Therese Chaney Of The Corcoran Group

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.

Before it became the polished metropolitan neighborhood we all know and love, the Upper East Side was considered a rural enclave, home to a series of villas. Gracie Mansion in Carl Schurz Park is the only relic of that period, but that mode of home perhaps set the stage for the refined residences of the present day. Aside from its adored architecture, the Upper East Side is nowadays renowned for its Museum Mile. Precisely what it sounds like, this near-30 block section of Fifth Avenue is inhabited by some of the world’s foremost cultural institutions. From 82nd to 110th Street, you’ll pass by The Metropolitan Museum of Art, the Guggenheim, the Africa Center, and several other halls of stature in between. There’s also no ignoring Central Park. Since all the grass and trees span the Upper East Side’s entire western border, there’s nothing in that green wonderland that is beyond reach.

There’s shopping in any city, there’s shopping in New York City, and then there’s shopping on the Upper East Side. Fashion’s foremost names have established outposts in this section of Manhattan, becoming as celebrated as any museum or gallery. Someone could spend an entire day on Madison Avenue alone, hopping back and forth from distinguished designer to lauded label until finding the particular piece they’re looking for. While nearly every neighborhood worth its weight in salt can lay claim to being the city’s peak of dining, the Upper East Side certainly set the standard for what it takes to reach the summit. Top chefs from all over the cuisine map put a pin down in the area, with eateries ranking among the world’s best. Just don’t think the UES is too stuffy for the simpler things; you can always head around the corner to grab a slice in this town.

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.

Some of the city’s absolute premier shopping and dining destinations anchor each end of Central Park South. The Shops at Columbus Circle bless the west with Michelin-starred restaurants and a whole host of shopping options — clothes, food, etc. Down the other end of 59th Street, the retail wonders of Fifth and Madison Avenues on the Upper East Side are close at hand. Even in between, this brief section of Manhattan teems with some of the city’s finest dining establishments. You also cannot do much better than Central Park South in terms of proximity to revered cultural institutions. Columbus Circle is the site of the Museum of Arts and Design, Carnegie Hall is on the corner of Seventh Avenue and 57th Street — no practice is required to get there — and the wondrous Museum of Modern Art is only a few blocks to the southeast.