Kids often have the choice of their regular high school, plus a few others for magnet programs, plus the state run Vocational Technical schools. The CTECS school system is selective and does reject middle schoolers applying. But at the end they have a high school diploma plus apprenticeship completed in a trade and they usually work part time senior year in their field.

Kids in my town have a choice of 11 high schools. Pretty good deal. Spending per student is also pretty decent in comparison to FL education budget.

All homes are "historic" compared to Florida (which really didnt start building in mass until after the invention of air conditioning.) But you know 1950's homes don't have anything special about them.

Really the question is Bigger City or more Country. Eastern CT is surprisingly rural, and I didn't realize that until I moved up here. You also may be limited by reasonable commute to jobs, and that may narrow things down. Southeastern CT's main employers are Pfizer, Electric Boat (and the Subbase), and the Mohegan and Foxwoods Casinos plus two hospitals. There is also a Dupont plant in there as well. But NE CT is much more sparse on major employers. Western CT has its own deal. And SW CT is basically NY to me, a non-native CT person who has lived here a little bit.