HOLLYWOOD, Fla. (JTA) — When Orthodox Jewish clients approach local real estate agent Sharon Brandt looking for a home in this South Florida area, she tells them to make sure they have spots for their children in school before they buy.

When Rabbi Yoni Fein, head of school at the Brauser Maimonides Academy in Hollywood, gets inquiries from prospective parents from out of state, he asks them to make sure they can find a house before enrolling their children.

This Catch-22 of a simultaneous housing shortage and waitlists at area schools is no coincidence: Hollywood may be one of the fastest...