The George Tyler Homestead appears on West Stockbridge maps as early as 1855. This charming 3-bedroom cottage exudes warmth and character with plenty of original detail. The wood-paneled living room features a handsome brick hearth with beehive oven and beautifully aged pine floors. The L-shaped kitchen offers ample storage and opens to a formal dining room, where a large window overlooks the lush backyard, framed by towering hydrangeas. The 1st-floor bedroom has a closed off fireplace and sits conveniently across the hall from a full bath. The rear entry mudroom has sliding doors that lead to an enclosed wood deck, an ideal spot for summer gatherings. Upstairs 2 bedrooms with wide-plank pine floors share a full bath, completing this timeless gem. Seller to install new heating system.

Perched ''on the hill'' this fully renovated cottage is bright, chic, and effortlessly livable. Thoughtfully redesigned from top to bottom, this home offers a smart, efficient layout that lives comfortably and is completely move-in ready.The interiors feel fresh and calm, with well-proportioned rooms, updated finishes, and an easy flow. The eat-in kitchen has been carefully reworked to be both functional and welcoming; opening directly to a stone patio and seasonal views of East Mountain. An ideal setting for morning coffee, casual dinners, or quiet time outdoors.Featuring two bedrooms, a beautifully updated full bath with generous natural light, and details throughout that make

Renovated, well-maintained, multi-use building perfect for a live-work situation in prime location! All 4 floors offer opportunity for offices, a studio, storage, retail showroom and more! Highlights include: a large parking lot, handicap accessible ramp, 2 half baths & finished 3rd floor attic. Finished basement w/ vault & video security system. The current retail space is bright & sunny with a large quartz sales counter, display shelves, spot lights, fresh paint, with modern pendant lighting. The impressive metal roof & boiler were both installed in 2019, along with the emergency generator & mini splits throughout. The building's total of 3000 sq ft is based upon renovations. (See floor plans in documents.) B2 zoning offers many options for permitted use! (See GB bylaws in documents.)

Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra storage. Inside, enjoy abundant natural light in the glassed-in sunroom or relax on the multiple porches and decks. A key feature is the large, private in-law apartment, perfect for multi-generational living or rental income. Ideally located in the heart of Sheffield village, you'll enjoy the comforts of downtown just steps from your doorstep.

Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra storage. Inside, enjoy abundant natural light in the glassed-in sunroom or relax on the multiple porches and decks. A key feature is the large, private in-law apartment, perfect for multi-generational living or rental income. Ideally located in the heart of Sheffield village, you'll enjoy the comforts of downtown just steps from your doorstep.

Fully renovated, well-maintained, multi-use building in prime location with sparkling retail space, offices and more! The current showroom is bright & sunny with a large quartz sales counter, display shelves, spot lights, fresh paint & modern pendant lighting. All four floors are finished, creating an ideal setup for a live-work opportunity. Highlights include: large parking lot, handicap accessible ramp, handicap 1/2 bath on main floor, & finished attic. Finished basement w/ vault & video security system has ample room for storage. The metal roof, boiler, emergency generator & mini splits were all installed in 2019. The building's total of 3000 sq ft is based upon renovations. (See floor plans in documents.) B2 zoning offers many options for permitted use! (See GB bylaws in documents

Tucked into the rolling hills of Great Barrington, The Turning Point has been welcoming travelers for more than two centuries. In the 1800s, stagecoaches once paused here--horses rested, stories were traded, and journeys quietly shifted direction. That spirit of arrival still lingers.Now spanning 3,600 square feet, this historic Berkshire retreat has lived many lives: a bustling inn, a beloved home, a place where people gathered, stayed a while, and never quite forgot how it made them feel. With 7 bedrooms and 6.5 baths, the house unfolds with an ease that invites connection and retreat in equal measure.The bones are here--wide-plank floors, glowing fireplaces, generous rooms, and a layout designed for connection. What it needs is someone who sees beyond what it is today and imagines

Tucked into the rolling hills of Great Barrington, The Turning Point has been welcoming travelers for more than two centuries. In the 1800s, stagecoaches once paused here--horses rested, stories were traded, and journeys quietly shifted direction. That spirit of arrival still lingers.Now spanning 3,600 square feet, this historic Berkshire retreat has lived many lives: a bustling inn, a beloved home, a place where people gathered, stayed a while, and never quite forgot how it made them feel. With 7 bedrooms and 6.5 baths, the house unfolds with an ease that invites connection and retreat in equal measure.The bones are here--wide-plank floors, glowing fireplaces, generous rooms, and a layout designed for connection. What it needs is someone who sees beyond what it is today and imagines

A rare opportunity awaits in the heart of historic Sheffield. This exceptional multi-unit property, originally a classic 1740s farmhouse, has been thoughtfully converted into a lucrative income-producing asset while retaining its timeless New England charm. Perfectly positioned just south of Great Barrington, it offers both tenants and owners a convenient commute to local attractions, work, and restaurants. Nestled amidst beautiful, well-maintained grounds, this residence exudes curb appeal. The apartments have all been thoughtfully updated and come equipped with outdoor space, access to laundry facilities, and exceptional parking.

A rare opportunity awaits in the heart of historic Sheffield. This exceptional multi-unit property, originally a classic 1740s farmhouse, has been thoughtfully converted into a lucrative income-producing asset while retaining its timeless New England charm. Perfectly positioned just south of Great Barrington, it offers both tenants and owners a convenient commute to local attractions, work, and restaurants. Nestled amidst beautiful, well-maintained grounds, this residence exudes curb appeal. The apartments have all been thoughtfully updated and come equipped with outdoor space, access to laundry facilities, and exceptional parking.

Many residents are drawn to Ashley Falls for its historical charm, welcoming community and seasonal events. With picturesque landscapes and a blend of tradition and opportunity, Ashley Falls remains a desirable location for families and individuals alike. Ashley Falls is not only a haven for history enthusiasts but also a community teeming with potential for new ventures and creative enterprises. The centrally located 'Post Office' building, constructed in 1860, presents a unique opportunity for both residential and commercial use. Entrepreneurs and investors could find this setting ideal for establishing shops or studios that compliment the village charm and attract both locals and visitors. Its strategic position ensures consistent foot traffic, making it an invaluable resource.

Immaculately maintained and thoughtfully custom-built, this inviting home offers the perfect blend of comfort, craftsmanship, and seclusion. The open-concept kitchen, living, and dining area features soaring ceilings, custom display windows, and three sliding glass doors that welcome natural light and open to a 1,350 sq ft wraparound deck - the ideal vantage point for taking in the tranquil, wooded landscape and seasonal views of Snyder Pond. The main level includes two bedrooms and two full baths, each with private access to the deck, creating a harmonious indoor/outdoor flow. A cozy loft adds charm while also providing entry to additional unfinished space already plumbed for a future primary en-suiteoffering exciting potential for expansion.

Old Historic Village downtown location! The centrally located Post Office building constructed in 1860, presents a unique opportunity for both residential and commercial use. Its strategic location ensures consistent foot traffic, making it an invaluable cornerstone of village life. With no mail delivery service in Ashley Falls, the Post Office attracts local residents daily. This building is offered for sale with 3 business rentals and 2 apartments creating a living and income opportunity.

Prime commercial frontage on Great Barringtons South Main Street. This Large building has been actively run as retail, manufacturing and residential housing for many years. This property is a perfect spot for a live/work scenario or to produce income.Currently this space has been used as two retail fronts, one space for manufacturing, one space for machine repair and two residential rental units on the second floor. With lots of parking the possibilities are endless!

Set in a small country neighborhood, this stunning 4 Bedroom is perfect for entertaining friends and family. The 1st floor includes an open kitchen and dining area with granite countertops and high ceilings, a cozy sunken living room with propane fireplace, and a spacious first floor bedroom suite. Sliding French doors throughout the 1st floor bring in plenty of light and lead onto a 50' mahogany deck overlooking the back yard. The 2nd floor offers a large primary bedroom suite with walk-in closet, and two additional bedrooms sharing a full bath with laundry. The insulated third floor with high ceilings provides potential for an extra 1620 square feet of living space.

Beautifully Built New Construction in SheffieldMove-in ready and thoughtfully crafted by a local custom builder, this 3-bedroom, 2-bath home sits on 1.64 private acres. The open-concept living, dining, and kitchen area flows seamlessly to a lovely backyard patio--perfect for indoor-outdoor living. Nearby hiking, biking, and skiing offer endless recreation, or simply relax and enjoy the peaceful surroundings. Conveniently located just minutes from Sheffield village, Canaan (CT), and Great Barrington, this versatile property works beautifully as a full-time residence, vacation retreat, or investment opportunity in the heart of the Berkshires. This is a new build, and taxes have not yet been determined.

Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless interaction during meals and gatherings. The living area extends outward to two distinct private spaces: a screened-in porch for three-season relaxation and a separate private deck. Designed for convenience and longevity, the first floor features a primary bedroom suite complete with a spacious en-suite bathroom and laundry.

Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless interaction during meals and gatherings. The living area extends outward to two distinct private spaces: a screened-in porch for three-season relaxation & separate private deck. Designed for convenience and longevity, the first floor features a primary bedroom suite complete with a spacious en-suite bathroom and laundry.

Embrace the extraordinary at 395 Park St. North, where history meets opportunity. This stunning red brick 6,833 sq.ft. warehouse, once a bustling trolley barn, boasts high ceilings and a rich industrial charm, with river views while exploring the spacious layout, featuring 3 updated bathrooms, a newer roof and building updates. It has versatile separate offices and garage/shop areas. With ample parking and loading docks, envision endless possibilities from manufacturing to art gallery or more. Conveniently located near dining, parks, and cultural attractions, this property invites you to re-imagine living or workspace with style and creativity. Total acreage and assessment include two lots.

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.