10 Madison Square W, 5A Flatiron, Manhattan, NY 10010

Even though the formal designation of the Flatiron District only dates to the mid-1980s, its namesake building has been a fixture for far longer. The distinctively triangular Flatiron Building rises above the area, an unmistakable landmark and indelible icon of NYC architecture. It stands as one of this city’s oldest skyscrapers and, though it may seem diminutive by today’s standards, was the tallest building in the world for a brief period following its c.1909 construction. However, don’t reduce the neighborhood to simply one structure. While various industries used to define it — namely toy manufacturing and photography — present-day Flatiron is bustling with restaurants and shopping, and the residents living there in Beaux-Arts, Neo-Renaissance, and Romanesque Revival apartment and loft buildings. Madison Square Park provides that leafy green peace everyone desires their neighborhood to have — finding a patch of grass to relax on after a long day cannot be underrated.