East 59 St, Upper East Side

East 59th really marks the divider between commerce and the official Upper East Side. This is where the real estate goes from expensive to old money ridiculously expensive. I prefer the architecture of the Upper West Side, myself. But, the homes on the east side starting on this street mean business. Like, "I have servants" kind of business.
The Sherry- Netherland Hotel is at the corner of 59th and 5th. It was erected in 1927 and is excessively opulent. Frank Sinatra, Dean Martin, Francis Ford Coppola and George Burns have all stayed here. Coppola actually lived here for a time. Cipriani's is the hotel restaurant and it is famous for upscale / celebrity clientele. This Cipriani's is, in my opinion, the only one in the city that is still respectable. The other ones seem to have drawn in a trashier, faux money crowd. This one is still incredibly uppity but deservedly so.
The corner of 59 and Madison houses a watch store that used to be a high end brothel that was frequented by the elite of literary, social and celebrity sects. Apparently, Dorothy Parker used to just hang out here. It reminds me of scenes from Boardwalk Empire but maybe just a bit more upscale. The coner of Park and 59th is the former Hotel Delmonico. This was quite a famous hotel but is now one of Trump's residential buildings. This site has always marked the border of Park Avenue between the ritzy upper east side residential above and the commercial part of Park Avenue below. Directly across Park is the current home to the famous Sherry - Lehman Liquor Store. This shop was started by ex-bootleggers and it is responsible for the introduction of Dom Perignon to New York City. Directly across Madison from that is Bloomingdales. There is another Bloomingdales in Manhattan (on Broadway in Soho), but as far as I'm concerned, this is The Bloomingdales. There's something about the uptown location that just makes this store a little bit more magical than the downtown location. I love this store and it is massive.
There are some beautiful and incredibly expensive apartments lining the south side of East 59th. This area surrounding Sutton Place is one of the most expensive squares in New York City.
The Roosevelt Island Tram -- an interesting ride that I suggest every one try -- is right here as is the Queensboro Bridge.