East 53 St, Turtle Bay

53rd starts off with quite the bang on the East River. The south side of the street holds River House which has been often noted as one of the nicest apartment buildings in New York. With the Beekman area butting up on Sutton Place, this is a really serious stretch of real estate where the richest of the rich live. This is much more of an old timey, old money sort of area so the demographic isn't exactly wild and wooly. But, the buildings are beautiful and you feel like you've been transported to another era when you walk down this street. River House used to have a yacht dock (crazy, right?). The inventor of FM radio killed himself by jumping out of his window here so it even has a ghostly sort of status outside of the fact that Cornelius Vanderbilt, Henry Kissinger and Marshall Field have all lived in this building. The rest of the apartment buildings are all lovely on this block (and ridiculously opulent and expensive) but none have the draw that River House has.
The next block is interesting because it holds two wooden structures which there are hardly any of in Manhattan. They stand out like sore thumbs but they're lovely and it's nice that they're still around. There are some other old timey, luxury apartments on this block in addition to a quaint little Irish pub, a diner -- which is weird for this part of town, and a piano bar. This is definitely an older people area if you catch my drift.
The next block is very commercial with the very identifiable Lipstick building next door to a townhouse that is now used as a commercial space. Across 53rd there are more high rises and a very swift departure from the uptown neighborhood feel of the two more eastern blocks of this street. The block up to Lexington follows suit and ups the ante with a boring looking Marriott, a Citicorp massive structure and some other massive commercial structure. The neighborhood feel is non existent here and it feels very midtown bustle during the day and ghost town- like at night. It's like you have to have millions of dollars to live in a cute two block area that's next to an urban nightmare. But, apparently, the apartments around Beekman are worth it.