Waterbury, Connecticut
Average housing cost: $750
Population age 65 or older: 12.6 percent
Walkability score: 48
Safety score: 8
Despite being near expensive metropolitan areas, Waterbury, Conn., has managed to keep its cost of living — and monthly rent prices — down. Waterbury, which starts our countdown of the top five cities, is located about 90 minutes outside of New York City on the Naugatuck River.
The city has a small-town feel to it, but it provides easy access to the hustle and bustle of Manhattan. You’ll also have access to quality healthcare, thanks to the proximity to Yale University. Lower crime, a thriving senior community (the third-highest senior citizen population on this list), good walkability (the second-highest on this list) and modern shops and amenities make Waterbury one of the best places to retire.