Introducing 
FREE QUARTER FARMNearly 1,500 Acres | Sandisfield, the Southern Berkshires | $4,500,000Miles of private trails for hiking, hunting, fishing, horseback riding - your own wilderness preserve134+ acres not in conservation with 1,489 feet of road frontage - craft your legacy5BR/5BA timeless home built for this wildly beautiful placeStand 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.

East Hill Farm offers 227 acres of protected quiet, anchored by the elegant 1798 Thomas Shepard House. A private hilltop world.Main house: Georgian-Federal; 5 BR, 5.5 BA, ~5,000 SF; 5 fireplaces; unusually high ceilings, wide-board floors, antique glass, rooms that hold the light, views that connect. Graceful, welcoming.A complete estate that also can be a working-farm or equine property: barns + outbuildings, pastures, private trails + roads, 4+ acre pond, gardens + orchard, pool, pool house, greenhouse, tennis.A vast former Arabian horse barn, now guest compound, or for you to reimagine. Preserved with rigor, lived in with joy, and rooted in the land and history that defines the Berkshires. Read the whole story. Read the whole story

Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of future for generations to come. Set on 67 +/- park-like acres this property offers 3 unique residences, a mature specimen tree farm, a spring-fed pond, wooded walking trails, and captivating views of the distant mountains all just a stone's throw away to restaurants and shops. At the heart of the estate stands The Tullar House; a well-preserved and substantial 6-bedroom 5,000+ sq ft antique Dutch Gambrel dating back

Experience a rare Zen-inspired retreat in the heart of the Berkshires, brilliantly designed to exist in harmony with its natural surroundings. Set on nearly 120 acres of protected land with striking rock outcroppings, sweeping mountain views, and frontage along the Williams River, this architecturally significant contemporary offers a true sense of privacy, tranquility, and escape- all just minutes from downtown Great Barrington. Designed by renowned architect Steven Haas and constructed of steel, glass, concrete, and wood, the main residence is defined by dramatic volumes and German Sorpetaler door and window systems that dissolve the boundary between indoors and out.

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 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. It is awaiting buyers final finishes.

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!

Majestic 71 acre Tudor Estate atop Tom Ball Mountain in the quaint hamlet of Alford, MA. Enjoy total privacy and breathtaking views from nearly every room. The main house features 5 en-suite bedrooms, a gourmet kitchen, formal living and dining rooms, den, family room, gym, billiard room and massage room. A separate 2-bedroom Guest House offers beamed ceilings and full amenities. Manicured grounds include an infinity pool, hot tub, pool house with full bath, tennis and pickleball courts, 7 garage bays, and a barn. State-of-the-art lighting, whole-house generator, smart tech, and security. Fully furnished and ready to enjoy.