My MIL and 2 of my SILs live in Winter Park, north of Orlando. The homes there are pretty pricey, $300,000 plus for a modest home. You pay more to be close to the city than if you are WAY OUT in the newer areas, just like anywhere else. We would move there if DH could get a job in his field there, which is highly unlikely. The schools vary depending on which county you are in, and which area of town you live in. We would love the weather, we are from the south, but the traffic around the theme parks would be awful, you would have to live away from all of that.