Gramercy & Flatiron Overview

In the middle of New York, Gramercy and Flatiron are neighborhoods hidden in plain sight. While most people pass through on their way to and from work, the people who live there appreciate them for their distinctive architecture, great greenspace, and ease of getting around. Union Square Park and Madison Square Park are popular with locals and tourists alike, while Gramercy Park, as the only private park in the city, is admired... from afar. 

In the the sections below, you'll get a glimpse into life in Gramercy and Flatiron. But before you go anywhere, make sure you scroll through the photos in the gallery below. Nothing can tell the story of a neighborhood as well as a few good photos. 


Manhattan's Flatiron district receives its unusual name from the triangular building that sits at its heart. In 1902, Daniel Burnham, a popular American architect, was faced with a difficult design challenge: how to fit a building in between the intersection of Fifth Avenue & Broadway. Even over a hundred years ago, that was some precious real estate.
So what do you do with a triangle plot? Build a triangle-shaped building of course! Formally known as the Fuller Building, and informally known as "Burnham's Folly" (Burnham's contemporaries didn't have a lot of faith in the building's structural integrity), the building eventually took on a more affable nickname based on its resemblance to a common household item: the Flatiron building. 

Before the Flatiron was built, the neighborhood had a different distinction: the "Ladies Mile." Now a historic district, it was once one of the most prestigious retail areas in the United States. Although many of the original store locations have long since closed, well-known retailers such as Lord & Taylor and Bergdorf Goodman first made their start in this upscale shopping area. 

Like much of New York City, the neighborhood's fortunes ebbed and flowed in the second-half of the twentieth century, but has since emerged as a vibrant commercial and residential area. 

Whereas Flatiron has only recently become a popular spot for affluent residents, neighboring Gramercy has held bourgeoisie residential appeal for over one hundred and fifty years. 

During the 1840s and 1850s, brick and brownstone row houses sprung up all over Gramercy based on the keen design sense of developer Samuel Ruggles. Ruggles led the effort to drain the area (the name Gramercy is an Anglicized version of the Dutch words for "little crooked swamp") and then divided the land into 108 lots: 42 for a private park and 66 for homes. Because of strict zoning laws, no building taller than 20 stories can be found in this part of the city, creating a bit of an oasis in an otherwise very vertical city. 


Gramercy, the quieter, more posh eastern section of the neighborhood, is centered on Gramercy Park, the only private park in Manhattan that is accessible exclusively to those who hold a key. Lovely, intricate details on landmarked houses, and actual backyards and even mansions (a rare sight in Manhattan) make it pretty apparent that most residents are well heeled. Indeed, the list of homeowners around Gramercy Park includes the likes of Julia Roberts, Uma Thurman, and Jimmy Fallon.

Besides the gated park and the beautiful homes that surround it, the area around Gramercy Park is home to two private arts clubs, the Players and the National Arts Club. But not everything around here is accessible only to those who can afford the annual members' fees. There are restaurants, bars, and stores along the north-south avenues, like in most of the rest of Manhattan. One classic spot is Pete's Tavern, where writer O. Henry spent time in the early 1900s.

Further from the iconic park are hospitals, schools, and public parks. Housing in the wider neighborhood of Gramercy is a mix of historic townhouses and both classic apartment buildings, and newer high-rises with doormen. Due to zoning laws, tall buildings don't get any higher than about twenty floors in this area.

Flatiron, on the western side of the neighborhood, is still somewhat upscale but is also well trafficked by college students, tourists, shoppers, and after-work crowds. Its main hubs of activity are Union Square, the famous wedge-shaped Flatiron Building, and shopping along Broadway, Fifth Avenue, and Sixth Avenue.

The shopping options, ranging from boutiques to chains, draw many people to the neighborhood, which occupies a sweet spot between the cool of downtown and the convenience of Midtown. Especially notable is the high concentration of bookstores in the Flatiron/Union Square area, from tiny themed indie booksellers to a huge Barnes & Noble. The neighborhood is a hotspot for food too - everything from fine dining to food trucks, plus a popular year-round farmers market.

Housing in Flatiron is interspersed with NYU dorms and other academic facilities, offices, and commercial spaces. Apartment buildings, which mostly offer doorman service in this area, range from historic to contemporary, and from four floors to about forty.

Overall, Gramercy and Flatiron represent a cultural blend between downtown and Midtown: upscale but accessible, hip but not edgy, family friendly but still possessing that fast-paced Manhattan vibe.

GRAMERCY & FLATIRON Transportation

Being centrally located in Manhattan just below Midtown means that commuter options are plentiful in Gramercy & Flatiron. Depending on which part of the neighborhood you live on, you will have very easy access to one side of the City and just be a short walk to transportation to the other side. 

Gramercy and Flatiron Subway & Walking Times

GRAMERCY & FLATIRON Guidebook Landmarks

Flatiron Building
The Flatiron Building is perfectly suited to its unique location: the intersection of Broadway and Fifth Avenue. Because Broadway runs diagonally through the city, it left the Flatiron a triangle lot for construction. The resulting wedge-shaped building was originally called the Fuller Building, but its resemblence to a clothing iron was too compelling for New Yorkers, and its "Flatiron" name has since stuck, not just for the building, but the whole neighborhood. When it was built, it was one of the tallest buildings in New York and towered over its surroundings at 22 stories.

National Arts Club
The National Arts Club is located in the Samuel Tilden mansion on the south side of exclusive Gramercy Park. The lavish brownstone was built in 1845, occupied by Tilden (the 25th Governor of New York) from 1860 to 1886, and acquired by the private arts club in 1906. The club, which works to foster public interest in the arts, is notable for allowing women as full and equal members since its inception in 1898—and also for giving its members much-coveted keys to Gramercy Park, the only private park in Manhattan.

Teddy Roosevelt Birthplace
Theodore Roosevelt was one of the most popular presidents in U.S. history. Even with that popularity, it would probably be a little bit of a surprise to today's New Yorkers that his birthplace has become a National Park. Shortly before his death, his childhood home was actually razed, so the Women's Roosevelt Memorial Association bought the property and built a replica. The new home was designed by Theodate Pope Riddle, one of the first female architects in the United States.


Pete's Tavern
Pete's Tavern has the prestigious distinction of being "the oldest continually operating bar" in New York City since its opening in 1864. The tavern avoided the fate of many of its Prohibition era competitors by opening a cover-up florist shop in the front of the store. The only way to get to the back rooms where the liquor flowed freely was to go through a fake refrigerator door. It probably didn't hurt that the bar was a favorite of some of the city's most influential politicians.

Stars of Madison Park
Los Angeles may be known for its stars on Hollywood Boulevard, but in New York, the stars aren't in the sidewalk… you actually have to look up. On 23rd Street, there are two illuminated elevated stars. The first one is at Fifth Avenue, built in 1918 as a memorial to World War I veterans. Just down the road, a second star had been constructed two years earlier. This "Star of Hope" memorializes a very unique New York first—the first community Christmas Tree in the country. Today, the stars blend a little bit into their urban surroundings, but when they were first constructed, they surely caught the eyes of passerbys. 

GRAMERCY & FLATIRON Parks & Recreation

Gramercy Park (2 acres)

It might not make sense to include Gramercy Park on this list because there are so few people that can actually enter it, but given its notoriety, we thought it deserved a quick mention. Gramercy Park is the only private park in New York City. Only those living in the lots surrounding the Park are granted a key (the locks are changed every year) and the Park is only open to the public once a year. Even for those who can't enter the Park, it does offer a bit of serenity in an otherwise crowded area of the City.

Madison Square Park (6.2 acres)

Madison Square Park features an amenity that is equally satisfying and disturbing: free public Wifi. Although New York's parks have long been a haven to get away from it all (including work), if you are going to have to work anyways, it might as well be in the shade of Madison Square Park's trees with a delicious milkshake in hand. In that regard, the Park features another modern luxury: Shake Shack. With lines that wrap around the Park, Shake Shack delivers some of the city's tastiest milk shakes, hamburgers, and (often under-rated) hot dogs. For those who are looking for more traditional park activities, you will certainly enjoy the playground, popular dog run, and an array of sculptures. 

Stuyvesant Square (3.8 acres)

Even back in 1836, New Yorkers realized that a little bit of free space was going to be hard to come by in the upcoming years. Peter Gerard Stuyvesant, the great-great-grandson of the last Director of the Dutch Colony of New Netherlands, sold the space to the City of New York for just five dollars to create a park.  Stuyvesant Square is protected by the oldest cast iron gates in New York City, dating back to 1847. Since the Park is bisected by second avenue, you can always be assured of a bit of hustle and bustle, but even amid the nearby cars you're sure to find some tranquility. And nature lovers can find Monarch Butterflies passing through the Park on their annual migration to feed on the Park's Buddleia davidii, aka, "Butterfly Bush".

Union Square (6.5 acres)

Union Square is named for its prominent place in the City's traffic grid, the "union" of Broadway and Fourth Avenue. The Park is surrounded by the hustle and bustle of the City, which gives it much of its character. Throughout it's history, it has been a popular rallying point for crowds and protests. In fact, it recently became a National Historic Landmark for it's history as an important meeting place for early labor parties. Today, the Park is best known for it's Farmer's Market which is open Monday, Wednesday, Friday, and Saturday all year-round.


Gramercy and Flatiron Cost of Living

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