4. Fort Tryon Hall, CKG Billings Estate

With over $2 million lying around, Cornelius King Garrison Billings (1861-1937) built an estate overlooking the Hudson River that fit right into the excessive culture of the Gilded Age. Completed in 1907, the Billings estate on Fort Tryon at Washington Avenue and Riverside Drive, was originally meant to only be his summer dwelling and included a bowling alley, a heated indoor swimming pool, and a maple squash court among the living quarters.

Soon after finishing an elaborate stable for 60 horses in 1903, Lowell started designing an estate for the millionaire and his family in the lavish style of Louis XIV. Completed in 1907 and named Tryon Hall, it included 21 rooms and was centered around a courtyard of flowers. Since the mansion was 250 feet above the Hudson River, the Statue of Liberty could be spotted from the observatory. To keep up with all the chores and maintenance, Billings had 23 live-in servants.

Despite his extravagant surroundings, Billings didn’t enjoy living in Upper Manhattan so in 1917, only 9 years after construction was completed, he sold the property to John D. Rockefeller, Jr. for $35,000 per acre. Rockefeller planned to turn the estate into a park, while demolishing the estate, which was met with resistance. A fire took down the house in 1918 while it was being rented out. Today, there are still remnants of the estate you can find in Fort Tryon Park!