In 2021, The Freeman was transformed utilizing high-quality materials from an aging nineteenth-century estate to a clean and modern getaway and top-performing rental property. The main house, renovated to be 100% carbon-neutral, features six fireplaces, two dining rooms, a library, 1500sqft bluestone deck and more. The Freeman sits atop 40 acres of greenery to explore, containing a tennis court, four-acre vineyard, mountain views and a dock to access Harman Marsh Pond. Individuals, wedding parties, and corporate retreats alike have come to The Freeman to enjoy its secluded feel while being close to key Berkshire attractions like Catamount Ski Area, Bash Bish Falls, and downtown Great Barrington. This property is just over 100 miles from both Boston and New York City.

The Kemble, a registered ''Great Estate'' built in 1881 is located in the heart of the thriving downtown Lenox business district. This classic Colonial Revival building has recently been refreshed with modern furnishings and decor, repurposed as a luxury rental property, and is being offered as a turn key operation. With grand gathering spaces, a well equipped kitchen, handsome mahogany bar, and 13 en-suite bedrooms, the property can easily accommodate groups of 20+ and is frequently rented to wedding parties, corporate retreat groups, and multi-generational family retreats. Stays can vary from a weekend to month or longer. Guests can choose to bring in cooks, bartenders, and waitstaff, if desired. Manicured lawns and gardens. Breathtaking views to the west. Fully ADA compliant.

Nestled in the Berkshires on a quiet road this 1958 Ranch with 3 Bedrooms and 2 full baths on approximately 1+ acres fully restored yet retains the warmth of its past with original wood floors and wood paneling. Updates include new kitchen, all new appliances, washer/dryer, windows, doors, septic, HVAC,insulation, electrical, plumbing, tile, and more. Partially finished basement with full bath. storage shed/shop large enough for machines. Beautiful backyard, with flowing trees, mountain views and abundant wildlife. Close to charming town center, family park and nearby schools. Whether you're looking to retire, raise a family, or gather for the weekends, this immaculate remodeled home offers the comfort of updated systems and the beauty of the natural scenery.

Stunning Circa 1850's renovated with seven bedrooms and nine full baths. Classic Greek Revival with strong lines and lovingly preserved details; three period fireplaces, generous gourmet eat-in cook's kitchen and the comfort and style of today's living in the perfect location just a short drive to Tanglewood and in between Stockbridge and Lenox!! This property offers gracious common spaces and six en-suite guest bedrooms. New first floor guest suite with separate entrance

NOW UNDER $3M! Calling all creative minds - artists, musicians, recording artists, producers, makers, and lovers of historic mill building restorations! STUNNING, ONE-OF-A-KIND, modern and historic mill building in the dynamic village of Housatonic, MA is THE PLACE for you to Make Art | Make Music | Live Life in the heart of the Berkshires. Seize the moment to make this extraordinary property yours! Utterly unique in the Berkshires. Light-filled, three stories of open space. 1st FLR includes studio, recording studio, kitchen and bath w adjoining private, walled gardens at each side. 2nd FLR comprises gallery space, living room, primary bedroom suite and guest bedroom with private bath. 3rd FLR is fully open loft space. Finished basement. Central AC. Residential and comm possible.

NOW UNDER $3M! Calling all creative minds - artists, musicians, recording artists, producers, makers, and lovers of historic mill building restorations! STUNNING, ONE-OF-A-KIND, modern and historic mill building in the dynamic village of Housatonic, MA is THE PLACE for you to Make Art | Make Music | Live Life in the heart of the Berkshires. Seize the moment to make this extraordinary property yours! Utterly unique in the Berkshires. Light-filled, three stories of open space. 1st FLR includes studio, recording studio, kitchen and bath w adjoining private, walled gardens at each side. 2nd FLR comprises gallery space, living room, primary bedroom suite and guest bedroom with private bath. 3rd FLR is fully open loft space. Finished basement. Central AC. Residential and comm possible.

FARMHOUSE FRESH | EGREMONTWelcome home! Nestled in the picturesque low-tax town of Egremont, just minutes from the vibrant town center of Great Barrington experience contemporary living with a rustic charm in this light and bright haven that promises the best of country life with all modern conveniences at your fingertips.PROPERTY HIGHLIGHTSSTYLISH COMFORT | Embrace the warmth of this inviting home featuring clean lines, open spaces, generous bedrooms and an abundance of natural light streaming through generous windows, illuminating each carefully considered space. GATHER AND UNWIND | Step outside into your own private sanctuary of lush gardens, thoughtfully landscaped to create intimate

Set on 20 private acres of pasture & woods, w/riding trails & pond, this fully equipped equestrian farm consists of a 4 bedroom residence, stable with apartment, indoor arena & bucolic grounds. This stunning contemporary home features a gorgeous, well-outfitted chefs kitchen w/walk-in pantry, towering ceilings & wall of glass. Formal dining room is accessed through butler's pantry. Bright & inviting den w/cathedral ceiling. Anchored by stone fireplace, the living room opens to wood deck w/stone walls & hot tub overlooking the pastoral scene. A custom built office, half bath & small den w/door to outside complete the first floor. Upstairs, a dramatic primary suite w/fireplace, balcony, skylights, cathedral ceiling, 2 walk-in closets & bathroom w/soaking tub. Also on this floor is a 2nd

Located at the base of Beartown Mountain, a 12,000-acre state forest. Looking for a large farmhouse, one family or two? This lovely home awaits your finishing touches. Five total bedrooms, three total bathrooms, 2 kitchens, living room, den, dining room, first floor primary with primary full bath. Second floor offers 4 additional bedrooms and two full bathrooms. Front & Back staircase. Beautiful fireplace in large back kitchen. Oversized sunporch overlooking fenced in yard with above ground pool, 2- story barn w/car port, 2 paved driveways. Rocking chair front porch. Great Location with tons of space. Close proximity to Beartown Mountain with recreation parkland, Great Barrington, Monterey, Tyringham, downtown Stockbridge, Tanglewood in Lenox & much more! Fantastic Location!

Located at the base of Beartown Mountain, a 12,000-acre state forest. Looking for a large farmhouse, one family or two? This lovely home awaits your finishing touches. Five total bedrooms, three total bathrooms, 2 kitchens, living room, den, dining room, first floor primary with primary full bath. Second floor offers 4 additional bedrooms and two full bathrooms. Front & Back staircase. Beautiful fireplace in large back kitchen. Oversized sunporch overlooking fenced in yard with above ground pool, 2- story barn w/car port, 2 paved driveways. Rocking chair front porch. Great Location with tons of space. Close proximity to Beartown Mountain with recreation parkland, Great Barrington, Monterey, Tyringham, downtown Stockbridge, Tanglewood in Lenox & much more! Fantastic Location!

''ROLL AWAY HILL'', A RARE BERKSHIRE OASIS! Waterfront on Prospect Lake, an incredible property and one of a kind. With over 500' of waterfront on 59 acres, this property boasts scenic Lake & Mountain views. Trails meander past stone walls and through the trees to the water's edge. Relax on the expansive front porch. A lodge like home with rooms of considerable size, offering casual comfort for daily living, entertaining and Summer fun. Nestled up a private drive, there is total seclusion where you can immerse yourself in the natural surroundings. Five Bedrooms, 4.5 Baths, two fireplaces. The charm of yesteryear remains intact. Enjoy Berkshire living at its finest in this truly magnificent setting. So much potential!

This lovely 1825 colonial has many of its original features in place - wide plank floors, beamed ceiling and original hardware. Combine this with newer windows, foam insulation in the basement and a well insulated attic and you have the best of both worlds. Also, the house is a legal two family offering a multitude of options - incorporate it into the main house to have a first floor bedroom suite, rent it year 'round or use it as an AirBnB (current owner did so quite successfully.) The adjacent barn/garage is currently being used as a woodworking studio but it can easily be converted to its original use. There is a carport, as well. The yard is partially fenced for dogs and the meadow view is beautiful. Tons of history here - in the late 1800's this was the post office for Housatonic

Lightly wooded 8 acres. Part of a two lot subdivision just outside the quintessential New England village of New Marlborough. Minutes to Gt. Barrington and the South County food, shopping and cultural scene. Benefit from some of the work that has already been done on the adjacent lot (which is also for sale for $260,000, see MLS #242788)

In the heart of the Berkshires, nestled on 21 picturesque acres, you'll find this grand Estate steeped in rich history and meticulously restored with an unwavering commitment to preserving its original character and splendor. Comprised of handcrafted European textiles that blend seamlessly with modern appointments and luxurious amenities sure to appeal to the discerning tastes of contemporary living. Marvel at the grand foyer with intricate moldings, gleaming hardwood floors, and a sweeping staircase. The formal living and dining rooms exude refined elegance and lend itself to gracious entertaining. The stunning library with its handsome woodwork is the embodiment of what one would expect in a fine home. The gourmet kitchen is the heart of the home, and a culinary haven boasting SubZero

This gorgeous estate parcel in the heart of the Berkshires is ready to be built on. A magical parcel of land that has to be experienced to appreciate how special it is. All the hard work has been done!! A total of three parcels, each with power and wells in place. Main building site also has a 4 bedroom septic in place and buried propane tank. Could be a perfect family compound or main building site with guest house and accessory building. Call today to schedule a tour!