The property for the Roslyn High School and its athletic field was donated by financier Clarence Mackay and Katherine Mackay in 1923. The building was designed by architect William Bunker Tubby in the Colonial Revival Style. Tubby was best known as the architect for the Pratt family and their estates. Among his other prominent buildings were the Nassau County Courthouse and the Roslyn National Bank and Trust. Tubby's family had a residence at 1401 Old Northern Boulevard in Roslyn.

Tubby's original Roslyn High School consisted of a columned main entrance with symmetrical wings. The main entrance was located at the intersection of Roslyn Road and Lincoln Avenue highlighted by a concrete staircase from Roslyn Road.

From 1970 to 1971, the original building was demolished and replaced by the current structure. Several remnants remain including the middle section of the entrance staircase, a small piece of the wall surrounding the entrance and a plaque commemorating Clarence Mackay's 1923 donation.

The Mackay Horse Tamer statue was moved from its original location at Mackay's former Harbor Hill Estate in 1959 to the Roslyn High School with the assistance of local assistance George Gach. After being damaged by weather and vandals, it was removed in 2012. The restored statue was reinstalled on a new pedestal on October 10, 2019.

1946

As seen on October 2, 2020 with remaining remnants.

The plaque commemorating Clarence Mackay

The restored Mackay Horse Tamer Statue which was reinstalled on October 10, 2019.

The Mackay Horse Tamer Statue as seen in its original location at Clarence Mackay's Harbor Hill Estate.