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.

Modern Country Home on nearly 14 acres. Refined country haven offering privacy .. exceptional location between Berkshires & Hudson.. perfectly positioned for enjoyment of everything in between. Modern farmhouse blends volume, light and quiet luxury. Cathedral-ceiling LR opens to beautifully appointed kitchen w/breakfast area creating an effortless flow for daily living. 1st flr primary ensuite is private sanctuary w/walk-in closet, dbl vanity, Jacuzzi soak tub, sep shower & encl water closet. Guest quarters thoughtfully placed on 2nd flr w/loft library, 2 generous BDRS, full bath & expansive studio or creative space. Finished walk-out lower level remarkable versatility for work, wellness or recreation. Outdoors low-maintenance acreage unfolds w/open land, wooded edges & meandering brook. A

Convenient one-level ranch in a prime location close to town. This well-maintained home offers four bedrooms and two full bathrooms, ideal for comfortable living. The updated kitchen features modern finishes and plenty of workspace. Enjoy energy efficiency with owned solar panels that significantly reduce utility costs, plus a pellet stove for supplemental heating. A generator ensures uninterrupted power during outages--peace of mind year-round. Situated on a private road, the property provides tranquility while remaining minutes from shopping and dining. Additional highlights include ample storage, a functional layout and move-in-ready condition. Whether you're downsizing, seeking your first home or looking for a smart investment, this turnkey property delivers.

Classic lakefront cottage with frontage on quiet Benton Pond plus deeded rights to Big Pond. Four season contemporary Cape with an open plan featuring a window wall facing the lake and a brick fireplace. There are three bedrooms and two full baths plus a small loft. The screened porch is next to the kitchen, convenient for al fresco dining. Exterior access to the basement is perfect for storage of your canoes and kayaks. The home is located on over an acre and is the 2nd to the last on the road so very quiet. Less than 3 hours to NYC and 2 1/2 to Boston, near Tanglewood, Jacobs Pillow and most other Berkshire cultural attractions, as well as several state forests. If you have been looking for a reasonably priced lake home, this is your chance.

Exceptional lakeside commercial opportunity with ~820 ft of frontage abutting the Cheshire Reservoir & the Ashuwilticook Rail Trail. Set on 4.71 acres w/ prominent Rte 8 visibility, expansive water views, & immediate trail access along one of the Berkshires' most active recreational trails. AADT 11,200+; w/ addt'l annual foot/bike traffic of 70,000+. Main building ~6,200 sq ft, formerly a popular restaurant, two lakeview cottages (one recently renovated), finished storage garage w/ covered pavilion area, & addt'l outdoor space. Includes a small waterfront piece on the lake side of the rail trail. Located within the marijuana overlay district. Zoning allows a broad mix of commercial, hospitality, recreational, residential, retail & mixed-use options, subject to approvals. Being sold AS-IS.

Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The main level boasts vaulted ceilings with open bright common areas, great room with wood flooring and gas fireplace, updated kitchen, dining room with views, primary bedroom with newly renovated en suite bath, oversized garage, half bathroom and private screened porch and deck to take in the fresh air and serenity.Second level has ample space with three guest bedrooms, two full baths and loft/office space open to the great room.The lower level walkout family room is gracious in size and has direct access to your private stone patio. Additionally, you have the fifth bedroom, full bath, laundry room and bonus storage room.Enjoy the association pool, Bousquet Mountain next door and all of the

Discover your dream retreat in this stunning log home, nestled on 37 acres of breathtaking land that adjoins over 1,000 acres of serene state forest. This oasis offers an unmatched blend of tranquility and natural beauty, allowing you to escape from the hustle and bustle of everyday life. Imagine sipping your morning coffee on the wrap-around deck, soaking in the picturesque mountain views. Indulge in the ultimate relaxation experience with a soak in your wood-fired hot tub or a rejuvenating session in your outdoor sauna. Step inside and be captivated by the charming open floor plan. The chef's kitchen is a culinary enthusiast's dream, featuring a large island, elegant granite countertops, and a high-end Viking stove, perfect for entertaining guests or creating culinary masterpieces.

Enjoy this beautifully updated, move-in ready home set on 26.9 acres of private, scenic land. Offering a warm and open floor plan, the home is enhanced by tall ceilings and expansive windows that flood the space with natural light throughout the first floor.Designed for both comfort and efficiency, the property features multiple heating zones, propane heat, an outdoor wood stove, updated air conditioning unit, & a newer roof. The open-concept kitchen, appointed with custom Millbrook Cabinetry and high-end appliances, flows effortlessly into the dining and living areas, creating a cohesive & inviting space ideal for both everyday living & entertaining.

Welcome to 4 Birch Hill Rd. By appointment only. This private retreat set on over 44 acres is the perfect fit for the Auto enthusiast, woodcraft, cabinet making, Hobby farm, the options are endless!Live off the grid with solar power. The owner has not had an electric bill in over 10 years. There is an Eversource credit as well as quarterly renewable energy credits that transfer with the property. The wood furnace will heat the house and Steel garage. There is also oil and propane. Live the easy life in the 3/4 bedroom home with a beautiful three season room to enjoy your morning coffee, Hot tub on the back maintenance free Trex deck to savor the beautiful starry sky and peaceful nights.The owner of this home is the original builder. Pride in homeownership is evident throughout.

Located on a peaceful cul-de-sac, this beautifully refreshed 4-bedroom, 2.5-bathroom Colonial perfectly blends New England charm with modern updates. This home is privately situated on a 1.01 acre lot. This move-in-ready home features a bright, airy interior with fresh paint, new contemporary light fixtures, and elegant updated wooden floors. The heart of the home is the expansive kitchen, complete with newer stainless-steel appliances, which flows seamlessly into a dining area and family room anchored by a cozy wood-burning fireplace. Off the family room is a spacious screened porch overlooking a private backyard. The main level includes formal living and dining rooms, powder room and laundry.

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!

Lovingly maintained contemporary Cape set on just over an acre with beautiful mountain views, ideally located on a paved country road just minutes from everything the Berkshires has to offer. This comfortable home is surrounded by established perennial gardens and fruit trees, creating a peaceful and private setting. The front entry welcomes you into a relaxing three-season screened porch-perfect for morning coffee or unwinding at night. Inside, the open-concept first floor features a bright, light-filled kitchen with cherry cabinets, stainless steel appliances, and a double oven, seamlessly flowing into the dining area with custom cherry built-ins and direct access to the deck overlooking the landscaped yard. The living room offers a cozy gas fireplace & room to gather.

Welcome to your private retreat in the Crystal Pond community, set on just over 2 acres of beautifully wooded privacy. This 4-bedroom, 3.5-bath residence blends refined comfort with natural serenity, offering a true Berkshire escape.Soaring cathedral ceilings, skylights, and expansive windows fill the home with natural light, highlighting rich wood plank flooring and a warm, elevated design throughout. The main living area features a fireplace, while a separate den is enhanced by a wood stove insert that provides efficient, comfortable heat and a cozy atmosphere.The thoughtfully designed layout includes generously sized bedrooms, including a second-floor bedroom with a private loft space, ideal for a reading nook, office, or creative retreat. Two upstairs bedrooms each enjoy access to

Loft 309 at Greylock WORKS is a distinctive north-facing 1BR | 1.5BA Berkshires residence with a generously scaled study, offering approximately 1,340 SF of thoughtfully designed living space. Set on the third floor of the region's most celebrated mill conversion, this home is defined by its warm wood ceilings, varied ceiling heights, and refined blend of historic character and modern finishes.The open living, dining, and kitchen area creates an inviting central gathering space, grounded by restored materials and an easy, functional flow for everyday living and entertaining. Energy Star appliances, Kohler and Grohe fixtures, energy-efficient windows, and an in-unit washer and dryer support both comfort and sustainability.

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.

OUTSTANDING COUNTY LIVING in idyllic Monterey with its low real estate taxes and easy access to Lake Garfield and Lake Buel. Butternut Ski Area is only 5 minutes away. 8 minutes to downtown Great Barrington. This Timber Fame (open floor plan) contemporary home features beautiful (wide-plank) pinewood floors, a cathedral ceiling Great Room, and a bonus sleeping loft area. A fireplace on the main level, and a wood stove on the lower level, add warmth and charm. Ready to move right in? With relatively low inventory level, particularly in Monterey, this listing is a lucky strike extra. Schedule your showing today.

Lenox MA Colonial on 0.92 acres with 4 bedrooms, 2.5 baths, and 2,184 sq ft of well maintained living space. This move in ready Berkshire home features a spacious eat-in kitchen, formal dining room, bright living room with wood floors, and a screened porch overlooking the yard. Enjoy outdoor living with two decks, a paver patio with BBQ area, and beautiful perennial gardens. Upstairs offers four bedrooms, two full baths, and second floor laundry. Additional highlights include updated kitchen and baths, newer propane boiler, central air, partially finished basement, and two car under garage. Convenient to downtown Lenox, Tanglewood, shopping, dining, and Berkshire cultural attractions.

Steps from the Association beach on Otis Reservoir--the largest recreational lake in Massachusetts--this mint-condition 2005 home offers 4 bedrooms and 3 baths over three levels. Large windows and glass doors open to a deck and a bedroom balcony for year-round enjoyment. The first floor features an open kitchen, dining and living room with a fireplace; a primary bedroom; a full bath and laundry. Upstairs are two bedrooms and a full bath. The walkout lower level has a family room with a fireplace and wet bar, a fourth bedroom, a full bath and a utility room. Impeccably maintained by the sellers and offered furnished with central A/C and fiber internet. Association fee: $100/year for access to two nearby lake lots. A lovely community on a beautiful Berkshire lake, just in time for summer.