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63 Photos
ALTON & WESTALL REAL ESTATE AGENCY, LLC
$1,950,000
4 BD | 4 BA
Residential - Single Family

Exceptional custom-built contemporary home with magnificent views. Featuring multi-level living including a beautiful great room/living room with floor-to-ceiling stone wood burning fireplace, expansive well-appointed kitchen with large breakfast area and walk-in pantry, and a formal dining room. The first floor also offers a primary suite with walk-in closets, an office with laundry room, a mudroom, and a half bath. The second floor has two bedrooms, one bathroom and an office overlooking the great room. The lower level offers a large family room, bedroom (currently used as an exercise room) a bath, and a two-room workshop. There is a separate screened porch on the wraparound porch and a hot tub to take in all the amazing views.


40 Photos
BERKSHIRE BUSINESS PROPERTIES
$2,490,000
11 BD | 5 BA
Residential - Single Family

HISTORIC BERKSHIRE FARM 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.


77 Photos
LANCE VERMEULEN RE, INC
$2,495,000
4 BD | 5 BA
Residential - Single Family

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


64 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$2,500,000
4 BD | 6 BA
Residential - Single Family

Tucked in the Berkshires of Western Massachusetts, this Williamstown contemporary boasts over 7,000 sq. ft. of undeniable form and function mixed with the highest degree of finishes. It's been said that homes can be duplicated anywhere, but a setting with unique and rare attributes cannot. Gently Sited amidst a spectacular 34-acre backdrop bordering 8,000 +/- acres of protected land is incredibly rare. Architecturally designed to contour with the natural topography of the site greatly reduced disturbance when built. This multi-tiered footprint affords picturesque sunset views of the village below and Berkshire hills beyond. Watch a soccer game at Cole field from your Gunite pool, walk to the village for dinner or go hiking on Chestnut/Pine Cobble Trails right off your property...


52 Photos
BIRCH PROPERTIES
$2,950,000
6 BD | 7 BA
Residential - Single Family

CONTEMPORARY ESTATE | LENOXLOCATION, LOCATION....SECONDS, not minutes, not miles to the main gates of Tanglewood, this secluded and private contemporary, renovated and expanded in 2020 (built 2017) by master craftsmen offers expansive and impressive entertaining spaces indoors and out. Soaring ceiling heights and upper level gallery invite light from every direction balanced by the warmth of mahogany and cherry woods. Designed for easy and elegant living from the chef's kitchen to dining areas, to exquisite bathrooms and guest rooms this wonderful property offers a truly luxurious primary suite, three guest bedrooms, a ''bunk room'' with private access a lower level for exercise, movies, state-of-the-art wine storage and more.


62 Photos
LANCE VERMEULEN RE, INC
$2,975,000
5 BD | 4 BA
Residential - Single Family

Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it offers plenty of room to entertain and relax. The large cook's kitchen is perfect for preparing meals for large gatherings, while the heated sun room provides a cozy spot to enjoy your morning coffee and take in the stunning views of the surrounding fields. This home also features 5 spacious bedrooms (primary with en-suite, four jack-and-jill), each with their own unique charm and character.


51 Photos
STONE HOUSE PROPERTIES, LLC
$3,485,000
5 BD | 6 BA
Residential - Single Family

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.


62 Photos
COHEN & WHITE ASSOCIATES
$4,450,000
5 BD | 8 BA
Residential - Single Family

The Birches....welcome to your new oasis in the Berkshires where every season is memorable. This magical compound has been architecturally redesigned & renovated using the finest materials offering all the modern amenities a buyer wants to live, play, relax and work from, surrounded by 20+ acres of privacy & far reaching protected views in all directions. This stunning contemporary has big open common areas for gathering, first floor primary en suite, guest bedrooms en suite and a private two bedroom guest quarters w/kitchenette, custom crafted wine room, and an exercise room all offering plenty of space for a large crowd or intimacy for a few. Just arrive with your suitcase and enjoy all this impeccably maintained estate has to offer; a beautiful gunite heated pool w/waterfall &


66 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$4,675,000
10 BD | 12 BA
Residential - Single Family

Set on 36 acres in the Berkshires' most coveted town, this stunning 8600 sq ft home is completely turnkey, tastefully designed, and a mere 12 years old. Turning off of bucolic West Rd, a gently winding driveway brings you past two beautiful ponds, through the woods, and arrives on a sunny plateau - nicknamed ''Ebbets Field'' and the site of this spectacular retreat. Abutting 899 acre Alford Springs Reserve, this custom-built home was thoughtfully designed to host family, friends, and guests across multiple discrete living areas. Main House. A striking glass walkway leads from the three-car garage to the vaulted-ceiling kitchen, which boasts a double-oven Wolf range and plenty of space for cooking and gathering. A light-filled dining area adjoins the kitchen, along with a large living


43 Photos
COMPASS MASSACHUSETTS, LLC.
$4,750,000
7 BD | 7 BA
Residential - Single Family

Significantly restored in 2024! Sellers have masterfully updated this legacy home w/ a cool & fresh aesthetic that preserves the integrity of its Mid-century Modern design. Updates to the 1st floor primary suite, kit, entertainment kit, bathrooms & freshly painted interiors are just a few of the improvements. The airy main living spaces w/ their expansive sliding glass doors offer sublime views of the resort-like grounds complete w/ manicured lawns, patios, in-ground pool, playground, newly resurfaced tennis/pickle ball court, gardens curated by a Master Gardener & distant mountain views. The 7 bedroom, 7 bathroom estate w/ 8200 sq ft of versatile living space prominently sited on 57+ acres is 3 hours to NYC and 2 Hours to Boston!


49 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$4,999,000
5 BD | 7 BA
Residential - Single Family

Exquisite Lakefront Sanctuary in the Heart of the Berkshires. Nestled amidst the ancient boulders of Goose Pond's pristine shores, rare opportunity to own a quintessential Berkshire Lake Estate. This gated haven offers 877 feet of lake frontage and 35 acres of untouched woodland, ensuring complete privacy and a connection with nature that is both rare and invigorating.The residence, an embodiment of energy efficiency and architectural elegance, features five bedrooms and 6 1/2 baths, each space thoughtfully designed to frame the breathtaking water vistas.The home boasts two primary suites on the first level and three guest rooms with en suite baths, one with a separate entrance all offering water views and access to stone patios. A vast screened porch further enhances the living experience.


50 Photos
STONE HOUSE PROPERTIES, LLC
$5,485,000
13 BD | 14 BA
Residential - Single Family

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.


49 Photos
NEPONSET VALLEY REAL ESTATE, INC.
$6,200,000
11 BD | 15 BA
Residential - Single Family

Houses like this do not come along often! Two magnificent houses on 2.7 acres of serenity. The 17 Room mansion boasts Victorian architecture with modern luxuries. Named the Taggart house, this property has hosted celebrities and guests for many years. Almost 9000 square feet including a ballroom! Continue operating the business or live in it as your dream home. The rear guest house is a 4,500 square foot modern post and beam farmhouse built in 2006 with many beautiful recent renovations. Kayak from your private beach on the Housatonic River, stroll into Town and all that Stockbridge has to offer.


75 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$6,390,000
14 BD | 13 BA
Residential - Single Family

On the crest of Woodruff Mountain, moments from The Southfield Store, York Lake, and area amenities, a classic country estate awaits. Its centerpiece is a stately 5BR, 5000sf, c. 1798, Georgian-Federal home, set on a 232-acre property encompassing a 3,550sf historic barn, smaller barns & run-ins, gardens & green house, Gunite pool & pool house, tennis court, fields, pastures, stream, mile-long trail abutting Sandisfield State Forest, and 5-acre spring-fed pond, all arranged for maximum livability and delight. You'll be pleased with the elevator, generator, & other mod cons, and charmed by historic details, stunning vistas, & untrammeled view of the star-studded night sky. Not enough? A 6,000sf guest house with four apartments suggests myriad uses for guests or income. Perfectly beautiful.


74 Photos
BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
$6,500,000
3 BD | 6 BA
Residential - Single Family

Atwater Pond is an exceptional retreat in the Berkshires of western Massachusetts. At the heart of the property lies the namesake 32-acre pond, which dates to 1892 when it was dug by hand and horses. More than 130 years later, the pond anchors the property, and the improvements and owner's homes are clustered on its eastern shore. The house and guest house recently underwent extensive renovations, and the immaculate structures have an effortless, contemporary aesthetic that honors the property's casual country roots while incorporating modern conveniences.Surrounding the pond are 321+/- acres of pristine woodlands, and the undulating topography is interspersed with trails, streams, wetlands, and remnants of the area's extensive history. It is a true four-season destination.


60 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$12,995,000
6 BD | 7 BA
Residential - Single Family

Nestled in the heart of the Hudson Valley, this unparalleled 227 acre compound in Copake, NY is a masterpiece of luxury and sophistication. The sprawling private grounds are a haven of natural beauty, with serene water frontage on 46 acre Chrysler Pond, lush woodlands for outdoor adventures, farm facilities for animals, and open fields that create a canvas for potential future development. Each corner of the property offers breathtaking mountain views and a sense of tranquility.The masterfully handcrafted 6-bedroom lodge, constructed with timber from British Columbia, offers over 8000 SF for year round entertainment. The residence exudes elegance with a chef's kitchen, gracious dining room and exquisite living room, complete with commanding fireplace - see supplement for full remarks


16 Photos
LANDVEST, INC.
$15,000,000
19 BD | 23 BA
Residential - Single Family

Wheatleigh is the perfect marriage of the grandeur of a 16th century Florentine palazzo and the comfort and elegance of the twenty first century. Imagine living in desirable Lenox on 22 acres overlooking Stockbridge Bowl and the mountains and being within a short stroll to Tanglewood! Henry Cook in 1893 commissioned Peabody and Sterns to construct this Italianate style home. It has since been updated by famed architects Tsao and McKown for contemporary living. The 19 suites, guest rooms and baths set a new standard of style and sophistication and can accommodate many friends, business guests and family. Each of the bedrooms have high speed internet and Bang and Olufsen TV's . The state of the art fitness center, heated pool, and tennis court keep every one active.

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