Don't miss this Lenox beauty! Tucked away on a quiet street and abutting preserved land, this colonial is a must see. Main level features hardwood flooring, living room with crown molding, formal dining w. large bay window, open updated kitchen with extensive storage. Family room with gas fireplace opens to spacious screened porch. First floor laundry and half bath. Three bedrooms on the upper level; primary suite w adjoining dressing room/ primary bath with soaking tub and separate shower. Two additional bedrooms and full bath; all w hardwood flooring. Central a/c; natural gas heat/hot water. If you enjoy nature and gardening- perennial gardens and specimen plantings bloom continuously to wow sight and scent. Abutting preserved land with year-round brook-your own magical retreat!

Just outside the charming village of Housatonic, this extraordinary Queen Anne Victorian stands as a true architectural gem, nested amid lush gardens and beautifully landscaped grounds. From its distinctive urn shaped columns to its twin towers, gables and wrap around porch, every detail reflects the grace and grandeur of a bygone era - balanced perfectly with thoughtful modern updates. Sweeping lawn with private patio and mature plantings. Currently configured as a two family residence, the layout offers easy conversion back to a magnificent single-family home, making it ideal for a grand Berkshire retreat, full time residence, or multi-generational living. Inside you will find historical character, original millwork & trim, and updated kitchens & baths. Whether you're seeking a stately

Immaculate Contemporary Cape Cod home in the desirable Fox Run neighborhood, tucked just off a scenic country road. This inviting property offers four bedrooms and 2.5 baths, featuring an open-plan kitchen, living, and dining area perfect for everyday living and entertaining. A first-floor primary en-suite provides comfort and convenience. The stunning sun porch overlooks a peaceful, bucolic pasture--an ideal spot to relax and unwind. With charming curb appeal and a prime location close to all the Berkshires has to offer, this home combines tranquility with accessibility. A truly special opportunity you won't want to miss.

Over 4500 square foot commercial space set on over 3 acres in New Marlborough. 10 Minutes to Main Street Great Barrington. The possibilities are endless with this property.

Located in one of Lenox most sought after neighborhoods. Surrounded by woods, it gives you a rural feel, yet you're only minutes to the center of town. This Home features 5 bedrooms 3 Full Bathrooms and a Den with a connecting door to the 1st floor bath which gives you the options of a 6th Bedroom / Suite, Large finished sunroom, Family room with fireplace, a beautiful Kitchen, Combined Formal Dining room and Living room area great holiday and entertaining, nice details like Pocket doors and Walk-in closets and large private yard. Whether you're planning to move here or already call it home, you know why we live in the beautiful Berkshires! A picture is worth a thousand words, please enjoy them.

First time on market in almost 50 years. Located on the north end of Gt. Barrington at Belcher Square is this exceptional opportunity. Boasting two curb cuts, one on Rt 7 aka Stockbridge Rd and the other on Rt 23 aka State Rd. This property is ready for new owners. Situated on .47 +/_ acres are two buildings. At 215 State Rd is a post and beam two story barn with one story additions on two sides. Two garage doors for ease of access. There is a 1/2 bath (cold water only). Utilities are town water, town sewer, 200-amp fuses, natural gas hot air furnace. The second building contains three rental units. Upstairs at 8A Stockbridge Rd is a three-room apartment with galley kitchen and full bath. Heat is oil fired hot water. Electric is 200-amp circuit breakers. Main level at 8 Stockbridge Rd

Located on a quiet country road, this 18.5-acre parcel offers beautiful mountain views, privacy, and a peaceful setting. Just minutes from Williams College, the Clark Art Institute, and town amenities, it's the perfect place to create your ideal retreat in the heart of the Berkshires. The property is under Chapter 61A.

Custom built home! Embrace the eastern views and warmth of New England's Mountains from the beautiful open front porch! Amazing custom home built by a true craftsman. Beautiful natural wood elements & exposed beams throughout, make for a wonderful Berkshire retreat! Large custom kitchen with granite & butcher block countertops, open dining room for easy entertaining with double French doors lead to an inviting screened porch/sunroom. Large private deck overlooking patio with firepit and meticulous lawn. Large mudroom/office. Beautiful living room with bay window, cozy den/family room with wood burning fireplace. Large first floor full bathroom with washer/dryer hook-up. Thoughtful design throughout.

Experience refined country living in this completely reimagined masterpiece by Wingate Ltd. Spanning 3 floors of gracious living space, 594 Shunpike offers architectural drama and modern efficiency on a truly scenic Berkshire corridor. Inside, a sculptural staircase leads to a sun-drenched open living area with white oak floors and a gas fireplace. This open plan flows into the chef's kitchen with stone counters, and high-end SS appliances with multiple deck access points. Three independent suites offer flexibility and true privacy. The main suite being an oasis of comfort and relaxation. The walk-out lower level serves as the guest wing and includes a billiard room, wet bar, and plenty of sleeping accommodations. One could even turn it into an in-law apartment.

This fully renovated 3-bedroom, 2-bath home on Peppermint Brook, an estuary of Lake Garfield, offers bright, open living with a seamless indoor/outdoor feel. Renovated in 2019 with thoughtful design, it includes a sleeping loft and a flexible third bedroom that can double as a den. Launch your kayak, canoe, or paddleboard right from the backyard into the brook or to the lake. While part of Sylvan Road HOA, this property is exempt from road maintenance dues, yet still enjoys deeded access to private, quiet, southwest-facing Lad's Beach for a fee of $275/yr. Tucked away in a quiet natural sanctuary, this home is a serene escape in beautiful Monterey -- perfect for relaxing weekends, hosting guests, and enjoying nature. Move-in ready with nothing left to do. Fiber internet.

Modernist retreat in a pastoral Berkshire setting; an artful sanctuary where design, landscape, and light exist in quiet harmony. Designed by acclaimed architect Debra K. Reiser, this light-filled two-bedroom, three-bath home blends refined urban modernism with the stillness of the countryside. Set along a quiet dirt road beside Moon In The Pond Farm, (an eco-conscious farm) a landscape of grazing sheep and open fields exists outside your window. The home feels private yet deeply connected to nature. Completely reimagined and meticulously renovated, it offers low-maintenance luxury within an intimate, thoughtfully designed footprint. Clean architectural lines, natural textures, and carefully placed windows frame the surrounding landscape like living artwork.

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.

Pride of ownership reasonates through this disctinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut St. near the esteemed Pittsfield Country Club, BUpstreet Cultural District and is ideally just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character boasting five bedrooms, two and half baths thoughtfully improved over this long term owners' commitment to preservation and restoration. This prominent manor style home MAY BE coupled with the neighboring guest house featuring 3 bedrooms, 1 bath plus a first floor in-law bedroom suite and a 2 car garage, if one so chooses to accommodate extended family, friends or caregiver

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.

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.

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!

Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. This sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms and two baths on the second floor. The primary suite comes with an oversized walk out deck large enough to place your summer lounge furniture, the perfect spot for your morning coffee. Amenities at Winden Hill include a heated pool and a tennis and pickleball court....all this and and only a 20 minute stroll to the center of Lenox. This truly is the perfect place to call home.

Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. The sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms and two baths on the second floor. The primary suite comes with an oversized walk out deck large enough to place your summer lounge furniture, the perfect spot for your morning coffee. Amenities at Winden Hill include a heated pool and a tennis and pickleball court....all this and and only a 20 minute stroll to the center of Lenox. This truly is the perfect place to call home.

Immaculate 4800 square foot, 5BR, 4 full bath jewel located at arguably the finest condominium community in The Berkshires. Enjoy looking at spectacular foliage with private panoramic wooded views and open space from the magnificent all seasons room, great room and primary suite. The garden level features a full kitchen as well as a screened in porch. The Buterus furnace system powers baseboard heating/3 zone HVAC. The home has a water filter and water softening system. The oversized garage has a washable neoprene rubber surface and two full car mats. There is an attached workshop and stairwell to a spacious attic. SMF is surrounded by mature landscaping an offers the following amenities: pickleball, tennis, swimming pool, basketball, fitness center, clubhouse and library.

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.