation and advanced mini-split climate systems, this home delivers modern efficiency in a serene Berkshire setting, convenient to CT and the Great Barrington.


60 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$1,250,000
3 BD | 3 BA
Residential - Single Family

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.


41 Photos
ELYSE HARNEY REAL ESTATE
$1,275,000
4 BD | 5 BA
Residential - Single Family

Experience breathtaking panoramic vistas over protected land from every angle in this renovated Classic American Farmhouse. Nestled on two parcels, this residence boasts a pool, a detached garage, and gracious proportions throughout. Relax in the majestic long-range mountain vistas. The house is perfectly positioned to experience both sunrise and sunset views.Step inside to discover an extra-large chef's kitchen seamlessly connected to a delightful breakfast room, sunroom, and screened porch, each offering tranquil views of the pool and raised garden beds. The inviting living room, complete with a cozy fireplace, flows effortlessly into the dining area, creating an ideal space for entertaining. Adjacent, find a sunlit den and office area, bathed in natural light.


37 Photos
COMPASS MASSACHUSETTS , LLC GB
$1,350,000
3 BD | 3 BA
Residential - Single Family

Custom modern home with open plan living area, high ceilings and oversized windows everywhere bringing in tremendous natural light. One level living with large gorgeous marble kitchen, great working island and wall pantry. Guest wing off entry with two bedrooms and a hall bath. Entry hall has a powder room, hooks for coats and closet. The primary suite, on the south side, has french doors to private backyard with saltwater pool, walk-in closet, soaking tub and separate shower. Sited at the back of the 1.5 acres the house sits nicely above the front yard and allows for a more private backyard area to enjoy the pool, patio and fire pit. Large full basement and custom shed are just a few more of the perks of this thoughtful home.


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HOUSATONIC REAL ESTATE
$1,475,000
1 BD | 2 BA
Residential - Single Family

A total 41 acres includes a 2nd building lot of 26 acres allowing one to build ones own home with mountain views. A 36x52 work shop. One full time residence and a separate summer studio. Some land does go into New Marlborough. Surrounded by conservation land. Passive solar views facing South and West. Property has been a sculpture park for many years. Trails throughout. Views to Connecticut.


61 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$2,500,000
4 BD | 5 BA
Residential - Single Family

The ULTIMATE LIVE-WORK-PLAY RETREATStep onto a property as striking as the Berkshires themselves--where innovative design meets natural splendor, creating an extraordinary canvas for your ideal lifestyle. The 13,738 sq ft retreat fondly known as ''The Factory'' spans 5+ acres with views of rolling hills & protected fields. 10,000 sq ft of versatile commercial and creative space below and flanked by 3,000-sq ft of stunning living spaces that seamlessly blend design, sophistication, comfort. From the glass walls that open to sweeping views, to its bespoke kitchen or design forward guest suite, every inch has been crafted to inspire. Host gatherings on the spacious screened deck, unwind by the 360 glass fireplace, find solitude in the ''Tower'' - and redefine living, creating, & thriving.


53 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$2,690,000
4 BD | 4 BA
Residential - Single Family

The Quarry - A One-of-a-Kind Berkshire Estate on 60 Private Acres!Singular, stunning, and secluded--the quarry pool at the heart of this 60-acre Berkshire estate is truly one of its kind: the culmination of geology, industry, and artistry. Carved into a reclaimed limestone quarry and framed by towering stone walls and a 16-foot waterfall, the quarry pool is a marvel in and of itself--equal parts art installation, private resort, and natural wonder.Measuring approximately 20 by 40 feet, the quarry pool sits within a landscape of curated gardens, open lawn, and forested acreage--entirely private and protected. The property offers the potential for additional dwellings, making it as versatile as it is visually striking.

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