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.

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.

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 - Click!

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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.

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.

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.

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

The Definition of Ultimate Privacy! A masterpiece of a home invites the most fastidious prospect. Built with the utmost dedication to detail that no item too small was overlooked. The ability to expand and build to your heart's desire is here. Perhaps a pool, tennis court, even a football field is within your reach. This property consists of 200+ acres, a 6,700 sq. ft home, Primary En-Suite on the first level, 2 bay garage, Extra Large Enclosed Barn capable of sheltering a bulldozer with a private space up above. Nestled in the foothills of the Berkshires on beautiful winding country roads. A lovely vineyard just around the corner, a short 25 minute drive to BDL International airport and just under 3 hours to NYC and 2 to hours to Boston. Come make this your dream get-away!

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.

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!

Offered with Seller Financing, this Majestic Tudor Berkshire Estate sits on 71 Acres atop Tom Ball Mountain in quaint Alford, MA. Privacy and Breathtaking views. Formal Entry and Foyer. Stately Living Room and Dining Room. Great Room with Gourmet Kitchen. Den, Family Room, Gym and Massage Room. 5 en-suite Bedrooms in the Main House. 2 Bedroom Tudor Guest House w beamed ceilings and full amenities. Manicured grounds, infinity Pool and Hot Tub, Pool House with full Bath, Tennis Court and Pickleball Court. 7 Garages and additional Barn. Exquisite architectural touches, state-of-the-art home technology and security, in the most peaceful of surroundings. Easy access by road, rail and private Airport. Close to Tanglewood and Berkshire attractions. *Fully Furnished and ready to enjoy.

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.