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!

Rare Investment Opportunity: 14-Unit Residential PortfolioWhy buy just one multi-family investment property when you can own the whole neighborhood?Presenting a truly unique real estate package: seven contiguous duplexes situated on their own private street in Pittsfield. This portfolio offers a total of 14 high-demand apartments, providing immediate scale and streamlined management for the savvy investor.Each of the seven duplexes features two spacious units. Every apartment offers a comfortable 2-bedroom, 1-bathroom floor plan. Built in 1986, these structures offer modern construction standards compared to older area stock. Whether you are looking to expand an existing portfolio or make a significant entry into the Berkshire County rental market!

Stunning contemporary nestled in tranquility. The main level boasts a gracious great room with cathedral ceilings, fireplace and walls of windows that wash the common spaces with natural light and bring nature in. Gourmet chefs kitchen with ample storage and dining room with direct access to the oversized porch that features a gas stove for the chillier days. First floor primary en suite with walk in closet, direct access to your deck and primary bath with beautiful textures throughout. The second level has three guest bedrooms and two full baths. Lower level features a large family room walkout, additional guest bedroom and full bath. Two car oversized garage with studio space above that gives flexibility in its use. Private setting with expansive lawn and professionally

Welcome to your ultimate country retreat, where the charm of history meets the ease of modern living. Here, timeless beauty and serenity reign--an escape where silence is broken only by the wind in the fields and the song of birds.The 1828 brick colonial, a masterpiece of its era, has been exquisitely restored to showcase spacious, light-filled rooms that draw the outdoors in, framing views of meadows, a sparkling pool, and the stately barn. The barn itself is a wonder, waiting to be reimagined--perhaps as a guest house, an artist's studio, or a setting for unforgettable gatherings.Surrounded by farms and opening to distant hills, the landscape feels both boundless and intimate. The pool, perfectly placed, invites leisurely afternoons and is graced with its own elegant pool house.

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.

Welcome to the historic Wyandotte Woolen Mills in Pittsfield, MA. This woolen mill operated from 1824 to 1963 in the Berkshires and was one of the oldest woolen manufacturing mills in Western Massachusetts. Currently, the complex is home to 14 businesses engaged in production, distribution, flex, & storage space. The property spans 14.79 acres, including both sides of the river, and comprises 15 buildings with a total of 228,611 sq. ft. of space. 14 overhead doors, 11 loading docks, 3 freight elevators & 10' to 16' high ceilings. The area adjacent to the property is zoned for multifamily housing, making it ideal for residential development with the necessary permits and approvals. The turn-of-the-century construction features chestnut beams and maple and concrete flooring throughout.

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.

Set on 21.5 acres at the end of a long, winding private drive, this extraordinary residence is a true architectural gem--where art, landscape, and modern living converge. Originally designed by Robert McMahon and built by Lou Boxer and later reimagined through a contemporary project by Deborah Reiser of the award-winning RUR Architecture with Hird Design and Construction as the builder, the home reflects a sophisticated, transitional approach to residential architecture and interior design. With five bedrooms and four baths, the home is defined by its dramatic walls of glass, seamlessly framing bucolic country views, a classic red barn, and thoughtfully designed gardens. Natural light pours into every space, creating an ever-changing connection to the surrounding landscape. The kitchen is

Set against the rolling beauty of the Berkshires, Constitutional Hill Farm offers a rare chance to own a truly iconic New England estate. Spanning 196 picturesque acres of hardwood forests and open meadows, this remarkable property blends natural beauty with rich agricultural heritage. Directly abutting the Berkshire Natural Resource Constitution Hill Trail, the land provides immediate access to miles of scenic outdoor recreation.The main residence features 3 bedrooms and 2.5 full baths, complemented by a 1 bedroom, 1-bath suite above the garage--ideal for guests, extended family, or rental income. Inside, the renovated home is filled with timeless character, including wide plank flooring, a classic stone fireplace, and both front and back staircases that add to its historic appeal

Commercial building in high-traffic location on the corner of Route 7 & 23. Current tenants include Trotta's Fine Wine & Spirits and Manhattan Pizza. Great investment opportunity.

44.43 acre parcel adjacent to BJs Club on busy Hubbard Ave. High traffic in this commercial/industrial area. Property is zoned for most any use, as it is IG zone, General Industrial. This would be an excellent place to locate a large cannabis operation, commercial store, business, or multiple smaller shops. Property also is adjacent to Downing III within the Downing Industrial Park.

Located in the heart of Sheffield, 113 Silver Street is a premier manufacturing facility that defines ''turn-key.'' Spanning over 49,000 square feet, this building combines industrial functionality with a warehouse component. The building, originally established in 1957, has undergone additions and modifications over the years.From the ample office area to the expansive production floors and warehouse space, this 7.3-acre property has been impeccably maintained. Its location offers a strategic ''sweet spot'' for businesses requiring proximity to both the New York and Boston corridors without the metropolitan price tag. Ready for immediate occupancy, 113 Silver Street is prepared to house the Berkshires' next great industry leader.

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

17,000 sf, $124.sf, WAREHOUSE/OFFICE FOR SALE IN BOSTON - ALBANY CORRIDOR, AVAILABLE FOR OCCUPANCY EARLY APRIL. .92-acre, Located 1 mile from Mass Pike, interstate 90, convenient access to Boston, NYC, Albany, Hartford. New heat pump, main building, LED lighting and foam insulation. Business has been sold, all merch being removed, shelving can remain or be removed. Features reception area, employee kitchen and break room. 9 private offices and large conference room, 3 half bathrooms, 1 full bathroom plus steam room and exercise room. 3 overhead doors, 1 is loading dock, 2 are ground level.

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.

A RARE BEAUTY ON HISTORIC YALE HILL! Discover an historically significant gem in this perfectly renovated home! Peacefully tucked away from it all, yet close enough to enjoy a stroll to town, tennis, Library, golf & restaurants.Chef's Kitchen, large flexible living spaces, 4 Bedrooms, 4 Baths, tall ceilings and charm galore. The Mill House, transformed into a cozy Guest quarters, with 3 Bedrooms,, 3 Baths, has a lovely brookside courtyard w/Pergola, rustic charm maintained. Quiet your mind and embody perfect country living. Overlook the Kampoosa Brook, with private swimming area from your backyard! Cultural & recreational activities nearby. Great income potential. Solar powers Main house, car charger & Mill House. A MUST SEE!

This historic farmhouse, originally built in the 1790s, underwent a complete renovation in 2012, including a new foundation, septic system, roof, updated plumbing and electrical, 5-zone heating, central air, and other modern systems. In 2022, a new well and a boiler for radiant heat were also added.Step inside to find timeless Colonial charm--exposed beams, three original fireplaces, and gorgeous antique floors--seamlessly paired with an expansion which added a large family room with a fourth fireplace, finished basement storage, mudroom, first-floor laundry, and partially screened wraparound porch.

A rare Berkshire offering w/ space, privacy, & exceptional versatility. Fabulous home & separate studio minutes from Tanglewood & Stockbridge Bowl. Charming 3 BR, 2.5 BA, 2,952 sq ft home - complemented by a beautifully renovated 1,800 sq ft studio barn w/ loft & full BA - rests on 8 picturesque acres with beautiful western views. Perfect for outdoor enthusiasts, culture lovers, or anyone seeking a peaceful Berkshire retreat. This location offers easy access to hiking, yoga & wellness centers, boating, skiing, & excellent dining & shopping. Inside, bright & inviting spaces include a living room w/ cathedral ceiling, fireplace, & abundant natural light. A renovated kitchen opens to a cozy den & breakfast nook, pantry, laundry, mudroom & garage.

Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side captures the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere you look you stop to take in the view, large bath with walk-in closet and laundry. The inner courtyard has a heated pool, sunken jacuzzi, outdoor shower, screen porch with fireplace and beautiful perennial gardens. Hidden off the drive is a guest cottage with open living area, bedroom and full bath.

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.