Annandale is said to be the oldest farm in the premium red-wine producing Helderberg Valley. Governor Simon van der Stel granted the title to Jan Wismaar, the property’s first owner, in 1688.

The farm was known as Brakelsdal until the early 1800s, when the then the owner fell in love with a girl from the Annan River Valley in Scotland, and changed the name of the property accordingly. A manor house built in the middle of the 1700s and a cellar which predates 1700 can be found on Annandale to this day, adding to the old world charm of the estate. At the height of its production in the early 20th century, Annandale supported over 500,000 vines on about 100 hectares of land.

After the Second World War, part of the Annandale property became a shelter for abandoned and abused horses and home to a riding school. In 1996 Hempies du Toit purchased the property and restored it to its winemaking roots, although the horse image on the Annandale logo still reflects this part of the farm’s heritage.