This charming bungalow offers the Lenox lifestyle you've been dreaming of. Tucked on a quiet dead-end street just steps from downtown, you can grab morning coffee, enjoy dinner at local favorites, or spend an evening at Tanglewood before strolling home under the stars.Inside, about 1,700 square feet of warm, inviting space blends character and comfort, creating a perfect retreat for every season. Ideal as a second home, weekend escape, or year-round residence. The property also offers the option to be purchased fully furnished, making it an easy, turnkey opportunity.With shops, dining, and cultural attractions moments away--and Lee and Stockbridge just a short drive--you'll enjoy the very best of Berkshire living.

Escape to this stunning four-bedroom contemporary retreat, nestled on 4.7 serene acres along a quiet country road. The open-concept living area boasts soaring cathedral ceilings, rich hardwood floors, and French doors that lead to an expansive upper deck. The sleek kitchen features stainless appliances, quartz countertops, and a bay window with picturesque views of the wooded backyard. The luxurious primary suite showcases double closets, a jetted tub, double sink vanity, and spacious tiled shower. 2 additional bedrooms on the upper level share a bathroom with a full tub and separate tiled shower. The second level offers flexibility with a 4th bedroom or office and a full bathroom, flowing seamlessly into the expansive 35-foot family room with French doors to the lower deck.

Home on a dream lot--over 7 secluded acres framed by mountains and backing to the Chalet Wildlife Management Area (7,000+ acres of protected state land). Enjoy total privacy, wide-open views, and dark-night skies away from city lights. Step inside to a grand entrance with a glistening chandelier. The main level features a flowing layout: a spacious kitchen with sufficient storage and generous counter space leading to the bright living room. Another feature on the first floor is that there is an option for private living quarters/in-law suite with its own entrance. The large primary suite offers a cozy fireplace, two walk-in closets, and an en suite bath with shower and jetted tub. Additionally, there is a first-floor laundry off the two-car garage, and an extra room great for an office.

Two multi-family homes on one lot, a two family and a four family. An apartment in each in needs updating. A short distance to downtown. All separate utilities

Berkshire Beauty set on quiet cul de sac near open protected land. Meticulously cared for, topped with a new 2024 roof so step onto the covered front porch and see: an open floor plan with comfortable spaces, start with the gracious and spacious kitchen centering the home's joy of cooking and entertaining. Finished with maple cabinetry topped with granite counters, stainless appliances and a Viking gas stove to prepare custom cuisine day after day. An abundance of cabinetry fitting for a baker with farm to table food: fresh eggs and vegetables at historic Brattle Farm just up the road. Open living dining area concept offers bar seating for a quick bite, a cozy nook for afternoon snacks, quiet reading or knitting with local Tunis yarn and view afternoon sunsets on the west facing porch.

Nestled on a serene private 5.52 -acre lot with a picturesque brook running through, this beautifully updated brick ranch offers the perfect blend of comfort, style, and nature. Located in desirable Dalton, this home features 4 spacious bedrooms with a versatile office space ideal for remote work -- and 2 full bathrooms. Step into the heart of the home with a chef's kitchen with stunning granite countertops, ideal for cooking and entertaining. Recent updates include a new roof (2018), new furnace (2025) and fresh paint throughout, giving the home a warm, bright and welcoming feel. The finished lower level provides a generous family room perfect for gatherings with a wood burning fireplace insert, along with laundry hookups and a two-car garage tucked beneath the house.

Nestled in the peaceful hills of Becket, this charming ranch offers the perfect Berkshire escape as winter fades into spring. Imagine enjoying fresh mountain air, morning coffee with birdsong, and quiet wooded views just outside your door. Surrounded by tall pines and serene forest, the setting provides wonderful privacy and calm. Inside, the easy single-level layout features an open living area and a kitchen perfect for relaxed weekend breakfasts or gathering after a day outdoors. Located a short drive from Otis Ridge, Bousquet Mountain, and Jiminy Peak, you'll enjoy year-round recreation--from late-season skiing to spring hikes. Ideal as a full-time home or seasonal retreat, this Becket gem is ready for peaceful mornings and relaxing evenings.

Welcome to 7 Park Street a sun-filled, classic New England home tucked on a quiet dead-end lane right in the heart of Stockbridge. With 2 bedrooms, 1 bath, and 1,300 sq ft, this 1900 charmer blends historic warmth with thoughtful updates: wide rooms washed in natural light, an inviting screened porch for morning coffee, and an easy, intuitive layout that lives larger than its footprint. The setting is exceptional, stroll just minutes to the Red Lion Inn, cafes, shops, and the library; at the end of the street, pick up beloved local trails toward Laura's Tower for quick nature escapes. A manageable 6,970 sq ft lot keeps weekends free for play, gardening, or launching out to the Berkshires' cultural highlights: Tanglewood, Norman Rockwell Museum, Naumkeag, and more.

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.

Discover this spacious, updated home offering year-round recreation just steps from Otis Reservoir, MA's largest recreational lake. Enjoy an open floor plan, a modern kitchen, and a quiet yard for outdoor fun. A two-minute walk leads to your included private dock and storage locker. Features include a main floor primary bedroom with a full bath, plus two large upstairs bedrooms with a second full bath. The property's location offers easy access to swimming, boating, skiing, snowmobiling, and hiking. This turn-key retreat is ready for you to start making memories as you relish the ultimate blend of modern comfort and natural beauty!

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.

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.

The ideal Berkshire escape can be yours. Prime location between historic Stockbridge & vibrant West Stockbridge, minutes to Tanglewood. This turnkey 4-bed, 3-bath home is a sanctuary of light where thoughtful upgrades ensure peace of mind. Key systems are new: a lifetime metal roof, 3 year old re-engineered and designed septic, high-efficiency Buderus boiler, and oversized windows that connect you to the landscape. Your backyard is a protected nature preserve, guaranteeing permanent privacy. The property features a handsome 24x30 horse barn with 2+ acres of paddocks, plus a separate lower-level guest apartment--perfect for weekend visitors or a private home office. A complete package blending modern convenience with pastoral beauty and cultural access.

Set in a peaceful, bucolic setting just minutes from Plunkett and Ashmere Lakes, this new construction home presents a rare opportunity to bring your own vision to life. The structure is in place, offering a blank canvas for customization, with the interior framed, unfinished and ready for your personal design choices. The floor plan can be easily reimagined, as plumbing has not yet been installed, allowing for flexibility in layout. Electrical has been roughed in, with final connection to be pulled from the street. A substantial HVAC credit is included in list price, providing added value and freedom to select the system that best suits your needs. An exceptional chance to create a bespoke home in a serene location close to outdoor recreation and natural beauty.

4,008+/- sqft 1850 Greek Revival in excellent condition w/large, open, bright rooms on 1st level incl wood-burning F/P, eat-in Cherry kitchen w/Shaker cabinetry - updated/bright lighting thuout- 2nd flr w/4lg BRS. 1 full, 2 half baths, period hardwood floors throughout, private rear deck. POST & BEAM BARN. Lg parking area... in hamlet center moments to Old Chatham, Berkshires, Chatham Village and half-hour to Capital District via I90/Parkway exit one mile away. Property leased through November 2027. Arrangements for earlier availability may be possible but not guaranteed. As a matter of brkrage policy, any co-op brokr comm, if offered, is payable solely and exclusively to a lic re brkr/brkrage company. Showings M-F 9AM-3PM, no wknd showings granted.

PRIME VISIBILITY off main route to Berkshires. 4,000 sqft Building in excellent condition w/large, open rooms on first level incl wood-burning fireplace and eat-in Cherry kitchen w/Shaker cabinetry. All new, bright lighting throughout. 2nd flr w/4 large BRS/offices. 4 baths. H/w flrs throughout. Private rear deck. POST & BEAM BARN. Large parking lot. In hamlet center moments to Old Chatham, Berkshires. Oil heat/2 furnaces, add'l Mitsubishi HV/AC first floor. Property leased thru 11/2027. Earlier availability possible but not guaranteed. As a matter of brkrage policy, any co-op brokr comm, if offered, is payable solely and exclusively to a lic re brkr/brkrage company. 48-72HR NOTICE. TENANTS MUST APPROVE. Showings possible by appt Mon-Fri 9am-3pm, no weekend showings granted.

Commercially zoned, high traffic count, 265' frontage on Rte 2 now being called 'the Cultural Corridor' between Williamstown and North Adams. 265' frontage on Rte 2,, .8 acre. This is the only undeveloped Main St. commercial site. Zoned Planned Business District ideal for retail, professional, service, or mixed use business and 2nd floor residential condos or apartments.. The lot is level, has all utilities to the site including natural gas, ideal southern exposure for solar as well as views in every direction. Directly across the street from Wild Oats Food Co-op, next door to Dunkin Donuts, a short walk to the pharmacy and public bus service right to the location.

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.

Experience relaxed lakefront living at the sought-after Lakecrest Condominiums on beautiful Pontoosuc Lake. This inviting home offers a first-floor primary suite with a curb less shower, a fully updated cherry cabinet kitchen with wine fridge and updated guest baths. Enjoy this light filled move-in ready end unit with expanded deck providing a private oasis. It is the perfect blend of comfort, recreation, and scenic surroundings in one of Pittsfield's premier waterfront communities. Residents of Lakecrest enjoy an exceptional lifestyle with outstanding community amenities, including a sparkling in-ground pool, tennis and pickleball courts, and a welcoming clubhouse featuring a fully equipped fitness center -- ideal for both relaxation and staying active year-round