Flatiron, Gramercy & Union Square

The area is also filled with trendy fine restaurants, swank retail and abundant transportation.

Welcome to Flatiron, Gramercy & Union Square

Flatiron District

The Flatiron District is bounded on the North by the wedge-shaped Flatiron Building (otherwise known as the Fuller Building), which was built in 1902, at the corner of 23rd Street, goes south to 15th Street, extends as far east as Park Avenue South and west to 6th Avenue. Union Square sits on the southern boundary of the Flatiron neighborhood.

At the time it was built, the 20-story Flatiron building was New York City’s first skyscraper, and thought to be not only the tallest building in the world, but the first skyscraper ever created. Designed by architect Daniel Burnham, it was nicknamed by New Yorkers for its skinny, triangular, iron-like shape, hence The Flatiron Building vs. its original name, The Fuller Building. Whatever its name, it is undoubtedly one of New York’s most photographed buildings. It is also the centerpiece of what has become a booming, vibrant neighborhood. In recent years, the surrounding area has undergone a major rejuvenation following the creation of Midtown South in the 1970s by advertising agencies and publishers who descended upon the area from Midtown seeking lesser rents. The Flatiron is now a hot and trendy destination for residents of all ages, and a convenient location to all of Manhattan. The neighborhoods’ massive buildings, the last of the pre-skyscraper era and remnants of New York’s Gilded Age, have had their ornate Romanesque facades gloriously restored. Chic boutiques and some of the city’s best restaurants occupy their street levels, while new media companies, ad agencies, publishing houses, architects’ offices, graphic design firms, and residential lofts occupy the upper stories.


Very residential Gramercy is close to the hustle and bustle of the nearby commercial Flatiron District, and boasts new restaurants and services on its western side known as Silicon Alley, which became popular and hoisted rents in the 1980s when many advertising agencies and computer start-up companies fled south. However, the neighborhood appeal, community solidarity and adherence to rules of conduct still ring true for all who live here. Residents feel they have the best of both worlds, and have no intention of ever changing the things that so loyally maintain Gramercy’s rich past and pristine charm., Elegant pre-war brownstones and luxury post-war high-rises with doormen preside along the tree-lined streets of this very desirable neighborhood. A variety of 19th century residences are found in the Historic District that spans roughly from East 18th to 21st Streets between Park Avenue South and Third Avenue, ranging from 1840s row houses and brownstones to Victorian Era Queen Annes and neo- Gothics.

Its clean streets stretch from 20th Street until the start of Murray Hill at 34th Street, and are bordered by the East River and Park Avenue to the west. The Gramercy Park area serves as home to typically more established, successful professionals. The townhouses around the park, built before the Civil War, are among the oldest and most outstanding in the city. Many tend to be handed down through the generations, making home hunting quite a challenge, unless of course you’re willing to spend.

Yet even if you live in this posh, uncluttered community, only those living right around Gramercy Park itself, the last private park in NYC, are allowed access to this green oasis. Others must settle for peering through its wrought-iron fence, and daydreaming. The beautiful park design is further complemented by the grandeur of the park’s surrounding architecture, and coherence of its physical and ambient character. Many who are not fortunate enough to be park-side, however, are happy just to live in the tidy, quiet atmospheres afforded in Stuyvesant Town and Peter Cooper Village, the area’s most salient features, which house 25,000 residents in their 9,000 apartments.

Union Square

This park, meeting place and outdoor shopping area is the focus of a bustling residential neighborhood. It’s name, “Union,” originally meant the union of two cross streets – Broadway and 4th Avenue – but took on a new meaning in the 19th and early 20th centuries when it became a rallying spot for labor protests and mass demonstrations.

In recent years, it has gained in popularity as a safe and secure haven for neighborhood residents and visitors. On Mondays, Wednesdays, Fridays and Saturdays, farmers and food purveyors from all over the Northeast sell fresh produce, flowers and plants, homemade baked goods, cheeses, wines, and other goodies in the square. The area is also filled with trendy fine restaurants, swank retail and abundant transportation.

Neighborhood History

Part of the Brevoort farm in the 18th century, Union Square was designated as a park in 1815 and laid out in 1831. It opened in 1839 and was enjoyed by prominent local families like the Roosevelts and Goelets. Aristocratic houses were later replaced by restaurants, shops, theaters and concert halls. During the later part of the century, 14th Street became the midpoint of Ladies’ Mile, a promenade of fashionable stores that spanned from Broadway & 8th Street to 23rd Street, but by 1900 Madison Square had taken over as the center for commerce and art. Needle trade workers subsequently moved into Union Square during the early years of the 20th century, when many homes became tenements, housing laborers and the occasional artist. During the 1930s, various radical, progressive and labor groups set up headquarters there, such as the Socialist Party, Communist Party, American Civil Liberties Union, Amalgamated Clothing Workers of America, and International Ladies Garment Workers Union.

The park was redesigned in 1985, and it has been transformed beautifully in recent years to become a safe and secure haven for neighborhood residents and visitors. The area is also filled with trendy restaurants and retail. Honoring its political roots, the square is full of statues of former politicians: George Washington (1856, by Henry Kirke Brown), Abraham Lincoln (1866, by Henry Kirke Brown), the Marquis de Lafayette (1875, by Frederic Auguste Bartholdi, who also sculpted the Statue of Liberty), and Ghandi (1986, by Kantilal B. Patel). Serene and upscale, the Gramercy Park neighoorhood was named for the elegant one-square-block-sized park of the same name created by Samuel B. Ruggles in 1831. From when Sam Ruggles purchased the property in 1831 through 1845, this prime piece of Manhattan real estate was once swampland referred to as Crommashie by the Dutch. Ruggles drained the swamp, planted willow, elm and chestnut trees, roses and lilacs, and added herbaceous borders, until gradually his lot became so beautiful that it served as a popular leisure spot to which Knickerbocker New York was drawn.

As not too many New Yorkers wanted to live up this far, there were only two houses on the square in 1845. Yet Ruggles had a vision and kept on planting…knowing that the city folk would certainly want a park. Hence, he set aside 42 lots for his exquisite Gramercy Park, developed specifically for those fortunate enough to buy the surrounding building lots in his planned residential square. His deed dated December 17, 1831 set forth these rules, which still apply today, though residents of surrounding blocks can now also buy visiting privileges. The park, with a tax exemption arranged for by Samuel Ruggles, is still owned by the residents of the surrounding streets. In his master plan, Ruggles also laid out Irving Place, named for friend Washington Irving, as well as Lexington Avenue, running it South to North knowing full well that a maritime city’s main thoroughfares should run East and West between the rivers. He foresaw that the city would expand northward, and that people would flock here. When they did, each resident received golden keys for unlocking the gate to their park paradise. Eventually, renowned New Yorkers, like his own son-in-law George Templeton Strong; the social lion Stuyvesant Fishes; inventor (and founder of Cooper Union) Peter Cooper; architect Stanford White; future New York Governor Samuel Tilden; book publisher and Mayor of New York James Harper; sister poets Phoebe and Alice Cary; concert singer Emma Thursby; novelist and critic Carl Van Vechten; Paul Rosenfeld, music editor of The Dial; Wall Street broker, critic and poet Edmund Clarence Stedman (who refused to attend a Gramercy Park dinner in honor of Oscar Wilde); Herman Melville and John Barrymore all came to reside on the square or along neighboring park streets. Even President John F. Kennedy lived here as a boy before his father was named ambassador to England. During the initial development period in the 1840s and 50s, the streets of Gramercy Park became solidly lined with brick and brownstone row houses and mansions, plus such institutional buildings as churches that were likely found in residential areas. The lots facing the park itself were among pre-Civil War New York’s most prestigious. Gramercy Park West and South today feature fine examples of houses erected during this period. Row houses also lined most of the side streets between 14th and 23rd Streets, and many still survive on the blocks to the south of the park. Some are within the designated district, notably those on East 18th & 19th Streets between Irving Place & Third Avenue. Additional row houses on East 19th Street are within the proposed Gramercy Park Historic District Extension; others on East 17th Street are within the proposed 17th Street/Irving Place Historic District; and a few on East 15th and 16th Streets are being considered for individual designation.

North of the park on East 22nd Street sat a mix of row houses and carriage houses, while Lexington Avenue between the park and East 23rd Street had two mansions. Very little dates from this early period of development remains to the North or East of the park, except for some simple mid-19th-century Greek Revival and early Italianate mixed-use residential/commercial buildings on Third Avenue, all within the proposed Gramercy Park Historic District Extension. A new period of development in the area came about in 1869 with the construction of the since-demolished Stuyvesant Apartments on East 18th Street, designed by Richard Morris Hunt. The building was known as the earliest apartment complex to attract a middle-class clientele. In the 1870s and 80s, other early apartment houses went up, notably 129 East 17th Street (1978), thought to be the city’s oldest intact apartment house. Other important dwellings were erected in the 1880s, including the Gramercy at 34 Gramercy Park East, one of the earliest cooperatives in New York, and 155 East 22nd Street, the earliest existing multiple dwelling erected in the section of the neighborhood North of the park. In subsequent decades, apartment-house construction abounded on East 22nd Street and Gramercy Park North, and to a lesser extent, on the streets South of the park. Early in the 20th century, two other interesting apartment houses were built: Sass Smallheiser’s Beaux-Arts building at 144 East 22nd Street (1901) and Bernstein Bernstein’s unusual building at 152-156 East 22nd Street (1907) with its five-stepped gables and extensive terra-cotta detail. In 1912, a multiple dwelling planned specifically for bachelors appeared at 52 Irving Place. This Colonial Revival-style structure with kitchen-less suites was one of a handful of New York apartment houses for single men in the early 20th century.

During the 1920s, Gramercy Park North’s character was totally transformed as row houses were replaced by luxury high-rise apartment houses and a hotel. The first apartment house along the park’s northern side was One Lexington Avenue, begun in 1910. Three other large-scale buildings also began between 1926 and 1929, and in 1924 work started on the Gramercy Park Hotel at the northwest corner of Gramercy Park North and Lexington Avenue. The flamboyant apartment house at 81 Irving Place at 19th Street, designed by George Pelham, rivaled other Gramercy Park North buildings with its fantastical terra-cotta detail. While large apartment houses were going up throughout the second and third decades of the 20th century, a change occurred in the design and use of many of the surviving side-street row houses. Few of these houses were being maintained as single-family dwellings, as the affluent families who had lived there moved elsewhere, and the area’s social standing slipped somewhat. Most row houses were converted into boarding houses or into apartments. Many had their facades redesigned, as on East 19th Street in the historic district, or were given less radical renovation. While some of the facades of many surviving row houses to the South of the park remain intact, others are evident of these early 20th-century alterations.

The changing neighborhood character brought about by the moving of prosperous residents had yet another result – the redevelopment of certain sites into loft and factory buildings. Commercial redevelopment moved eastward into Gramercy Park from the Ladies’ Mile along Broadway. By the early 20th century, loft buildings were being erected on Fourth Avenue (now Park Avenue South) and on many adjacent side streets as far East as Irving Place. The most interesting development to the North of Gramercy Park took place just south of 23rd Street, which became a center for charitable institutions. In the late 19th century, such organizations grew in number and size in response to the growing interest that middle- and upper-class reformers had in trying to change conditions in the city’s growing poor and immigrant communities.

There were four buildings in the proposed historic district extension that were built to house the headquarters of important institutions: the United Charities Building, the Association for the Prevention of Cruelty to Children Building, the Church Missions House (a designated individual landmark), all built in 1892-93, and the Russell Sage Foundation Building, begun in 1912 and completed in 1931. It is believed that Gramercy Park attracted these charitable institutions because it not only remained a respectable neighborhood, but it was centrally located, convenient to mass transit, and less expensive than in newly-fashionable areas to the North.

Besides headquarters buildings for philanthropic organizations, four buildings were erected as centers of progressive social programs: the Manhattan Trade School for Girls (1915-19), the Children’s Court (1912-16), and the Domestic Relations Court Building (1937-39), all within the boundaries of the proposed historic district extension, and Washington Irving High School, in the proposed 17th Street/Irving Place Historic District. Each building erected for charitable or civic purposes is of historical and/or architectural interest in its own right, and combined create an important complex of major social service buildings. The designation of the proposed historic district extension, and of the additional district and series of individual buildings, as proposed by Gramercy Neighborhood Associates, Inc., will preserve the comprehensive history of the architectural and social development of Gramercy Park.

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