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.

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

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.

As seen in Architectural Digest, this meticulously reimagined 1875 farmhouse compound unfolds across 11.5 lush acres on a quiet, bucolic dead-end country road, with protected views. Brought to life in collaboration with AD100 design firm Sachs Lindores and landscape design by Judy Murphy, the property is full of historic character with refined modern comfort. The compound includes a four-bedroom, four-bath main house, a one-bedroom, one-bath guest house and a large barn relocated from New York State. Outdoors, a private heated in-ground pool, gas-fired pizza oven and fire pit, orchard, fenced vegetable garden, and poolside outdoor shower create an idyllic country retreat. All systems were replaced in 2019, with high-speed internet and central A/C, just minutes from Great Barrington.

SUN DRENCHED MODERN HOME WITH POOL AND PRIVACY, A SHORT WALK TO THE WALDORF SCHOOL AND THE GREEN RIVER. This gorgeous property consists of 2 separate building lots and is on a lovely, quiet road ideal for walking and biking, and only 7 minutes drive to Guido's. The house, which has been recently completely reimagined and added onto, is an ode to sophistication, beauty, and practicality. 4+ bedrooms, 3.5 baths, Open plan sun filled kitchen/dining/living, walk in pantry, generous entry with built in benches and storage, TV room with custom shelving, bright office, and a loft like studio above the 3 car garage. For outdoor living, the mahogany deck runs along the back of the house and connects to a comfortable screened porch with plenty of room for dining and lounging.

NODIN FARM. A spectacular 130 acre property, rich in history, and lovingly maintained by only four owners during the past 225 years. Perhaps the word ''Farm'' understates the true magnificent character and charm of this outstanding home that has been carefully expanded and preserved and updated with premium appliances, the highest quality cabinetry, and with state-of-the art heating and AC equipment. True to its history the ''farm'' encompasses a large barn complex with one wooden and one main gambrel roof brick barn. There is a separate brick ''bull barn'' with architectural plans for a guest house. Did I mention the 7 bay brick car garage with an office and a gym? The entire barn complex was repaired and shingled with premium asphalt shingles in 2024! This is a must see property.

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.

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.

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.

Set on 35.6 acres in the heart of Alford, this exceptional estate offers privacy, sweeping western views to the Catskills, and direct access to the Tom Ball Mountain Trail, abutting hundreds of acres of protected land. Located just minutes from Great Barrington and approximately 10 minutes to the Massachusetts Turnpike, the property combines seclusion with convenient access to the region's top destinations. Built in 2003 and thoughtfully updated beginning in 2020, the main residence spans approximately 9,400 square feet with 5 bedrooms, 5 full baths, and 3 half baths. The home is designed for both grand entertaining and comfortable daily living, featuring expansive living areas with a fieldstone fireplace and full bar, a custom mural highlighting local landmarks, and a gourmet kitch

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.

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.