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Windsor is one of the oldest towns in Australia with a colonial heritage which dates back to 1789, just one year after the First Fleet arrived in Australia. With great need for good agricultural land in the first decade of the fledgling colony, the well-watered plains of Windsor were immediately recognised for their farming potential. In 1794, 22 settlers were given land grants in the area to cultivate this fertile land and produce food for the colony. Despite being 60kms away from the main township of Sydney, Windsor's position on the Hawkesbury River made it easily accessible by boat and had the settlement a key part of the Hawkesbury trade route.

Windsor was one of the early townships which Governor Lachlan Macquarie would use to enact his new emancipation laws, in this case using former convict architect Francis Greenway to design a number of key buildings for the suburb including St. Matthews Anglican Church and the Windsor Courthouse.

One of Windsor's most prominent life-long residents would be Australia's first Astronomer John Tebbut who used his Windsor property to set up a number of observatories in 1863 and began the series of key observations which would have him renowned both at home and overseas. After undergoing restoration in the 1990s led by his great grandson, Tebbut’s observatory which is still situated on his Windsor property was opened to the public.

The railway line extension to Windsor in 1864 would increase the town accessibility and made the town more attractive to Sydneysiders looking for an escape from the cities pollution and overcrowding. With a specific interest in preserving the suburbs colonial heritage, many of the towns original houses and buildings still remain and continue to serve the purpose they always have. The Macquarie Inn is still the local pub and the public school run alongside St. Matthews Anglican Church is still teaching students. With a rich history in food production, Windsor has continued to be Sydney's agricultural heartland with the town's key industry remaining on the land. However, with the housing crisis currently facing Sydney, there is talk of substantial portions of Windsor’s farming land be turned into residential development, yet this is being strongly opposed by the local community with pride in the heritage value of both the suburbs buildings and industry.