In 1895, Frederick W. Vanderbilt purchased the Langdon estate, comprised of 153 acres, a structurally unsound house, a farm and 459 acres on the east side of Post Road. Hyde Park was the name of the stately home he commissioned for himself and his wife, Louise and it was built between 1896 and 1899 on approximately 600 acres. The mansion on a bluff overlooking the Hudson River in Hyde Park, N.Y., this was one of several homes owned by the couple.

William Gillette was a successful actor and playwright mostly known for his portrayals of Sherlock Holmes on stage. Gillette originated and popularized many common features of the character: the cap and cape, curved pipe, magnifying glass and the phrase “elementary, my dear fellow (which later evolved to “elementary, my dear Watson”. He took his money and ran for the hills overlooking the Connecticut River where he built his 24-room mansion, called the Seventh Sister, on 122 acres.

Frederick Gilbert Bourne was a self-made millionaire who resided at the Dakota Apartments in Manhattan and had a 1,000-acre estate in Oakdale, Long Island, called Indian Hall. Bourne became the fifth president of the Singer Sewing Machine Company, which is where the current name “Singer Castle” comes from. While the Bourne’s summered here, they called the castle, “The Towers” and the island, “Dark Island”.