Your private Berkshire retreat! Sweeping views of Squaw Peak, surrounding mountains, 42 beautiful sub-dividable acres with trails, seasonal brook, room for pool, tennis court, family compound. Warm, welcoming 4BR, 4.5 bath, home with room for family, friends, gathering or quiet escapes. Sun-filled fireplaced LR with picture window, cozy window seat framing the view; elegant formal DR with window wall and fireplace. Spacious chef's kitchen with island, dining area, TV area, comfy wood stove, leading to the large screened porch and expansive deck--perfect for morning coffee, summer dinners or simply relaxing. 3 main-level BRs include ensuite primary. Above-grade LL offers office, 4th BR, bath, inviting fireplaced family room. 2-car garage. 1 mile to downtown Great Barrington.

Nestled among spectacular rhododendrons that burst into bloom each spring, this architect-designed contemporary home offers a seamless blend of natural beauty and timeless mid-century modern inspiration. Designed byarchitect Andrew Daland, the residence features expansive windows that frame peaceful pastoral views and fill the home with natural light. Designed for comfortable one-level living, the main floor includes the primary living spaces, while the lower level provides exceptional accommodations for family and guests with two bedrooms each with en suite full baths, and a spacious family room. The open-concept great room boasts a cathedral ceiling, a fireplace, built-in bookcases, and flows effortlessly into the kitchen. . . .

Located in a ''hidden'' neighborhood behind a stonewall entrance, this newly built home offers tranquil living just 5 minutes from the heart of Great Barrington. The spacious farmhouse front porch is the perfect spot to enjoy quiet mornings or gather in evenings with family and friends. Light-filled and open, the main level features an elegant living and dining area framed by French doors, a gas fireplace, and a chef's kitchen designed for effortless entertaining. Also on the 1st floor, a guest bedroom suite enjoys a private bath with shower and soaking tub. On the 2nd floor the generous primary suite offers dual walk-in closets as well as an luxuriously oversized shower and soaking tub.

Winding country roads lead you to this secluded sanctuary on Rote Hill Road--an address synonymous with estate-caliber living and undisturbed serenity. Crafted from the ground up by its original owner, this beautiful post-and-beam residence stands as a profound labor of love on over 15 private acres. From the main-level wood floors hewn from a single stately oak tree found on the property, to the dramatic two-story stone fireplace, the home was brought to life in collaboration with local craftsman. Car collectors and hobbyists alike will appreciate the custom-built, aprox. 1,080-square-foot barn/workshop.

Originally a gift from Williams College President Harry A. Garfield, the son of United States President James Garfield, to his daughter, this elegant and gracious South Street home is available for the first time in over thirty years. Fine architectural details abound with beautiful crown moldings and woodwork, six panel doors, gleaming oak flooring, abundant built-in shelving and cabinetry, and large, light-filled floor-to-ceiling windows. The spacious entrance hall opens on your left to a stunning wood-paneled library lined with ample book-shelving and warmed by a corner fireplace with wood mantel and slate hearth. Ahead, the lovely living room, with another handsome fireplace with decorative mantel, side pilasters and marble hearth, provides access to a covered slate side terrace.

Professional Light Industrial Office Park located in Central Berkshire County for ease and 7 mnute access to Major Routes 7 & 20 and Routes 8 & 9. Heavy Trucking Hauling, Ideal for Mail Distribution, Customer Service Offices & Entrance, Warehouse Space, Two Loading Docks, Room for Expansion on the Second Level. 23' -26' Ceiling Height. Refurbished Front End Office Space, Conference Room, Lunch Room, Private Offices, Conference Room, Employee Break Room, Mechanic Room in Warehouse. Redesign Options available for Individual Use upon Request. City Water,Sewer, Natural Gas. Rear Loading Docks, Reception Area, Bus Line and close to Major Routes for Ease of Transportation to Albany or Northhamptom 40 miles Pittsfield Amtrak Station 3.5 Miles.

LOCATION, LOCATION, LOCATION. This terrific home is in low-tax Egremont, setback from road, & is a short walk to French Park which sports new tennis/pickleball courts, a playground, hiking trails, a basketball court, and a dog park. The town also features two of the more popular restaurants in the Berkshires. But, what about the house? This well maintained 4 bedroom/3 bathroom home is wheelchair accessible, and meticulously maintained. There is an in-apartment that might be rented as an apartment or a professional office. Ever been inconvenienced by a power outage? Not at this house because it has a 10kW generator. Worried about roof conditions? Not a concern at this house. The steel roof should be good for another 40 to 50 years. Schedule a showing today! SEE MORE...

Exceptional Federal style reproduction farmhouse located in a peaceful setting on a scenic country road. Offering 3-4 bedrooms, 3.5 bathrooms, beautiful hardwood and marble floors. The kitchen with Viking range, custom cherry cabinets, granite countertops and walk-in pantry opens to a family room with a brick Rumford fireplace. The formal dining room opens into the living room. There are French doors to a heated sunroom that connects to a barn/garage with 2nd floor great room and full bathroom. The grounds include a bluestone patio and Goshen steps to the home. Property setting has mature landscaping and perennial gardens. Adjacent undeveloped 2.5 acre lot included.

Rarely will you see a beautiful, undisturbed major land parcel totaling 118 acres anywhere in Berkshire County. This parcel has 91 acres in Richmond and the remaining 27 acres in West Stockbridge. The land is bisected by Furnace brook. There are wetlands in one section. Property is currently in Chapter 61A Forest Management.

Loft 402 is one of Greylock WORKS' most sought-after residences: a large, south-facing 2BR | 2BA + Study Berkshires loft with soaring 16-foot ceilings, luminous all-day light, and sweeping views of the hills. Set within the region's most celebrated mill conversion, this exceptional home blends architectural authenticity with contemporary design in a way that defines modern Berkshire living. The expansive living and dining area features regionally sourced schist countertops, gorgeously restored original hardwood floors, and hand-burnished structural elements that anchor the home in its mill history. South-facing windows flood the space with natural light and frame tranquil hill views that shift with each season.

Excellent 8-Unit Investment Opportunity-5 minute walk to the Lake! Clean, well-maintained multifamily property featuring 8 total units with separate utilities. Each unit includes central A/C. Property offers private, dedicated parking for tenants. Prime location—just minutes from major hospitals, large employers, shopping, and public transit. High-demand rental area with strong occupancy history. Ideal for investors seeking turnkey income with upside potential. Great long-term hold in a desirable neighborhood.

Looking for a Berkshire getaway that can help pay for itself? This unique 6-unit property in Lee offers the rare opportunity to enjoy a spacious 4BR/2BA home of your own while generating income from 5 additional apartments. Full of character, the property retains many of its beautiful original features with significant updates, including renovations to 5 of the 6 units, a newer roof, updated electrical and newer heating systems. Set on a spacious property with ample parking, public water and sewer, and separate utilities, it offers tremendous flexibility for seasonal, short-term or year-round rentals. Centrally located near the Mass Pike, downtown Lee, Outlets, Tanglewood and all that the Berkshires have to offer. An ideal combination of Berkshire lifestyle, character and income potential!

A rare opportunity on Lake Garfield, this mid-century A-frame and two-story barn are being offered for the first time since the home was built in 1965. Renovated over the years, the home features a dramatic cathedral-ceilinged great room with a wood-burning fireplace, a wonderful kitchen with butcher-block countertops, three bedrooms, two full baths, and a comfortable TV room in the second-floor loft. The property comprises two separate parcels: one with the house and barn, and the other providing direct waterfront access. Long considered one of the Berkshires' most desirable lakes, Lake Garfield has been the setting for generations of cherished summer memories. Now, a new owner has the opportunity to create a distinctive lakeside compound and begin a tradition of their own.

Cross the charming historic-style covered bridge and enter a world of privacy, nature, and endless possibilities. This remarkable 94-acre sportsman's estate offers river frontage on the Farmington River, expansive woods, trails, and room to roam. At the heart of it all is a spacious split-level home with 3 bedrooms and 2.5 baths, featuring fresh paint, new flooring, and a new roof. A 5-bay barn/garage provides incredible space for vehicles, equipment, hobbies, and toys. A separate mobile home offers flexible additional space for a studio, guest quarters, office, or creative retreat. Whether you're seeking a private Berkshire escape, outdoor adventure, or simply a place where the woods are truly your own, 132 North Main Road is a rare opportunity to own your very own Hundred Acre Wood!

A Truly Inspired Berkshire Retreat. The perfect home to relax, create, and be inspired, this remarkable Egremont property offers an exceptional blend of luxury, comfort, and creativity--truly unlike anything else on the market. The main residence features three spacious bedrooms and three full baths, enhanced by radiant in-floor heating beneath stunning reclaimed ancient teak floors. The thoughtfully designed first-floor primary suite serves as a private sanctuary, complete with direct access to a personal sauna, hot tub, and greenhouse--an ideal setting for rest and rejuvenation. Outdoors, the property transforms into a private resort. A heated Gunite pool is surrounded by lush, curated gardens, elegant stone patios, a fire pit, and a charming gazebo. A dedicated pickleball court adds

Privately sited across 10.37 park-like acres, this fully updated residence stands as an elevated countryside sanctuary, positioned moments from historic Rhinebeck Village and ten minutes from the Taconic State Parkway. The interiors express a refined architectural warmth, anchored on the main level by a primary suite with full bath, a striking floor-to-ceiling stone fireplace with an integrated wood stove, and a thoughtfully updated chef's kitchen designed around a generous central island. The upper level offers private guest quarters featuring two spacious bedrooms, a full bath, and a dedicated laundry room, while an attached two-car garage affords subtle everyday convenience.

Step into history at 1001 Canaan Southfield Rd, a rare 1797 Colonial estate set on over 23 breathtaking acres of mature, landscaped grounds. This extraordinary property features two serene ponds with fountains, over 300 feet of classic stone walls, and the scenic Umpachene River winding through the land. Extensive landscaping, stone patios, and picturesque outdoor spaces create a private retreat unlike any other. The home offers 4 bedrooms, including a spacious primary suite, blending timeless character with natural beauty. Included are three separate parcels, with an additional lot located across the street, offering endless possibilities for expansion, recreation, or investment. A truly one-of-a-kind Berkshire property rich in history, charm, and unmatched natural surroundings.

Properties of this magnitude and character are becoming a true rarity in today's market. Brookmede Farm, isn't just a listing; it is a magnificent blank canvas of 22 beautiful scenic acres, defined by sweeping mountain views and a profound sense of quiet serenity. From the moment you arrive, the silence and the scale of the landscape invite you to imagine the unlimited possibilities. Whether you envision a world-class equestrian estate, a sustainable organic farm with cows and chickens, or a sophisticated multi-structure family compound, this land provides the space and the soul to make it a reality. Standing as a centerpiece to this vision is a towering, three-story Timber Frame barn. With its incredible volume and structural presence, it offers a

Four-bedroom homes are a rarity at Coldbrooke, where most residences offer three. This one combines that hard-to-find layout and one of the community's more generous floor plans with a location beside the Miraval Berkshires resort and the historic Wyndhurst estate, putting world-class spa, dining, and golf just steps from the door. Inside, vaulted ceilings and an open layout fill the home with light. A thoughtfully updated kitchen anchors the main level, opening to a spacious great room with adjoining dining and living areas built for gathering. Out back, a screened porch and deck overlook the golf course, an easy setting for summer cookouts or a drink after a round.

A once-in-a-lifetime opportunity to build your dream home on a large waterfront parcel in Lenox. This spectacular 14-acre property offers privacy, tranquility, and direct frontage on beautiful Laurel Lake while remaining just minutes from downtown Lenox, Tanglewood, shopping, dining, and all the Berkshires has to offer. Enter through the stone and metal electric gate, cross the stone bridge, and arrive at a cleared, manicured homesite ready for your custom estate or compound. A scenic boardwalk winds to your private dock and lakeside sitting area. Truly a rare Berkshire offering combining natural beauty, convenience, and waterfront living.