5) Weston, Connecticut
Actors Bette Davis and Robert Redford and Rolling Stones’ musician Keith Richards have all owned homes in Weston. In 2011, Connecticut Magazine named it the number one town of all Connecticut towns with populations between 10,000 and 15,000. The current population is 10,388. The median household income is $209,630 versus the state median of $71,346. Weston High School has been highly ranked by Newsweek and U.S. News & World Report. The school district has also been noted as one of the most affluent in the state by 247wallst.com and the Connecticut State Department of Education. Many residents commute to work in New York City 45 miles away. The town has minimal commercial development and boasts a lot of green space. Devil’s Den Preserve has a 20-mile trail system. Katherine Ordway Preserve consists of 62 acres, and Saugatuck Reservoir has fishing.
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