Tucked away in a peaceful, private setting off scenic Oblong Rd and overlooking a meadow with limited distant views of Mt. Greylock, this converted barn redesigned in 1994 by local architect Anne Mccallum,offers an inviting year-round retreat. The cathedral ceiling greatroom showcases exposed, hand-pegged beams from the original 1948 barn structure, creating a warm and timeless gathering space. An expansive deck to the east extends the living area outdoors, ideal for relaxing or dining while taking in the surrounding landscape. The first floor is an open floor plan with kitchen, adjacent comfortable living room and dining area. This level includes 2 comfortably sized bedrooms and a full bath, while the entire upper level is devoted to the primary suite. A full walkout basement provides

Welcome to easy single floor living in a highly desirable Southeast Pittsfield neighborhood! Built in 2003, this exceptionally well-maintained contemporary home features 3 spacious bedrooms, 2 full baths, soaring vaulted ceilings, and beautiful hardwood floors. The light-filled primary suite includes a private ensuite bath, while the enclosed 3-season room and front porch offer ideal spots to relax overlooking a low-maintenance yard. Complete with a newer roof, central air, a massive unfinished basement with endless potential, and city-maintained street access, this move-in-ready property is a standout Berkshire home!

Timeless elegance meets modern luxury in this beautifully maintained Victorian home, where historic charm and exceptional craftsmanship shine throughout. Lovingly cared for and thoughtfully updated, this stunning residence showcases exquisite architectural details, original character, and an abundance of natural light. High-end finishes are found at every turn, including a beautifully appointed kitchen and luxurious bathrooms. Spacious living and entertaining areas blend seamlessly with inviting private spaces, creating a home that is as functional as it is beautiful. Every detail reflects pride of ownership, offering a rare opportunity to own a truly exceptional Victorian that combines classic sophistication with today's modern comforts

Large home with room for everyone! This 5 bed 4 bath (2 full upstairs, 2 half baths on the first floor) home features 2 kitchens, 2 living rooms, and 2 dining rooms as it was once a 2 family home. It's spacious and bright, has a beautiful wrap around rocking chair porch, two enclosed porches, a barn, and just under 3.5 acres. Sit by the fire at night, walk across the street to the Corkscrew Rail Trail which extends all the way up through Stephentown. Very close to all the restaurants, brew pubs, and stores in town including the wonderful year-round farmer's market store. Minutes to Berkshire County, @ 30 minutes to Albany, and 15-20 minutes to Jiminy Peak where you can enjoy year-round adventures. Enjoy a beach membership at Queechy Lake, just minutes away! Zoned Commercial & Residential.

Cable Mills, industrial mill buildings restored into beautiful homes with 12ft to 16ft ceilings, massive windows, and exposed brick and beam, steel and timber throughout, stainless appliances, granite countertops, gas ranges, generous closets and in home laundry. Cable Mills offers stunning views of the 'Purple Mountains' and the Green River. Homes are one, two or three bedrooms in single level flats, lofts and townhome styles totaling 61 residences. Outdoor spaces including the Outdoor Living Room with a fire pit, grills and seating along the river walk. The main building offers a community lounge, fitness center, interior bike storage, package delivery room, dog wash and on-site professional management. Photos of similar home. #GardenCondoWilliamstownMA #BerkshiresRealEstate

Here's a rare opportunity to own a classic roadside motel with strong potential in a popular small-town tourist destination. This 17-room property, complete with an on-site owner's quarters, offers a solid option for renovation or rebranding or to convert to housing. The motel has been operating for many years and continues to welcome repeat travelers, but it would benefit from fresh energy and cosmetic updates to reach its full potential. With steady local tourism and limited lodging competition, there's plenty of room to grow revenue through improved marketing, refreshed rooms, and updated amenities. Located near shops, restaurants, and popular area attractions such as Tanglewood, Edith Wharton House, Norman Rockwell Museum, and many others.

Enjoy the beauty of the Berkshires in your own country home on a dead end road. Thirty acres of privacy with possible views to the east. Roof was done in 2011 and foundation was redone in 1991. This nearly 100 yr old home has been loved for many years by one family. The 31' x 50' great room with large stone fireplace has seen generations come and go playing games and warming by the crackling fire. The oil furnace is not working, but the original duct work is in place for a new unit to be installed. This home will be sold as is, where is. Most contents will remain. There is a drilled well. Septic will be inspected. New electric breaker panel. Chimney was repointed. With some love and care, this colonial will become a delightful home for years to come!

Have you been dreaming of fun on Stockbridge Bowl? The time is now! Built in 2011, this lovely home is directly across the street from the beloved town beach and affords water views from most windows. Offering 4 seasons of single-level living, 3 BR, 1 full BA, a well appointed kitchen and gracious living spaces. The unfinished walk-out lower level is the perfect place to store your kayaks, and could be finished to offer more living space. There is plenty of off-street parking above and below the home. You are mere moments to Tanglewood's Lions Gate and the very best of the Berkshires. Would make a great rental, or a wonderful family retreat to make memories for years to come. Town sewer, private well, radiant heat, and energy efficient construction, all in a location that can't be be beat!

Don't miss this one. Prime downtown Great Barrington. Over 5000sq ft, land with building.Can be expanded. Private Parking. Ready for your finishing. Why rent- invest.

Meticulously maintained and lovingly cared for, this spacious four-bedroom, two-and-a-half-bath home offers the perfect combination of comfort, quality, and location. Featuring generously sized rooms throughout, this home provides ample space for both everyday living and entertaining. Pristine wood floors lie beneath the carpeting, offering the opportunity to uncover their timeless beauty. Recent improvements, including a new roof, providing peace of mind, while gas heat and central air conditioning ensure year-round comfort. Set in one of the area's most desirable neighborhoods and within a highly sought after school district, this property offers a truly special connection to its surroundings.

Discover a prime investment opportunity at 110-118 Lincoln Street in Pittsfield! This well-maintained property features four spacious units, each offering three bedrooms and one bath--perfect for attracting reliable tenants. With separate utilities for each unit, managing expenses is seamless. Ample off-street parking ensures convenience for all residents, enhancing the living experience. Ideal for investors or those looking to enter the rental market, this property will be delivered vacant at closing, allowing for immediate occupancy or renovations. Don't miss out on this fantastic chance to secure this valuable asset.

Well-maintained 3-bedroom, 2.5-bath ranch offering over 1,800 sq ft of comfortable living space. This home features a spacious upper-level bonus room with a fireplace, perfect for a family room, office, or entertaining space. The main level offers a functional layout with bright living areas and three bedrooms, providing flexibility for a variety of uses. A finished basement adds even more living space, ideal for a rec room, gym, or additional lounge area.Additional highlights include a one-car garage, convenient mudroom/laundry area, and a beautifully maintained interior throughout. Situated on just over a half-acre, the property offers a generous yard with room to enjoy the outdoors.A versatile home with space across multiple levels, offering flexibility and functionality.

Welcome to 551 Tamarack Road! A beautifully updated and maintained Cape-style home, nestled on 1.28 acres in picturesque Pittsfield, MA!This charming 4-bedroom,2-bath residence boasts a perfect blend of modern amenities and classic charm. Step inside to discover a spacious, light-filled living area, ideal for gatherings and relaxation.The eat in kitchen features contemporary finishes and ample storage, seamlessly connecting to the dining area. Enjoy the convenience of 2 well-appointed bathrooms and generously sized bedrooms, perfect for family and guests.Outside, the expansive yard offers endless possibilities for outdoor activities, gardening, or simply enjoying nature.Meticulously maintained and set in a peaceful setting, this home is a true gem just waiting for you to make it your own!

Building has been used as an antique business for the last 50 years. Seller had previously lived in the upstairs apartment. Located across the street from Mend and Calgary's and .5 miles from downtown Great Barrington. Selling as is, business and inventory for sale separately - negotiable with owner.

An iconic Great Barrington landmark, the beloved ''Little Store'' offers a rare opportunity to own a high-visibility commercial property on Main Street in one of the Berkshires' most vibrant downtown corridors. Ideally positioned just a short stroll to the center of Great Barrington, this property enjoys steady foot traffic and exceptional exposure among restaurants, boutiques, galleries, and year-round community activity. Home to a well-established antique business for over 50 years, the space offers flexibility for a wide range of future uses — retail, gallery, studio, specialty food shop, office space, or a creative mixed-use concept (buyer to verify use). An upstairs apartment was previously owner-occupied, presenting potential for live/work convenience or additional income.

Tucked away on 4 acres of wooded and partially cleared land, this lovingly maintained 1960 cape-style home offers the perfect blend of privacy, character, and opportunity. Set back from the road by a long driveway, the property creates a peaceful retreat just minutes from the heart of Lenox and outdoor destinations like October Mountain State Forest & Kennedy Park. Inside, the home is ready for its next chapter with spacious and inviting living areas including a formal living room, dining room, kitchen, and a cozy family room with gas fireplace and slider access to the private backyard. A sunroom off the kitchen is perfect for seasonal enjoyment. The first-floor primary bedroom features a connected full bath with convenient hall access, while upstairs offers two additional bedrooms,

The drive to this beautiful parcel takes you off the main road, past farms, cottages, and estates--all within a mile or two. Hidden away in one of the most scenic parts of Monterey and surrounded by larger holdings and hundreds of acres of conserved, trust-protected land, this property offers peace and privacy rarely found. The land is mostly level before gently sloping down to a brook on the east and a stream and pond to the south. Located just down the road from the Gould Farm Harvest Barn and the beloved Roadside Store Cafe, this is a great area for walking a dog, on the surrounding roads or on nearby hiking trails. With conservation lands and established homes all around, this is a truly exceptional and enduring setting.

Discover single level living in 160 Water Street Home 203, Williamstown, MA. Cable Mills consists of three former industrial mill buildings restored into beautiful homes featuring 12'-16' tall ceilings, massive windows, and exposed brick and beam, steel & timber throughout, stainless steel appliances, granite countertops, gas ranges and in home laundry. Cable Mills offers stunning views of the 'Purple Mountains' and the rolling Green River. Homes are one, two or three bedrooms in single level flats, lofts and townhome styles totaling 61 residences. Outdoor spaces include Outdoor Living Room w/fire pit, grills, seating along the river. Main building offers community lounge, gym, interior bike storage and prof. management. #BerkshiresLofts #WaterfrontCondoMA #WilliamstownMACondo

Welcome to the historic Simmons Cottage located at 2 Melrose Street in Adams, MA. This Victorian gem, completed in 1901, perfectly blends its 19th-century character with modern convenience. Situated on a .24-acre lot in the heart of Adams, the 2,406-square-foot residence features 4 bedrooms, three bathrooms, office, and full attic. The home's historic elegance shines through its preserved curved front porch, original woodwork, stained-glass windows, and rare Lincrusta ceilings. This home has been updated to provide efficiency, including a new roof, upgraded heating system, and a modernized kitchen with top appliances. A standout feature is the unique historic carriage barn, relocated and repurposed into an incredible five-car detached garage for your vehicles and hobbies!

Two remarkable properties being offered together! Combined, the adjoining 3-acre homesite and 10-acre parcel create a remarkable 13-acre offering--an expansive canvas to design and build your ultimate Berkshire retreat. With open meadows, sweeping mountain views, mature woodlands, stone walls, and exceptional privacy, this rare property offers endless possibilities for a custom estate, equestrian pursuits, or a secluded country sanctuary. Conveniently located near the area's renowned cultural attractions, outdoor recreation, and Williams College. Recently surveyed and successfully perc tested, with a driveway already installed, this extraordinary property is ready for your vision to become reality.