Fifth Avenue apartment buildings reflected in Central Park’s Conservatory Water © Getty

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For more than a century, Fifth Avenue has been the epicentre of Manhattan high society. The Age of Innocence, Edith Wharton’s 1920 novel, chronicles the lives of the Gilded Age’s super-rich, families whose social comings and goings are overseen by the aristocratic matriarch Mrs Manson Mingott of Fifth Avenue. It was a life that Wharton knew well: the inspiration for Mingott came from her own great-aunt, Mary Mason Jones, who in the late 1860s built a series of matching marble-clad houses on Fifth Avenue between 57th and 58th Streets known as Marble Row — about 20 blocks north of what was then “respectable” Manhattan.

In the novel, Mingott does likewise and Wharton describes the character’s confidence in her end of the street. “She was sure that presently the hoardings, the quarries, the one-story saloons, the wooden green-houses in ragged gardens, and the rocks from which goats surveyed the scene, would vanish before the advance of residences as stately as her own.”

If Jones had a similar thought, she was right. By the end of the century The New York Times had nicknamed the junction of 57th and Fifth “the palace corners”. Surrounding Marble Row were the grand houses of business magnates Cornelius Vanderbilt II, Collis P Huntington and the Whitney family.

None of these homes remains. Yet the opulence of Fifth Avenue — and its appeal to homebuyers — is undimmed. “A Fifth Avenue address means that you’ve pretty much arrived in terms of Manhattan’s elite circles,” says Daniel Douglas, an estate agent with Corcoran.

In August, a five-bedroom apartment at 1040 Fifth Avenue sold for $32m. The 17-storey limestone building includes views of Central Park and the Jacqueline Kennedy Onassis Reservoir. One person who no doubt enjoyed the view was Onassis herself, who lived in the building from 1964 until her death in 1994. The reservoir was named after her when she died.

Empire State Building, c1962 © Rolls Press/Popperfoto/Getty Images

Corcoran is selling a two-bedroom apartment overlooking Central Park at 60th Street for $27.5m. The property, which measures about 5,000 sq ft, is owned by David Geffen, the record and film company founder.

Fifth Avenue starts about 50 blocks to the south at the Washington Square Arch in Greenwich Village. This end of the street began its transformation in the 1850s when members of the Astor family moved in. More of New York’s moneyed families soon followed and the seven-block stretch of Fifth Avenue between 14th Street and Washington Square Park eventually came to be known as the Gold Coast because of its wealthy clientele.

Edith Wharton © Bettmann Archive

The Astor house began as a modest brownstone, but extensive interior renovations in the French Rococo style added a ballroom with floor-to-ceiling artwork and a large chandelier. The home came to be known as the meeting place for the “famous 400”, because that is how many of the Manhattan elite it was thought could fit inside.

Manhattan became more developed in the late 19th century, and as lower Fifth Avenue gradually began to attract commercial activity, New York society started to move north towards Central Park and the newly built mansions of Jones and Vanderbilt.

© Evan Joseph Images
Reception room and exterior of six-bedroom beaux arts townhouse on East 62nd Street, $84.5m © Evan Joseph Images

Around the time Vanderbilt started work on his home on the corner of 57th Street, plans were under way for another project on Fifth Avenue. Called the Triple Palace, three adjoining townhouses were built for Vanderbilt’s granddaughters in 1882. The buildings occupied the entire block between 51st and 52nd Streets.

“Their appeal was their size, their staid grandeur, and the quality of their design and construction,” says author and historian Michael Gross. Like the grandfather’s mansion, the Triple Palace fell to the wrecking ball and was demolished in the 1940s.

Staircase at the Dommerich Mansion on 69th Street, $72m © Cary Horowitz

Gross works as an “in-house historian” for 12 East 88th Street, a 29-unit condominium built in 1931 between Fifth Avenue and Madison Avenue, currently being restored by developer Simon Baron. Prices range from $1.49m for a one-bedroom apartment to $7.87m for a four-bedroom home, available through Douglas Elliman.

While sales of Manhattan’s super-prime condos have been patchy — in March, Extell Development, the builder of the One57 tower, reduced its projected sellout value by $162m from 2013 estimates to $2.56bn — historic buildings on Fifth tend to hold their value.

Dommerich Mansion reception room © Cary Horowitz

After all, some of these homes weathered the Great Depression, during which the value of Manhattan property plummeted more than 50 per cent — double the fall that followed the 2008 financial crisis.

On both occasions prices recovered. “Buyers who could afford luxury preferred history and pedigree,” says Jeremy Stein of Sotheby’s International Realty. “That’s still true today and that’s why a Fifth Avenue apartment will always keep its value.”

Exterior of the Dommerich Mansion © Cary Horowitz

If any of today’s super-rich feel like imitating the Astors, the Vanderbilts or Mary Mason Jones by buying their own grand townhouse, they might consider the beaux arts home for sale just off Fifth on East 62nd Street. On the market with Modlin Group for $84.5m, the house includes six bedrooms and 15,000 sq ft of living space.

A few blocks north, the Dommerich Mansion, a century-old limestone building on 69th Street between Park and Madison Avenues is on the market for $72m. The 21,000 sq ft home has seven storeys, two residents’ and one service lift, multiple terraces and a roof deck with views of Central Park. Brown Harris Stevens has the listing.

Cornelius Vanderbilt II’s house on 57th Street, c1885 © Kean Collection/Getty Images

Astor v Vanderbilt: battle of the belles

Even prominent society figures of New York’s Gilded Age were not above displays of petty one-upmanship, writes Georgina Varley. The feud between society belles Caroline Astor and Alva Vanderbilt in 1883 is a famous example.

Vanderbilt had recently moved to a grand house on Fifth Avenue, which her descendant Arthur T Vanderbilt II described as “a battering ram to crash through the gates of society”. To celebrate she held a masquerade ball for more than 1,000 guests, costing a reported $250,000 (equivalent to more than $5m today).

Not only was the housewarming a rather brash display of Vanderbilt’s wealth, it was also a powerful societal move that challenged Astor’s position as “the Queen of New York”. Until then, it had been Astor who held the city’s most lavish parties at her home at 350 Fifth Avenue — now the site of the Empire State Building. Astor’s ballroom could only hold 400 guests, alas, and what was worse, Vanderbilt refused to invite Astor’s daughter Carrie to her party.

Such was the hype surrounding Vanderbilt’s upcoming soirée that Astor was forced to take the humiliating step of sending a calling card to Vanderbilt in order to secure an invitation for Carrie.

The power had shifted at the top of high society. Yet Astor wasn’t ready to admit defeat. In 1894, she moved to 840 Fifth Avenue, a bigger house with an even bigger ballroom that could host 1,200 people. She continued to hold functions until a fall at the age of 77, which affected her so badly she was later seen wandering through her home greeting guests who weren’t there and hosting imaginary soirées. She died a year later in 1908.

Buying guide

● Fifth Avenue from 82nd to 105th Streets is known as the Museum Mile because it is home to eight museums

● Architect Rosario Candela designed some of New York’s most coveted addresses in the 1920s, including 1040 Fifth Avenue

● Construction of the Empire State Building on Fifth Avenue was completed in 1931

● Fifth Avenue between 49th and 60th Streets is home to some of the most expensive commercial space in the world. Retailers include Louis Vuitton, Gucci and Tiffany & Co

What you can buy for . . . 

$10m A four-bedroom home on Fifth Avenue near Washington Square Park

$20m A smart duplex apartment with four bedrooms near Central Park

$70m A grand six-storey townhouse with six bedrooms just off Fifth Avenue

More homes at propertylistings.ft.com

Photographs: Getty Images; Rolls Press/Popperfoto/Getty Images; Bettmann Archive; Evan Joseph Images; Cary Horowitz; Kean Collection/Getty Images

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