33rd St Between 2nd Ave and 1st Ave

While there's much that could be said about what one finds on this block, it's all over-shadowed by the presence of the monumentally strange Kips Bay Towers. Designed by world-famous architect, I.M. Pei, and built in the early 1960's, the geometric towers represent a rather conservative example of his work. When compared to his designs for The Louvre, The Bank of China Tower, even the Jacob Javits Center across town, or any number of other structures, The Kips Bay towers seem simply ordinary. There's an argument to be made that they fit in to the geometric nature of his body of work, but even with that considered, the towers seem more like monolithic eyesores than works of a great architect.

Directly across the street (and indeed overshadowed – literally – in the right light by the aforementioned towers) a row of tenement apartments are slowly being replaced by more expensive condos. It seems that developers are working their way inward as the east and west ends of the block bookend the street with new condos and office buildings. 

Though there's quite a bit to find on 2nd Ave in terms of restaurants and shopping (not to mention the AMC Theater which sits on the same property as the apartment towers), 1st Avenue is dominated by the consistently-under-construction NYU Medical Center...and it's a dead-end, so you're pretty much stuck in a sea of doctors.