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Westleigh is near the western border of Hornsby Shire, on a plateau surrounded by wooded valleys to the north and southwest.
The first inhabitants of the district were Dharug people.
As with all the Hornsby suburbs, Westleigh was originally timbered. Much of the bushland appeal still remains, as clearing for houses has been carried out carefully to preserve native vegetation. The bush setting is also evoked with streets named after native trees, such as Stringy Bark Close and Spotted Gum Road.
The first Europeans to explore the area were a party led by Governor Arthur Phillip in 1788. They probably travelled along the ridge close to where Duffy Avenue is today.
Thorn and Horne were given grants of land in the district for their efforts in capturing a band of bushrangers. Patrick Duffy was granted 100 acres (40 hectares) to the north of Thorn's grant in 1830. When access to his land was cut off by another landholder, James Milson, the Colonial Secretary's Office ordered that the track be kept open, and this later became known as Duffy Avenue. 
In the 1860s, with the subdivision of these early grants, new settlers arrived.
Much of the area was orchards and bushland until the 1960s, when it was opened for residential development.
The name Westleigh was proposed by Max Ruddock, the president of Hornsby Council, from a suggestion he received in 1967, and from 1968 the area has been steadily developed as a self-contained suburb.
All the roads in Westleigh were designed to reduce through traffic, with the exception of Duffy Avenue and Quarter Sessions Road. Because of fears of bushfires or other emergencies, residents have petitioned for an alternative to Duffy Avenue, the only main road into the suburb.