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I would go with Bridgeport, CT as the cheapest to buy or rent.

But expect higher taxes and not as pretty neighborhood.

But you have 45 min to drive to New York City and its the cheapest town of fairfield county. Not the best schools though if you have kids not recommended. I would look into the North end bridgeport, ct

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11y ago
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Q: In Connecticut where is the cheapest place to live?
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