There are quite a few personal weather stations in The Villages on the Wunderground
Charlotte Weather | Personal Weather Station: KFLWILDW30 by Wunderground.com | Weather Underground weather network. Can't tell if any of them are on the roof.
I doubt there are any laws against roof mounted weather stations but your deed restrictions might restrict them. The restrictions vary throughout The Villages so you will have to check the restrictions for your house You can look them up on line at districtgov.org site
Village Community Development Districts