Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it offers plenty of room to entertain and relax. The large cook's kitchen is perfect for preparing meals for large gatherings, while the heated sun room provides a cozy spot to enjoy your morning coffee and take in the stunning views of the surrounding fields. This home also features 5 spacious bedrooms (primary with en-suite, four jack-and-jill), each with their own unique charm and character.

Some homes are purchased. Others become part of a family's legacy. Welcome to 109 Under Mountain Road. There is something unmistakably special about a Berkshire summer- evening stroll to Tanglewood, morning coffee overlooking protected meadows, or relaxing on the patio as the music of the Boston Symphony Orchestra drifts softly through the evening air. Bathed in extraordinary natural light, this architect-designed home embraces its breathtaking setting with soaring walls of glass, vaulted ceilings, exposed beams, skylights, and exquisite gardens. Thoughtfully designed for gracious entertaining and comfortable everyday living, the spacious first-floor primary suite allows you to enjoy the home with ease for years to come, while family and friends gather in beautifully appointed guest rooms.

Seize this rare opportunity to complete a 55-unit expansion within an existing condo association. With a majority of infrastructure in place and high demand in the area, this semi-completed development offers exceptional return potential. Originally approved in 2002 as a 40B development, this project is ready to be picked back up where it left off. All current permits, site plans, and engineering documents on hand shall be transferred as part of sale, providing a streamlined path for completion. Don't miss the chance to capitalize on this ready-to-go project in desirable Great barrington.

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.

A UNIQUE NEW HOME UNDER CONSTRUCTION IN THE HEART OF STOCKBRIDGE, MASSACHUSETTS Historic Living: In an era of increasingly homogenized architecture, this extraordinary timber frame Dutch house replica offers something rare: a true sense of place. Rooted in the early traditions of the surrounding Housatonic Valley, the home is a thoughtful homage to the region's European heritage--crafted with authenticity, integrity, and many locally sourced materials designed to age gracefully. Inspired by early 18th-century Dutch design, the residence features massive anchor beam construction, a steeply pitched roof, thick plank floors and richly textured materials that develop warmth and patina over time. Traditional casement windows with deep sills, exposed timber framing, and masonry fireplaces

Expertly crafted by Gregg Wellenkamp, this stunning property pairs everyday wellness with sweeping views. Begin your morning in the private fitness and pilates studio, complete with steam shower. The primary suite is a retreat unto itself, with two separate sleeping spaces, a spacious walk in closet, and two private bathrooms. Three additional en-suite bathrooms round out the home, each framing its own sweeping view. Entertain on the oversized deck, where sunsets are the main event. Inside, the chef's kitchen anchors the home with custom hardwood cabinetry, recycled glass countertops and high end appliances, while a custom fireplace brings warmth to the main living area. Mature, professionally landscaped grounds frame the home. Enjoy nearby Lake Garfield from this Berkshire masterpiece.

Perched high on one of Egremont's most desirable country roads, this exceptional estate offers breathtaking panoramic views stretching more than 30 miles across rolling meadows, mountain ranges and Prospect Lake. Facing south and surrounded by approximately 15 private acres, the property combines natural beauty, privacy and convenience just minutes from downtown Great Barrington and major Berkshire attractions. This contemporary residence was thoughtfully designed to capture the spectacular scenery from nearly every room. Soaring ceilings and sun filled living spaces create a warm and inviting atmosphere throughout the home.The residence features:5 bedrooms,5 full and 1 half bathrooms,A dramatic great room flooded with natural light,Three fireplaces, A charming three-season screened porch

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.

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.

Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living experience unlike anything else on the market. The first floor features an impressive great room with soaring timber beams, an elevated Malm fireplace, and floor-to-ceiling glass that captures the surrounding vistas. A gourmet kitchen imported in its entirety from Germany anchors the main living space with exceptional craftsmanship and modern sophistication. Radiant heat throughout the main

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

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 house that stops people mid-sentence! At the Lenox/Stockbridge line on the western shore of Lily Pond, discover this one-of-a-kind home. A rare architectural sanctuary where nature, privacy, and imagination quietly redefine Berkshire living. Embraced by woods and water, this 4br, 4ba contemporary is bathed in extraordinary light. Enter and you'll find over 5000 sf. living space. Bedrooms are spaced apart for maximum privacy; the open living area takes center stage for entertaining. Post-and-beam great-room/atrium w stone floor. Open kitchen w custom cherry cabinetry. First floor primary suite. Outside, enjoy over 4 acres of privacy: lawn, gardens and your own nature trails! Deeded rights to the White Pines beach on Stockbridge Bowl. Walking distance to Tanglewood! Must see!