Originally named "Buckingham" the property now "Gledswood" was a grant of 400 acres made to Gabriel Louis Marie Huon de Kerillian in 1810. De Kerillian was a French nobleman who fled the Revolution and joined the N.S.W. Corps as Gabriel Lewis, arriving on the "Surprise" in 1794. He was at one time a tutor to John Macarthur's sons.De Kerillian was issued with 8 convicts who constructed a residence on the property. This first building later became the kitchen for the homestead. The second building was a coach house and the third a cottage for the convicts in which they were chained at night. These buildings still stand and are distinguished from later buildings because they are made from local sandstone.
In 1816 the property was sold to James Chisholm for 250 pounds. Convict labour was also used to build the Homestead. There is no record of the Architect or completion date. Conjecture puts the date at c.1829, the time of Chisholm's marriage to Elizabeth Kinghorne.
Extensions and renovations were last done in the 1860's. Chisholms and their descendants lived at "Gledswood" for approx. 120 years.
There are close ties to the Macarthur family through marriages and wine growing. There is a story that James Chisholm was bailed up by Jack Donahoe the "Wild Colonial Boy" but was allowed to proceed on his way because he was good to his convicts "of which I was once one".