The traditional inhabitants of the land are thought to be originally the Dharug peoples, specifically the Toongagal clan.

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.

In 2009, the last remaining large parcel of vacant land, at Buckleys Hill, started to be developed.

Other group of streets are named after great scientists Einstein, Volta, Lister, Edison and Marconi[2] or Biblical figures such as Goliath, Gideon and Esther.

The building on the site was once the accommodation for the staff who worked on the dairy situated on Oakes Road up to what is now Rebecca Parade.

Previously, a stone homestead named "Casuarina" built for George Oakes in 1861 was located on the site,[5] and demolished in 1962.

Winston Hills has Girl Guides, Scouts, rugby league, baseball, football and netballclubs.

WHBC started playing at Col Sutton Park, just down the road from Model Farms High School.