I'm in Madison, WI. The house I'm currently in was 180k back in '09. It has appreciated some since then. My neighbors have each turned over in the past decade and have sold their house for ~$300k.
If you go with 500k, you're in a very nice part of town or one of the extremely large corner lots. Most of the houses are in the 300k - 350k range.
https://www.zillow.com/homedetails/1305-N-Thompson-Dr-Madiso... isn't uncommon.
> And the worse the weather is, the better the real-estate value.
That's a big consideration for many people. Little tolerance for the winter.
But, for example, while Boston/Cambridge are very pricey in general as are some of the more exclusive suburbs with good school systems, there's almost certainly housing in that general range within an hour drive (or even on a commuter rail).