New Canaan, CT
Lake Forest, IL
In 2008, CNN Money evaluated the nation for its 25 top earning towns. 4 out of the 25 were located in Fairfield County, Connecticut, with 3 of the top 5 also in Fairfield County. New Canaan and Darien (pronounced "Darian") are about 35 minutes from New York City, and Westport is about 50 minutes. Greenwich which is number 14, is quite possibly known as one of the wealthiest areas in the nation, and used in countless movies (Stepford Wives, etc). Westport or Darien might be a little bit more "original" for a story. Most people commute to NYC for work, the whole area is considered an affluent bedroom community, with countless country clubs, beaches, vast estates, etc.
F. Scott Fitzgerald spent many summers in Westport, and many believe inspired the Great Gatsby (to some extent). Other notable celebrities to make Westport their home are Martha Stewart, and Michael Bolton.
Keep in mind the affectation of Greenwich, Darien, and New Canaan, is VERY "old money", whereas Westport is considered a little bit more "nouveau riche"
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