The Northwest corner is very sheltered as far as values on property go anywhere you want to actually live. I have no issue living in Torrington or Winsted... however many people see it as a stigma. People joke around and call Winsted Wincest. I for one have zero issues investing there or Torrington. You just have to realize what you are getting into. Winsted was a factory town for the most part and you can see the shells of buildings downtown that used to be the factories.
The prices in places like New Hartford, Canton, Avon, Burlington etc are much higher because they have better schools and probably attract a much higher rent and possibly a better tenant. The only issue nobody wants to talk about in this entire area is heroin. It is here like any other place and nobody wants to talk about it. Shoot me a PM and I am happy to kind of draw out a map of where I would invest and where I wouldn't in the Winsted area. If the price is right I do not think you can go wrong. That being said I house hack in New Hartford and I am losing a tenant of 3 years as he bought his own home. I am going to renovate and probably relist my unit for 1250. If I was single I would rent out my extra bedroom for another 650... unfortunately I am not lol