by Anne Motto, F.M. Kirby Curator of Collections
April 27, 2026
Originally a “white Colonial” built for Thomas Pinckney, Cherrycroft was extensively altered and expanded by its second owners, Mr. And Mrs. Dudley Olcott II, in 1909. Later that same year, the gardens were designed for the couple by Italian landscape architect Ferruccio Vitale and soon found their way into several national publications of the most beautiful gardens in America. In the years that followed, the Normandy Park estate was the scene of frequent soirées hosted by the Olcotts, culminating in a June 1911 “bal masqué” attended by 300 guests. Purchased by Eugene V. Brewster in 1924 for himself and his mistress, Cherrycroft would be in need of a new owner a mere two years later. A booklet printed by Brewster for potential buyers displays the house in all its magnificence, but shows no signs of the dramatic scenes it witnessed under either of its most recent owners. The asking price for this hotbed of scandal and roses? $635,000 (~$11.8 million today).
