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 has always been pretty special, although you’d probably never guess that it began with a rather ordinary and functional name: Middle Road. Like the 1811 Commissioner’s Plan for Manhattan, which laid out the city’s future expansion in a rational manner, Middle Road was part of an earlier real estate plan by the City Council.

As its name suggests, Middle Road was situated in the middle of a large land parcel that was sold by the council in 1785 to raise municipal funds for new newly established nation. Initially, it was the only road to provide access to this yet-undeveloped portion of Manhattan, but two additional roads were built later (eventually becoming Park Avenue and Sixth Avenue).

The steady northwards march of upscale residences on New York City’s Fifth Avenue, and the retail to match, has its origins where the street literally begins: in the mansions on Washington Square Park. Madison Square was next, but it would take a combination of real-estate clairvoyance and social standing to firmly establish Fifth Avenue as the center of society. The AIA Guide to New York City calls this area of Fifth Avenue from 59th Street to 78th Street the “Gold Coast,” and rightly so.

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

The catalyst for Fifth Avenue’s transformation came in the form of the Astor family. Patriarch John Jacob Astor had purchased large swaths of Manhattan in the aforementioned land sales, allowing William Backhouse Astor Sr. to present his son and the new Caroline Astor (née Webster Schermerhorn) with a parcel of land on 34th Street and 5th Avenue as a wedding gift in 1854.

Old money didn’t need to flaunt however, so the resulting home was a rather modest brownstone. But the arrival of upstarts A.T. Stewart across the street forced Caroline into action. Following extensive interior renovations in the French Rococo style, the first “Mrs. Astor’s House” was born. It was also here that societal standing was attained and lost, amidst the famous 400 (named so because it was simply how many people could fit into Mrs. Astor’s ballroom). The ballroom, sumptuously appointed with floor to ceiling artwork and a massive chandelier, was built in a new wing which replaced the stables.

With new fortunes being made overnight in the new center of world commerce that was New York, it was only logical that the new millionaires each needed their own mansions along 5th Avenue.