In the winter, snowfall is frequent, and a blanket of white covers the state. This New Haven County city is located smack dab in between two of the most expensive cities on our list, New Haven (40th place on our list) and Bridgeport (36th), making Milford the obvious affordable … We took a look at data from the most recent American Community Survey from the Census Department to identify which of the 100 biggest places in Connecticut … They are places where people have jobs, can live comfortably, and then enjoy things like family and friends. 2 CT Towns Among Money's Best Places To Live In 2020 - Across Connecticut, CT - The 50 Best Places To Live offer great jobs, safe streets and homes you can really afford, according to the … The … 46,473) For more Connecticut reading, check out: Richest Cities In Connecticut; Safest Places In Connecticut In the spring, … The Best Time to Move to Connecticut. If you're curious enough, here are the best cities to live in Connecticut: Milford (Pop. The micropolitan is home to about 36,000 people within city limits and has been rated as one of the best … More Economy. And in the end, Hartford ranks as the worst city to live in Connecticut for 2020. 52,349) Shelton (Pop. The rankings were created by … 41,155) Middletown (Pop. COST OF LIVING Compared to the rest of the country, Connecticut's cost of living is 7.8% higher than the U.S. average. More Cost of Living or Compare Connecticut… Tucked into the Northwest corner of Connecticut, Torrington has the most affordable home price to income ratio on this list. Connecticut experiences all four seasons in their definitive form. We’ll give you a head start as these cities are our top picks for the best places to live in Connecticut. A report ranked the top 25 best places to live in Connecticut.. Here Are The 10 Best Places To Live In Connecticut…And Why. Recent job growth is Negative. The unemployment rate in Connecticut is 3.6% (U.S. avg. 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