I am from Watertown, CT. My brother and his wife still live in Waterbury and cousins in Thomaston. Sounds like you are interested in making a similar move that I made and never looked back. There are things to be considered in Condo purchases and home purchases. If it's the condo life you like, great there are some excellent deals. If it's the cost that attracts you, there are homes that you can buy in that same price range.
As far as each of the communities, it would be wise to work with a Realtor. After finding a home or condo that might interest you, they can tell you all about the association, fee etc. I have left a link to a site that you can search out those and then put a search criteria in and it will email home that match that criteria on a daily basis.
AAA Realty LLC