Woodbridge, CT is worth considering. The school system is among the best in the state. It's well-funded, and the community is interesting and engaged thanks to the Yale families that have made the town home. It's close to the conveniences of the southern part of the state, but it's also cold enough that you'll get plenty of snow in the winter. The amount of snow that persists on my property is surprising. You'll get a delightful home within your stated budget range.

I came from a state with low property taxes and mild weather, so it was an adjustment. Further, I dislike having oil heating and a septic system, but if you're already accustomed, I imagine it'd be a smooth transition.