In the late 19th century, a radical architectural shift permanently altered our city skylines. As cities were rapidly outgrowing their horizontal boundaries, architects began to look up. Facilitated by the invention of the safety elevator and structural steel, a generation of visionary engineers began constructing “buildings that scraped the sky.” More than just a necessity, these buildings were a statement of progress. The first skyscrapers were bold, intricate, and unapologetically grand.
While many of these pioneering high-rises fell victim to the wrecking ball over the last century, a select few historic structures remain standing. Here are 12 of the oldest skyscrapers that redefined city skylines.
1. Temple Court Building, New York (1883)
The Temple Court Building, located at 5 Beekman Street in Manhattan’s Financial District, was originally completed in 1883. Designed by Benjamin Silliman Jr. and James M. Farnsworth, it displays a blend of Queen Anne, neo-Grec, and Renaissance Revival styles. Its distinctive red-brick façade, adorned with tan stone and terracotta accents, is complemented by two pyramidal towers at the corners.
In 1889, a Romanesque Revival style annex was added to the building. Its limestone façade seamlessly integrates with the original structure. The structure has a nine-story atrium, crowned by a pyramidal skylight, which floods the interior with natural light and highlights the intricate iron railings and detailed ornamentation. The atrium was designated as an interior landmark by the New York City Landmarks Preservation Commission in 2024.
After a period of vacancy starting in 2001, the building underwent significant restoration and redevelopment. In 2016, it reopened as part of The Beekman Hotel and Residences complex. This project included the addition of a 51-story condominium tower, known as the Beekman Residences, designed by Gerner Kronick + Valcarcel Architects.
2. Hotel Chelsea, New York (1884)
The Hotel Chelsea, or Chelsea Hotel, is a historic landmark located at 222 West 23rd Street in Manhattan, New York City. Constructed between 1883 and 1884, it was initially designed as one of the city’s first cooperative apartment complexes. Designed by architect Philip Hubert, its style is described as Queen Anne Revival and Victorian Gothic. The 12-story red brick building, adorned with wrought-iron balconies, was, for a time, the tallest structure in New York City.
In 1905, the building transitioned into a hotel, quickly becoming a haven for artists, writers, musicians, and actors. Its bohemian atmosphere attracted a plethora of notable residents, including literary figures such as Mark Twain, Arthur C. Clarke, and Jack Kerouac, who penned “On the Road” during his stay. The hotel also hosted musical legends like Bob Dylan, Jimi Hendrix, Janis Joplin, and Patti Smith. Andy Warhol filmed his iconic movie “Chelsea Girls” at the hotel in 1966.
Throughout its history, the Chelsea Hotel has been a backdrop for both artistic creation and tumultuous events. The poet Dylan Thomas fell ill at the hotel before his death in 1953, and in 1978, punk rock musician Sid Vicious was implicated in the death of his girlfriend, Nancy Spungen, in one of its rooms.
3. Osborne Apartments, New York (1885)
The Osborne Apartments, located at 205 West 57th Street in Manhattan, New York City, was constructed between 1883 and 1885. Designed by architect James Edward Ware, the luxury apartment building uses a Romanesque Revival style with a façade clad in rusticated brownstone. The building’s southern section facing 57th Street rises 11 stories, while the northern section extends to 15 stories. The interior is notable for its elaborate lobby, adorned with stuccoed and mosaic-tiled walls, reflecting the opulence of the Gilded Age.
Commissioned by stone contractor Thomas Osborne as a speculative investment, building costs soon spun out of control, resulting in its acquisition by the Taylor family in 1889. Situated directly across from Carnegie Hall and in close proximity to Central Park, it sits within Manhattan’s “Billionaires’ Row,” a stretch known for its luxury real estate and cultural institutions.
Today, the Osborne operates as a cooperative residential building, maintaining its historic charm while offering modern amenities. In 1991, it was designated a New York City landmark, and in 1993, it was added to the National Register of Historic Places.
4. Sun Building, Washington, DC (1887)
Nestled at 1317 F Street NW in Washington, DC, the Sun Building stands as a testament to architectural innovation. Designed by Alfred B. Mullett and constructed between 1885 and 1887, it originally served as the Washington bureau for The Baltimore Sun. When it was completed, the nine-story edifice was among the city’s earliest skyscrapers. The pioneering iron-and-masonry structure has a façade adorned with sun motifs and sunflowers, an early example of corporate branding through architecture.
The building was equipped with steam-powered elevators, later upgraded to hydraulic systems in 1909 and electric elevators in 1922. In 1904, architect B. Stanley Simmons oversaw modifications for the American Bank, including the addition of a ninth floor in 1907 to accommodate the Interstate Commerce Commission’s hearing room. Other notable tenants have included Woodrow Wilson’s law firm and the early offices of the Federal Bureau of Investigation under J. Edgar Hoover.
Recognized for its architectural and historical value, the Sun Building was added to the National Register of Historic Places on March 27, 1985.
5. Rookery Building, Chicago (1888)
Nestled at the corner of LaSalle and Adams Streets in Chicago, the Rookery Building was completed in 1888 by the renowned partnership of Daniel Burnham and John Wellborn Root. This iconic structure seamlessly blends masonry and skeletal frame construction. Root devised a “grillage foundation,” a network of iron rails encased in concrete. This results in an underground floating platform that distributed the building’s enormous weight evenly across the soft earth, a technique that changed how skyscrapers were anchored around the world
The building’s name, “The Rookery,” harks back to a time when the site housed a temporary city hall teeming with crows and pigeons, as well as politicians, leading locals to dub it a “rookery.” Embracing this moniker, Root incorporated bird motifs into the building’s ornamental design, adding a whimsical touch to its grandeur.
One of the Rookery’s most captivating features is its central light court. Originally designed to flood the interior with natural light, this two-story atrium was reimagined in 1905 by the legendary Frank Lloyd Wright. He introduced white Carrara marble, intricate Persian-inspired patterns, and elegant bronze chandeliers, transforming the space into a luminous blend of form and function.
6. Wilder Building, Rochester (1888)
Constructed between 1887 and 1888, this eleven-story structure is considered Rochester’s first modern skyscraper. Designed by the prominent Rochester architectural firm Warner & Brockett, the building showcases a modified Romanesque style. Its original design featured spires at each corner of the roof, which have since been removed.
A notable feature of the Wilder Building is its association with the invention of the mail chute. James Goold Cutler, who received U.S. Patent 284,951 on September 11, 1883, for the mail chute, installed a perfected version in the Wilder Building during its construction. With the demolition of the Elwood Building in 1965, the Wilder Building’s mail chute is currently the oldest surviving example of this innovation.
Today, the Wilder Building continues to serve as a functional office space, housing various businesses and organizations. Its prime location at the Four Corners in downtown Rochester makes it a central and accessible hub for commerce.
7. APA Building, Melbourne, Australia (1889)
Completed in 1889 at the corner of Elizabeth Street and Flinders Lane in Melbourne, Australia, this structure was an absolute monolith for its time. It wasn’t just the Southern Hemisphere’s first skyscraper. For a brief period, the 12-story, 173-foot structure was one of the tallest commercial buildings in the entire world.
Fueled by the Victorian gold rush, the city was one of the wealthiest in the British Empire, earning the nickname “Marvelous Melbourne.” The building was commissioned by the Australian Property and Investment Company and designed by the architectural firm Oakden, Addison & Kemp in association with John Beswicke. It was designed in Queen Anne Revival style with a highly decorative exterior made of contrasting red brick and cream-colored freestone bandings. The top of the building was a chaotic, beautiful masterpiece of picturesque gables, dormer windows, steep roofs, and a soaring, corner turret spire that made it look like a medieval castle stacked on top of a modern office block. The building was “scalped” of these features in the 1950s.
Unfortunately, by the mid-20th century, the Victorian Queen Anne style had fallen heavily out of architectural favor and lacked modern fire isolation standards. In 1980, despite fierce protests, the building was demolished.
8. New York Times Building (41 Park Row), New York (1889)
The New York Times was founded in 1851 and initially operated from 113 Nassau Street. As the newspaper’s influence grew, it relocated to a newly constructed building at 41 Park Row in 1858, making it the first structure in New York City designed specifically for a newspaper. By the late 1880s, to accommodate its expanding operations, the Times commissioned architect George B. Post to design a larger Romanesque Revival-style building on the same site. This new 13-story structure was completed in 1889, showcasing advanced construction techniques of the period.
The 1889 building featured a façade adorned with intricate stonework and large arched windows, reflecting the Romanesque Revival style. Its construction was notable for being executed around the existing operations of the newspaper, allowing The New York Times to continue publishing without interruption. This engineering feat demonstrated innovative building practices of the time.
In 1905, The New York Times relocated to a new building at One Times Square, and 41 Park Row underwent modifications, including the addition of four stories. Pace University acquired the building in 1951, repurposing it for academic use. The structure has since been designated a New York City landmark and contributes to the Fulton–Nassau Historic District.
9. Old Chronicle Building, San Francisco (1889)
The Old Chronicle Building, also known as the de Young Building, is a historic landmark located at 690 Market Street in San Francisco, California. Completed in 1889, it was designed by the renowned Chicago architectural firm Burnham and Root in the Richardsonian Romanesque style. At the time of its completion, the ten-story building, featuring a clock tower reaching 218 feet, was the tallest structure on the West Coast and is considered San Francisco’s first skyscraper.
Commissioned by M. H. de Young, owner of the San Francisco Chronicle, the building served as the newspaper’s headquarters and was a prominent feature of the city’s “Newspaper Row,” sharing the area with other major publications. In 1905, during a mayoral victory celebration, fireworks ignited the wooden clock tower, leading to its removal. Despite suffering significant damage during the 1906 earthquake and subsequent fires, the building was rebuilt under the supervision of architect Willis Polk, preserving its historical significance.
Over the years, the Old Chronicle Building underwent several transformations. In 1962, an attempt to modernize its appearance led to the original masonry façade being covered with a contemporary exterior. However, in 2004, efforts were made to restore its historic character, and the building was converted into the Ritz-Carlton Club and Residences.
10. Manhattan Building, Chicago (1891)
Located at 431 South Dearborn Street in Chicago, Illinois, the Manhattan Building was designed by architect William Le Baron Jenney and constructed between 1889 and 1891. Upon its completion, the 16-story structure was the tallest building globally and is recognized as the oldest surviving skyscraper with a purely skeletal steel frame.
The building’s distinctive design features bow windows that enhance natural light within its interior spaces. The façade combines a granite base for the lower floors with brick on the upper stories, reducing the load on the internal steel framework. This innovative approach addressed concerns about wind-induced sway, with Jenney incorporating structural elements to ensure stability. The Manhattan Building was also constructed wedged between two existing seven-to-eight-story buildings. Traditional foundations would have destabilized their walls, so Jenney used cantilevered foundation beams. He placed the building’s massive structural columns 15 feet inside the property line, and then balanced the exterior walls out over the edges like a see-saw.
Today, the Manhattan Building continues to serve as a commercial office space, retaining its historical significance and architectural charm. Visitors and architecture enthusiasts can admire its exterior, which showcases the early adoption of steel-frame construction; a pivotal development in skyscraper design. Situated in Chicago’s Loop neighborhood, the building is part of the historic Printing House Row District, offering a glimpse into the city’s rich architectural heritage.
11. Ames Building, Boston (1893)
Nestled at 1 Court Street in Boston, Massachusetts, the Ames Building stands as a testament to the city’s architectural evolution. Completed in 1893, it was designed by the esteemed firm Shepley, Rutan, and Coolidge in the Richardsonian Romanesque style. At 14 stories, it was Boston’s tallest building upon completion and is considered Beantown’s first skyscraper.
Commissioned by industrialist Frederick Lothrop Ames, the building showcases a façade adorned with granite and sandstone, featuring grand arches and intricate carvings. Its construction marked a significant achievement as the second-tallest masonry load-bearing wall structure globally at the time, surpassed only by Chicago’s Monadnock Building.
Over the years, the Ames Building has undergone several transformations. Initially serving as office space, it was converted into a luxury boutique hotel in 2009. In 2020, Suffolk University acquired the building, repurposing it as a student residence hall.
12. The Witte Huis, Rotterdam, Netherlands (1898)
This 11-story, 141-foot-tall building was Europe’s first skyscraper. In the late 1890s, Rotterdam was rapidly expanding into a world-class port city. Two wealthy brothers, Gerrit and Jan-Hendrik van der Schuyt, traveled to the United States and were spellbound by the soaring skyscrapers of New York and Chicago. They returned to the Netherlands determined to bring that vertical ambition to Europe.
Locals believed that their soft, marshy ground could not support a skyscraper. To prove them wrong, architect Willem Molenbroek engineered a massive underground foundation, driving 1,000 thick pine piles deep into the soft swampy soil to anchor the structure securely.
Different from its American cousins, the building used Art Nouveau and Jugendstil styles. The exterior was clad in brilliant white glazed bricks, which gave the building its name, and the facade is decorated with ornamental mosaics and stone statues. It has a steep mansard roof featuring a magnificent rooftop viewing platform, which became an instant tourist attraction in 1898.
