2. Central Park West Historic District
New York, NY
New York's Upper West Side isn't a bastion of all that's cool in the Big Apple, but when you've got the kind of money to own real estate here, well, you don't have to care what other people find "cool." Old money is its own kinda cool.
This chunk of Manhattan's UWS is packed to the gills with landmarks, including some of the earliest apartment buildings in the city -- from the neoclassicist towers of the San Remo to the German Renaissance gables of the Dakota. Then there's the imposing and prestigious American Museum of Natural History; founded by Teddy Roosevelt, it's essentially what smaller museums dream of being when they grow up. Finally, if architectural pedigree and cultural education aren't enough (seriously, tough crowd...), consider that the entire neighborhood is bordered on its east side by Central-freaking-Park, the most famous public park in the country. If this doesn't do it for you, nothing will.