The link below will give you information on schools here in Connecticut. For good schools, look for those that perform above the state averages on the Connecticut Mastery and Connecticut Academic Performance Tests and have reasonable class sizes (generally under 24 per class).
State Department of Education - CEDaR
Longmeadow should have homes in your price range but you are right they will be older. East Longmeadow would have newer homes but I am not sure about their schools. You might check on the Massachusetts board for information.
In Connecticut, I would recommend looking into Granby, East Granby, Ellington, Suffield and Somers. These towns all have schools that perform above the state averages so the schools could be considered good. These are smaller, more rural towns but they should also offer newer homes. The commute to Springfield and Windsor will depend on where in each town you live but should not be horrible. Good luck, Jay