I think there’s two middle schools but one high school, but from what I’ve heard all public schools there are great. There’s a really nice downtown shopping area with a few restaurants right on a river. If you Google maps the town library it’s right there. All very walkable! The town as a whole you need a car. I think Darien has a similar downtown area. I grew up in the town next to Westport so I know that area better.

Also not sure if the commute to NYC is by train or car but they used to have a small shuttle that would pick you up at your house and bring you to the train station.