Also, you may find it easier to locate a home in Winchester because most homes for sale in that area are listed in the Lexington Area MLS, whereas many homes for sale in Mt. Sterling aren't listed in any central database (many agents in Mt. Sterling aren't members of the area MLS) so it's harder for you to get a true idea of everything that's on the market in Mt. Sterling, especially from far away.
Obviously, you can tell that as an agent, I favor Winchester, but having said that, both communities are nice smaller towns to live in and I don't think you could go wrong with either one.
If you'd like to search the MLS for homes for sale in Winchester, KY, just visit my website below.
Good luck with your hunt,