A luxurious home on one of the most scenic roads in The Berkshires, surrounded by 15 pastoral acres, with picturesque mountain views. Enter a sun-drenched living room with a soaring cathedral ceiling and an elegant fireplace centerpiece. Enjoy an expansive 3-season porch, with panoramic windows and classic mahogany floors. A recently updated eat-in kitchen features Sub Zero appliances and a beautiful butler's pantry. Relax in the newly renovated family room with wall-to-wall casement windows. This 5 bedroom home offers a bonus game room and home office equipped with fiber internet and a spacious private master bedroom with ensuite bath. An additional wing features a separate guest suite with living room, kitchen, dining area, full bathroom and 2 bedrooms. In Alford, renowned for low taxes

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

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

Incredible opportunity to own 367 acres of privacy with your own 6-acre lake, trails, streams, and direct access to Beebe Hill State Forest and its 30 miles of hiking trails. The property includes a classic single-family home (ready for a full renovation), a 40' x 50' Morton shed, and a heated garden shed.An approved second homesite with septic, underground electric/data lines, and a transformer is already in place on the north side of the lake. Ideal for building your dream home, a private retreat, or an eco-conscious compound. Enjoy stunning natural beauty, dark skies for stargazing, and endless potential--all just steps from nature.

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 Truly Inspired Berkshire RetreatThe perfect home to relax, create, and be inspired! This remarkable Egremont property offers an exceptional combination of luxury, comfort, and creativity--far beyond anything else on the market.The main house features three spacious bedrooms and three full baths, with radiant in-floor heat beneath reclaimed ancient teak floors. The first-floor primary suite provides direct access to a private sauna, hot tub, and personal greenhouse--ideal for moments of relaxation and rejuvenation.Step outside to discover a heated Gunite pool, surrounded by lush gardens, stone patios, a fire pit, gazebo, and even a pickleball court, creating the ultimate outdoor oasis.The clubhouse, a separate structure designed for gatherings, features an open floor plan with a

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.

BERKSHIRE LAKE FRONT WITH BEAUTIFUL WESTERN VIEWS ACROSS THE LENGTH OF LAKE BUEL. Premiere motor boat lake. With 6 bedrooms and 3 full baths there is room for your extended family or friends. Walls of windows allow lake views from most rooms. Open plan for relaxing after a long day swimming, boating, fishing or relaxing on the water. Lovely out door areas include a deck, patio and steps to your dock. Under 10 minutes to downtown Great Barrington and a short drive to Berkshire County culture, dining and entertainment.

Nestled in the center of Williamstown, just steps from Williams College, this stunning two-story Colonial stucco home offers timeless charm and modern comfort. Built in 1907, this 4,100 sq. ft. residence features five spacious bedrooms, three full baths, and one half bath.Set on 1.35 picturesque acres, the property boasts a large post-and-beam barn, a beautifully covered stone patio, and breathtaking western views of the Taconic Mountains. The expansive, level backyard is adorned with mature gardens and majestic old-growth trees, creating a serene and private retreat.Don't miss this rare opportunity--call today for your private showing!

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.

Perched atop a gentle hill with distant Berkshire views, this distinguished former Lenox school building known as ''Crystal Hill'' has been thoughtfully converted into 10 residential apartments plus one office space.The historic masonry structure combines character and stability with modern updates, including hardwood floors, spacious layouts, and separate hot water and electric meters for each unit. Strong rental income and solid cap rate make this an attractive investment in one of the county's most sought-after towns.Set on two scenic acres, the property offers ample parking, coin-operated laundry, three storage rooms, and a boiler room. Capital improvements include a Simplex fire alarm system (2014), roof replacements (2015 & 2016), apartment upgrades (2019)

Perched atop a gentle hill with distant Berkshire views, this distinguished former Lenox school building known as ''Crystal Hill'' has been thoughtfully converted into 10 residential apartments plus one office space.The historic masonry structure combines character and stability with modern updates, including hardwood floors, spacious layouts, and separate hot water and electric meters for each unit. Strong rental income and solid cap rate make this an attractive investment in one of the county's most sought-after towns.Set on two scenic acres, the property offers ample parking, coin-operated laundry, three storage rooms, and a boiler room. Capital improvements include a Simplex fire alarm system (2014), roof replacements (2015 & 2016), apartment upgrades (2019)

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.

Nestled in a secluded, serene setting and surrounded by lush gardens, fruit trees, wildlife and Nature Conservancy on 3 sides, custom-built home offers extraordinary privacy and tranquility. Crafted using wood milled directly from the property, this rustic yet contemporary home boasts a wealth of unique details that highlight exceptional craftsmanship. Moose, deer, bear, turtles, fox and more visit mature grounds tended by master gardener. Incorporates a native stone fireplace, ash sapling banister, antique leaded glass accents, & reclaimed 18th-century tavern doors from historic Egremont Tavern. These elements blend seamlessly with the open-concept floor plan, highlighted by soaring vaulted ceilings and oversized windows. 5 Brs, 5BA w/ attached separate apartment w/ balcony.

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

The Nine- Square house is, at its core, an authentic country house. On the ground floor are the double living room, dining area, & kitchen, all flowing into each other & anchored by a marble fireplace & 3 large glass doors opening to the exterior terrace with a breathtaking view. A kitchen, office/painting studio, a washroom, a dry bar, & laundry room complete the main level.The central architectural piece of the home is the solid white oak staircase leading up to the second floor. The 4 bedrooms upstairs, though spacious, are much more private & intimate, each with large windows on 2 sides, communing with the serene & quiet landscape outside.

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!

Set on a quiet country road w/ private driveway, this charming 3 BR, 2.5 BA home sits on 8 picturesque acres just minutes from Tanglewood, Stockbridge Bowl & the villages of Stockbridge, Lenox & West Stockbridge. Perfect for outdoor enthusiasts, culture lovers or anyone seeking a peaceful Berkshire retreat. The location offers hiking, yoga & wellness centers, boating, skiing, & convenient access to dining & shopping. Inside, bright & inviting spaces include living room w/ cathedral ceiling, fireplace, & is filled w/ natural light. Primary suite with vaulted ceiling & balcony w/ stunning mountain views. Renovated kitchen opens to a cozy den & breakfast nook connecting seamlessly to the pantry, laundry & mudroom. Lower level with flexible bonus space for family room, gym, office or

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.

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.