William Kissam Vanderbilt came to Oakdale in the last quarter of the 19th century seeking an escape from New York City for himself and his family. He was the son of William H. Vanderbilt, and the grandson of the famous Commodore Cornelius Vanderbilt who amassed a $100,000,000 fortune in railroads.

William K. Vanderbilt's introduction to Oakdale was through the Southside Sportsmens Club. He joined the Club along with members of the Tiffany, Hyde, Hunt and Belmont families who came to Oakdale to enjoy the hunting and fishing together. Hoping to secure his family's position in New York City's elite social set, Willie K. (as his family called him) chose to build a country retreat in the company of his peers. He began to assemble a large plot of land in 1876.

The northern perimeter was Montauk Highway, its western boundary was the Connetquot River, eastern was what is now Vanderbilt Boulevard, and the Great South Bay formed the southern boundary. When purchasing the land, Vanderbilt was represented by a discrete agent because a Vanderbilt purchase would have caused a substantial price inflation in the area. The plot encompassed 862 acres dense with maple, pine, locust and oak trees. He and his wife, Alva, began construction of "the most beautiful private home in the world."

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