Great Barrington A masterful rebuild with reverence for Great Barrington's past and a bold reimagining for modern living. This 5-bedroom, 4-1/2 bath colonial sits in-town and blends historic charm with contemporary luxury for effortless, years-long comfort. Property Highlights 5 Bedrooms | 4 Full Baths + 1 Half Bath** Complex rebuild from the ground up** - preserved nod to the town's heritage with a fresh, modern interior Chef's Kitchen** - high-end appliances, ample prep space, and thoughtful layout for entertaining Radiant Floor Heating** - in entry Dual Fuel Heat throughout High Velocity Central Air Conditioning** - efficient, quiet climate control Solid Heavy Doors with Emtek Hardware** - substantial, timeless feel with premium finishes 4-Season Porch**

Why rent when you can own in a delightful neighborhood. Immaculate ground level unit in the private country community of Forest Row., located just a few minutes from downtown Great Barrington. Forest Row is a Community Land Trust Neighborhood. Easy care one level living with an open floor plan, private screened porch and a patio bordered by gardens and woods, surrounded by 21 acres of protected land for your enjoyment. Carport and garden shed. Easy access to Rudolf Steiner School, Great Barrington town center, Tanglewood, Skiing and other local attractions. This is a community land trust neighborhood for full-time year round living.

Charming, Move-In Ready Side Hall Colonial - A True ''Dollhouse!'' Welcome home to this absolutely stunning, meticulously maintained side hall colonial nestled in a super quiet, peaceful neighborhood. Combining classic charm with a long list of modern, high-ticket upgrades, this home is the definition of a turnkey property and is ready for its next chapter. Step inside to find a warm and inviting living space featuring a cozy wood-burning fireplace, perfect for chilly evenings. Classic hardwood floors run throughout the home, currently protected by brand new, plush carpeting that offers a fresh feel while preserving the beautiful wood underneath. The beautifully updated kitchen and dining area flow seamlessly together, creating an entertainer's dream space that is sure to please hosting f

Discover the perfect blend of privacy and country living at 1340 North Street in Windsor. Situated on 6 scenic acres, this well-maintained raised ranch offers 2 bedrooms, 1.5 bathrooms, and a spacious two-car garage beneath. The inviting open-concept layout features Harwood floors and seamlessly connects the kitchen, dining, and living areas, creating a comfortable space for everyday living and entertaining. The lower level offers excellent potential for additional finished space. Outside, enjoy the peaceful surroundings from the deck or patio. Enjoy the tranquility of country living while still having the comfort of a well-cared-for home.

Step into a home where light dances through every room and the whisper of Pontoosuc Lake lingers in the air. This enchanting 3 bedroom, 2 bathroom sanctuary offers both a spacious living room and a warm, inviting family room—spaces made for laughter, quiet moments, and memories waiting to be born. Drift onto the breezy 3 season porch and savor mornings in the treetops or peaceful twilight conversations. A freshly updated kitchen shines with new life, a brand new roof brings lasting peace of mind, and a generous 2 car garage adds effortless ease. Just steps from the shimmering lake, this home feels like a gentle spell—welcoming, uplifting, and pure Berkshire magic.

A rare opportunity to acquire one of Pittsfield's most established and recognizable cocktail destinations. For more than a decade, Methuselah Bar & Lounge has served as a neighborhood gathering place known for its craft cocktails, themed events, live entertainment, and a loyal following. The sale includes a fully operational, turnkey business with an extensive inventory of owned equipment, transferable liquor license, a built-out bar, prep kitchen, walk-in cooler, commercial refrigeration, sound system, and POS infrastructure. Originally transformed from a nearly empty space through a substantial investment , the venue offers an inviting atmosphere that has become a fixture of Pittsfield's nightlife scene.

Within walking distance to Main Street, this adorable home has been lovingly cared for. Immaculate condition, wood floors throughout, cozy fireplace and a detached garage. A sweet place to call home in a convenient location.

A refreshed split-level home set on four level acres just outside the quaint village of Egremont! Enjoy low taxes, peaceful surroundings and plenty of usable outdoor space for gardening, recreation, or future possibilities. Inside, the home offers comfortable living with additional flexible space in the lower level featuring ample windows and a walk-out, creating excellent potential for office, gym, or family room. The property also includes a one car garage and a separate garden shed for added storage. A wonderful opportunity to enjoy country living with easy access to the charm and amenities of Egremont and the surrounding Berkshires. Ski Catamount & Great Barrington minutes away.

COMMANDING VIEWS OVER LAKE GARFIELD WITH A STUNNING MOUNTAIN BACKDROP, this beautifully updated home offers charm with modern refinement. Original architectural character has been thoughtfully preserved, while expansive windows fill the home with light and frame the breathtaking scenery. Recently renovated chef's kitchen, first floor primary bedroom, and loads of closet space address today's needs. And could there be any better spot to watch sunsets than the expansive front porch? What's more, a well-appointed suite in the separate carriage house offers flexible space for guests, a home office, or artist's studio. Features include eight private acres, high speed internet, low Monterey taxes, and proximity to the Monterey bathing beach and the incomparable tomatoes at Anna's farm stand.

Tucked into a peaceful wooded setting in Lenox, this architecturally distinctive contemporary home offers 2,189 square feet of living space on a private half acre lot. Designed with an asymmetrical exterior and a split level floor plan spanning three levels, this home offers unique character. Large windows fill the interior with natural light, while the open living areas create an inviting space. With its distinctive contemporary design and solid architecture, this property presents an exciting opportunity for thoughtful updates that can enhance both style and value. A rare chance to create something truly special in one of Lenox's most desirable settings. View in person and experience the warmth, character, and connection to nature that make this home so unique.

Beautiful 4-bedroom, 2.5-bath Colonial set on 1.78 private acres in desirable New Lebanon. This spacious home offers a bright, open floor plan with hardwood floors, abundant natural light, and comfortable living spaces ideal for everyday living and entertaining. The generous primary suite features a walk-in closet and private bath, while three additional bedrooms provide plenty of space for family, guests, or a home office. Enjoy the walk-out lower level, expansive deck, whole-house backup generator, and peaceful country setting. A standout feature is the exceptional garage space with both an attached garage and detached garage for storage, hobbies, or vehicles. Located just ''seconds'' from the Massachusetts border and convenient to the Berkshires, skiing, dining, and cultural attractions

Not for the faint of heart, this unique 2BR/2BA property near downtown Stockbridge is pulled back to the studs and ready for a total revival. Currently uninhabitable, but brimming with whimsical potential, its one-of-a-kind footprint features unique octagonal rooms, a central fireplace and a detached garage with an adjacent mini studio--perfect for an artist nook or home office. Located in a highly sought-after prime location, the heavy demo is done, leaving a blank canvas for your contractor and imagination. Grab this tremendous opportunity to create a bespoke masterpiece in the heart of the Berkshires. Bring your creative spirit!

Custom-designed Lenox Woods townhome with direct access to Kennedy Park! This beautifully maintained, one-owner residence offers 4 bedrooms, 3.5 baths, and an exceptional blend of comfort, quality, and convenience. Thoughtfully upgraded throughout, the open-concept main level features a stunning kitchen with custom cabinetry, granite countertops, tile flooring, stainless steel appliances, a walk-in pantry, and an expansive breakfast bar that flows seamlessly into the dining area and Great Room. A striking stone gas fireplace serves as the heart of the home, while the adjacent screened porch opens to a private patio surrounded by professionally designed native pollinator gardens and the natural beauty of Kennedy Park beyond. The first-floor en-suite bedroom provides ideal one-level living

A house that stops people mid-sentence! At the Lenox/Stockbridge line on the western shore of Lily Pond, discover this one-of-a-kind home. A rare architectural sanctuary where nature, privacy, and imagination quietly redefine Berkshire living. Embraced by woods and water, this 4br, 4ba contemporary is bathed in extraordinary light. Enter and you'll find over 5000 sf. living space. Bedrooms are spaced apart for maximum privacy; the open living area takes center stage for entertaining. Post-and-beam great-room/atrium w stone floor. Open kitchen w custom cherry cabinetry. First floor primary suite. Outside, enjoy over 4 acres of privacy: lawn, gardens and your own nature trails! Deeded rights to the White Pines beach on Stockbridge Bowl. Walking distance to Tanglewood! Must see!

This wooded lot is the perfect location to build your dream home or weekend getaway. Nestled near the end of a cul-de-sac in a desirable subdivision in Lanesborough and only minutes away from Jiminy Peak skiing and Onota and Pontoosuc Lake boating and fishing. Homeowner's Association owns and maintains the well water system and common areas and the Town maintains the road.