Nestled in the heart of West Stockbridge, this stunning 5-bedroom, 5.5-bath Federal/Greek Revival style home at 4 Stockbridge Road combines historic charm with modern luxury. Built in 1825, the residence has been beautifully renovated, maintaining its classic character while offering contemporary amenities. The spacious interior features generous living areas, perfect for family gatherings and entertaining. Outside, you'll find a large barn, a greenhouse and impeccable gardens ideal for gardening enthusiasts or creative projects. This property is not just a home; it's an opportunity to enjoy the tranquil beauty of West Stockbridge, with its vibrant community and picturesque surroundings. Located minutes from many local attractions including Tanglewood and minutes from the highway.

Steeped in American history, Burn Brae Cottage is a rare and enchanting estate. Built circa 1750 and gifted by Adonijah Bidwell to his daughter Theodosia in 1793 on her wedding day, this beautifully updated home sits on just under 7 sunny acres just one mile from Lake Garfield in low-tax Monterey. The 4-bedroom, 3.5-bath residence features gorgeous wood floors, abundant natural light, and nearly all new windows. The main level offers a kitchen with a 6-burner Bertazzoni range and stainless appliances, a family room with two wood-burning fireplaces, and two enclosed porches (one heated). Outside enjoy pastoral views and open land, private trails to a babbling brook, a new 14.7kW solar array with whole-house battery backup, a 3-car garage with EV charger, and a recently built storage shed.

Set beyond the ordinary, this extraordinary private retreat blends historic character with refined modern living on 2.25 scenic acres in the hills of Granville. Originally transformed from a classic New England schoolhouse, the home now offers a truly one-of-a-kind lifestyle surrounded by privacy, nature, and breathtaking beauty. The property features expansive open spaces, soaring ceilings, dramatic architectural details, and walls of windows that bring the outdoors in. The chef's kitchen flows seamlessly into inviting gathering areas, while outdoor spaces encourage relaxation and connection with the peaceful setting. Ideal as a full-time residence, weekend escape, multigenerational property, or live/work retreat. Worth the drive, impossible to duplicate!

Turnkey Berkshire sophistication meets absolute privacy. Reimagined from the studs up, this 3BR, 3.5BA architectural retreat sits on 2.32 level acres in Sheffield. The sun-drenched open main floor features wide-plank oak, a gas fireplace, and a chef's kitchen flowing to a wrap-around deck. The 2,748 sq ft footprint offers 3 independent living suites across 3 levels--including a luxury primary, private loft, and walk-out lower level with a wet bar--making it a premier, lucrative vacation rental or private escape. New multi-zone HVAC, full spray foam, UV filtration, and a whole-home generator offer total peace of mind. Just 15 mins to Great Barrington and 45 mins to the Wassaic NYC train. Fully furnished option available!

Beautifully renovated historic farm house available in Lenox Massachusetts. A charming 1840s clapboard house located on the estate of ''Brookhurst'', one of the famed Berkshire ''cottages'', this former guest house has 3 or 4 bedrooms and 2 full baths spread over three floors (primary bedroom and bath on main floor). It has a private gated driveway and an attached 2 car garage.. Luxurious traditional decor throughout the home but with all the modern conveniences including AC, WiFi, whole house generator and more. A flagstone terrace overlooks the lush backyard and fully planted walled garden. The house benefits from the rolling landscaped vistas of the beautifully maintained estate property it abuts. Steps to the town of Lenox and to Tanglewood!...Call Today!

Berkshires Luxury & New Lakeside Living. Enjoy distant lake and mountain views from each first floor room. This elevated ranch style home creates one level living with grand open sunfilled spaces. This floorplan features open floor plan capturing lakeviews from each room on the main living level. This beauty is what you have been waiting for - a brand new never lived in newly constructed home is ready for you to live and enjoy the Berkshires at it's best now. Expansive gourmet kitchen topped with quartz quality counters, stainless appliances, breakfast bar and oversized walk-in pantry. Dining room flows to living room with sliders leading to a glorious continuous wrap-around upper level deck. Custom wire railings enhance views and is oversized for outside dining and chaise lounging.

Discover a rare opportunity to own 181 extraordinary acres in the picturesque town of Adams. Available for the first time, this expansive property features an ideal blend of open meadows, rolling hills, mature woodlands and stunning views - perfect for nature lovers, outdoor enthusiasts, or visionary developers. The land boasts gently sloping topography from east to west, creating a dynamic landscape rich in wildlife and diverse ecosystems. Property borders Savoy Mountain State Forest to the east, providing direct access to hundreds of acres of protected land. Extensive frontage on East Hoosac Street and additional right-of-way access from East Road opens the door to potential development. Priced at just under $5,000 per acre, this is a unique opportunity in the heart of the Berkshires.

Situated on Great Barrington's highly sought after neighborhood of 'The Hill', 11 Prospect delivers on style, convenience and of course, location! This four bedroom home with two and a half baths over three floors and hardwood floors throughout, offers lots of room for family and friends. An oversized screened in porch, attached two car garage and a finished basement are just some of the 'must haves' to enjoy in this recently updated property. Steps away from the shoreline of Lake Mansfield and a simple stroll to downtown Great Barrington's many coffee shops, restaurants, bakeries and theaters, this property is the perfect move in ready home!

An exceptional commercial opportunity on busy Route 7 at the Sheffield-Great Barrington line, this 7.29-acre property offers over 1,000 feet of frontage and unmatched visibility. Formerly a GMC dealership and auto repair shop, the site includes a 5,540 sq ft garage with five oversized service bays and heavy-duty power—ideal for automotive, fleet, or light industrial use. An additional storage building on-site expands functionality. The expansive paved lot can accommodate over 100 vehicles, making it ideal for dealerships, rentals, or display. The location benefits from steady traffic, close proximity to tri-state area schools & businesses, and easy access to downtown Great Barrington's shops, restaurants, and cultural venues.

Welcome to 3 Cone Hill in the heart of the Berkshires. This rustic retreat is the epitome of a classic country compound that's been lovingly cared for and enjoyed by the same family for many years. Minutes to Tanglewood, this 2+ acre lot hold more fun and relaxation than most large estates. Sitting over Cone Brook, you'll enjoy listening to the babbling water from your screened-in gazebo. After playing a game of tennis or pickle ball, take a soak in the hot tub before guests come, which will be plenty as you can easily sleep 14 people. The house has 5 BR/3BA with an open concept on the main level. The detached garage has 1 BR/1 BA guests quarters where they can come and go as they please. Let the lasting memories begin today!

Offered for the first time in more than forty years, this c.1880 residence presents a rare opportunity to own a substantial property on coveted Prospect Hill Road, one of Stockbridge's most desirable addresses. Set privately on 3.5 acres just moments from the center of Stockbridge, the property offers the increasingly rare combination of privacy, acreage, and location that defines some of the most sought-after luxury real estate in the Berkshires and Berkshire County.

12.84 Acres of Prime development Land. Ideal for possible Commercial and/or Residential projects. Close to Shopping and Transportation. Curb cut and some engineering done.

LAND. 12.84 Acres of Prime Development Land. Abuts several Commercial Properties. High Traffic. Centrally located. Lot not cleared. Some engineering done.

Escape to your own private retreat in Williamstown, 'The Village Beautiful.' This spacious 5-bedroom, 4.5-bath home sits on 7.5 private acres and offers over 4,000 sq. ft. of living space throughout three levels, plus a finished basement with full bath and sauna. This home blends classic and modern features: exposed wood beam ceilings and a new, private primary suite with soaking tub. The home features a second primary suite, a third floor bedroom or loft space, and an abundance of natural light throughout. There are two woodstoves and a wood-burning fireplace for staying warm, and mini-splits for cooling in the summer. The expansive property boasts a designated garden area, a large garage with loft space above, and two large decks for entertaining and enjoying the surrounding nature.

Wake up to breathtaking panoramic waterfront views & end every day with spectacular sunsets from this exceptional ranch offering approx. 170' of waterfront frontage.This well-maintained home features 3 bedrooms, 2 full baths & an inviting open layout designed to showcase the stunning scenery.The sunroom, with walls of glass sliders, opens to an expansive deck-perfect for entertaining, relaxing or simply enjoying the peaceful waterfront setting.Inside, a beautiful stone gas fireplace creates a warm focal point, while radiant heat in the upper level & basement floors provides year-round comfort.Additional features include central a/c, new windows throughout & a walkout basement offering easy access to the outdoors & possibility of an ADU. The business zoning provides added flexibility for

Prime Commercial space in the center of Sheffield. 9500 +- versatile square footage to work with. Prior food processing and cafe center. Offices, (3) restrooms, multiple large spaces to work from. Huge storage area and garage spaces. Outdoor patio area with fireplace off what was once a cafe that seats 36. Lots of natural light throughout the building. 3-phase electric. Many improvements were done in 2012. Make your vision a reality with this property.

Set on four private acres along a quiet stretch of road by the Housatonic, this is the kind of place that reveals itself slowly. The driveway is lined with rhododendrons that light up every spring, and the rest of the landscape is paced to bloom straight through summer - fruit trees, azaleas, perennials, blueberries, raspberries, all of it planted by someone who clearly knew what they were doing. Out back, a brook babbles through the yard. The Sheffield covered bridge, about as scenic as New England gets, is an easy walk away. Inside, the first floor opens up and flows - wood floors throughout, and a wood-burning fireplace that anchors the whole space. There's a full bath on the main level. Upstairs, the primary has its own en suite, and the other two bedrooms share a half bath.

Fully occupied-Opportunity to own 2 commercial buildings on the same 2.9 acre lot in a desirable location located on Main St. in Egremont. Both are well maintained buildings with attractive curb appeal and a prominent stone retaining wall and paved driveway with plenty of parking. Roofs are under 10 years old. Front building has a 950 sq.ft. of professional office space on ground floor. The second floor has a well maintained 750 sq.ft. apartment with 1 bedroom, living room, kitchen and bathroom. In addition, a detached, 300 sq.ft. suite to accommodate a business with smaller space needs. Each unit has it's own private entrance and bathroom. The second building boasts 5 commercial spaces ranging from 100 to 750 sq.ft.. of professional office space.

A Stunning Hilltop Retreat with Breathtaking Views for an Easy Care Lifestyle in the Berkshires. Majestic and magical perfectly describe this exquisite three-story mountain top home, designed to capture the stunning and distant views of the Berkshire skyline. With over 5,000 square feet of expansive living space, this centrally located residence offers the perfect opportunity to either escape, join a quaint community or work at home with glorious views of the Berkshire Hills. Prime Location for Nature and Culture. Nestled in a charming small-town neighborhood, this home is bordered by beautiful woodlands, providing direct access to hiking trails and the nearby Appalachian Trail. Its central location places you at the heart of the area's vibrant culture and great outdoors.

Whether you're looking for a weekend retreat or a year-round home, this beautifully maintained, five-year-old ranch offers the perfect blend of modern comfort and peaceful Berkshire living.Thoughtfully designed with an open floor plan, vaulted ceilings, and abundant natural light, the home is ideal for entertaining and everyday living. The inviting living room features a gas insert fireplace with a stunning floor-to-ceiling stone hearth. The spacious kitchen boasts granite countertops and ample workspace, while the primary suite includes an accessible bath with 36-inch doorways. Two additional bedrooms and a full bath are located on the opposite side of the home for added privacy.