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60 Photos
COLDWELL BANKER COMMUNITY REALTORS
$6,900,000
6 BD | 5 BA
Residential - Single Family

An extraordinary country estate spanning approximately 150 acres of open meadows, woodlands and spectacular long-range views to the Mount Holyoke Range. The beautifully reimagined antique residence blends original timber framing, stone fireplaces and reclaimed floors with exceptional craftsmanship and refined finishes. A private two-story guest wing offers added flexibility. The remarkable converted barn features beautifully appointed offices, gathering spaces, full kitchen, balconies, gym and extensive car and equipment storage. Stunning grounds include gardens, ponds, stonework, outdoor kitchen, fire pit and outbuildings. Just 10 minutes to I-91 and Shelburne Falls. This extraordinary property must be experienced in person to fully appreciate its remarkable setting and all it offers.


65 Photos
BROWN HARRIS STEVENS HUDSON
$6,995,000
8 BD | 8 BA
Residential - Single Family

1775 -WHITE BRIDGE FARM - A True Hudson Valley Fairytale. White Bridge Farm is an extraordinary 18th-century estate set on 160 acres, where history, architecture and landscape come together in a way that feels almost cinematic. It's a property so rare, that it needs to be experienced -- there is a moment waiting around every corner, from the restored original hand forged iron gates and stone walls to winding stone paths, gardens, streams, waterfall and miles of trails. The Main House feels transported from the English countryside -- perhaps even a fairytale château -- with an enchanting courtyard, dripping with original details dating to before the birth of the nation, including her pristine wide-plank floors, original wavy glass and wood-burning fireplaces. A beautifully crafted kitch


46 Photos
BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
$7,250,000
6 BD | 6 BA
Residential - Single Family

A rare French Manor estate gracing one of South Berkshire's most scenic and sought-after country roads, this extraordinary 45+/- acre sanctuary is awaiting buyers final finishes and offers unmatched privacy, panoramic mountain views, and a setting of timeless beauty. Bordering protected state forest, the property unfolds across rolling meadows, tranquil ponds, and a gently flowing brook--creating a secluded retreat that feels worlds away, yet remains moments from the cultural heart of the Berkshires. SEE LIST OF ITEMS TO BE FINISHED IN DOCUMENTS.


50 Photos
COMPASS MASSACHUSETTS , LLC GB
$7,975,000
8 BD | 7 BA
Residential - Single Family

Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket doors that provide charm and flexibility. Every detail has been curated to embody warmth and sophistication, creating an inviting ambiance that is both refined and welcoming. Ideally located just moments from downtown Lenox, Tanglewood, a local municipal airport and a charming farm, HomeFarm, directly across the street. Highwick offers an unparalleled sanctuary in the heart of the Berkshires!


56 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$14,500,000
19 BD | 23 BA
Residential - Single Family

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody & Stearns, this 16th-century Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.


60 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$14,500,000

Commercial

The Wheatleigh: Former 5 Star Forbes Travel Property and 'Leading Hotel of the World', this Gilded Age masterpiece sits on over 21 acres overlooking Stockbridge Bowl. Designed in 1893 by Peabody & Stearns, this 16th-century Florentine palazzo features stunning grounds by Frederick Law Olmsted. At Tanglewood's doorstep, this 25,000+SF architectural sanctuary marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, Parlor, 3 formal Dining Rooms, Wine Cellar (6,500-bottle cap.), meeting rooms, Gym, and 19 Guest suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the Pool and Tennis Court. This iconic Inn offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.


52 Photos
STONE HOUSE PROPERTIES, LLC
$21,000,000
5 BD | 6 BA
Residential - Single Family

There are beautiful homes in the Hudson Valley, and then there are properties that seem to occupy a world entirely their own. Set at one of the most extraordinary vantage points in the region, this exceptional contemporary estate presides over 135 private acres with sweeping, unobstructed views across the Hudson Valley to the Catskill Mountains. The sense of scale is remarkable: open sky, rolling land, distant mountains, and complete privacy in every direction--yet Hudson and Great Barrington are each only 25 minutes away. The residence was designed around this landscape; dramatic walls of glass frame the Catskills throughout the house, while soaring ceilings and expansive, open living spaces give the interiors a sense of volume without sacrificing warmth.

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