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Greg,
$250,000 bought you a pretty nice home in CT. 15 years ago now those same homes go for $450,000 and up.
It is not all doom and gloom $250,000 will still buy you a decent home in CT. it just takes alot of looking, networking.
If you want to live in picture post card land (Litchfield) you are going to have to pay for the priviledge. Anything west, south or north of Waterbury and they know they have you by the short hairs and you are going to have to pay.
I do not know if you have checked out S. Windsor or Ellington both really nice towns, good schools, plenty of shopping for the wife and safe neighborhoods for the kids and nice homes are affordable.
