Eighteen acres on the quitest dirt road with its own exceptional landscape feature: a boulder-strewn, mossy-rocked cobble. The cobble bisects a flat, three acre cleared field to the east, and a wooded forest with old stone wall remnants to the west. Live amongst the ancient spirits in whatever beautiful house you build. Fifteen wooded acres in Chapter 61A.

This property offers a blend of comfort, style, and spaciousness, set within the picturesque landscape of Sheffield. The 16-acre property provides an idyllic country setting, ensuring privacy and a connection with nature. The residence, a charming 3-bedroom, 2-bath home, has been thoughtfully updated to combine modern amenities with rustic charm, new hardwood floors and bathrooms complement the cozy living spaces. The primary bedroom, with its oversized closet and adjacent full bath with custom tile, separate glass shower and luxurious soaking tub, promises a retreat within the home. The additional bedroom or office space adds flexibility to the floor plan. And the 3rd bedroom has great room separation off the living room.

A rare & authentic 1842 post & beam farmhouse w/ many original details. This one-of-a-kind antique home awaits the reinvention & stewardship of it's next owners. In the same family for the last 125 years, and with just two prior owners since being built, the structure features post & beam construction, two original fireplaces, antique hardware, woodwork and doors that exemplify early American craftsmanship. The home offers a spacious first floor with two kitchens (once used as a two-family), dining room & parlor, and 2nd floor offers 4 bedrooms and two baths. The 1.5 acre parcel offers extraordinary western sunset views towards Mt. Everett overlooking the Housatonic river valley. A once-in-a-lifetime opportunity to own and restore an iconic home.

Sugar & Rye: A vibrant market and deli located on Main Street in Sheffield, this turnkey business is beloved for its freshly prepared foods, including custom sandwiches, grab-and-go meals, and baked goods. Key features include a liquor license, ice cream bar, and a coffee bar, attracting a wide range of customers. The store offers both casual seating and takeout, ensuring steady traffic from locals and visitors alike. With an established customer base, supplier relationships, and popular items such as rotisserie chickens and baked goods, Sugar & Rye is perfectly positioned for continued success. Real Estate Details: In addition to the business, this listing includes two 2-bedroom apartments and a carriage house apartment, offering additional income potential or a residence for the owner.

Experience the serenity of 594 Shunpike Rd. This cozy 2600 sq. ft. Gambrel-style home, set on 2.32 acres, has been meticulously & extensively renovated for modern living. Enter through a bright, open foyer & enjoy central air/heat, a full house generator, & new wood flooring. The home features all new kitchen, bathrooms, gas fire place, plumbing, electric, windows & more. The newly finished lower level w/ walkout offers additional living space. Relax on the spacious deck, surrounded by a beautiful clearing in the woods. The primary suite w/ a spa-like bathroom & walk-in closet. This property is ideal for year-round living, vacation home, or potential rental income. Located on a quiet country road, minutes from town, enjoy location for recreation & cultural attractions.

Welcome to 856 Barnum, a stunning residence born from the creative vision of a talented photographer and acclaimed New York architect, Debora K. Reiser. What was once a modest Cape Cod has been transformed into a sophisticated modern masterpiece.The exterior showcases sleek lines and elegant copper details, with a striking turret adding depth to its profile. Upon entering, you are greeted by a grand room featuring a soaring vaulted ceiling and expansive windows that seamlessly connect the interior with the picturesque countryside. Custom-built, spacious closets line the front wall, providing generous storage solutions. The back wall is anchored by a cozy fireplace, complemented by built-in bookshelves.

Investment opportunity in Sheffield. Set way back from the main road, this multi family dwelling awaits its new Stewards after almost 40 years in the same family. The property consists of 3 separate buildings, The main house with four 1 BR apts.In the rear of the main house is a semi attached 2 BR apt with its own separate entrance. You then have an additional 3 bedroom 2 bath home with 3 season room and rear garden. There is also a separate 2 bay garage with maintenance room. The grounds are beautifully manicured with flowering bushes and trees with lovely mountain views. Its really a little bit of paradise just off the beaten path yet close to everything. 15 minutes in Great Barrington, 10 minutes to N Canaan CT. This lovely Homestead is set on almost 13 secluded acres.

This modern country property is beautifully sited offering a natural woodland setting w/ privacy, and only 10 minutes to Great Barrington. The Impeccable design and quality construction stem from the talents of Creative Building Solutions and noted designer, Carly Shafiroff of Carly Jane Design. The open and inviting floor plan seamlessly integrates indoor and outdoor living with large windows providing plentiful natural light. This wonderful lifestyle design allows for easy Berkshire living and offers a luxe chef's kitchen with walk-in pantry along with a large primary suite w/ steam shower & 2 additional guest rooms. Finished walk out multi purpose lower level is rough plumbed for a bathroom. Thoughtful outdoor living spaces including an oversized screened porch and courtyard patio

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.

Large 5 Bay Auto / Truck Sales and Service Center on Route 7 (Garage over 5000 sq ft - room for @ 100 cars). On Sheffield-Great Barrington border. Huge Parking Lot, High Visibility, Heavy Power. Additional Storage Building on over 8 Acres of Land. Ideal for a multitude of uses.(Former GMC Dealership location.)

Classic American Farmhouse With Epic Views - 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.