Charles M. Schwab House-Riverside Drive-Demolished-NYCImage via Library of Congress

Like everywhere else in Manhattan, the Upper West Side and Manhattan began as bucolic farmland, settled with farmhouses and later large mansions away from the commercial fray downtown. Grand mansions were built from the Revolutionary era through the Gilded Age, by a variety of characters ranging from robber barons to respected surgeons. Famous names like Boss Tweed, John James Audubon, A.T. Tewaert, CKG Billings and Charles Ward Apthrop once graced these halls, but their homes all fell to the same fate–the wrecking ball.

1. Charles M. Schwab Mansion

Charles W. Schwab was president of U.S. Steel (founded by Andrew Carnegie) and also founded Bethlehem Steel Company. On Riverside Drive between 73rd Street and 74th Street, he built a 75-room mansion in a French chateau style over the course of four years from 1902 to 1906. He dubbed it Riverside, giving a nod to its great views of the Hudson River. Schwab was also the first to acquire an entire block in Manhattan, according to The New York TimesThe 50,000 square foot abode came replete with a pool, a bowling alley, a gaym and three elevators. As late as 1930, Schwab still staffed the mansion with 20 servants, mostly English-born. Schwab ended up going bankrupt, and according to this personal story, a Boticelli was smuggled out of the mansion and sold, which kept Schwab going financially for the remainder of his life.

Schwab tried to sell his home and property to the city as a mayoral residence but Fiorelli LaGuardia refused to live in it. In 1948, it was demolished and replaced with an apartment building.