Ernest Flagg was a prolific and honored architect, mostly known for the US Naval Academy in Annapolis and the Singer Tower -Manhattan's first notable skyscraper-. He was one of Staten Island's largest landowners, developing a series of houses which combined the knowledge he acquired during his years of study in Paris with his desire to improve construction methods in a cost-effective manner. His goal was to make single- family houses affordable for a broader segment of the country's population. This estate was his residence and laboratory for over four decades, resulting in a unique group of structures that reflect his distinctive interpretation of architectural styles and design principles. Part of the property was designated as a NYC Landmark in 1967, with boundaries extended in 1983 to include other structures. At this time, a developer working with architect Robert A. M. Stern made modifications to some of the existing buildings, added 10 new residences, and made the pool into a formal garden. In 1987, three more buildings from the Estate were designated as NYC Individual Landmarks. With the exception of Stone Court, all of the buildings are currently used as private residences.