6. Eastover

The Eastover estate, owned by New York City stockbroker Harris Fahnestock Jr., was designed by Hoppin & Koen, the same firm that built Edith Wharton’s The Mount, with the gardens by Wharton’s niece, the famed landscape designer Beatrix Farrand. The Georgian-style mansion has 30 rooms and the property also contained a stable, tennis courts, a pool, “a chauffer’s home, an eight-car garage, and a pump house used to store 20,000 gallons of water for use on the property,” according to the history on the Eastover website. Like other Gilded Age mansions in the Berkshires, it was once used as a school, but continues to be privately owned to this day. From 1947 to 2005, it was operated as a resort by the Bisacca family, and sold in 2010. The original 1,500 acre estate is now 450 acres in size, and is used as a resort and holistic retreat.