Winston Hills was originally part of the “Toongabbie” area. The traditional inhabitants of the land are thought to be originally the
Dharug peoples, specifically the Toongagal clan. As the colony spread out, the Toongabbie area grew and was later divided up into separate suburbs. Winston Hills was named after Britain's Prime Minister
Winston Churchill (1874–1965) during
World War II. With the name being preferred to
Churchill Hills. In the early days, this area was named
Model Farms (a name retained in a locality of the suburb and
local high school) as this was the area where a model farm was developed to show settlers the types of crops that could be grown in different seasons. Development of the suburb began in the 1960s by
Hooker Rex, and there is little undeveloped land left. In 2009, the last remaining large parcel of vacant land, at Buckleys Hill, started to be developed. There is not much natural
bushland left in the suburb, except for the creek corridors, like Toongabbie Creek. It was transferred from the
local government area of the
City of Blacktown to the
City of Parramatta in 1972. . Some streets are named after writers such as
Bronte Place,
Shelley Street,
Twain Street,
Voltaire Road == Heritage listings ==