I am a connecticut resident, who has lived in NY for the past 15 years. I grew up in Windsor and have recently returned. I AM NOT a realtor
As some of the realtors point out, you can find a "deal" in any town right now depending your needs, desires and what you will compromise on. For instance, if public school education is HUGE on your list, it may affect which towns you include/exclude from your search. You will need to investigate the school systems as well as the current trend of suburban students attending magnet schools in Hartford. (That last fact may minimize your need to limit towns).
There are many older homes in established communities, such as windsor, CT for sale. They range in price from $150K for a 1950's 2br room in need up updating to 2700+ square ft. 4 br. homes built after 2000 that go up to $450K. There are also brand new "hi-end" townhouse & freestanding condos available at the Country Walk at Windsor. I live there and if "affordable" ($325-$360k) condo is what you seek, try there.
As far as slightly older homes, some are move in ready, some need updating. There are many listing depending on your need.
The town settled in 1633 is remarkably middle class. No real pockets of great wealth (i.e net wealth over $1,5 mil, nor any projects. But should do your research. http://www.townofwindsorct.com/
Bloomfield is similarly situated, and is closer to the more affluent town of W. Hartford. However finding a nicer 2000+ sq. ft home in Bloomfield will mean that you have to be further from Hartford. Windsor is very convenient due to the Major highway that runs through it. (You can still get a very very rural feeling home within 3 min of the highway and 20 min of Hartford).
I mentioned W. Hartford. It is a much wealthier and larger town than windsor. It has pluses and minuses. i.e. i would imagine that the public school system is ranked higher than Windsor or Bloomfield (but you should check this out on your own). It has a population of 60K versus windsor 22K. As a result, there is a downtown with many good reasturants as well as several grocery stores (including two whole foods). That said, real estate if generally far more expensive, even though similar older homes (across town) will still often need upgrading or come with same maintenance cost. Check the mil rate (property taxes) as they differ between towns.
There many factors...so it is hard to give you more information with knowing your needs. I have a friend who scored big time. He purchased a 1958 2br/2ba cape in W. Hartford for $202K with a great yard. It was a great deal because the house was in pristine condition considering its age and least expensive surrounding homes (expect 1 with lazy neighbors) is valued above $300K. The point is that finding some thing that is a good market value will require effort (and if you are not from here), an honest friend that knows the area or hopefully a decent realtor who knows all the towns in the area well, and who will be brutally honest about each and every listing that they show you. (I freely admit that my knowledge of towns on the east side of the Ct River is limited).