Elegance Meets History on 1 Eaton Lane! Tucked away on a quiet, sought-after street just minutes from the Country Club of Pittsfield & only 10 minutes to vibrant downtown Lenox, this remarkable Colonial seamlessly blends timeless character with extraordinary versatility. Offering just under 5,000 square feet of living space, this historic estate presents a rare opportunity for those seeking a home with a story. The main house is a masterclass in classic architecture, featuring period details enhanced by thoughtful modern updates. High ceilings, gleaming hardwood floors, & charming front & back staircases ground the home in history, while the spacious layout provides endless room to breathe. The heart of the home is a sophisticated kitchen, featuring rich cherry cabinetry, new SS appliance

Charming, beautifully maintained, and ideally located, this gorgeous Four Square home sits directly across the street from the Mohawk Trail Multi-Use Path and is at the base of the Pine Cobble Trail System, offering an exceptional combination of classic character and outdoor adventure right outside your door. The home features 4 bedrooms and 1.5 baths, beautiful wood floors, and a finished attic that provides additional flexible living, office, or recreational space. A stunning wraparound front porch welcomes you home and offers the perfect spot to enjoy your morning coffee or gather with friends and family. The cozy back deck overlooks a fenced in back yard for those pet lovers and provides even more outdoor living space. Both the front porch and back deck are crafted from beautiful,

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

Just the right size, this lovely contemporary home captures the ease and beauty of Berkshire living, with beautiful westerly views and a sunny, open-sky setting. A stone's throw from the charming village of West Stockbridge and just minutes from downtown Lenox and Tanglewood, the location offers an ideal blend of country living, culture, and convenience. Inside, three bedrooms and two baths complement an inviting open floor plan anchored by a dramatic floor-to-ceiling fieldstone fireplace. The kitchen and dining areas flow naturally into the living space, while a cozy den and lovely screened porch offer additional places to relax and enjoy the surroundings. A large deck, detached garage and storage shed complete the property. Effortless and inviting, this is the perfect Berkshire getaway.

Beautifully tucked away in one of Pittsfield's most established neighborhoods, this stately 5-bedroom, 5-bath home is a rare offering filled with warmth, character, and endless potential. From its gracious proportions to its timeless architectural details, this is a home that makes a lasting impression. Sun-filled living spaces, generously sized rooms, and a thoughtful layout provide the perfect balance of elegance and everyday comfort. Whether you're gathering with family, entertaining friends, or simply enjoying a quiet evening at home, there's room for every occasion. Rich in original character and beautifully maintained, this home also offers an exciting opportunity for its next owner to add their own style and create something truly extraordinary.

Come see this Stockbridge home with land, multiple fireplaces, all electric service, and close to everything the Berkshires has to offer! You'll be minutes to historic downtown Stockbridge, Tanglewood, and all the entertainment venues that you love, in a quiet country setting. All the comforts of home, available to you right now! Come be a part of the Berkshires lifestyle, you'll be glad you did!

Welcome to 354 Notch Road, a well-maintained and move-in ready Colonial situated on a combined 13.75 acres in a desirable North Adams neighborhood. This 3-bedroom, 2.5-bath home offers a spacious primary suite with private bathroom, an attached and heated 3-car garage, and convenient access to downtown North Adams, MASS MoCA, Williamstown, and nearby hiking trails. Enjoy outdoor living with an in-ground saltwater pool, pool house, and a newly constructed 1,872-square-foot barn offering endless possibilities for storage, a workshop, studio, or future customization. The property includes the main 7.35-acre lot plus an adjacent 6.4-acre parcel, providing privacy, space, and a rare opportunity to own a substantial piece of North Adams real estate.

Outdoor Living Meets In-Town Convenience! Rarely does a property offer such an exceptional balance of outdoor living and in-town accessibility. Located at the end of Elm Street, this home provides a peaceful retreat while remaining just minutes from downtown Williamstown, Williams College, and local amenities. Set on approximately 1.3 acres and bordering protected conservation land and the Green River Linear Park trail network, the property enjoys a rare sense of privacy and connection to nature, with direct trail access from the rear yard, all just moments from downtown Williamstown. At the heart of the home is a stunning cathedral-screened porch featuring exposed timber framing and mahogany flooring, creating an inviting three-season great room and a natural extension (click on more)

Welcome home to this spacious raised ranch located in a highly desirable neighborhood! This well-maintained property offers five bedrooms and two full baths, providing plenty of room for family, guests, or a home office. The inviting family room is perfect for gathering and entertaining, while the two-car garage adds convenience and storage. Step outside and enjoy the oversized deck overlooking the beautiful built-in pool an ideal setting for summer fun, outdoor dining, and relaxing with friends and family. With generous living space, great amenities, and a sought-after location close to schools, shopping, and local attractions, this home is a wonderful opportunity you wont want to miss.

This charming Colonial is set back from the road and perched on a hill overlooking a beautiful, sun-filled yard. The private setting features mature landscaping, including apple, peach, and cherry trees, a lovely garden, and a wonderful patio perfect for relaxing or entertaining. Inside, enjoy the open living, kitchen and dining , heated sunroom, bonus room off the kitchen for an office, playroom or laundry room along with 3 bedrooms upstairs and 2.5 baths. Recent improvements include new kitchen and primary bathroom updates, mini-splits, new windows, 200-amp electrical panel, owned solar panels, a five-year-old roof, and an EV charger.

Step out your back door and onto the mountain--this unique slopeside condo offers direct access to skiing and hiking trails right from your backyard. Offering 2,750 sq. ft., this beautifully updated 3-bedroom, 2½-bath home features a gas fireplace and refreshed kitchen with quartz countertops, subway tile backsplash, and GE Profile appliances. Updates include newer carpeting and paint, California Closets, and USB/USB-C outlets. The unfinished basement offers generous storage, home gym or future living space and is stubbed for plumbing. Enjoy peaceful mountain surroundings and a community pool in warmer months. Just a short drive from Lenox and Tanglewood, with easy access to dining, shopping and the best of the Berkshires.

Enjoy comfortable, move-in-ready living at this inviting Sheffield property, complete with a barn and access to a nearby pond for fishing and kayaking. The versatile layout is ideal for extended family, guests, a home office, or supplemental rental income. Sheffield Center is approximately two miles away, offering restaurants, the Bushnell-Sage Library, the Sheffield Historical Society, and the welcoming character of this historic Berkshire village. Great Barrington's restaurants, shopping, and everyday conveniences are just 15 minutes away, while Canaan, Connecticut, is approximately 10 minutes away.

Beautiful 4 bedroom contemporary on Lilybrook Road. Vaulted entry way leads to living (sitting) room flanked by formal dining room. Also on the first floor is oversized great (family) room with fireplace, large eat-in kitchen and private master (in-law) suite with full bath and jet tub. The second floor has another master suite with full private bath, two additional bedrooms, and a second full bath. This is perfect for a multi generational family. The basement has plenty of storage and a dry, carpeted rec room with a wet bar and a half bath. The grounds feature mature landscaping and privacy. The roof, skylights, and gas fireplace are newer (installed in 2016). Home is on a private street with a cul-de-sac and is within walking distance to BCC and the state forest. Bosquet and Jiminy Pe

Welcome to 12 Mountain St, a quintessential colonial masterpiece that blends classic elegance with modern functionality. Spanning over three expansive, light-filled floors, this stunning home offers five spacious bedrooms and 3.5 bathrooms, providing the ideal layout for those who love to entertain. The chef's kitchen is designed to inspire with high-end finishes, including a vast center island, a professional-grade Six-burner gas stove w/pot filler, chic quartz countertops. With an abundance of cabinetry and a dedicated, organized pantry featuring custom built-ins, this kitchen is as practical as it is beautiful. Gleaming hardwood floors flow throughout the main level, creating a seamless, inviting atmosphere. Ascend to the second floor, where you will find a tranquil primary en suite wit

Just over the hill from Tanglewood, down a quiet country road, this year-round Richmond retreat blends privacy, rustic character, and expert craftsmanship. The heart of the home is the vaulted great room, where exposed beams, a loft balcony, and a wood stove create a warm gathering space that flows seamlessly into a beautifully crafted three-season porch with interchangeable glass and screen panels overlooking the woodland. Thoughtfully designed to preserve the home's original rustic charm, the spacious primary suite is a private retreat featuring vaulted ceilings, a sitting area with a gas stove, an ensuite bath with a soaking tub, and laundry. Wraparound decks further extend the living space outdoors, embracing the natural landscape. The walk-out lower level provides excellent storage

Welcome to 28 Mountain Pond Lane, a stunning raised ranch nestled on a private 3.29-acre parcel in New Ashford, MA. This charming home features 3 bedrooms and 2.5 baths, eat in kitchen & great room currently used as a studio offering ample space for comfortable and flexible living. The oversized 3-car garage provides plenty of storage, while the large multi-tiered deck and beautiful concrete patio in the rear create the perfect outdoor oasis for entertaining or relaxing. Surrounded by mature gardens, this property exudes tranquility. Additional highlights include a backup generator and various other features that enhance the home's appeal. Experience serene living in this picturesque setting--your dream home awaits!

A One-of-a-Kind Contemporary Woodland Retreat with seasonal Mount Greylock Views, in town location and a stone's throw to everything Williams College and the ''Village Beautiful'' Williamstown. Discover a truly unique property in the heart of the Berkshires, offering the privacy and beauty of a woodland retreat with the distinctive character of a contemporary home and an extraordinary opportunity to own two contiguous original parcels of land. This three-level residence features 4 bedrooms, two full bathrooms, a spacious kitchen and dining area, and a large living room designed to take advantage of the surrounding natural beauty. The home's elevated setting provides views of Mount Greylock from the front windows in the spring, winter & fall seasons, bringing one of the Berkshires' most

Start showing: 9/18! Berkshire Hills at Leisure Lee! Welcome to this contemporary four-bedroom, two-bath home in this sought-after Goose Pond lake community. Bathed in natural light w large windows and slider to the wraparound deck, the living room features a vaulted ceiling, fireplace and hardwood flooring. Off the open kitchen/dining area, enjoy a spacious screened porch. The main floor includes two bedrooms, a full bath and laundry, making one-level living a reality. The second floor includes two more bedrooms, including one with a walk-in closet, and a full bath with a jet tub, shower and double sinks. Bonus: The unfinished walk-out lower level offers room to add more living space. Short walk to the swimming beach and boat launch. Amenities include canoe/kayak storage and tennis court

A tranquil oasis in the sought after Beachwood community with its private beach and kayak launch on Stockbridge Bowl. This ranch-style cottage with hardwood floors has a spacious living/dining area with double volume wood ceilings and a gas stove for added warmth in cooler weather. The renovated kitchen boasts stone counter tops and flows onto the private, shaded screened-in porch for effortless entertaining. A bonus deck with grill is accessed off the porch. There are three comfortable bedrooms (2 with king size beds) and two small refurbished bathrooms one with a tub and one with a walk-in shower. A large laundry closet is fitted with a washer and dryer. This 3-season home has a newer roof and primary bedroom en-suite addition. Ideally located between Stockbridge, Lenox and Tanglewood.

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, a 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.