Barns, Brook & Beautiful Living Uniquely spanning the Williamstown, MA and Pownal, VT state line, this inviting property combines New England charm with exceptional flexibility. The expanded 3,500 sq ft home offers 4 bedrooms and 2 full baths, including an option for a first-floor bedroom. Warm, connected living spaces include a stone-fireplaced family room, open kitchen and dining area, a cozy tavern room with wet bar, and a shaded patio for summer enjoyment. The 3.4-acre Vermont parcel features Broad Brook along its boundary plus two outstanding outbuildings: a 30'×40' insulated and finished barn with office and 12' ceilings, and a 30'×50' three-bay garage with 12' rafter clearance--ideal for vehicles, equipment, hobbies, or future conversion. With the house on 0.6 acres in MA and the

Set on four private acres along a quiet stretch of road near the Housatonic, this is a property that keeps to itself. No sightlines from the neighbors, no road noise to speak of, just the sound of the brook that runs through the back of the yard. This is a place built for quiet enjoyment, and the land delivers it in full. The gardens are the kind that take decades to get right, and someone got them right. The driveway is lined with rhododendrons that light up every spring, and from there the whole landscape is paced to bloom straight through summer. Fruit trees, azaleas, perennials, blueberries, raspberries. Walk it in July and you understand: this wasn't landscaping, it was devotion. And for all that's established, there's still room to put your own touch.

Some Berkshire homes are simply places to live. Others become part of the way you want to live. The Oronoque Villas are among those rare places. Built in the mid-1990s on the historic grounds of Oronoque--one of Stockbridge's great Berkshire cottages--just eight freestanding villas were thoughtfully sited within the estate landscape, complementing the original mansion, now home to distinctive condominium residences. Surrounded by mature trees, sweeping lawns, and established gardens, this villa offers the warmth and privacy of a house, the simplicity of one-level living, and the freedom to lock the door and leave whenever adventure calls. Whether as a year-round home or a favorite Berkshire retreat, life here has a wonderful way of slowing you down.

Sometimes fairy tales do come true... Tucked away on five private acres in Monterey, this singular handcrafted Berkshire cottage feels as though it emerged from a storybook. Natural-edge wood siding, steep rooflines, a massive fieldstone chimney and a tower-like upper level rise from a landscape of hydrangeas, woodland and a grape-covered arbor. Inside, the house is an irresistible mix of rustic character and thoughtful updates. Original wood floors, reclaimed hand-hewn beams, paneled walls, arched doors and unexpected architectural details give each room its own identity. The dramatic great room is the heart of the house, where soaring volume, exposed beams, richly paneled walls and an immense fieldstone fireplace create a space that feels far removed from everyday life.

Welcome home to an extraordinary blend of modern style, flexible living, and resort-quality outdoor amenities, perfectly located moments from the heart of downtown Lenox, top-notch dining, Tanglewood, & the local high school on a quiet cul-de-sac. Step inside to a bright, freshly painted open floor plan framed by updated windows that flood the space with natural light. The inviting living area features a cozy gas fireplace, creating a warm focal point for chilly evenings, while the kitchen comes equipped with sleek, modern appliances. This turnkey residence offers 3 spacious bedrooms plus a versatile 4th full-size room that's ideal for a fourth bedroom, dedicated home office, or quiet retreat along with 2.5 updated bathrooms.

Bring your BOAT and enjoy all that the Stockbridge Bowl has to offer. This charming home has deeded rights to the lake, as well as its own dock space! The house was recently renovated with all top of the line mechanicals and appliances. Bosch, Miele, & Fisher Paykel. Central AC. One level living with two bedrooms and two full baths. Open concept living with a large front deck and yard for entertaining. Inside is an original log fireplace for those chilly winter nights. All new cedar lined closets and freshly painted throughout. A three-minute walk to your boatslip and private neighborhood dock, you can sit and watch the sunset from the best spot on the bowl. Make an appointment to view this gem now.

These are the Berkshire views you've been dreaming of. Meadow, mountains and enormous sky surround you in nearly every direction, with stunning westerly views across preserved fields to the lower Taconic Mountains. Morning light moves across the meadow; evenings end with the sun dropping behind the ridgeline. Spring brings wildflowers and returning birds, summer fills the fields with native plants and pollinators, autumn moves across the mountains in color, and winter transforms it all to snow-covered meadow and white-capped peaks. Perhaps your greatest pleasure will be getting out into it--walking the fields, cross-country skiing after fresh snow, watching the birds and wildlife, or discovering what has changed in the meadow from one day to the next.

On 5 park-like acres this well maintained and thoughtfully designed home overlooks a tranquil pond and offers a serene getaway. Designed by architect Dennis Wedlick to maximize space and ease of living the home features 3-4 bedrooms and 3 full baths of which one is a separate guest suite. A renovated kitchen and updated bathrooms blend seamlessly with gleaming wood floors. A striking double sided fireplace connects the living room and den. Custom designed windows bring in sunlight while framing picturesque views. An exceptional property, ideal as a full time residence or a country retreat for those looking for both design and a quiet setting. Solar panels have been aesthetically placed to reduce energy bills, EV charger in garage. Full house generator too.

Discover a rare Berkshire property offering endless possibilities in one of New England's most sought-after destinations. Whether you're seeking a luxurious year-round residence, a four-season getaway, or a property designed for multigenerational living, this exceptional offering delivers the perfect blend of privacy, flexibility, and convenience. Ideally located in the heart of everything the Berkshires has to offer, you'll be just minutes from world-renowned attractions, including MASS MoCA, The Clark Art Museum, and the Williamstown Theatre Festival. Head south to enjoy concerts at Tanglewood, the renowned summer home of the Boston Symphony Orchestra, or take advantage of the area's abundant hiking, biking, and scenic trails. Autumn brings spectacular fall foliage and

ARRIVE FRIDAY NIGHT, UNLOCK THE DOOR & ENJOY THE WEEKEND! Turnkey Berkshire get-away in an exceptional location. Beautifully maintained and ready for immediate enjoyment, this inviting Egremont home requires no updates and offers comfort, privacy, and convenience. Features include a two-car attached garage and generator for effortless year-round living. Ideally positioned near skiing, scenic hiking, exceptional dining, and the vibrant villages of Great Barrington & Egremont, with easy access to New York and Connecticut. Egremont's attractive property taxes add to the appeal. A rare opportunity to simply arrive, settle in, and enjoy all that the Berkshires have to offer

Steeped in history and rich with character, this remarkable 1767 residence is the oldest home still standing on its original site in Williamstown.Thoughtfully expanded over time, it preserves its historic integrity while offering comfort for modern living.Set on nearly five meticulously maintained acres in one of the town's most desirable neighborhoods, the property feels both private and timeless, with mature plantings, perennial gardens, and sweeping lawns.The classic Cape Cod-style architecture features a wood shake roof, enhancing its New England charm. Inside are 5 bedrooms and 3.5 baths, blending intimate period rooms with light-filled living spaces. A dramatic living room with cathedral ceilings and French doors opens to beautiful Goshen stone patios, ideal for outdoor entertaining.

Beautifully designed for one level living and both pristine and charming...open floor plan with a cathedral ceiling in the great room (which is complete with gas fireplace, built ins and access to the patio); gorgeous kitchen with quartz counters and eating bar, formal dining room, hardwood floors in main living spaces, Primary Suite plus 2 additional bedrooms (one currently used as a solarium with access to the south facing deck) and an additional full bath. Powder room, mudroom and hook ups for laundry. The basement level is fully usable for a game room and other creative uses (wait til you see it!). Gorgeous gardens surround this property and the stone sitting porch and patio are highlighted by gardens and a privacy fence...absolutely charming! For ease of 1 level...this is it!

Dreaming of your own private sanctuary? 30+ acres await exploration! Enter between two stone pillars and the long winding driveway will take you past woodland glades, open spaces, mature tree stands, manicured lawns and a magnificent spring-fed swimming quarry! Acres of open cleared land afford additional usage options. Cedar log home, one-owner custom built. Large wrap-around deck and long covered porch; great for summer entertaining! Inside you'll enjoy over 2000 sf of relaxed country living. Great room with vaulted ceiling, massive stone fireplace. Open kitchen w. granite counters and island w seating. Two first floor bedrooms and full bath. Upper level with spacious primary suite and an open loft with fireplace. Finished walk-out lower level w. 2 car garage. Truly one-of-a-kind!

A rare opportunity to become the next steward of a remarkable piece of Sheffield history. Dating to 1819 and prominently situated on South Main Street in Sheffield's Historic District, this extraordinary antique is filled with the character, warmth, and craftsmanship of another era. Currently configured as a four-family residence, the property includes three beautiful apartments in addition to the spacious main portion of the home, allowing an owner to enjoy gracious historic living while rental income helps offset expenses. Alternatively, rent all four residences and take advantage of a distinctive investment opportunity. Gorgeous grounds and an exceptional historic setting make this a truly special Sheffield property.

A rare opportunity to become the next steward of a remarkable piece of Sheffield history. Dating to 1819 and prominently located on South Main Street in Sheffield's Historic District, this extraordinary antique is filled with the character, warmth and craftsmanship of another era. 16 rooms, 5 bedrooms, multiple baths and 4 fireplaces, the home features beautiful wide-board floors, period details, sun-filled rooms and gracious proportions. A large three-season porch and welcoming front deck extend the living spaces and add to the home's timeless village appeal. With its rich history, wonderful scale and multipurpose zoning offering intriguing possibilities, this is a property ready for its next chapter--an opportunity to preserve its past while creating a home for generations to come.

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-

Just two miles from the center of Stockbridge, this beautiful four bedroom, three and a half bathroom home offers privacy, space and exceptional indoor outdoor living. The spacious primary suite features a large ensuite bath and separate his and her closets, and an additional closet with direct access to a full length deck shared access with the living room. The open floor plan connects the living room, dining area and kitchen, highlighted by soaring beamed ceilings abundant natural light, and a gas fireplace. A bright sunroom to choose a book from its floor to ceiling bookcases. The deck overlooks the mature landscaping, pool, and pool house. The walkout lower level includes a second kitchen, providing space for guests. A Berkshire retreat just minutes from the cultural attractions!

Discover a peaceful retreat in Alford with this charming 4-bedroom, 2.5-bath Contemporary Cape set on more than 8 acres. Relax on the spacious screened-in porch while listening to the birdsong and the gentle flow of Scribner Brook. Offering an upscale cabin feel in every season, this inviting home provides the perfect escape from the pace of everyday life. Enjoy privacy, natural beauty, and the tranquility of your own wooded retreat.

Completely reimagined from top to bottom, 1790's Colonial blends historic New England character with modern luxury in a truly one-of-a-kind Berkshire setting. Located directly across from Pontoosuc Lake, the property offers stunning lake views, exceptional craftmanship and endless possibilities for live/work, business venture or investment in business/residential zone. Stunning kitchen featuring radiant heat, quartz countertops, high end appliances, oversized center island with dramatic full waterfall quartz sides flowing on every exposed edge. First-floor bath/laundry w/radiant heat. All three bathrooms have been fully renovated with spa like appeal and upscale design. Large living room/dining room, 1st floor bedroom with lake views, 2 sunporches all on main leve