Extraordinary and expansive estate property near the top of the hill on prestigious and desirable Bulkley Street. Consisting of three separate parcels over 11+ acres, this offering provides a rare opportunity to acquire an expanse of gorgeous acreage within minutes of Williamstown center, Williams College, the Clark Art Institute, the new Williams College Museum of Art, and close by the 2600 acres ecological reserve, Hopkins Memorial Forest. The four bedroom, three and one half bath main house, sitting atop the hill, has been beautifully updated while maintaining its gracious character and features an array of public spaces both intimate and open, with an especially appealing four season sunporch overlooking the lovely gardens, graceful and sweeping grounds, and the distant ridgeline.

Set in the heart of Old Chatham, this classic Colonial rests on an exceptional 101-acre landscape of rolling pasture, woodland, and wide-open country views. From its elevated vantage point, the home looks out over a 2.5-acre swimmable pond, open fields, and a stretch of Hudson Valley scenery that changes beautifully with the seasons. Flooded with natural light, the seven-bedroom home offers generous space to gather and unwind with family and friends. At its center, the kitchen and living areas are designed for connection. The open kitchen and dining space flows easily into the main living room, where a stone fireplace anchors the room and creates a natural place to come together after a day outdoors. Stainless steel appliances and ample workspace make the kitchen as functional as it is

A Landmark Berkshire Estate of Extraordinary Provenance, the Oliver Wendell Holmes summer cottage. Set on 15 private acres in the heart of the Berkshires, a rare American legacy estate commissioned in 1847 as the summer residence of renowned physician, poet, & author Oliver Wendell Holmes Sr. Two centuries later, this extraordinary property remains a testament to architectural elegance, literary heritage, & timeless craftsmanship. The offering preserves original hardwood floors, intricate millwork, & the grandeur of a distinguished era. Its storied halls welcomed literary icons including Longfellow, Melville, & Hawthorne. Surrounded by exceptional privacy, Holmesdale is more than a residence, it is an irreplaceable American landmark

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare colonial charm. The legendary c. 1776 estate boasts a well maintained main residence/Inn, three cottages and a great barn for entertaining. The residence/Inn features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. Its dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that caters to both intimate family gatherings and grand celebrations. For the serious equestrian, the estate offers multiple barns and paddocks. Training is a year-round luxury thanks to the 6,000 square foot heated indoor arena, which includes an owner's apartment and viewing area--and a professional-grade outdoor ring.

Brookside Acres awaits your arrival, privately sited on 15 + acres, on one of the most scenic country roads in Richmond. This exquisitely renovated Contemporary offers a plethora of amenities for the person looking for a private retreat for a few or someone that likes to entertain and gather with a crowd. From the moment you enter your monitored driveway you realize Brookside Acres has it all; beautiful woodlands, acres of groomed lawn, established flower gardens, mature landscaping and the private stone pathway to the running stream side patio. Owned solar system, a whole house generator, a lighting system that lights up the house with an evening arrival, in ceiling sound speakers on the main level and pool area...no detail has been left undone.The interior of this 5 br, 5 bth

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.

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.

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.

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.