Fabulous Property with ponds, rushing streams, huge acreage & a gem of a house. The 220 acres abuts state forest and beautiful Walker & Spark Brooks both run through the property. The 2BR/2.5B home has lovely views of the pond & hills beyond, and was totally renovated to the highest standards in 2023 & 2024. Native stone fireplace, heart pine floors, new kitchen, baths, heating, mahogany decks, outdoor shower, windows & insulation. There is a large post & beam barn plus stone foundations from an earlier barn. The fishing is great and trails have been cleared for hiking and horseback riding. Conveniently located near Tanglewood, Jacobs Pillow and most other Berkshire cultural attractions as well as state forests and wildlife management areas. Under 3 hrs. to NYC, 2.5 hrs. to Boston

A Classic Modern Farmhouse with Incredible Views - This home has been thoughtfully updated to provide a seamless blend of style and comfort. The property features a resplendent in-ground pool, a spacious swim pond, and a three-car garage with an inviting guest suite above. The main residence welcomes you with a charming wrap-around porch and an enchanting screened porch, both perfect for enjoying the dynamic and ever-changing views. The interior is bright and lively, with each space thoughtfully designed to capture the natural beauty of the surroundings. The gourmet kitchen, a convivial hub with a grand stone fireplace, offers direct access to the screened porch and serves as the perfect backdrop for culinary exploration and social gatherings. The first floor also includes a - see more

A Landmark Berkshire Estate of Extraordinary Provenance. 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 and a rare opportunity to become the next steward of Berkshire history.

PRISTINE LAKEFRONT SANCTUARY: Perfectly sited with generous frontage on the shores of Lake Windemere, this sprawling post and beam residence offers lakefront views from every room, with four bedrooms and three and a half baths, blending rustic elegance with timeless comfort. Windmere Lake is a privately owned lake flanked by homes tucked away along the waterfront. Designed for gathering and gracious living, the home provides expansive spaces for family and friends to come together while embracing the natural beauty that surrounds it. Whether enjoying peaceful mornings by the water or hosting memorable evenings in the warm, inviting interiors, this is country living at Enjoy four of the best restaurants the Berkshires has to offer just minutes away.

OFFERED FULLY FURNISHED AND TURNKEY. Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views. The main home, a modernist design collaboration between Bauhaus designer George Giusti and architect Crane De Camp, is a two-bedroom, three-and-a-half-bath masterpiece that features a gym, sauna, and gardens designed by a local landscape architect. For guests, they can choose between the three-bedroom, two-bath Cottage or the one-bedroom Cabin, both of which are intimate and offer plenty of privacy for family and friends. Whether it's poolside by day, trails in the afternoon, or hanging by the fire pit at night, there is something for everyone at this mid-century getaway set in the Berkshire hills and only minutes to Litchfield County

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

EXPANDED CONTEMPORARY CAPE Appointed with elegant detail, masterfully crafted, this stunning home is nestled on over 9 private acres offering 9 rooms, 4 bedrooms, 3 full and 2 half baths. An open floor plan flows seamlessly from the generous living room, featuring a striking coffered ceiling and a fireplace surrounded by natural raw granite, into a large kitchen and dining area perfect for entertaining. A stunning wrought iron detail by Ivan Bailey enhances the staircase.. A media room with glass-paned sliders and built-in bookcases completes the exceptional living space. The first floor primary ensuite is a true retreat, boasting a soaring vaulted ceiling and two large walk-in closets. The second floor offers three additional bed rooms, and two full baths.

At the Lenox/Stockbridge town line on the shore of Lily Pond, sits this architectural gem! Offering a rare combination of privacy artfully aligned with nature and a premier location. Set on six acres within the grounds of the original historic Wheatleigh estate, the property is within walking distance of Tanglewood, the Linde Center, Kripalu and Lenox village. Designed by Berkshire architect David Rothstein, the house is ideally positioned to engage its landscape. Large bay windows invite natural light and frame views of water, trees, and gardens. Custom cherry woodwork adds warmth and craftsmanship. The layout is both flexible and refined. First floor primary suite supports single level living, while 3 additional bedrooms and a library occupy the upper level. Lofts, towers and

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.

Set on 30 private acres bordering Beartown State Forest, this exceptional Berkshire estate offers a rare combination of timeless farmhouse architecture, refined craftsmanship, and complete privacy. Built in 2018, the 4,700-square-foot residence is thoughtfully designed to blend seamlessly into its surroundings, creating a home that feels both elegant and deeply connected to the landscape. Filled with natural light and beautifully proportioned throughout, the home offers four bedrooms, five bathrooms, and inviting spaces designed for both everyday living and effortless entertaining. At the heart of the home, the chef's kitchen features Vermont Danby marble countertops, a spacious pantry, and an inviting breakfast nook that opens to the surrounding gathering spaces.

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

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.

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.

Rare opportunity to acquire a four-building industrial complex totaling approximately 193,037 SF in a centrally located Pittsfield industrial corridor. The property consists of Building A (57,755 SF), Building B (18,125 SF), Building C (59,313 SF), and Building D (57,844 SF), offering a variety of configurations suitable for manufacturing, warehousing, distribution, and industrial users. The main building has 32 offices and conference spaces, plus at least 15 additional spaces throughout the warehouse. Buildings are fully sprinklered and feature clear heights ranging from 8'-30'. The site benefits from two truck-access entrances, providing efficient circulation and logistics capabilities. Building D offers potential for a separate parking area.

''A Perfect Place Farm'' - a Berkshires Masterpiece on 17+ Acres The one you've been waiting for...a preeminent build in a premier location. 37 Main Rd checks off the wish list: sweeping views, modern comforts, privacy, location, and colonial era character, but in an immaculately kept turnkey 2002 home. Located in Tyringham valley, one of the Berkshires' most majestic locations, 37 Main Rd is idyllically sited on the northern slope of Tyringham valley, and faces to the southwest. The expansive front porch, sunroom, and living and sleeping quarters all are positioned to track the sun's daily arc across this picturesque east-west valley.

Position your business for growth in one of Berkshire County's premier industrial locations. Situated on 5.96 acres within the established Downing Industrial Park, 21 Downing Three offers approximately 70,920 square feet of industrial, warehouse, manufacturing, and distribution space.The building is configured into three separate sections, providing exceptional flexibility for various ownership and occupancy strategies. Two established tenants currently occupy approximately 20,000 SF while the remaining space is divided into a 10,000 SF section and a 40,000 SF section. Industrial infrastructure includes seven loading docks, two overhead doors, ceiling heights ranging from 16 to 20 feet, ample parking, a sprinkler system and three-phase power.

Position your business in the heart of the Southern Berkshires with this exceptional 84,380 square foot industrial facility situated on approximately 6.9 acres in Sheffield. This former plastic manufacturing building offers scale, flexibility, and functionality for manufacturing, warehousing, distribution, or specialized industrial operations.

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.