Envision waking up in this beautifully renovated New England farmhouse in quaint Lenoxdale Village. Enjoy morning sunrises on the front patio and quiet evening dinners on the terrace, all just minutes from the world-class culture of Tanglewood and the iconic downtowns of Lenox and Stockbridge. Inside, original hardwood floors flow throughout a versatile layout featuring 3-4 bedrooms, a cozy office space, and a spacious, freshly updated kitchen with a breakfast nook and extra pantry space. Outside, the large open yard is anchored by a charming car barn--ideal for summer projects, kayaks, bicycles, and flexible loft space. Come make this home your Berkshire dream!

Offering the rare and coveted 'lake life' on Lake Buel, this unique property presents an extraordinary opportunity to establish your own Berkshire footprint on an expansive 2-acre parcel. Comprising 90% sun-drenched, open meadow, the large lot serves as the ultimate blank canvas with potential for a stunning architectural expansion, a custom family compound, or agricultural designs. While the existing cottage provides a peaceful, private retreat set back from the road, the true crown jewel is the property's dedicated lake access--offering the right to install your own private dock or boat slip on one of the Berkshires premier motorized lakes. Bring your vision to this exceptional property and start living the Berkshire lakeside dream today.

Tucked into the rolling hills of Great Barrington just minutes from downtown and the slopes of Ski Butternut, The Turning Point is a storied 3,600-square-foot Berkshire landmark operating as an active short-term rental. Steeped in history dating back to its 1800s stagecoach tavern roots, the property showcases an enduring dual-facade of classic New England brick and weathered clapboard. Inside, original period charm takes center stage with wide-plank wood floors and glowing fireplaces, perfectly paired with a rare, substantial footprint featuring 7 generous bedrooms and 6.5 bathrooms. Designed for effortless hosting, this expansive retreat offers an incredible canvas for a lucrative rental investment, a boutique bed-and-breakfast, or a magnificent private country compound.

Situated on highly desirable Mountain Drive, this expanded 3-bedroom, 2-bath Cape delivers classic Berkshire charm, thoughtful updates, and flexible living spaces. Step inside from the welcoming front porch into an inviting layout featuring hardwood floors and abundant natural light. The spacious living room is anchored by a wood-burning fireplace flanked by custom built-ins, flowing into the formal dining room and a tastefully remodeled kitchen. Enjoy year-round tranquility in the heated four-season sunroom or relax in the separate main-floor den featuring a cozy gas fireplace and sliders leading out to the rear deck. A generous first-floor bedroom, full bath, and dedicated laundry room offer effortless single-level living convenience.

Moments from Lake Mansfield and Main Street, this turnkey contemporary offers clean lines, natural light, and effortless Berkshire living. The main level features an open-concept floor plan anchored by a show-stopping Duvemåla tiled stove, serving as a striking centerpiece for gatherings and cozy evenings by the fire. Enjoy the convenience of a first-floor bedroom alongside one of the home's three well-appointed full baths. Upstairs, an expansive primary suite impresses with vast cathedral ceilings. The finished lower level adds a versatile bonus room, providing extra square footage for a home gym or game room. Outside, relax and entertain on the sun-soaked deck overlooking the oversized grounds of this rare double-sized parcel.

This new-construction Craftsman Contemporary on private Terra Ferma Drive delivers sharp lines and bright living spaces. Anchored by vaulted ceilings and custom details, the open-concept layout flows directly to an expansive deck overlooking serene wooded wildlife. The five-bedroom, three-bath footprint provides a highly flexible layout for remote work, hosting, and modern living, supported by an attached two-car garage and a large yard, perfect for outdoor summer entertainment. Situated on a premier South Egremont cul-de-sac, the roadway connects directly to the Karner Brook Wildlife Management Area for instant trail hiking access, while keeping you minutes from Catamount skiing, Great Barrington, and low Egremont taxes. Clean, current, and highly efficient.

Rare, renovated Berkshire investment compound on 0.59 acres in walkable Housatonic. This turnkey property features two separate legal duplexes (4 units total) offering stellar cash flow. The front home (392 Park St) features a 5BR/2BA unit, a sleek 2BR flat, and a prominent street-front walk-out lower level with incredible commercial/addition potential. The rear Swiss-Gothic home (394 Park St) hosts two updated 2BR units. Enjoy a sprawling backyard with mountain views, a community garden, and fruit-bearing trees. Fully insulated and optimized for easy management with 4 separate heating/electric systems, town sewer/water, and off-street parking for 10+ cars. Walk to Berkshire Mountain Bakery; minutes to Great Barrington & Tanglewood. A rare, turnkey find!

Special opportunity to take over the 5BR owners' unit as part of this 4-unit compound and let the other 3 pay your mortgage. Relaxing property in the center of Housatonic village with two charming, recently renovated duplex homes - each with historic details left intact. The front house has a flex 4/5BR 2200 sq. foot owners' unit which feels like its own house. Split on 2 floors, it has 2 full baths, privacy, its own screened-in porch and outdoor BBQ area. Currently operating as a high-end furnished rental. Use it as your FT residence, weekend home or mid-term rental (i.e. traveling nurses), turn-key and ready to go. The remaining 3 x 2BR units are filled with wonderful tenants; each home has their own W/D, outdoor space and there is an expansive shared yard-

Set quietly at the end of a private road in desirable South Egremont, this recent build delivers modern single-level living at its best. Designed with an easy, step-free floor plan, the home opens into a chef's kitchen that anchors the main living space. The layout features three well-appointed bedrooms-highlighted by a generous primary suite-plus a dedicated home office. Outdoor spaces are built for unwinding and entertaining, from the welcoming front porch to a broad stone patio, with wooded hiking trails waiting right outside your door.

Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The heart of the home is a dramatic, light-filled great room anchored by soaring cathedral ceilings and a brick fireplace paired with charming built-ins. The main level is designed for entertainment and ease, featuring a lavish first-floor primary suite with walk-in closets and a spacious ensuite bath. Upstairs, three additional guest bedrooms are complemented by a private, separate bonus studio

Tucked away on a peaceful private drive, this custom Craftsman home (built 2022) combines timeless architectural character with effortless modern living. Designed with accessibility and everyday ease in mind, the main level features zero-step entry and true single-level functionality. At the heart of the home is a bright, spacious cook's kitchen that flows seamlessly into welcoming living spaces. Outdoor living shines with both a classic front porch to take in quiet sunsets and a stunning screened porch designed for bug-free Berkshire evenings. The versatile 4-bedroom layout features a private primary suite alongside an attached in-law apartment-ideal for multigenerational living, long-term guests, or rental potential. A dedicated home office makes remote work a breeze,