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.

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.

Architecturally iconic and rich with history, this brick Federal home and its gracefully conceived mid-1990s expansion offer a rare opportunity for a buyer with vision. The last major renovation paired the 1830s structure with a deftly designed addition that respects the home's proportions while opening new possibilities for contemporary living. Set along the Stockbridge-Lenox corridor on 13+/- acres (including 9 conserved), the property is ready for a thoughtful, design-forward restoration that brings its next chapter to life.Originally built in the 1830s, the residence showcases beautiful proportions, abundant natural light, and the kind of craftsmanship impossible to replicate today. The interiors unfold across more than 5,000 sq ft, with high ceilings, generous rooms, and an

Stunning Post and Beam Home with Log Facade. Nestled in a park-like setting with views of Mount Washington. Outdoor Amenities Galore. Extensive patios and wraparound decks provide the perfect venues for outdoor gatherings including a private bocce ball court, outdoor hot tub, and private dog park. The first floor offers generous entertaining spaces, including two to three bedrooms that provide flexibility for guests or additional family members. The open kitchen/dining area is perfectly positioned to capture southeast-facing views. The primary suite includes a luxurious bath and expansive walk-in closets. On the lower level there is a private walkout suite, full bath, gym, and kitchenette. 3 car oversized garage/shop and generator.

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

The equestrian elegance of this 55 acre property starts at the gated driveway. Perched on the hilltop is a fully equipped custom build multi use barn entirely heated by radiant floor heat and includes 8 14x14 stalls w/ autowaterers perfect for the breeder or veterinarian. Includes kitchenette, office, laundry and bathroom. Also included is a heated equipment shed and workshop, a heated drive through aisle for large trucks, washstalls and more! The grounds include 8 paddocks with waterers, an exercise track, 3 large pastures. A second barn offers 12 additional stalls. The meticulously kept grounds is professionally landscaped and a covered wrap around porch greets guests into the home. Kitchen has quartz counters, GE profile appliances and a slider out to a large patio

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.

Welcome to your ultimate country retreat, where the charm of history meets the ease of modern living. Here, timeless beauty and serenity reign--an escape where silence is broken only by the wind in the fields and the song of birds.The 1828 brick colonial, a masterpiece of its era, has been exquisitely restored to showcase spacious, light-filled rooms that draw the outdoors in, framing views of meadows, a sparkling pool, and the stately barn. The barn itself is a wonder, waiting to be reimagined--perhaps as a guest house, an artist's studio, or a setting for unforgettable gatherings.Surrounded by farms and opening to distant hills, the landscape feels both boundless and intimate. The pool, perfectly placed, invites leisurely afternoons and is graced with its own elegant pool house.

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 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.

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!

Set on a quiet country road w/ private driveway, this charming 3 BR, 2.5 BA home sits on 8 picturesque acres just minutes from Tanglewood, Stockbridge Bowl & the villages of Stockbridge, Lenox & West Stockbridge. Perfect for outdoor enthusiasts, culture lovers or anyone seeking a peaceful Berkshire retreat. The location offers hiking, yoga & wellness centers, boating, skiing, & convenient access to dining & shopping. Inside, bright & inviting spaces include living room w/ cathedral ceiling, fireplace, & is filled w/ natural light. Primary suite with vaulted ceiling & balcony w/ stunning mountain views. Renovated kitchen opens to a cozy den & breakfast nook connecting seamlessly to the pantry, laundry & mudroom. Lower level with flexible bonus space for family room, gym, office or

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.

BREATHTAKING 360 DEGREE VIEWS Rarely does such a magical property come along with so much to offer. A well built and spacious home with Pickle Ball, Tennis, Swimming Pool, Gazebo, Lake frontage, Lush Green Lawn, Pastures, A Three Car Garage, Outbuildings, VIEWS FROM EVERY ROOM. Kitchen has Sub-Zero refrigerator, Wolf cooktop, large center island and a wall of windows overlook the gorgeous gardens and view. Formal dining room with wet bar and 500 bottle temperature controlled wine storage. A formal living room w/ a fireplace, a spacious family room for watching movies, a gym with a wall of windows looking to Mt Greylock, It is one of the most beautiful properties in the Berkshires. Equidistant to north & south Berkshire County. Close to all the Berkshires has to offer. Land conserved.

An Unrivaled 8-Acre Sanctuary of Beauty, Privacy & SophisticationNestled in the cultural heart of the Berkshires, just steps from downtown Lenox, this extraordinary property offers a rare and coveted blend of seclusion and sophistication set on an unheard-of 8 acres of wooded, professionally designed, and maturely landscaped grounds.Inside, the home has been completely reimagined, with every detail thoughtfully curated. Sunlight pours into the open-concept floor plan, seamlessly connecting the gourmet kitchen, grand great room with a striking stone fireplace, and elegant dining area. French doors on either side of the stone fireplace open to a spacious sunroom, where multiple sliding glass doors lead out to a Trex deck overlooking beautifully terraced gardens.

Set on 11 enchanting acres in the pastoral town of New Marlborough, Massachusetts, this exceptional Berkshires estate offers a rare convergence of architectural refinement, natural splendor, and modern luxury. Designed by an architect and originally built in 1984, the main house, guest house, and pool house were all fully renovated in early 2025 to create a cohesive, contemporary compound with timeless style and enduring grace.A long, private drive leads through an arboretum-like collection of mature trees to a secluded setting that feels both cultivated and wild. Here, heirloom stone walls, glacial rock formations, and a shimmering pond define the landscape. Master-crafted stone paths and terraces by local masons integrate the home with its natural surroundings, while new

Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure.Inside, the home is thoughtfully designed to host both family and guests in complete comfort, offering five well-appointed bedrooms, six full bathrooms, and a half bath, providing privacy and ease for all. The first-floor primary suite serves as a true sanctuary, complete with two separate full bathrooms for an elevated sense of luxury.

The Lakehouse enjoys a spectacular setting on a westerly facing cliff overlooking pristine Laurel Lake in the heart of The Berkshires. The Lakehouse is a classic three-story, shingle style mansion with 530' of lake frontage including its own dock. Built in 1903, the architecture denotes the unpretentious, timeless elegance of a turn-of-the-century lakeside cottage. There are 15 bedrooms and suites all with stunning, private bathrooms. The Lakehouse is exquisitely appointed and furnished with an eye toward showcasing the clean, graceful architectural details of the original lake cottage while adding modern ''creature comforts'' and ''cutting edge'' bathroom design. The Lakehouse is perfect for large families to gather for long weekends or extended vacations year 'round.

April Hill, an exquisite 1850 Greek Revival masterpiece. This architectural gem has been carefully restored and enhanced to exceptional standards, preserving its storied heritage while seamlessly integrating contemporary conveniences. The exceptional property features an elegant Main House, inviting Guest Cottage, Potting Shed/Studio and Barn. Framed by breathtaking panoramic vistas, the estate showcases classic stone walls, a serene spring-fed pond and a heated saltwater pool. The impeccably maintained lawns and expertly designed grounds establish a pristine country retreat. Premium upgrades include superior rock wool insulation throughout. Perfectly positioned just minutes from Tanglewood's celebrated performances, fine dining and thriving cultural attractions in the Berkshires.

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.