7. Gramercy
Walk a few blocks south of Kips Bay and it feels like you're in another world. Gramercy has a reputation for being well-to-do, but it's the perfect residential option near the bustling Union Square. Chances are you can't afford a place where you'll get access to the coveted key to Gramercy Park, but just being in the vicinity is worth it.
[Photo via @leatherandlacebyelyse]