I have a unique perspective, since I worked in NYC and commuted from Westport for 13 years. I also have children in the school system. It has been correctly noted that agents are not allowed to opine on one school system being better than another, but as a parent and a real estate agent here, I have been quite happy with the school system, and so have my clients who have moved from different communities all over the world. The system here offers excellent resources, including as many AP level classes as you would like to have. We have an abundance of students attending Ivy League schools every year, including this year, which was the most difficult one EVER. (I am not necessarily pushing Ivy League schools, but some parents use that as an indicator). I am also intimately familiar with the train system. The train is not 100% perfect, but in my opinion, it is consistent, reliable and punctual, even when the weather would predict something less than perfect. I would prefer the train to the freeway any day! Westport has two stations and a number of express trains (3 stops to Grand Central Station or less). Nearby Fairfield has 2 stations as well, and is a slightly longer ride, but Fairfield also has many express trains. A Westport ride is about an hour and a Fairfield ride is maybe 10 minutes longer. Wilton is also a lovely community. The trains in Wilton run on a spur line, so it is slightly more complicated, but many commuters are very happy in Wilton. Weston is another likely choice for a wonderful community. Depending on where you are in Weston, you can commute via the Westport station, or cut over to the Wilton line. Regarding houses under $1 million, now is the best time EVER to take advantage of some inventory that has been reduced in price! I am seeing this all the time, as sellers realize that we are getting to the close of the busy spring season. There are some great houses out there! Have a good agent check into Westport, Weston, Wilton and Fairfield - you would be surprised what is available!