37-acre, ROCK RIDGE FARM, with early mid 20th century roots. Built in 1785, steeped in local history, Property has remained a working and residential farmstead today and reflects the regions long tradition of working farms. Offering a blend of local heritage and timeless New England character. Along with the main house there are several outbuildings that could be renovated, repurposed or redesigned to your vision. Original house boasts multiple living quarters. Continue this as a working farm, wedding venue, country inn or primary residence. Frontage on Dublin Rd and State Rd. Close to Tanglewood, Bousquet Ski-Sport and other cultural attractions. Easy access to routes in and out of the Berkshires. 37 acres that offer a rare freedom to build, invest or preserve something truly lasting.

COMMANDING VIEWS OVER LAKE GARFIELD WITH A STUNNING MOUNTAIN BACKDROP, this beautifully updated home offers charm with modern refinement. Original architectural character has been thoughtfully preserved, while expansive windows fill the home with light and frame the breathtaking scenery. Recently renovated chef's kitchen, first floor primary bedroom, and loads of closet space address today's needs. And could there be any better spot to watch sunsets than the expansive front porch? What's more, a well-appointed suite in the separate carriage house offers flexible space for guests, a home office, or artist's studio. Features include eight private acres, high speed internet, low Monterey taxes, and proximity to the Monterey bathing beach and the incomparable tomatoes at Anna's farm stand.

Nestled beside 900 acres of Alford Springs Nature Preserve, this contemporary colonial is sited on 5.8 acres. Built in 2005 and fully renovated in 2021, it boasts high-efficiency HVAC and hot water, 14GW of seller-owned solar, an open main floor plan, gorgeous kitchen with top-of-the-line appliances, front porch, screened porch, large 2-car garage, and generously-sized rooms throughout. Two spacious additional rooms adjacent to the primary and a guest suite are currently used as a gym and office/studio. Move-in ready with incredible privacy yet 15min to the center of Great Barrington.

A completely transformed barn renovated into a chic home with every modern convenience. Located in the desirable town of Egremont and just minutes from Great Barrington, this delightful property offers long-range pasture views with the Green River just beyond.Thoughtful living spaces for every walk of life featuring a roomy primary suite on the first floor, an additional primary suite that occupies the entire third floor, and inviting spaces for guests and gatherings. Key features include top brands like Waterworks, Wolf, Schluter, Graff, Bertazzoni, and Kohler, along with Danby marble, Italian stone, and oak floors. Every window offers views of the expansive 13.5 acres, fully fenced and lush, with endless possibilities for nature lovers, hobby farmers, or equestrians. Super low taxes.

Luxurious, fully-modernized 1850s Victorian in the heart of Great Barrington. Elegant, four-story 3600 sq. ft. newly renovated clapboard and shingle house with covered porch. Meticulous gut-renovation features chef's kitchen, four+ bedrooms, 4.5 bath, second floor and basement laundry, walk-out finished basement with private entrance and bathroom, perfect for guest suite or professional office. High-end appliances, including 6-burner Wolf stove and Bosch French door refrigerator with two freezer drawers, Bosch dishwasher, wine cooler and microwave in the island. Full-size prep sink in the kitchen island, 36'' farmhouse sink in the main counter. Cabinets are all-wood with soft-close drawers and doors; vented whole-house A/C and heat pump with propane back-up; primary bath with heated floor

Originally built in the 1700s, this historic post-and-beam barn has been thoughtfully renovated over time while maintaining its unique character and charm. A recently installed solar energy system allows for highly efficient living with the potential for an off-grid lifestyle.The home features an open floor plan filled with natural light from numerous oversized windows. A chef's kitchen adjoins the dining area, creating an ideal space for entertaining. With three full floors of living space, the home offers four ensuite bedrooms plus an additional bedroom, providing comfort and privacy for family and guests. Enjoy seamless indoor-outdoor living with a screened porch off the main level leading to spacious decks and a hot tub. The lower level includes a media room and sauna for relaxation

Welcome to Camp Mohawk, a pristine lakefront property in the heart of the Berkshires. Set on Cheshire Reservoir--a serene, largely uninhabited lake--the property offers both privacy and convenient access just off Berkshire County's main north-south route.Once a summer camp, the estate features an existing main house and barns listed on the National Register of Historic Places, dating back to the late 1700s. There are also numerous sleeping cabins that could be restored.Ideal as a private family compound or for development as a spa or resort, corporate or wellness retreat, or condominium, single-family, or retirement community--the possibilities are truly endless. Can be subdivided.

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

Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views to the northern Connecticut hills. 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.

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.

Blue Hill Farm: an 1820 Center Hall Colonial farm and farmhouse in excellent condition on 249 high acres with organic hay meadows and pastureland, an apple orchard, woodlands, gardens, tennis court, a 1970's caretaker/farmer's house and multiple barns. The main house has 6/7 bedrooms and three baths, along with a three-car attached garage. The property consists of seven parcels of contiguous land surrounded by the Umpachene River on three sides. There are long views to the west of the Taconic Range from inside and outside of the home, and a grouping of supportive barns to the south across a very rarely traveled, narrow dirt road. Offered for the first time since 1967, this is truly an unusual and rare offering with development possibilities featuring extraordinary views.

Brooke Astor's COBBLE HOUSEWhere Land, Light, and Legacy ConvergeTYRINGHAM VALLEY BERKSHIRE COUNTY MASSACHUSETTS$3,900,0005,885 square feet7 bedrooms8.5 bathrooms27.9 private acres1909 Harrie T. Lindeberg design2,321 +/- feet road frontageThe Valley That Time ForgotThe drive through Tyringham Valley never fails to quiet the soul. Past stone walls that have marked these fields for centuries, through meadows where The Shakers once pastured their sheep, toward the ancient drama of the Cobble--206 acres of exposed bedrock thrust skyward by tectonic forces that shifted the very bones of the earth millions of years ago. Here you find what Tyringham Valley has always offered--that profound quiet that restores and renews.MORE OF THE STORY BELOW

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.

Come relax amid sweeping pastoral and mountain views in this exceptional retreat designed for both entertaining and everyday comfort. The impressive great room, anchored by a massive stone fireplace, offers a welcoming focal point and flows into a spacious well-designed kitchen/dining area. A screened porch with fireplace overlooks the pool and rolling landscape, creating a seamless indoor-outdoor experience. The first-floor primary suite features a luxurious bath and tranquil views. An exceptional cinema room includes theater-style reclining seats and a half bath. Generous guest accommodations throughout. A private office suite with full bath. Outdoors, enjoy an infinity pool, bluestone patios, lush gardens, a charming pool house -- all just three miles from downtown Great Barrington.

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.

Pine Needles.Built circa 1900 as a Berkshire ''cottage'' in the era of grand summer estates, this historic property blends the dignity of Colonial Revival architecture with the relaxed elegance of an Italian villa and the artisanal detail of the Arts & Crafts movement. Sited on 80 private acres just minutes from the heart of Lenox, the estate offers breathtaking southern views, rolling forest, and a rare level of privacy and provenance.Arrival.Approached via a long private drive, the property unfolds gradually--passing a sun-kissed meadow, through a grove of majestic pines, past a stunning carriage house, before arriving at an inviting courtyard. The house itself is beautifully sited to capture natural light and frame the sweeping mountain and pastoral views.

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!

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 minutesfrom Great Barrington and approximately 10 minutes to the Massachusetts Turnpike, the property combines seclusionwith 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 feetwith 5 bedrooms, 5 full baths, and 3 half baths. The home is designed for both grand entertaining and comfortable dailyliving, featuring expansive living areas with a fieldstone fireplace and full bar, a custom mural highlighting locallandmarks, and a gourmet kitch

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!