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The Magazine

Northshore October 2025
For years, Bill and Joyce Cummings were undercover billionaires. They lived well, but not large, maintaining their relatively modest Winchester home (along with a smallish condo in Florida), driving decade-old cars, and flying economy class. When Bill, ever frugal, said hello to his neighbors, he would complain about the money he spent keeping his yard maintained. People generally knew that Bill did well for himself as the founder, president, and eventual chairman of Cummings Properties, but most didn’t suspect that he was one of the wealthiest people in America. That all changed around a decade ago, when he and his wife signed onto The
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