Also I used to shop at Whole Foods regularly in VA, but don't here. There are other options though I do go to that area of the Post Road once or twice a month for Costco and Trader Joe's

I'd definitely recommend coming up and driving around a bit to see the different towns suggested. I think Orange/Woodbridge or Madison/Guilford (though farther from Whole Foods) fit the bill, but I also want to mention that Connecticut suburbia is very different from Virginia. There aren't a lot of subdivisions here,l; the towns themselves are older (though Woodbridge and Orange don't have much of a town like Guilford and Madison do) bit then outside of that the houses are a lot more spread out. A lot of these areas are wooded with no sidewalks. I have one coworker who lives on a neighborhood in Orange where kids can walk to friends' houses, but that is not common. Again not sure if that's something you want, but wanted to make that distinction.

You should definitely try for the public school lottery, which is coming up soon for next year. They used to provide both before and after care, that got cut, but I think some schools have added it back in. They are free and our children had a very positive experience. If you live in a neighborhood with a school with Pre-K, you have neighborhood preference and your child is likely to get in. Even if you don't live in a neighborhood with a school with Pre-K, it's still worth trying.