The property portfolio of the Vanderbilt family, once one of the wealthiest families in America, boomed on Fifth Avenue during the Gilded Age, when nearly a dozen mansions, more akin to palaces, were erected by multiple descendants of Cornelius "The Commodore" Vanderbilt.
From the 1880s to early 1900s, the Vanderbilts spent nearly half a billion dollars in today's rate building their homes, but by the 1940s, most of them had been demolished. Their empty lots soon were making way for the modern skyscrapers the legendary avenue has become known for today, such as the Buchmann Tower and the Tishman Building, which today host retail stores like Swarovski and Nike at their base.
The Vanderbilts, and their fellow millionaire socialites, first landed on Fifth Avenue when their previous Lower Manhattan neighborhoods became increasingly commercialized.
"Fifth Avenue was a wider street, and many wealthy families had bought land there early on as investment property," architect and historian Gary Lawrence, who runs the blogs Mansions of the Gilded Age as well as The Gilded Age Society, tells HELLO!. "The avenue began to fill in with fine residences designed in an eclectic mix of architectural styles, often surrounded by small gardens and space."
"By the 1850s, the older families, preferring solid, unpretentious homes, built boxy brownstone dwellings that looked formidable on the outside but were opulently decorated inside," he adds. "From the 1890s on, the area of Fifth Avenue above 59th street, which fronted Central Park, was the place for some of the grandest, more classical style mansions."
However, the expert notes, the Vanderbilts and other families eventually were ready to move on to newer properties. "The next generation of the builders of these magnificent homes found they no longer desired to live in their parents' houses, or they preferred more modern, easier to care for homes." Rising real estate taxes and monied, hungry developers didn't help either.
Today we can see that these Fifth Avenue properties mirror the evolution of New York City, and tell a story that still rings true today: residents forced out by rising property taxes, and homebuyers, who prioritize space and privacy, driven away from their first homes as commercial development encroached on residential areas.
It's the reason the Vanderbilts — whose first mansions were built on Staten Island — arrived on Fifth Avenue, and the very reason they left.
The Vanderbilts' Fifth Avenue - then and now
Below, take a before-and-after look at the legendary homes the family built along Fifth Avenue's "Vanderbilt Row," and what rose in their place.
854 Fifth Avenue — The $50 million former Cold War enclave
This residence is one of Manhattan's last intact Gilded Age mansions, built further up from Vanderbilt Row on 67th Street in 1905 for stockbroker Robert Livingston Beeckman.
Emily Thorn Vanderbilt Sloane White (William Henry Vanderbilt's daughter) and her husband Henry White purchased the house in 1925 for $450,000, around $8 million today.
The Vanderbilt Mansion today
Following Emily's 1946 death, Yugoslavia bought the six-story Beaux-Arts mansion for $350,000; it served as the country's U.N. mission before it again became a private residence. The building was sold for $50 million in 2022 after first being put on the market in 2017. Surprisingly, at the time the 32-room, 20,000 square-foot home still had many of its original details and splendor, including ceiling frescoes, hand-carved marble balustrades and even an original working oven. Plus the mansion had a secret top-floor as well as a Cold War-era metal-padded room known as a Faraday Cage, which allowed officials of the former Soviet ally to converse or make calls without the risk of being wiretapped.
640 and 642 Fifth Avenue and 2 West 52nd St — The Triple Palace
Also known as the Triple Palace, this hulking manor, built for the Commodore's son William Henry Vanderbilt, consisted of three brownstones taking up almost an entire block between 51st and 52nd Streets; he paid $700,000 (over $23 million today) for the lot. William inhabited one townhome (and its 58 rooms) with his wife Maria Louisa and their son George, while his daughters Emily and Margaret took up the other home, which was split in two. His residence alone boasted 27,000 square feet, while his daughters' had 11,000 square feet each; the entire complex had 135,000 square feet of living space, and cost $2 million to build — around $69 million today.
Following William's sudden death in 1885, the mansion was passed down to his children, and part of it was for a time leased to fellow business mogul Henry Clay Frick. Cornelius Vanderbilt III later took ownership of the house and eventually sold it to politician and hotelier William Waldorf Astor, cousin of John Jacob Astor IV. Also once one of the wealthiest people in the world, Astor IV died when the Titanic sank in 1912.
The Vanderbilt mansion today
By the 1940s, the home — as was Fifth Avenue — was increasingly surrounded by commercial developments, and was ultimately demolished in 1947. In its place currently are two office buildings, 640 Fifth Avenue, at the bottom of which is a Victoria's Secret, and 650 Fifth Avenue, anchored by a Nike store.
660 Fifth Avenue — Petit Château
Across the street from the Triple Palace was Petit Château, a Châteauesque mansion built by Richard Morris Hunt in 1882 for William Henry's son William Kissam Vanderbilt and his wife Alva Vanderbilt. (Alva was famously determined to break into the society scene ruled by old money gatekeeper Caroline Astor, who developed, along with fellow society arbiter Ward McAllister, the notorious 400 List, an exclusive index of New York City's social elite). The home cost $3 million to construct, about $98 million today. When the home was first built, in order to capture the public — and Mrs. Astor's — attention, Alva hosted her famed Fancy Dress Ball, inviting 1,200 guests from New York's high society… except Mrs. Astor herself. The society doyenne reportedly ultimately called personally for an invite, officially making way for the new-money guard.
The Vanderbilt mansion today
For all the efforts to make it to Fifth Avenue, by the 1920s the grandiose homes and the avenue as a residence had fallen out of vogue. Petit Château shared the fate of many Vanderbilt homes; it was demolished in 1926 after being sold to a developer. In its place is now the Tishman Building, a 41-story building completed in 1957, which in part houses Zara, Uniqlo and Abercrombie & Fitch.
742-748 Fifth Avenue — New York City's largest ever residence
William Henry's other son, his eldest Cornelius Vanderbilt II, reportedly the Commodore's favorite grandson, also had his own Châteauesque mansion built. Completed in 1883, it occupied the northwest corner of Fifth Avenue and West 57th Street, and was also designed by Richard Morris Hunt along with George B. Post, with interiors by French design firm of Jules Allard and Sons; it was and still is the largest private residence ever built in New York City, boasting over 130 rooms.
The Vanderbilt mansion today
Following Cornelius II's death in 1899, for a time his wife Alice Claypoole Vanderbilt was able to maintain both their mega-mansions, the Fifth Avenue home and the famed Breakers mansion in Newport, Rhode Island thanks to the trust fund her husband left behind. However, she was eventually forced to sell in 1926, with developers paying $7 million (around $130 million today) for the land. After the home was demolished, it became the site of the iconic Bergdorf Goodman Building.
871 Fifth Avenue — The William C. Whitney House
The home at 871 Fifth Avenue was a townhouse known as the William C. Whitney House. It was inhabited by his son Harry Payne Whitney's widow Gertrude Vanderbilt Whitney - the second daughter of Cornelius Vanderbilt II and the namesake founder of the Whitney Museum, who was also an esteemed sculptor. Originally built in 1883 for Robert L. Stuart, who died before the home was completed, it came into the ownership of William C. around 1897. The property was later passed down to Harry, who lived there until his death in 1930, after which Gertrude owned it until her death 12 years later.
When William C acquired the home, he employed beloved Gilded Age architect Stanford White to transform it into a Beaux-Arts palace — a renovation which at the time cost $3.5 million, an equivalent in purchasing power to approximately $140 million today. He incorporated a grand ballroom, measuring 63 feet long by 45 feet high, into a brand-new wing. Including the basement and servants' quarters, the home sprawled across 54,000 square feet of living space.
The Vanderbilt mansion today
The William C. Whitney House was demolished in 1942, and a residential building is now in its place.
680 and 684 Fifth Avenue — Florence Adele Vanderbilt Twombly and Eliza Osgood Vanderbilt Webb Townhomes
Even a residence as large as William Henry Vanderbilt's Triple Palaces wasn't enough (by Vanderbilt standards) to house all of his children, and therefore his daughters Florence Adele Vanderbilt Twombly and Eliza Osgood Vanderbilt Webb also got their own mansions on Fifth Avenue. The townhouses, described as brick and stone mansions featuring a jumble of historical styles, were created in 1884 by John B. Snook, known for designing many of SoHo's signature cast iron commercial buildings. Eliza lived at 680 Fifth with her husband William Seward Webb, and her sister Florence lived in 684 with her husband Hamilton McKown Twombly.
The Vanderbilt mansion today
The Webbs left the city in favor of their other mansions around 1913, and 680 was sold to John D. Rockefeller for a reported $1.25 million shortly after. It was demolished in 1917 in favor of a French-inspired store and office building known as the Rockefeller Building. Florence remained in 684 until around 1925, when Rockefeller also bought the home, demolishing it and adding to his adjacent building. That structure was taken down in 1956, and in its place rose the Buchmann Tower, which today houses a Swarovski store.
677 Fifth Avenue — Cornelius Vanderbilt III Townhome
Little is known about the origins of 677 Fifth Avenue. The townhouse, built in 1904, is where Cornelius Vanderbilt III lived with his wife Grace Vanderbilt for a time, before they inherited one of the Triple Palaces townhomes.
The Vanderbilt mansion today
The townhouse was razed sometime in the 1940s, and in its place today is the Microsoft flagship store.
645 and 647 Fifth Avenue — Marble Twins
Not far from where the Triple Palaces stood, William Henry Vanderbilt's son George Washington Vanderbilt built his own (double) mansions, the Marble Twins, between 1902 and 1905. Designed by Hunt & Hunt in a French Renaissance Revival style, the buildings stood on an L-shaped lot that has the Cartier mansion in the corner. The Cartier mansion also consists of conjoined residences, also built in 1905: the Morton F. Plant residence designed by Robert W. Gibson, and the Edward Holbrook residence designed by C. P. H. Gilbert.
The Vanderbilt mansion today
Of the Marble Twins, only one remains, 647. The home was altered for commercial use in 1916, and today houses Kim Kardashian's shapewear brand Skims' store. The "twin" 645 was demolished in 1944, and in its place now stands Olympic Tower. The 51-story skyscraper — designed by Skidmore, Owings & Merrill and completed in 1974 — currently houses residences, offices and shops.






















