The Cornelius Vanderbilt II Mansion on 57th Street and 5th Avenue, now demolished. Photo from Library of Congress, Prints & Photographs Division, Detroit Publishing Company Collection

New York City’s Fifth Avenue in Manhattan has been associated with glamour and wealth since the 1800s. However, when this now-iconic street was first laid out, it was given a rather humdrum name, Middle Road. The undeveloped parcel of land Middle Road cut through, which was sold in 1785 to raise municipal funds for the newly established nation, would become the epicenter of New York City’s high society. As the 18th-century turned into the 19th-century and the Gilded Age began, the 1811 Commissioner’s Plan renamed Middle Road Fifth Avenue. Development of the city moved northward, led by millionaires who built palatial homes on the largely empty swaths of land. The string of fabulous Gilded Age 5th Avenue mansions that stretched from 59th to 78th Street was dubbed the “Gold Coast,” and “Millionaire’s Row.” While many of the grandiose 5th Avenue mansions of New York City’s 19th and early 20th-century millionaires have been lost to time, there are some that remain intact today, serving as homes for non-profits, museums, and cultural organizations.

Lost NY: Mansions of Fifth Avenue

You can uncover the stories of forgotten Gilded Age 5th Avenue Mansions in our next Lost New York virtual talk! Tickets to this talk are just $10. You can gain access to unlimited free virtual events per month and unlock a video archive of 100+ past events as an Untapped New York Insider starting at $10/month. Already an Insider? Register here! Can’t make it live? Register for this virtual talk and we’ll email you a recording of it after it ends!

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

The Astor family started the trend of building 5th Avenue 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.