Anywhere in Fairfield County. They're all bangers outside of the cities.

Here's what you need to understand, especially with schools: a school system may be ranked #40 in CT, but CT schools are really, really good. The gap between a #1 ranked school and a #25 in CT is tiny.

So, what it's going to boil down to, is if you want a rural feel or you want a more urban/suburb-ish feel. Do you want to be 10 minutes away from everything or is 20-30 OK?

The one thing I will advise is don't be within 2-3 blocks of the shoreline. During hurricanes and strong tropical storms water tends to stack up in Long Island Sound and the majority of it gets pushed down that way. Leads to a lot of surface street flooding and damaging waves.