There were people settled in the Ashtead area from prehistoric times and on Ashtead Common there is the site of a Roman villa and tileworks, which was excavated in the 1920s. Ashtead is recorded in the Domesday Survey of 1086 as 'Stede' and it is 'Estede' in a document of about 1150, the name meaning 'place of the ash trees'.

By the second half of the 13th century Ashtead had become the property of the De Montfort family, whose most famous member, Simon, lead the Barons' Revolt against King Henry III and was killed at the Battle of Evesham in 1265. The Manor of Ashtead passed to the Dukes of Norfolk who, in 1680, sold it to Sir Robert Howard. Howard was a poet, playwright, M.P. and also held the lucrative post of 'Auditor of the Exchequer'. He was a great friend of the composer, Henry Purcell, and his sister, Elizabeth, married the poet, John Dryden.

Howard rebuilt Ashtead Manor House, which was visited by most of the wealthy and famous of the Restoration Period. Charles II, James II and William III all came to be entertained at Ashtead. As 'Ashtead Park' the house was rebuilt in the early 1790s and in 1926 it became the home of City of London Freemen's School.

Ashtead continued to be held by the Howard family until 1877, but two years later the estate was sold and broken up. The sale coincided with a depression in agriculture and the estate was worth little as farmland, but much more as land for housing. Ashtead Station had already opened in 1859 and thus, by the late 19th century, there were all the right ingredients for the development of the thriving commuter village that is Ashtead today.