Set on six picturesque acres in Stockbridge, this beautiful contemporary home offers privacy, comfort and stunning views. The thoughtfully designed layout features five bedrooms and 4.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The chef's kitchen is equipped with premium Wolf and Sub-Zero appliances, perfect for entertaining or everyday living. An oversized three-car garage and finished lower level provide ample storage, while expansive windows showcase the surrounding landscape. Available furnished. This exceptional property is move-in ready and an ideal Berkshire retreat.

349 Old Stockbridge Road and 40 Frothingham Crossing together represent a rare 16.76± acre contiguous institutional campus and redevelopment opportunity in the heart of Lenox--one of the Berkshires' most established and sought-after destination markets. At the center of the offering is Overlee, a distinguished Berkshire estate built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan / Jacobean Revival style. Over time, the estate evolved into a fully integrated campus, thoughtfully organized around the original mansion and supported by a collection of dormitory residences, academic and administrative buildings, dining infrastructure, and recreational facilities.

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. MORE

Welcome to NEWGRANGE, a grand 1920s Manor House capturing the golden age of lakeside country living. This historic estate echoes the effortless elegance of an early 20th-century summer retreat. Imagine hosting lavish gatherings in the formal dining room, or retiring by original, roaring stone fireplaces after a leisurely day on the water or the slopes. Encompassing over 10,000 sqft, the sprawling residence boasts ten spacious bedrooms, a classic country kitchen, and sweeping living areas. Stroll the 7.7-acre grounds--past the guest house, pond, and gardens originally designed by Frederick Law Olmsted--down to your private dock on Lake Garfield. Ideally located near Tanglewood and premier skiing, and low Monterey taxes, this Berkshire gem is a rare invitation to reclaim a masterpiece.

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.

The thoughtfully renovated and expanded 1940s Main House is full of exceptional spaces--elegant formal dining and living rooms in front, informal sitting area and spacious eat-in kitchen at the back, stunning central stairwell, cozy den/bar, and media room. Five comfortable bedrooms, including two luxurious primary suites. Every material, sightline, and design element has been curated with care and sensitivity. Delightful outdoor spaces abound--front and rear goshen stone patios, rolling lawns, balconies and roof spaces. Cozy historic sunroom off the living room. Above the oversized two-car garage, is a stunning light-filled studio with intricate ceiling details, exterior balcony and bathroom. The in-ground pool is surrounded by a huge patio area, gardens and pastoral views.

STILL HOUSE brings next-level contemporary design and a new kind of elegance to the Berkshires--quietly luxurious, exquisitely detailed, and made to be lived in. Minutes from the center of Great Barrington, this newly completed home of more than 5,000 square feet pairs the distinctive vision of acclaimed Brooklyn studio Me & General Design with superb craftsmanship and exceptional materials throughout. Four bedrooms, five-and-a-half baths, a heated saltwater pool, bespoke spa and fitness spaces, solar energy and exceptional privacy make this as much a retreat as a home. Preserved stone walls from the original structure bring history, texture and character to the new architecture--and keep something distinctly Berkshire at its heart.

Set along the shores of beautiful Pontoosuc Lake, this extraordinary private estate captures the very best of Berkshire waterfront living. Enjoy sweeping lake and mountain views, a private dock, heated pool, outdoor kitchen and fire pits designed for unforgettable entertaining. Inside, open-concept living showcases the views, while a chef's kitchen with Wolf and Sub-Zero appliances anchors the home. Multiple private living quarters, a game room, loft and home office offer exceptional flexibility. Extensive garage and parking space provides room for cars, boats and recreational toys, while gated and fenced grounds offer privacy. Come for the views. Stay for the lifestyle. Make Pontoosuc Lake home.

Beautifully sited to capture light and long-range views, this architect-designed residence offers timeless elegance within a serene natural setting. Bright, sophisticated interiors open seamlessly to a screened porch and stone terraces overlooking the pool and manicured grounds. Generous proportions and refined architectural details define the living spaces, complemented by a beautifully reimagined library/office, dining, living media/den and kitchen. First-floor primary suite serves as a private retreat, while additional en-suite bedrooms provide comfort and discretion for guests. An upper-level loft (w/ elevator)offers space for gym, studio, or media. A rare offering of privacy, design, and distinction in the Berkshires.

Marcel Breuer partner Tician Papachristou designed this home as a private paradise for his three-generation family: a long driveway leads past a tennis court, guest house, swimming pool, gazebo, and gym shed to a three-level modern house evoking the New England barn. From the third-floor master loft suite with private terrace and kitchenette, a skylit central stair leads to the mid-level kitchen/dining room with fireplace nook, between stone patio and screened porch. An atrium living room includes cozy coffered-ceiling seating by a fireplace. A cherry-walled study with private porch, pass-through full bathroom, and family room complete the floor. Family or guests on the lower floor enjoy four bedrooms and three bathrooms, as well as laundry room and two-car internal garage.

Introducing 
 FREE QUARTER FARM Nearly 1,500 Acres | Sandisfield, the Southern Berkshires | $4,500,000 Miles of private trails for hiking, hunting, fishing, horseback riding - your own wilderness preserve 134+ acres not in conservation with 1,489 feet of road frontage - craft your legacy 5BR/5BA timeless home built for this wildly beautiful place Stand between your home, overlooking your private lake, and your barns, Turn 360 degrees—everything you see you could own. Pure sanctuary in the highest possible sense. Nearly 1,500 acres where Thorp Brook winds through marshlands, Seymour Mountain rises to 1,682 feet, and miles of trails beckon for every outdoor pursuit. The kind of American dream that exists now only because someone saved it, after they assembled this dream.

The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental. The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a strong performer for weddings, corporate retreats, and multi-generational stays. The grounds feature open lawns, established gardens, and west-facing views. Fully ADA compliant and walkable to Lenox's restaurants, shops, and cultural venues. A rare opportunity to own a large-scale, income-producing property in one of the Berkshires' most established locations.

Perched to capture sweeping vistas, this contemporary architectural masterpiece seamlessly balances the demands of a world-class art collection with an immersive natural experience. The residence is brilliantly composed of three intersecting bars: a single-room-deep main volume that captures the views, a service wing and a perpendicular upper level that hovers to create a sheltered dining terrace below. Guided by museum-quality principles, long stretches of UV-protected wall space give way to precisely framed vistas. Board-formed concrete walls mitigate winter winds, while the exterior is clad in enduring, low-maintenance Vermont slate. Embracing sustainable luxury, the three-bedroom, two-study home features triple-glazed windows, super-insulated envelopes, and geothermal climate control.

Tullar Farm is a rare opportunity to own a remarkable piece of Berkshire history--where timeless architecture, modern comfort, and natural beauty come together across 67+/- park-like acres in South Egremont. With three distinctive residences, a mature specimen tree farm, spring-fed pond, wooded walking trails, and captivating distant mountain views, the estate offers an extraordinary sense of privacy and place, while remaining just moments from restaurants, shops, and the many cultural and recreational offerings of the Berkshires. At the heart of the property is The Tullar House, a substantial 6-bedroom, 5,000+ square-foot antique Dutch Gambrel dating to 1761 and reported to be the second-oldest house in Egremont. Carefully preserved while thoughtfully adapted for modern living, the

Welcome to Meadow Wood This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lily pond, terraces, pastoral views, and privacy. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/ potting room and a studio space. The Gunite pool is surrounded by an espaliered apple tree fence & generous stone terrace. The large screened pool house includes 1/2 bath, outdoor shower, kitchenette & massive fireplace. Further from the house is the barn complex consisting of a 2 bedroom apartment with yard & patio, separate studio apartment and 4 garage bays, a barn, and cutting gardens.

A rare French Manor estate gracing one of South Berkshire's most scenic and sought-after country roads, this extraordinary 45+/- acre sanctuary is awaiting buyers final finishes and offers unmatched privacy, panoramic mountain views, and a setting of timeless beauty. Bordering protected state forest, the property unfolds across rolling meadows, tranquil ponds, and a gently flowing brook--creating a secluded retreat that feels worlds away, yet remains moments from the cultural heart of the Berkshires. SEE LIST OF ITEMS TO BE FINISHED IN DOCUMENTS.

Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket doors that provide charm and flexibility. Every detail has been curated to embody warmth and sophistication, creating an inviting ambiance that is both refined and welcoming. Ideally located just moments from downtown Lenox, Tanglewood, a local municipal airport and a charming farm, HomeFarm, directly across the street. Highwick offers an unparalleled sanctuary in the heart of the Berkshires!

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody & Stearns, this 16th-century Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.