2. Mrs. Astor’s House, 34th Street and 5th Avenue: Demolished

The Astor family started the trend of building 5th Avenue Gilded Age mansions uptown. The first popped up on a parcel of land at 34th Street and 5th Avenue. The land was a wedding gift to William Backhouse Astor Jr. and his new wife, Caroline Astor (née Webster Schermerhorn), from William Backhouse Aster Sr. in 1854. The house the couple had built on the property was a surprisingly modest four-bay brownstone, which was a stark contrast to the ornate A.T. Stewart mansion built across the street.

After William Backhouse Sr. died, Caroline became the reigning Mrs. Astor. In anticipation of increased entertaining duties, she made extensive renovations to the interior of their “humble” home. First, she transformed the Georgian drawing-room into a French Rococo style. The Astor family portrait was painted in the Rococo room. A new ballroom wing was added to the house, replacing the stables. In this ballroom, Caroline sat perched on a red silk divan, her “throne” as it would come to be known, and made or broke the dreams of New York City’s social climbers. Mrs. Astor’s ballroom famously held 400 guests, and to be one of “the 400,” meant you had made it into the highest echelon of New York City society. The Empire State Building now stands at the site of the Astor’s brownstone.