Once the cherished country residence of acclaimed wildlife artist & tableware designer Lynn Chase, this gracious 4-bedroom manor dates back to 1850, and had a major update in 1998. Set on 5.96 acres of rolling pasture framed by stone walls, this charming estate is spacious but manageable, complete with a garage/horse barn, larger barn, fenced paddocks, and a small pond. Rich in character and period detail, this Greek Revival home boasts wood paneling, exposed beams, built-in cabinetry, and antique flooring. The 1st floor offers plenty of space for entertaining, with a formal entry, spacious receiving room, library, and parlor - each with working fireplaces. A 1998 addition introduced a bright open kitchen/dining area with French doors opening onto an elegant south-facing bluestone patio.

Step into a piece of history with the once Iconic Card Lake Inn Tavern, now transformed into a stunning residential haven in the heart of downtown West Stockbridge. This property offers not only a prime location but also an exceptional living experience, combining modern amenities with charming historic character. The building houses six completely renovated high-end apartments, each thoughtfully designed to meet the needs of modern living. These units feature elegant wood floors and come equipped with all necessary appliances, including dishwashers and in-unit laundry facilities. Central air conditioning ensures comfort year-round, while tiled double-sink bathrooms add a touch of luxury. Ample storage space is available in each unit, allowing residents to keep their living areas tidy.

This impressive Italianate residence, dating back to 1880, has been meticulously restored for modern, turn-key living. This coveted location with a private backyard and off-street parking neighboring Talbot & Arding - offers a rare sense of quiet just a few blocks from the restaurants, galleries, and shops of the exciting city. Spanning three thoughtfully renovated stories, the turn-key property includes a large eat-in kitchen, sunny, and bright living and dining room, and a large mudroom. The top two floors contain bedrooms and bonus spaces ideally suited for year-round living and guest suites. The showcase of the home is the gorgeous staircase with a curved banister that enhances all three floors. Outside, there is a private backyard and side patio and a staircase to lower Hudson.

This classic 1920's masonry commercial building was the original Woolworth's Department store in Pittsfield's central downtown. At the corner of North Street and Depot Street, Crawford Square presents four prominent storefronts. Inside the main entrance is a high-ceiling wide public corridor housing a ''mini-mall''with six fully occupied tenants including a restaurant, a health club, a popular barber shop and a real estate offices. On the second floor of this sprinklered and elevator building is the headquarters of 1Berkshire, the long-standing Chamber Of Commerce for the county and a variety of smaller professional offices. The basement is also well utilized with a fine arts custom printer and a contemporary tattoo studio. The diverse mix of tenants offers a strong cash flow and is

A rare opportunity awaits! Own a developable mountain top in the Berkshires! Your 4B/2.5Bath home is 10 years young with custom kitchen and baths. An unobstructed view of Goose Pond and beyond, it's a 56 acre sanctuary mostly comprised of Oak and Mountain Laurel forest with trails. Enjoy a 40 mile view to Mt. Greylock and views of October Mt. State Park, and boating on Goose Pond (@1/2 mile to the the boat launch). Also viewable is Tyringham Valley, South Lee and Bear Town State Forest. Build another home on the property (ADU or a larger home and keep this as your guest house). Possibilities are endless here! Already in place is a 28'X48' building with 14' ceilings with it's own electric service, (could also be used for horses) and a small barn near the house. A one of a kind offering.

The equestrian elegance of this 55 acre property starts at the gated driveway. Perched on the hilltop is a fully equipped custom build multi use barn entirely heated by radiant floor heat and includes 8 14x14 stalls w/ autowaterers perfect for the breeder or veterinarian. Includes kitchenette, office, laundry and bathroom. Also included is a heated equipment shed and workshop, a heated drive through aisle for large trucks, washstalls and more! The grounds include 8 paddocks with waterers, an exercise track, 3 large pastures. A second barn offers 12 additional stalls. The meticulously kept grounds is professionally landscaped and a covered wrap around porch greets guests into the home. Kitchen has quartz counters, GE profile appliances and a slider out to a large patio

HISTORIC BERKSHIRE FARM Best bargain in the Berkshires! Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns and maintenance building. 161 acres with stunning views, mountain paths, and Jim Kelly's stunning giant stonewalls throughout. Gorgeous New England marble stone farmhouse built in 1780, with modern addition featuring vaulted ceiling and massive windows which flood the dining and kitchen area with light. Enormous custom built hearth and fireplace, mahogany full bar, artisan-made bookcases, wrap-around deck. Close to Williams College and Jiminy Peak. The property offers swimming in two private ponds, 6 bay carriage barn with second floor for offices, studios., or storage.

A lovely, winding approach to this gorgeous 21-acre estate ensuring serenity, privacy, and the beauty of living in the country. The main house includes 3-4 bed, 2 1/2 bath. An impressive architect-designed guest house has 2 ensuite bedrooms with balconies, dramatic exposed beams and vaulted ceilings. The guest house is an extraordinary place to host family and friends both winter and summer. With views of Tom Ball mountain, this property is a combination of gardens, fields, forest, and offers several outdoor living spaces, including a stone patio off the kitchen. A short jaunt to No. Six Depot, The Foundry performing arts, and Tanglewood. Central to Gt. Barrington, Lenox and Stockbridge for theatres, boutiques, skiing, golfing, museums and so much more at your fingertips!

A rare opportunity to own the most popular place in town. The iconic Hot Dog Ranch, an award-winning restaurant with decades of very profitable history, totally renovated building, large parking lot, full liquor license, lottery, seating for 99. ,fully staffed. Truly turnkey. With a menu that rivals the Berkshire finest restaurants, this is not your ordinary hot dog joint.

Surrounded on three sides by Nature Conservancy-protected land, 173 Hillsdale Road is one of the most private and extraordinary estates in the Berkshires -- a handcrafted sanctuary where the wilderness is literally your backyard. Moose, deer, bear, fox, and turtles roam master-gardened grounds tended with rare care; fruit trees, a garden pond, mature perennial beds, and lush native plantings make every season a revelation. Custom-built in 2000 from timber milled directly on the property, this 4,842 sq ft home carries an irreplaceable provenance that announces itself at every turn. A native stone fireplace anchors the soaring vaulted great room. An ash sapling banister curves to the interior balcony above. Antique leaded glass casts dappled light across wide-plank floors.

The subject property is a single story office use building that contains 14,440 square feet. Built in 1998, the property is on a slab on grade founda-tion with a decorative block and metal sided exte-rior; there are fixed framed windows and a pitched metal roof. The building has three 10 foot by 10 foot overhead doors and one, 14 foot by 10 foot overhead doors at ground level. The over-head doors are located at the rear of the building; this area is accessible through a fenced in portion of the site that is utilized by the anchor tenant for vehicle and equipment storage ,Spectrum. The interior is divided into two tenant occupied units. Pittsfield Community Television occupies 4,608 square feet of updated office type space and utilizes it as a television studio and office space. This unit

Commercial building in high-traffic location on the corner of Route 7 & 23. Current tenants include Trotta's Fine Wine & Spirits and Manhattan Pizza. All spaces in building currently rented. This price includes Trotta's Fine Wines and Spirits (excluding inventory). Great investment opportunity. The building will not be sold without the business.

Own a Living Masterpiece. Meticulously curated by the current stewards since 2006. This Colonial Revival offers rare fusion of 18th-century authenticity and cutting-edge modern comfort. Designed for both grand-scale entertaining and intimate family life, this c1930, 7,894 sq. ft., Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately fireplaces anchor the formal living spaces. Enjoy panoramic views and privacy from the grand porch overlooking 4 pristine acres. a state-of-the-art kitchen featuring Wolf and Sub-Zero, and no expense spared Geo-Thermal heating/cooling.

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

Just seconds not minutes from the main gates of Tanglewood, this stunning contemporary estate is tucked into a sunlit site surrounded by woodland, offering a rare blend of proximity and seclusion. In a region renowned for its natural beauty, it's almost unheard of to find a home this close to the cultural heart of the Berkshires that also feels so entirely removed.Perfectly positioned for four-season enjoyment of the Berkshires lifestyle--Tanglewood, Lenox village, farm-to-table dining, ski slopes, hiking-this custom-built 2017 home was fully reimagined and entirely updated in 2020 by master craftsmen. Every detail has been elevated to support both elegant entertaining and relaxed daily living.Dramatic ceiling heights and a sun-drenched upper gallery define ... see more

Privacy and tranquility define this exceptional Berkshire retreat. Perfectly sited with generous frontage on the pristine shores of Lake Windemere, this sprawling post and beam residence offers four bedrooms and three and a half baths, blending rustic elegance with timeless comfort. Windmere Lake is a privately owned lake with only 13 homes that have access to it. 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 its absolute finest in the heart of the Berkshires. Only 15 minutes from Butternut ski area, 2.5 hours from NYC.

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.

Hawks Nest Ridge. Quiet privacy on 8.6 acres. Decks, patio, screened porch and pool all enjoy the view and the natural setting. Dramatic open floor plan with walls of windows to the views, soaring stone wood burning fireplace spanning three stories. Cook's kitchen with walk-in pantry. First floor primary suite with gas fireplace and dressing room all abutting library and office. 4 private bedroom suites in total each with their own sitting areas and additional sleeping options. Family room with wet bar and gas fireplace. Exercise room with steam shower. 3-bay garage. A very special retreat with plenty of room for guests and entertaining. Just a short jaunt to dining, shopping, recreational and cultural venues in West Stockbridge, Lenox, Stockbridge and Great Barrington.

Position your business in the heart of the Southern Berkshires with this exceptional 84,380 square foot industrial facility situated on approximately 7.5 acres in Sheffield. This former plastic manufacturing building offers scale, flexibility, and functionality for manufacturing, warehousing, distribution, or specialized industrial operations.