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New London and Groton have some nice "old money" charm areas, but they can have a rough urban feel to them IMO.
Shoreline CT isn't cheap IMO, but there are some good compromises. I'm about a half hour north of the base, and $300K still buys a unique home.
I agree with Shaun, some of the outlying areas have a nice country feel to them, are close to I95, and can be some of the friendliest and quietest areas.
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