Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a warm and inviting escape. Two additional en-suite guest bedrooms occupy the second floor with sitting area between. Residents enjoy exclusive access to a resort-inspired amenity suite--pool, fitness center, clubhouse, and tennis--all just minutes from the cultural and culinary heart of Lenox. A rare blend of privacy, comfort, and sophistication. This is a truly outstanding home, must see.

A luxurious home on one of the most scenic roads in The Berkshires, surrounded by 15 pastoral acres, with picturesque mountain views. Enter a sun-drenched living room with a soaring cathedral ceiling and an elegant fireplace centerpiece. Enjoy an expansive 3-season porch, with panoramic windows and classic mahogany floors. A recently updated eat-in kitchen features Sub Zero appliances and a beautiful butler's pantry. Relax in the newly renovated family room with wall-to-wall casement windows. This 5 bedroom home offers a bonus game room and home office equipped with fiber internet and a spacious private master bedroom with ensuite bath. An additional wing features a separate guest suite with living room, kitchen, dining area, full bathroom and 2 bedrooms. In Alford, renowned for low taxes

Located on one of Egremont's most picturesque roads, this beautifully designed contemporary home offers panoramic views from nearly every room. Set in a low-tax town just minutes from Great Barrington, this home is private, comfortable and versatile. The main house has perfect flow, great scale rooms, tons of light, a beautiful stone fireplace, custom Kitchen, and the prettiest of outdoor spaces. The connected ADU/Guest suite has a private entry, ideal for guests, caretaker, or rental income. Perfect for primary residence, vacation retreat, or income producing property. A tranquil setting with easy access to area amenities. Come enjoy the view!

Luxury in Lenox......If you are looking for carefree living with fabulous amenities at a world class resort, this Fairwynds single family residence at Miraval/Wyndhurst may be the perfect spot for you. Beautifully renovated with sleek, clean lines, generous two volume great room with wood burning fireplace, direct access to screened porch and open decking; all open to the gourmet kitchen with high end appliances. Formal living and dining room, first floor luxurious primary with generous en suite, three guest bedrooms, two full baths, a loft lounge and attached two car garage for added convenience. The Association includes use of the tennis court, gym, indoor and outdoor pool and available membership to the beautiful 18 hole campus golf course.....BERKSHIRE PERFECT!!!

ICE HOUSE HILL FARM. Richmond, MA There are properties with views in the Berkshires. Then there is Ice House Hill Farm270 degrees of sweeping, layered vistas, and exceptional distant views - guaranteed forever by 130 acres of land that can never be developed. The facts: Exceptional building parcel on one of the Berkshires most beautiful roads, commanding staggering views. | 143 total acres. | 12.96 buildable acres + 130 acres permanently protected | Nearly 1 mile of frontage along East Road; 559' serves the buildable area | Historic farm complex: 1922 dairy barn and silo, etc. + 1890 farmhouse that needs renovation - this is primarily a land listing due to the quality of the build site.Open land at elevation with Wide & Distant views that will never change. A landmark farm

HISTORIC BERKSHIRE FARM Best bargain in the Berkshires! Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns and maintenance building. 161 acres with stunning views, mountain paths, and Jim Kelly's stunning giant stonewalls throughout. Gorgeous New England marble stone farmhouse built in 1780, with modern addition featuring vaulted ceiling and massive windows which flood the dining and kitchen area with light. Enormous custom built hearth and fireplace, mahogany full bar, artisan-made bookcases, wrap-around deck. Close to Williams College and Jiminy Peak. The property offers swimming in two private ponds, 6 bay carriage barn with second floor for offices, studios., or storage.

BERKSHIRE LAKE FRONT WITH BEAUTIFUL WESTERN VIEWS ACROSS THE LENGTH OF LAKE BUEL. Premiere motor boat lake. With 6 bedrooms and 3 full baths there is room for your extended family or friends. Walls of windows allow lake views from most rooms. Open plan for relaxing after a long day swimming, boating, fishing or relaxing on the water. Lovely out door areas include a deck, patio and steps to your dock. Under 10 minutes to downtown Great Barrington and a short drive to Berkshire County culture, dining and entertainment.

A RARE BEAUTY ON HISTORIC YALE HILL! Discover an historically significant gem in this perfectly renovated home! Peacefully tucked away from it all, yet close enough to enjoy a stroll to town, tennis, Library, golf & restaurants.Chef's Kitchen, large flexible living spaces, 4 Bedrooms, 4 Baths, tall ceilings and charm galore. The Mill House, transformed into a cozy Guest quarters, with 3 Bedrooms,, 3 Baths, has a lovely brookside courtyard w/Pergola, rustic charm maintained. Quiet your mind and embody perfect country living. Overlook the Kampoosa Brook, with private swimming area from your backyard! Cultural & recreational activities nearby. Great income potential. Solar powers Main house, car charger & Mill House. A MUST SEE!

Nestled in a secluded, serene setting and surrounded by lush gardens, fruit trees, wildlife and Nature Conservancy on 3 sides, custom-built home offers extraordinary privacy and tranquility. Crafted using wood milled directly from the property, this rustic yet contemporary home boasts a wealth of unique details that highlight exceptional craftsmanship. Moose, deer, bear, turtles, fox and more visit mature grounds tended by master gardener. Incorporates a native stone fireplace, ash sapling banister, antique leaded glass accents, & reclaimed 18th-century tavern doors from historic Egremont Tavern. These elements blend seamlessly with the open-concept floor plan, highlighted by soaring vaulted ceilings and oversized windows. 5 Brs, 5BA w/ attached separate apartment w/ balcony.

Nestled in the center of Williamstown, just steps from Williams College, this stunning two-story Colonial stucco home offers timeless charm and modern comfort. Built in 1907, this 4,100 sq. ft. residence features five spacious bedrooms, three full baths, and one half bath.Set on 1.35 picturesque acres, the property boasts a large post-and-beam barn, a beautifully covered stone patio, and breathtaking western views of the Taconic Mountains. The expansive, level backyard is adorned with mature gardens and majestic old-growth trees, creating a serene and private retreat.Don't miss this rare opportunity--call today for your private showing!

Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it offers plenty of room to entertain and relax. The large cook's kitchen is perfect for preparing meals for large gatherings, while the heated sun room provides a cozy spot to enjoy your morning coffee and take in the stunning views of the surrounding fields. This home also features 5 spacious bedrooms (primary with en-suite, four jack-and-jill), each with their own unique charm and character.

An elegant Berkshires residence, 813 East Street in Lenox, MA is a fully renovated seven-bedroom home designed for both sophistication and ease of living. Built in 2004 and extensively reimagined over the past few years, this Lenox property offers the rare combination of privacy, luxury, and seamless indoor-outdoor living--all in the cultural heart of the Berkshires.Professionally landscaped grounds with hand-laid stone walls mark the elegant entry, setting the stage for this distinctive Berkshire home. Inside, a soaring double-height foyer introduces a layout that is both intuitive and expansive, ideal for year-round living. The centerpiece kitchen features granite countertops, dual islands, a fireplace, and effortless flow into the living room,

Custom Built Craftsman Contemporary Home nestled in a beautifully landscaped property with an orchard, gardens and path to a seasonal brook. Inside this well appointed home you will find large rooms Vaulted ceilings, whimsical lighting, Fireplaces, Indoor pool, hot tub and sauna, radiant floor & forced air throughout. Two primary suites on main floor and 2/3 more bedrooms in the lower walkout portion of the home. Large Timber Frame screen porch and deck overlooking rear of the property. Media room and recreation room with more space for added entertainment. A four car plus heated garage with an ample unfinished area above for storage or create your own space. Option to this property is a new 2 bedroom contemporary guest house at an additional cost. See additional disclosure.

MODERN LUXURY-NO UTILITY BILLS. A net zero home. Framed by sweeping walls of glass, nature itself becomes part of the design in this single-level modernist retreat. The seamless indoor-outdoor flow invites you to take in mountain views from every angle. Refined simplicity define the space, with sleek lines, a cohesive palette, and high-end finishes creating effortless sophistication. Created by the award-winning firm Res4 Architecture, this modern masterpiece exemplifies precision and innovation. The open living area centers on a chef's kitchen with Gaggenau and SubZero appliances, bespoke cabinetry, and a striking Stuv fireplace. A plush media suite offers an immersive theater experience with a retractable screen and surround sound -- perfect for entertaining or quiet nights in.

Blue Hill Farm: an 1820 Center Hall Colonial farm and farmhouse in excellent condition on 249 high acres with organic hay meadows and pastureland, an apple orchard, woodlands, gardens, tennis court, a 1970's caretaker/farmer's house and multiple barns. The main house has 6/7 bedrooms and three baths, along with a three-car attached garage. The property consists of seven parcels of contiguous land surrounded by the Umpachene River on three sides. There are long views to the west of the Taconic Range from inside and outside of the home, and a grouping of supportive barns to the south across a very rarely traveled, narrow dirt road. Offered for the first time since 1967, this is truly an unusual and rare offering with development possibilities featuring extraordinary views.

Iconic only begins to describe this rare union of sophistication & natural splendor. Spanning 40+ secluded acres of rolling meadows, forested trails, & sweeping mountain views, this remarkable estate has welcomed world-renowned artists & hosted unforgettable gatherings, from summer soirees to intimate retreats.At its heart is the Great House--a 6,000 sq. ft. architectural masterpiece by renowned sustainable architect Allan Shope. Thoughtfully placed within the landscape, the residence reveals itself at the end of a winding, art-lined drive. Inside, soaring ceilings, an open & airy floor plan, & an indoor pool create an atmosphere of timeless elegance. With 5 bdrms, 7 bths, & separate guest or staff quarters, the home is designed for both hospitality & privacy.

STUNNING LONG VIEWS, RARE 330+ ACRE PARCEL, ABUTS CONSERVATION LAND! Total seclusion and privacy, bucolic countryside with some open meadows and wooded hillside. Once a grand Berkshire estate, the property is comprised of the main Tudor style residence with indoor pool, shingled barn, Dutch colonial multi family dwelling, a guest house & several smaller sheds and workshop. The buildings are all in need of upgrades, but restoration to former glory, a most worthwhile project. Indoor heated pool room opens to beautiful sunken gardens with Contemplation Bench , Stone Walls and perennial gardens. A unique and wonderful opportunity, within close proximity to Gedney Farm, Old Inn on the Green, Southfield Store, and just minutes to ski Butternut and Great Barrington. Being sold AS-IS.

Gated Berkshire Stone Estate in exclusive Pinecroft compound with Canyon Ranch Living and its 125 maintenance-free acres. Optional membership. Turnkey home features elevator, 300-year-old reclaimed timber floors and large gourmet kitchen. Great room boasts floor-to-ceiling stone fireplace, wet bar, Nano doors to screened lanai. Two primary en suite bedrooms with cedar closets. Lower level: gym, sauna, 8-seat hi-def theater, wine cellar, massage room, en suite bedroom/office and a soda fountain. Elegant outdoor living includes heated gunite saltwater pool/spa, firepit, pool house with guest suite and fully equipped kitchen. Heated driveway and garage. Near Lenox, Tanglewood and Berkshire arts.