Before white settlement this was the land of the Tharawal and Gundungurra peoples. In 1810 Governor Macquarie granted 400 acres of land to Count Huon who had been a tutor to William and James Macarthur, sons of John Macarthur. Huon named his property Buckingham. He sold the property to James Chisholm, one of the founders of the Bank of NSW, in 1816 after a series of bad agricultural seasons. Chisholm built the homestead and out buildings on the property now named Gledswood by the second James Chisholm’s wife Elizabeth. Chisholm planted vines for wine and ran cattle and sheep. The Chisholms owned Gledswood for 128 years. From 1914 to 1971 Gledswood had a number of owners including Anthony Hordern. In 1971 the Testoni family bought Gledswood and opened the property as a tourist attraction. The present owners the Nasso family continue this tradition.
On part of the original Gledswood property bordering Camden Valley Way, El Caballo Blanco school for dancing Spanish Andalusian horses ran from 1979 to 1998. At its height this popular tourist attraction had an indoor seating arena holding 800 people.
The new suburb of Gledswood Hills, gazetted on 9th December 2011, is bounded by Camden Valley Way, Raby Rd and Gregory Hills Drive. It includes a 27 hole golf course and will eventually have 3000 houses. The first estate to be released is The Hermitage and includes the historic homestead of Gledswood as a central feature.