They call Fifth Avenue the “Street of Dreams” a place where grand ambitions collide with unapologetic opulence. It’s a sobriquet that has held true well over a century now, back when the avenue was witness to an unofficial race as to who could outdo their neighbor with just more marble, more mahogany, and good measure-just more rooms than one could conceivably use.

Built in 1916 by Marjorie Merriweather Post, heiress to the Postum cereal fortune, this impressive five-story mansion with 54 rooms was located at the corner of Fifth Avenue and 92nd Street, right in the center of what was known as Millionaires’ Mile. This wasn’t an ordinary neighborhood; it was where the most influential families of America lived—the Carnegies, Dukes, Vanderbilts, and Woolworths. This was a street ruled by status, where strict social codes were practically etched into the stone of the grand facades.

Competition for prestige wasn’t just intense—it was almost ruthless. Families fought to design the most impressive, extravagant homes in the area, drawing inspiration from European architecture: part British manor, part French château, with a touch of Italian villa. This wasn’t just about keeping up with the neighbors; it was about outshining them with glittering chandeliers and jaw-dropping grandeur.

A Private Palace for Miss Post

Ms. Post’s mansion was no modest undertaking. She went all out, decking it in Louis XVI furniture, tapestries from Beauvais, and enough Sevres porcelain to make even the Louvre a little jealous. While most people have a closet, she had a gown room. Yes, a whole room. And this was not a closet on steroids-it had dress space, display spots, and probably needed its own zip code.

As one biographer noted, Post was unafraid of wealth. That might be the understatement of the century. With her husband, E.F. Hutton, she took her daddy’s company and made it General Foods, snatching up Birdseye Frozen Foods in the bargain. By the time her mansion reached high gear, Post was swimming in it. But she wasn’t the only one who set up shop along this swath of New York City real estate.

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Fifth Avenue: Home to the Rich and Powerful

It was through the Gilded Age-a period roughly spanning the late 1800s to early 1900s-that Fifth Avenue became the address. Old money families, railway tycoons, and bankers flocked there, drawn by a desire to show off wealth that was new, shiny, and practically begging for attention. According to historian Andrew S. Dolkart, nearly all the land between 59th and 96th Streets was mansion territory.

As the saying goes, money moves mountains-or in this case, Manhattan neighborhoods. In and of itself, Fifth Avenue dragged New York society’s center north and left everything else in its shade.

But this was to be the golden age of the Fifth Avenue estates, which would fade as fast as it had arrived. World War II introduced new demands and a new taste for apartment living rather than full-scale palaces. Ms. Post’s mansion and most of Millionaires’ Mile became private clubs, museums, and swanky luxury apartment buildings that still remain among the most expensive addresses in the world.

Origins: From Main Street to Fifth Avenue

Before it was an internationally known name and brand, Fifth Avenue was known simply as Middle Road-the name of which does have a pretty humble sound to it, doesn’t it? Just a stretch of dirt serving as a direct route to the outskirts of the city, each plot of land sliced up into five-acre parcels in the interest of raising capital for growth.

So when the 1811 street grid commission mapped out New York’s future, Middle Road got its upgrade to Fifth Avenue. Most of Manhattan’s population used to hang south, where the city buzzed with the trade of finance, goods, and anything you could haul in on horseback-or the 40,000 horses themselves-no shortage of aroma there. Uptown was still a whole lot of openness.

But Henry J. Brevoort broke the ice north in 1834, erecting a Greek Revival house on the site of his father’s farm. The dam had burst: one mansion begat another, and Fifth Avenue became the place to be for New York City’s haut monde. Federal rowhouses gave way to brownstones by the 1850s, lending the neighborhood some -comparatively-subdued homogeneity.

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The Astors, Vanderbilts, and the Social Tug-of-War

Fifth Avenue swelled in the 1890s with the most lavish residences from the crème de la crème of New York. Even Edith Wharton, chronicler of upper-crust society, weighed in.on her feelings-that New York was being overrun with brownstones. And so her verdict was that it was boring, a “chocolate-colored coating” covering the city’s most hideous buildings. Wharton mightn’t have liked them, but these houses represented an advances of status and money undeniably.

But nothing quite personified Fifth Avenue’s social one-upmanship like Vanderbilt Alley. William K. Vanderbilt and his wife Alva dropped a literal chateau into 52nd Street, kitted out with tapestries, armor, and medieval furniture. The mansion itself became a High Society power play, too- Alva famously left the formidable Mrs. Astor off her ball guest list, forcing her to invite Alva into the fold lest her daughter’s social disaster follow. Northbound, expressly around Central Park

Fifth Avenue’s great estates edged further uptown, crossing, at last, 59th Street into Central Park. Henry Flagler laid claim to 54th and Fifth, William Rockefeller snapped up the northeast corner and, handsomely, the greatest of these, the Carnegie Mansion, checked in at 91st Street. Carnegie’s mansion-a Georgian strongpoint with more than 60 rooms-was pretty much the last stop for most of these baronial palaces.

It was here that the shantytown holdouts received their marching orders, and soon only neighbors of a studied social cachet might be found in the environs.

But perhaps the most outlandish of these homes belonged to copper magnate William A. Clark. His house, at the corner of 77th Street, was over a decade in making and featured amongst other things, four art galleries, a Turkish bath, and an underground railway for coal. You know, as one does. But by the time it was complete, the age of the mansion was already on life support. The Rise of the Penthouse: A New Kind of Prestige

By the 1920s, the romance of Fifth Avenue’s sprawling mansions finally wore off. The upkeep was brutal, property taxes a killer, and New Yorkers were finally warming up to apartment living. Marjorie Merriweather Post felt this shift in sentiment first-hand.

Tired of the street noise and fumes, she struck a bargain to allow the mansion to be demolished on one condition: that she be given a triplex penthouse in the new 14-story luxury apartment building that would take its place. She wanted it all-her own private entrance, a terrace, 12 fireplaces, and 17 bathrooms. The penthouse thus became the newest status symbol for those chasing Fifth Avenue prestige. The palatial homes of Fifth Avenue may be long gone, but their spirits make their presence-mostly as museums: the Andrew Carnegie mansion is now the Cooper Hewitt, Smithsonian Design Museum; the Straight House was once a home of wealthy socialites, and it now houses the International Center of Photography; the Payne Whitney House at 972 Fifth Avenue is now serving French Embassy’s cultural services. Today, Fifth Avenue still will compete for one of the most expensive streets in the world. Gone are the mansions, replaced by billion-dollar penthouses and condos, but it is not a spell doomed to fade as time wears on. The next time you walk down this “Street of Dreams,” just remember those buildings are not just dwellings-they are monuments to an era when living large meant pulling out all stops and sometimes more.

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