Isleworth traces its roots to the Chase family, a group of citrus grove owners from Philadelphia who purchased land in the area after the U.S. Civil War.
Sidney and Joshua Chase referred to their property as the "Isle of Worth," because its citrus trees seemed naturally resistant to periodic cold snaps.
In 1993, the Tavistock Group purchased the golf course and surrounding area and began developing the large, expensive and magnificent mansions that are a hallmark of the community.
Isleworth is home to a championship 18-hole golf course originally designed by Arnold Palmer and Ed Seay, later re-designed and modified by Steve Smyers.
Late in 2007, the community became a bone of contention between Orange County officials and nearby Windermere when the city announced plans to annex Isleworth.