Isleworth has deep roots in Florida’s citrus heritage.  In 1884, Sydney Chase and his older brother, Joshua, formed a partnership which was the beginning of Chase & Co., one of Florida's most successful companies in the ensuing years.

After a severe freeze in 1886, the brothers were out looking for fruit to supplement the scarce supply in the Sanford area. While searching a section southwest of Orlando by horse and buggy, they wound up on an island by Lake Tibet-Butler and the sight of such bounty in those times led them to call it the ‘Isle of worth’.

Isleworth was expanded over the years through a number of additional land purchases. It was an illustration of the remarkable foresight of the Chases that, at the very time when other growers were bidding farewell to Florida, they were increasing their land holdings.

In 1913, Sydney Chase built a cypress bungalow on Lake Louise which was sometimes used for summer vacation visits. Sydney Chase's youngest son, Frank W. Chase, Sr., was sent to Windermere soon after finishing college in 1931 in order to oversee the company's activities there. Until his death in 1986, Frank lived in the lovely cypress home on Lake Louise to which he and his wife, Helen, moved as newlyweds in 1935.

The potential of Isleworth was envisioned by Arnold Palmer when he flew over the property in 1981. At that time orange trees covered the nearly 800 acres, part of the Isleworth Groves, some of the finest producing groves in Florida for close to 100 years.

Palmer recognized that this land, surrounded by seven pristine lakes, had the potential for being the site of a world class golf course and luxury residential community, a longtime goal of his. After purchasing the land in 1984, Palmer and his development partner - the Concord Corporation of San Antonio, Texas - carefully planned every aspect of Isleworth. Rather than limiting Palmer's golf course design genius by plotting the golf course, Palmer first planned the 18-hole course.

In 1993,  The 600-acre community was sold in 1993 to Aviva Land Holdings who have redeveloped the community to feature estate-type homes built upon one simple precept - only the best.