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.
Classic red farmhouse on 3.49 bucolic acres just minutes from the heart of Stockbridge. This updated 3BR/2.5BA home blends original charm with thoughtful upgrades. Post and beam construction, a sleek gas fireplace, and a sunny open layout connect the living, dining, and kitchen areas. The first-floor primary suite includes a walk-in closet and private bath. Upstairs, two more bedrooms and a full bath offer space and flexibility. A spacious 1BR/1BA apartment above the attached garage is perfect for guests, rental income, or studio use. Proven short-term rental history adds investment appeal. Enjoy a contemporary deck overlooking lawns and trees—ideal for relaxing or entertaining under Berkshire skies. The property offers privacy, convenience, and timeless appeal in the town Norman Rockwell called home. Just minutes to downtown Stockbridge, with Lenox, Tanglewood, and Great Barrington close by. A rare blend of character, versatility, and location in the Berkshires.
Stockbridge is located in Massachusetts. Stockbridge, Massachusetts has a population of 1,827. Stockbridge is less family-centric than the surrounding county with 17.88% of the households containing married families with children. The county average for households married with children is 21.74%.
The median household income in Stockbridge, Massachusetts is $46,458. The median household income for the surrounding county is $63,159 compared to the national median of $69,021. The median age of people living in Stockbridge is 60.1 years.
The average high temperature in July is 80.9 degrees, with an average low temperature in January of 11.9 degrees. The average rainfall is approximately 47.2 inches per year, with 56.2 inches of snow per year.
