Perched high above a serene, bucolic country setting, this warm and inviting three-level home perfectly blends private seclusion with everyday convenience. Offering spacious open-plan living, the home features a dramatic, floor-to-ceiling stone fireplace in the great room that anchors the space with timeless rustic elegance.The seamless flow connects the living area, dining space, and kitchen--ideal for both quiet evenings and effortless entertaining. Just off the first-floor primary suite, a dedicated hot tub room offers a private year-round retreat. Upstairs, an open office loft looks down over the great room, accompanied by two guest bedrooms and a full bath. The walk-out lower level expands your living space with a large family room and laundry room,complemented by abundant storage

Dating from the late eighteenth century, this handsome, hip-roofed Colonial home is a distinctive and stately presence gracing its two and one half acre site in historic South Williamstown and provides a glimpse into its storied past. The finely proportioned residence offers casual elegance with its three fireplaces, wide board flooring and extensive built-in cabinetry and shelving. With a unique hand-painted wall mural of Williamstown's iconic scenery complementing the warmth of the original old world architectural details, the spacious dining room awaits the hosting of many gatherings both intimate and large. The kitchen overlooks a bright solarium with woodburning stove and ample bookshelves, perfect for relaxation and reading or simply viewing the meadows beyond. Three to four bedrooms

Welcome to 365 Deer Run, a beautifully refreshed four bedroom, 3.5-bathroom home tucked into the sought-after Otis Woodlands community. Inside, 2,297 square feet of cedar-wrapped warmth unfolds beneath cathedral ceilings and skylights, with east-facing windows that bring beautiful morning light into the home throughout the year. A window-lined three-season porch extends the living space and offers an inviting place to linger through spring, summer, and fall. The home is designed for both comfort and ease, with features including soapstone countertops, gas heat with Nest controls, a private sauna, and a brand-new roof. Thoughtfully updated and move-in ready, it offers the rare combination of character, modern comfort, and minimal fuss.

Now offered at $715,000, exceptional opportunity for spacious, single-level living on 3.04 acres across two lots in desirable Woodmont Estates. This expansive 3,400 sq. ft. executive ranch offers 4 bedrooms, 2.5 baths, and a combination of comfort & privacy. Highlights include an updated kitchen, renovated primary bath, custom library, private office, and inviting four-season sunroom with newer Andersen windows. Recent improvements include retaining wall repairs and selective tree removal, enhancing natural light and curb appeal. Surrounded by mature landscaping, this peaceful Berkshire retreat features a picturesque brook, beautiful sunrise views, central air, and natural gas heat. The expansive walkout lower level provides abundant storage and possibilities for additional usable space.

Welcome to this large expansive dwelling that features great privacy! Enjoy outdoor cooking and refreshments on the enlarged deck for these hot summer days. Also featuring a separate personal deck off the Primary bedroom. This great home boasts an oversized living room with a Grand fireplace place that will impress any viewer. An interior balcony from the sizable Primary Bedroom overlooks the oversized living room. A large kitchen leading to your dining room that opens up to the back deck. Updated bathrooms with amazing tilework will be found throughout the home. An oversized garage to store your personal vehicle or off-road vehicles of your choice. The lower level including a bonus room that is currently being used a game room completes the interior. It's a Perfect opportunity to finish

A private retreat w/ mountain views, surrounded by natural beauty & offering convenient access to the best of the Berkshires. This inviting three bedroom, two & half bathroom home features an open living concept w/ the family room, kitchen & dining area flowing together while focusing on the views & creating a memorable backdrop for entertaining. The sunroom captures afternoon light offering a peaceful place to relax & enjoy the changing seasons. A cozy living room features a fireplace, while a second fireplace in the primary bedroom creates a comfortable haven for the end of the day. Ideally located w/ a beautiful walking trail through the woods along a winding river nearby, this home offers a rare combination of privacy & convenience w/ easy access to all the Berkshires have to offer!

Light, airy & effortlessly inviting this 4 bedroom & 3 full bath home is made for Berkshire Living. Walls of windows & a sun filled sunroom bring the surrounding woodlands into nearly every room, while a brand new oversized deck sets the stage for long summer dinners & relaxing afternoons. A separate grilling deck offers the perfect spot for outdoor cooking & easy entertaining. Spacious interior rooms, abundance of natural light & multiple gathering spaces make this an exceptional year round retreat. Then there's the Otis Wood Lands lifestyle w/ an incredible array of amenities including a private lake, clubhouse, swimming pool, tennis/pickleball & playground. It's the perfect pairing of a beautiful home & a welcoming community offering everything you need to relax, play and entertain.

Thoughtfully crafted custom home offering timeless New England character, quality craftmanship, and beautiful eastern mountain views. Rich natural woodwork and exposed beams create a warm, inviting atmosphere throughout. The custom kitchen with granite, marble and butcher block countertops opens to the dining area with French doors leading to a screened in sunroom. Enjoy the expansive deck, stone patio with firepit, and beautifully landscaped grounds. Spacious living and family rooms with woodburning fireplace and generous mudroom/office. Offering three bedrooms, three baths, plus a versatile creative space, studio/sitting room, endless possibilities. Minutes to downtown Lee, Stockbridge, Lenox, Tanglewood, shopping, dining and all that the Berkshires has to offer for year-round living.

Welcome to a custom-designed architectural haven where clean, modern design meets inviting warmth. Meticulously maintained and lightly lived-in, this spotless, move-in ready retreat offers the ultimate in effortless, single-floor living set against a backdrop of mature perennial gardens, custom walking paths, and complete privacy.Step through the inviting front porch into a bright, open-airy floor plan anchored by soaring ceilings, oversized windows, and rich bamboo floors that seamlessly bring the outdoors in. The heart of the home features a cozy gas fireplace and radiant-heated floors for year-round comfort. The chef's kitchen and main living spaces flow effortlessly onto an expansive wrap-around deck-perfect for alfresco dining while taking in views of the private grounds.

Drive in beneath the trees and the house appears in a pool of sunlight, set well back from a quiet road with gardens, lawn and woods gathered around it. There is an immediate sense of having arrived somewhere apart. Private and peaceful, yet not isolated, this one-owner West Stockbridge home has the easy spirit of a modern farmhouse and a distinctly relaxed way of living--a place to slow down and settle in. An inviting front porch, screened by the surrounding landscape, is private enough to become a place of its own--for morning coffee, reading or the pleasure of doing very little.

Beautifully updated and lovingly maintained Colonial in the heart of Great Barrington. Bright, sunny, and truly move-in ready, this inviting home offers a combination of classic charm and comfortable modern living. The first floor features a welcoming mudroom, updated kitchen, heated sunroom, dining room, living room, family room, laundry, and full bath, providing plenty of space for both everyday living and entertaining. Upstairs are three comfortable bedrooms and a second full bath. Outside, enjoy a lovely yard and charming covered porch--perfect for relaxing and enjoying the neighborhood. Ideally located with easy access to Great Barrington's vibrant town center, library, restaurants, shops, and churches. A warm and beautifully cared-for home in a wonderful convenient location.

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

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.

The original farmhouse at the bend in the road: a center chimney colonial of 1782, dearly loved and held in exceptional condition. The grounds are a work of art cultivated over many years, a garden you want to immerse yourself in. Seasonal eastern sunrise views, and protected land along the border. Inside, an addition framed around the home's own eighteenth century posts and beams opens the kitchen through to a sunroom. Two fireplaces and two wood stoves, one a wood cook stove in the mud room. Wide boards, stone counters, nothing waiting to be done. 500 feet of road frontage, and then the road ends. One neighbor, out of sight. The quiet is complete and the night sky extraordinary. 20 minutes to Lee, 30 to Great Barrington. What we call Heaven. An add'l 45 acres is available

With lake views from your porch, your own dock on the bowl, just minutes to walk/drive to Tanglewood, come and see what you're missing. The house sits on a a generous size lot, with plenty of room to expand if desired. This place packs a lot of punch! Newly renovated with top-of-the-line mechanicals and appliances. A new Bosch heating and cooling system for all year-round living. New Mielle, Fisher Paykel and Bosch appliances. Enjoy the wood burning fireplace on those chilly nights. The attic and roof have been fully insulated. The crawl space was renovated with a new sump pump and commercial dehumidifier. A primary bathroom was added giving you 2 full baths. Freshly painted throughout. The house was thoughtfully renovated to keep the mid-century cottage vibe. Did I miss anything?

Move right into this stunning single-family home at highly desirable Berkshire Country Meadows. Nearly new and impeccably maintained, this spacious home offers the ease of condominium living with the feel of a private residence. The open-concept design features a beautiful kitchen, dining area, and living room with a cozy gas fireplace, perfect for entertaining or everyday living, and a separate first floor office with French doors for privacy. The first-floor primary suite boasts a walk-in closet and en suite bath while the walkout lower level expands the living space with a generous family room, two additional bedrooms, full bath and private patio. With 4 bedrooms, 4 full baths, and exceptional space throughout, this home is simply gorgeous and ready to enjoy. Clubhouse, pool, tennis.

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.

FOR SALE: Prime Downtown Great Barrington Gem - Endless Possibilities! Welcome to 406 Main Street, a rare opportunity in the heart of downtown Great Barrington, MA. Just steps from bustling Main Street shops and restaurants, this versatile 5,180 sq ft building offers exceptional potential for residential, commercial, or creative mixed-use transformation. Zoned B2, the property allows for single-family, multi-unit, or live/work conversion—with no sprinkler system required for up to 3 residential units. Already equipped with 1 full bath and 4 powder rooms, and featuring two finished floors, the layout adapts effortlessly to your vision—be it modern apartments, stylish offices, retail space, or a dynamic studio. • Spacious and bright with 5,180 sq ft across two levels • Excellent bones

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

Berkshire Estate Near Jiminy Peak Experience the beauty, privacy, and charm of Berkshire country living at this remarkable estate, tucked away at the end of a quiet cul-de-sac on more than three beautifully landscaped sunny acres. Surrounded by expansive lawns, mature plantings, and scenic views of Savage Hill, this property offers an idyllic setting for both relaxation and recreation. Designed for enjoying every season, the grounds feature a stunning in-ground pool, a hot tub perfect for crisp Berkshire evenings, and direct access to outdoor pursuits. Bordering the Town Brook River, where excellent trout fishing awaits just beyond' your backyard. The impressive residence encompasses approximately 4,320 square feet of thoughtfully designed living space. Minutes to Jiminy Peak Ski Resort