New York Neighborhoods

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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 expanse 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.

An address on the Upper East Side has been a desirable asset for centuries. Names like Vanderbilt, Carnegie, Schermerhorn, and Lenox — ones familiar to anyone traveling around the city today — all secured their spot at one time or another. What was once vast farmland became subdivided by NYC’s street grid in the 19th century. Subsequently, construction began on the first wave of iconic apartments and townhouses, many of which continue to captivate us today. Elegant prewar buildings. Stunning Central Park vistas. Iconic cultural institutions. Endless shopping options. The setting of countless books, films, and television shows. For those living there, however, it’s all those things and more: it’s home.

Midtown East may very well be the only neighborhood in Manhattan where you can look up and see the stars. Of course, you’ll likely be staring at the muralled ceiling of Grand Central Terminal, but what’s wrong with that? The historic Beaux-Arts train hall is positively gorgeous and only one of several significant masterworks in Midtown East — a list including the Chrysler Building, Plaza Hotel, St. Patrick’s Cathedral, and more. Along with its sibling to the west, Midtown East also encompasses the world’s largest central business district. However, there is plenty of living room among the grand architecture and business offices. Luxe co-ops and condos — themselves often housed in impressive, towering structures — are the dominant type of residence. Still, you’ll find low-rise apartments and even townhouses further east into the Turtle Bay and Sutton areas. With stunning skyline and riverside views — plus bountiful transit options — Midtown East is a hub for Manhattan’s action. 

If you want to be in the range of Midtown but otherwise removed from the rush, find Kips Bay bounded by Lexington Avenue and the East River between 23rd and 34th streets. Kips Bay is nominally split into distinct sections by the avenues that run through it. Healthcare-related buildings dominate first Avenue. Second Avenue is home to the area’s characteristic brick high-rise towers, along with some brick rowhouses. (The I.M. Pei-designed Kips Bay Towers are off the avenue on 33rd street). Third and Lexington are where you’ll find local bars and restaurants, respectively. However, this does not mean that Kips Bay is without its curiosities. One of the last wooden houses in Manhattan is on 29th street, and there is a rare-for-NYC alley named Broadway Alley despite the fact it is nowhere near Broadway (the street or the industry). Look close enough, and you can find just about anything in Kips Bay.

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.

What is the key to Gramercy’s alluring aura? It could be its central location within short distances of multiple subway and bus stops. Or maybe it has to do with the culture — the performing arts venues and the countless excellent restaurants around every corner. Perhaps people are drawn by the history of famous residents, including icons of the stage, page, and screen. All are plausible, but everything comes back to the park in the end. Gramercy Park is literally held under lock and key, only accessible to those living in the immediately surrounding buildings, creating an unmistakable air of grandeur. However, it certainly helps that the exquisite townhouses and apartment buildings that border the renowned private square rise to meet its splendor, showing off celebrated 19th-century architectural styles. The Gramercy Park Historic District and local advocates help keep everything preserved, creating a neighborhood that feels the exact right amount of quaint.