Apps or Tips for Moving?

Guys, this is a very serious post. It's so serious that it doesn't even have a picture.

I'm going to be moving to the Stanford, CT area in June, and I'm looking for advice!

The biggest decision is where to live. Given that the area is well connected by trains, I have a pretty wide variety of options that would all work logistically. I know a bit about the areas I'm considering - Greenwich, Stanford, South Norwalk, and potentially New York City. But what I really want to know is less about cities and more about neighborhoods and connected areas within the cities.

Craigslist can locate places, as can Realtors. And Realtors can also give you a sense for the neighborhood. But my impression is that Realtors are more likely to tell you things such as "the schools are good in this area and have XYZ average SAT scores." While that's important, I want to know smaller tidbits like "there is a local A Capella group that meets down the block from this place" or "this place is within walking distance of the local Humane Society, which has a good volunteer program."

Does anyone know of good websites or apps or other tools to solve this problem? Does anyone want to work with me on making something if it doesn't exist yet? :-)

Let me know! And, if you're in the Boston area, we should see each other soon before I leave...