7. Harbor Hill

The now-demolished Harbor Hill, Clarence MacKay estate was once home to a mansion and expanse of stables. It was constructed from 1899-1902 in Roslyn, and was designed by prominent American architecture firm, McKim, Mead, and White, with Stanford White as the supervisor of the project.

All that remains of the estate in the stone drive entry and an original statue of a house and rider that now stands in front of Roslyn High School, which has since taken the mansion’s place. The estate is also now occupied by the Roslyn A.N.G. Station, a housing development, and the town pool.