240 Central Park South, 2K Central Park South, Manhattan, NY 10019

What it lacks in square blocks, Central Park South more than makes up for with name-brand cachet and eye-popping details. Central Park South’s borders are flanked by two iconic entrances into its namesake — Columbus Circle and the Maine Monument on the west side and Grand Army Plaza and the Pulitzer Fountain on the east. Verticality reigns in Central Park South, where a collection of supertall structures don’t so much scrape the sky as they pierce through it into the stratosphere. The view from the top surely isn’t half bad either, with the remarkable Manhattan skyline in one direction and the entire long view of Central Park in the other. However, these pencil-thin towers are not the be-all-end-all, as more classic buildings like the Art Deco-style Essex House or the French Renaissance-inspired château-style Plaza Hotel continue to define the area’s character.