The property was part of a large tract granted to local landowner Philip Philipse in 1686 by the British Crown. His son Frederick left to his daughter Mary Gouverneur in 1829, and she ultimately divided it three ways, taking the northern third and naming it Eagles' Rest. That portion was eventually sold to Louis Fitzgerald, a local businessman who served as an officer in the Union Army during the Civil War. His three daughters in turn sold the estate to Ruppert, who had made a fortune in his family's brewing business, served in Congress and bought the Yankees, 11 years later, in 1919. He commenced major building on the property in the early 1920s, tearing down the original mansion for the current Tudorbethan structure, which was finished in 1928. The Yankees and their "Murderers' Row" became champions under Ruppert's ownership, and many players were guests at the estate. Babe Ruth reportedly signed one of his most lucrative contracts there. The brewing business had also survived Prohibition by making near beer, and since real estate had become cheap after the Crash of 1929, Ruppert began expanding it, acquiring the land between the old and new alignments of NY 9D when the road was relocated east to its present route. In these buildings he kept a small personal zoo, with one of the largest collections of monkeys, wild birds and peacocks in the world at the time. In the mansion he had a collection of furniture, pottery, jade and Chinese porcelains. The estate employed 40 people. Construction continued through Ruppert's death in 1939, with smaller outbuildings added, bringing the estate to a total of 26 buildings. Many of these are considered contributing resources to the NRHP listing.
As school
After five years of vacancy, the Greek Orthodox Ladies Philoptochos Society bought the property in 1944 for $55,000. Property taxes were increasing on large estates, and as a nonprofit the church was exempt. At first, it was coeducational, but soon it was decided to limit admission to girls due to the limited space available. In addition to its secondary program, the academy was also, at first, a women's junior college, offering a three-year teacher training program, and an orphanage. Graduates went on to work for the church as teachers or secretaries. Later in the 1950s, the school decided to admit boys again, and in 1959 a former stable had been converted into a boys' dormitory. The American Hellenic Educational Progressive Association, which had raised money for the stable conversion, continued its efforts and built a new classroom building, just north of the mansion, which opened in 1962. The Pan-Arcadian Fraternal Association built a new gymnasium that doubled as an auditorium the next year, inspiring Archbishop Iakovos to call for money for more new dorms. This period of growth would lead to a slight contraction in the 1970s. In 1973 the junior college and its programs merged with Hellenic College in Brookline, Massachusetts. Three years later, in 1976, the Philoptochos sold the of marshland along the Hudson River to the Audubon Society, which has made it their Constitution Island Sanctuary for the protection of some of the river's bird species. Building began anew with a library in 1981 and swimming pool five years later, in 1986. Architect William Chirgotis designed and funded a new chapel in memory of his parents, in 1985. A playground was built with donated money in 1990, and in 1999 a medical and dental facility. Maintenance and renovation projects continue around campus as educational programs for students.
