Flatiron is bounded by 20th Street to the south, Sixth Avenue to the west, 26th Street to the north and Lexington Avenue to the east. Gramercy’s boundaries are roughly 14th Street to the south, Park Avenue South to the west, 23rd Street to the north, and First Avenue to the east.
While their boundaries may blur a bit, the Flatiron District and Gramercy Park boast distinctively different personalities all their own. Named for the striking, three-sided Flatiron Building that has dominated the intersection of Fifth Avenue and Broadway since 1902, Flatiron was primarily a bustling office and restaurant district. But over the last two decades, new residents—many of them families—have moved in, taking advantage of the recently remodeled Madison Square Park, the central transportation hub at Union Square and the mini-restaurant rows along West 21st, West 24th and West 26th Streets. Jewel-like parks and rows of charming townhouses dominate the landscape a few blocks away in Gramercy, named for the private gated park at its core. Visually, the neighborhood hasn’t changed much since Oscar Wilde and James Cagney resided here, and that’s a good thing, because this graceful neighborhood remains one of New York’s finest.
The Flatiron District is renowned for its 19th-century cast iron and Beaux-Arts buildings, many of which are part of the Ladies’ Mile Historic District. Completed in 2010, the 50-story luxury condominium known as One Madison Park towers over the neighborhood’s namesake. Nineteenth-century brownstones and carriage houses abound in Gramercy Park, along with low- and mid-rise apartment buildings along many side streets.
Theodore Roosevelt is the only U.S. president—thus far—to be born in New York City. A recreation of the family’s brownstone on East 20th Street is now a museum.
Pete’s Tavern in Gramercy Park survived Prohibition by operating as a “flower shop.” O. Henry famously penned “The Gift of the Magi” in a front booth.
A sidewalk plaque on 28th Street between Fifth Avenue and Broadway commemorates what was once Tin Pan Alley, where the major songwriters and music publishers the late 19th century gathered to create and sell their songs.