At the peak the Gilded Age, steel tycoons and other professional exploiters only built their mansions in the Hamptons or Newport if they couldn't get a property in Tuxedo Park, New York. Founded in the 1880s by a tobacco millionaire and "sportsman" who won a whole lotta acres in a poker game, the area became home to such notable Americans as Adele Colgate (heir to the Colgate/Palmolive fortune), William Waldorf Astor, and JP Morgan. It was also home to a finance dude with the totally ironic name of Henry Poor, otherwise known as the guy who begot half of the famous Standard & Poor stock index.
"Poor's Palace," which is also known as "Woodland," was designed by eminent era architect Henry T. Randall, who gave the place a grand limestone entrance, a smoking room for the gents, drawing and dining rooms with deep relief ceilings, hand-painted insets for the grand dames, ample terraces, and wood paneled hallways. All 17,265-square-feet of that is still there, if a little worse for wear. What's more, it's all on the market with 4.8 surrounding acres for $9.999M.