The Empire State Building rises majestically above the Manhattan skyline (Photo: Michael Discenza / WikiCommons)
Cover The Empire State Building rises majestically above the Manhattan skyline (Photo: Michael Discenza / WikiCommons)

The stomping ground of the affluent elites, New York City's Fifth Avenue is a living architectural museum

From the opulent displays of wealth along Millionaire’s Row in the Upper East Side during the Gilded Age, to the glamorous gatherings of chic aristocrats and fashion icons in Midtown’s trendiest spots to the modern-day elites who frequent the Museum Mile, the illustrious Fifth Avenue has been a stage for the rich and famous for generations. 

Many of these iconic moments have been immortalised in popular TV shows and Hollywood films, often filmed right on Fifth Avenue itself. Think Breakfast at Tiffany’s, The Godfather and The Great Gatsby, or the stylish antics of Blair Waldorf’s crew on the steps of The Met in Gossip Girl, and the legendary Black and White Ball thrown by Truman Capote at The Plaza, chronicled in Feud: Capote vs. The Swans.

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Photo 1 of 2 A scene from the famed Black and White Ball in 'Feud: Capote vs The Swans' (Photo: Courtesy of FX)
Photo 2 of 2 The scene was shot in The Plaza's Grand Ballroom where the Black and White Ball was held in 1966 (Photo: Courtesy of FX)

But it’s not just the elite society that captures attention—it’s also the architectural wonders that adorn the thoroughfare. From the breathtaking Châteauesque-style mansions to the grand Beaux-Arts buildings, Fifth Avenue is a living museum of a bygone era.

Explore six iconic buildings along Fifth Avenue, each a masterpiece of distinctive and timeless architecture, spanning from the Central Park Reservoir to the vibrant streets of the Flatiron District.

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1. Warburg Mansion

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Photo 1 of 2 The Warburg Mansion is today the Jewish Museum of New York (Photo: Gryffindor / WikiCommons)
Photo 2 of 2 C.P.H. Gilbert's Châteauesque style build was one of the many opulent Gilded Age mansions along Millionaire's Row (Photo: Epicgenius / WikiCommons)
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The Indiana limestone façade capped with an ornate French Gothic roofline (Photo: Epicgenius / WikiCommons)
Above The Indiana limestone façade capped with an ornate French Gothic roofline (Photo: Epicgenius / WikiCommons)
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One of the windows with bolded-scaled French Gothic detailing (Photo: Epicgenius / WikiCommons)
Above One of the windows with bolded-scaled French Gothic detailing (Photo: Epicgenius / WikiCommons)

The Warburg Mansion, now home to the Jewish Museum of New York, stands as a testament to the opulent Gilded Age era along Millionaire’s Row, where during the late 19th and early 20th centuries, the wealthy elite vied to outshine one another with grand mansions of various architectural styles; many of which were demolished in the following decades.

Commissioned by Felix M Warburg, a prominent Jewish financier and philanthropist, renowned architect Charles Pierrepont Henry Gilbert, known as C.P.H. Gilbert, began the mansion’s construction in 1907 on the Upper East Side of Manhattan, adjacent to Central Park Reservoir, drawing inspiration from the Châteauesque style of the Loire Valley and late Gothic architecture distinctive among European church designs.

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The Indiana limestone façade boasted bolded-scaled French Gothic detailing, particularly around the windows and roofline, with ornamentation on the upper floors and a sizable lawn extending from its 15-metre frontage.

The mansion spanned a staggering 82,000 square feet, with over 50 rooms across six floors inside. Each meticulously designed with rich wood panelling and intricate detailing, highlights included a grand staircase on the ground floor, formal spaces on the second floor with a music room fitted with a built-in organ, private quarters on the third floor, and even a squash court on the fifth floor.

Warburg, his wife Frieda, and their five children resided in the mansion until his passing in 1937. Following his death, Frieda transferred ownership to the Jewish Theological Seminary of America, leading to the establishment of the Jewish Museum in 1947.

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2. Solomon R Guggenheim Museum

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Photo 1 of 2 Frank Lloyd Wright’s swirling, organic-style marvel along Fifth Avenue (Photo: Bryan Ledgard / WikiCommons)
Photo 2 of 2 The circular leitmotif in the main gallery defies the convention museum layout (Photo: VillageHero / WikiCommons)

The Solomon R Guggenheim Museum emerges as a striking departure from Fifth Avenue’s Beaux-Arts grandeur that peppered Manhattan’s strict city grid. 

A swirling, organic-style marvel soaring skyward at the intersection of 88th and 89th Streets on the Upper East Side, it was one of Frank Lloyd Wright’s most recognisable icons that incorporated geometric motifs with symbolic significance for its exterior, which he described as “certain human ideas, moods, sentiments: the circle, infinity; the triangle, structural unity; the spiral, organic progress; the square, integrity.”

While Wright originally wanted a marble façade for The Guggenheim, budget constraints led to the adoption of the reinforced concrete gunite, sprayed in ivory and coated with vinyl plastic. 

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A continuous helical ramp that uncoils across six levels (Photo: Tbatb / WikiCommons)
Above A continuous helical ramp that uncoils across six levels (Photo: Tbatb / WikiCommons)
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The interior recalls the Bramante Staircase at the Vatican Museums (Photo: Gabriel Fernandes / WikiCommons)
Above The interior recalls the Bramante Staircase at the Vatican Museums (Photo: Gabriel Fernandes / WikiCommons)

Inside the main gallery with similarly hued walls, the circular leitmotif extends to the soaring six-storey atrium of 92 feet via a continuous ramp that uncoils more than a quarter-mile upward through the levels towards an expansive dome; a seamless design structure that recalled the nautilus shell, and that of the Bramante Staircase at the Vatican Museums designed by Giuseppe Momo in 1932.

The interior architecture was a departure from the traditional museum layout of interconnected rooms showcasing different exhibitions. With one level flowing into another, the helical ramp acts as an enormous structural arch in lieu of columns to prevent collapsing, as guests are able to observe displayed artworks on different levels along the open rotunda.

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3. The Plaza

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Photo 1 of 2 The majestic Plaza Hotel designed by Henry Janeway Hardenbergh (Photo: Jim.henderson / WIkiCommons)
Photo 2 of 2 The Beaux-Arts style lobby on Fifth Avenue (Photo: Jorge Royan / WikiCommons)
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The distinctive green-tile roof of the Corner Tower with copper accents (Photo: Reinhold Möller / WikiCommons)
Above The distinctive green-tile roof of the Corner Tower with copper accents (Photo: Reinhold Möller / WikiCommons)
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The Châteauesque style exterior that reaches 18 storeys in height (Photo: Sam /WikiCommons)
Above The Châteauesque style exterior that reaches 18 storeys in height (Photo: Sam /WikiCommons)

In the late 19th century, the corner of Central Park South and Fifth Avenue was lined with undeveloped brownstone row houses, an enclave untouched by the commercialisation until the turn of the century, when it became the upscale neighbourhood we know today, teeming with hotels, nightclubs and luxury stores.

One notable addition to this evolving landscape was The Plaza, originally the vision of three ambitious investors who acquired a 15-year-old hotel of the same name that occupied the site.

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Photo 1 of 2 The Palm Court of neoclassical elegance (Photo: Instagram / @theplazahotel)
Photo 2 of 2 The Oak Room of German Renaissance Revival style (Photo: Jazz Guy / WikiCommons)

They enlisted the expertise of architect Henry Janeway Hardenbergh, renowned then for setting the standard in luxury hotel design across America, to reimagine the property that spanned over 53,700 sq ft and soaring 18 stories high, hosting more than 280 hotel rooms and suites, and more than 180 condominium units.

It was a monumental undertaking, with a staggering USD$12 million investment—an unprecedented sum for its time.

Hardenbergh blended an array of architectural styles to create “New York’s most celebrated symbol of cosmopolitan and turn-of-the-century splendour.” Its Châteauesque exterior included elegantly adorned pilasters, balustrades, balconies and arches, all crowned by a distinctive green-tile mansard roof with copper accents.

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Inside, the grandeur continued through the Beaux-Arts style lobby vestibules with luxurious Breccia marble. Guests encountered a rich tapestry of design influences: from the German Renaissance Revival-style Oak Room, resplendent with wood panelled carvings and murals depicting mediaeval castles, to the Spanish Renaissance Revival-style Edwardian Room, distinguished by its ornate wainscoting and stencilled decor.

The journey through The Plaza also revealed the neoclassical elegance of the Palm Court, where towering marble pilasters commanded attention, and the opulent marble-clad grand ballroom with a magnificent coved ceiling, intricate roundels and sparkling chandeliers.

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4. Metropolitan Museum of Art

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Photo 1 of 2 The palatial Beaux-Arts style façade of The Met Fifth Avenue (Photo: Hugo Schneider / Flickr)
Photo 2 of 2 Beaux-Arts was a Parisian architectural trend of the late 19th century (Photo: Arad / WIkiCommons)

When the Metropolitan Museum of Art first opened its doors to the public in the 1880s, the original Ruskinian Gothic structure faced less than favourable reviews. Designed by Calvert Vaux and Jacob Wrey Mould, it was criticised as a “mausoleum,” a style already considered outdated upon its completion.

Situated along Museum Mile, on the eastern edge of Central Park, The Met has undergone significant expansion and redesign since its inception, particularly the revamped Fifth Avenue façade, Great Hall and Grand Staircase, which have become familiar to the 3.2 million annual visitors for more than a century.

École des Beaux-Arts alumni Richard Morris Hunt kickstarted the architectural overhaul, and whose son, Richard Howland Hunt, completed the project in 1902 following his father’s passing. They embraced the Beaux-Arts style, a Parisian architectural trend of the late 19th century, blending French neoclassical principles with Renaissance and Baroque elements, all while employing modern materials.

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Photo 1 of 2 One of the three arched with framed by sculptural festoons (Photo JavierDo WikiCommons)
Photo 2 of 2 Pairs of freestanding Corinthian columns (Photo: Annalisa Welinder / WikiCommons)

The central block, resembling a Palazzo, stretches a quarter of a mile and features tripartite colossal Roman arches with windows flanked by massive pairs of freestanding Corinthian columns resting on elevated pedestals. Atop these columns sit respective entablatures adorned with lion gargoyle sculptures and dentils decorating the cornices. 

Rounded niches with plain relief panels dot the façade evenly, recently enriched by the 2019 installation of four bronze sculptures titled The Seated I, II, III and IV. Created by Kenyan-American artist Wangechi Mutu, the modern figures juxtaposed with the conservative Neoclassical design, which also included portrait medallions of six art titans: Michelangelo, Bramante, Rembrandt, Raphael, Velázquez and Dürer.

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5. Empire State Building

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Photo 1 of 2 The Empire State Building stands at 1,250 feet tall with an additional 102-foot pinnacle (Photo: Daniel Dimitrov / WikiCommons)
Photo 2 of 2 6,514 geometric windows separated into several vertical bays by vertical nickel-chrome steel mullions (Photo: Kidfly182 / WikiCommons)

Strolling down Fifth Avenue, it’s impossible to miss the towering presence of the Empire State Building. This architectural giant, located in Midtown South, stands proudly at 1,250 feet tall with 102 storeys, and an additional 102-foot pinnacle crowned with a lightning rod.

Upon its completion in 1931, the Empire State Building was the world’s tallest building. Spanning over 2.1 million sq ft, its lower 85 floors house a mix of commercial and office spaces, while the 102nd level has an observatory deck.

Crafted by Shreve, Lamb and Harmon, the architectural firm known for their contributions to New York City’s Art Deco landscape, the Empire State Building rises majestically with a symmetrical massing atop a five-storey base, while the upper floors feature progressively smaller setbacks or recessed bays to enhance the stability of the entire build.

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The Art Deco-style façade was clad in Indiana limestone, granite, bricks, aluminium and stainless steel (Photo: CS Imming / WikiCommons)
Above The Art Deco-style façade was clad in Indiana limestone, granite, bricks, aluminium and stainless steel (Photo: CS Imming / WikiCommons)
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The original main lobby off Fifth Avenue with marble wainscoting and an aluminium relief of the skyscraper (Photo: DanielPenfield / WikiCommons)
Above The original main lobby off Fifth Avenue with marble wainscoting and an aluminium relief of the skyscraper (Photo: DanielPenfield / WikiCommons)

Typical of the pre-WWII architecture in the city, the signature blonde, Art Deco-style façade was clad in 200,000 cubic feet of Indiana limestone panels and granite, 10 million bricks and a mix of aluminium and stainless steel accents.

The building’s 6,514 geometric windows, less ornate and less expensive than its neighbouring counterparts, are separated into several vertical bays by vertical nickel-chrome steel mullions.

Visitors entering the original main lobby from Fifth Avenue are greeted by terrazzo-tiled floors arranged in a striking zigzag pattern and surrounded by wainscoting marble walls. This leads towards the resplendent aluminium relief at the end of the lobby at the security desk. It depicts the Empire State Building in its original form, sans antenna, with rays emanating from the spire and the sun behind it.

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6. Flatiron Building

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The 22-storey façade blended Renaissance aesthetics with Beaux-Arts styling (Photo: Lafleursauvage / WikiCommons)
Above The 22-storey façade blended Renaissance aesthetics with Beaux-Arts styling (Photo: Lafleursauvage / WikiCommons)
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The Flatiron Building nestled in the intersection of Fifth Avenue and Broadway (Photo: G Edward Johnson / WikiCommons)
Above The Flatiron Building nestled in the intersection of Fifth Avenue and Broadway (Photo: G Edward Johnson / WikiCommons)

As iconic as the Empire State Building just minutes away, the Flatiron Building is nestled in the sharp-angled intersection of Fifth Avenue and Broadway; previously an underdeveloped, residual piece of real estate acquired by Harry S. Black, CEO of the Fuller Company, for the headquarters of the steel and skyscraper construction firm.

Renowned Chicago architect Daniel Burnham was tasked with the design, and together with Pennsylvanian architect Frederick P Dinkelberg, they blended Renaissance aesthetics with Beaux-Arts styling, drawing structural and decorative inspirations from classical Greek columns.

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The Flatiron Building in the early 20th century (Photo: Detroit Publishing Co / WikiCommons)
Above The Flatiron Building in the early 20th century (Photo: Detroit Publishing Co / WikiCommons)

Originally named the Fuller Building, the Flatiron stands tall at 307 feet with 22 storeys, boasting a unique wedge-shaped pro referred to as “The Point,” measuring a mere six feet wide.

Vertically divided into three sections reminiscent of the antiquity columns, the building features a three-storey limestone-clad base and upper levels adorned with glazed terracotta.

While the materials contribute to its robust and rich appearance, the steel frame provides structural integrity, an innovative approach popularised by the Chicago School of Architecture pioneered steel-frame construction in commercial buildings.

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Structural and decorative inspirations from classical Greek columns (Photo: chrisinphilly5448 / Flickr)
Above Structural and decorative inspirations from classical Greek columns (Photo: chrisinphilly5448 / Flickr)
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The prow known as "The Point," measuring a mere six feet wide (Photo: Bob Collowan / WikiCommons)
Above The prow known as "The Point," measuring a mere six feet wide (Photo: Bob Collowan / WikiCommons)

Designed to withstand four times the maximum wind force of the area, the Flatiron Building proved its resilience despite early scepticism–locals dubbed it “Burnham’s folly” and placed bets on its collapse due to its tripartite structure.

Ranked as the fourth most beloved building in the United States in 2023 by Buildworld, its distinctive silhouette, reminiscent of a cast-iron clothes iron, also recalled decorative Grecian elements: cornices, frieze mouldings with dentils, columns holding up entablatures over the entrances, and an array of window shapes, from oriel to sash and oculus.

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