In 1683 land belonging to one of the Freeburgers, whose farms along the Liesbeek River supplied the Dutch East India Company, was sold to Herman Weeckens. The farm was named De Oude Wjinbergh (Old Wine Mountain). The Cape's rough seas in the winter months led to a formal winter anchorage in 1743 where ships would dock at Simons' Baai (present day Simons Town). A wagon route linking Cape Town to Simons Town went over the hill adjasent to De Oude Wjinbergh estate.
When the British took control of the Cape settlement on 16 Sept 1795 the small farming area of Wynberg developed rapidly into a garrison town, as the British settled a large number of troops in the area. A notable settler was Alexander Tennant who built a house still standing, named Sonnebloem. At Wynberg the Dutch had earlier made a show of resistance, but they were soon driven from their post by the British. Wynberg was a convenient half way point between Table Bay and False Bay and this led to a hub of commercial activity. The authorities had allotted places where large teams of oxen could be unyoked and graze which made this possible. The village provided farmers with an alternative to the market in Cape Town. As more farms were subdivided commercial and residential properties began to increase.
The famous astronomer John Herschel lived at Wynberg between 1834 and 1838, where he set up a telescope to study the southern hemispehere skies, and also did some botanical work on South African flowers together with his wife Margaret. In was at Wynberg that the young Charles Darwin met Herschel in 1836, a meeting which considerably influenced Darwin's later work.