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Remains of human settlements dating back to 3,000 B.C. were found in Keston. Roman ruins from the 3rd century A.D were found in the valley below the area. These seem to be remains of tombs and a mausoleum. Remains of a Roman villa were also found in this part of South East London. The villa was unearthed in 1854 but a sarcophagus was found in the 18th century. Proper excavations began 100 years later in the 19th century. Flint tools and other evidence that shows sign of Middle Iron age occupation were found here. Remains of a Saxon village from around AD 450 were discovered in Keston.

The medieval church in Keston does not bear a dedication to a saint like other churches. Instead, it has a sign saying “In hoc signo vinces” which means “In this sign you will conquer”. The sign dates from the 17th century. Keston Park gated community knew some famous residents over the years. Former prime minister Margaret Thatcher lived here with her husband and two children. Bass player Bill Wyman of the Rolling Stones, footballer Kenny Sansom, and entrepreneur Peter Wood are other well-known residents. Keston Common features an 18th-century mill.

Holwood House is a Keston Greek Revival style country house built in the 19th century. The remains of Caesar’s Camp, an Iron Age fort, were found within the manor’s grounds. Politician and abolitionist William Wilberforce visited his friend William Pitt the Younger who lived in Keston at Holwood House. The two discussed slavery abolition here under the famous “Wilberforce oak”. The old oak is mostly dead by now but its remains can be still seen. “Wilberforce seat” is a bench under the new oak that was planted here in recent times. The Keston Institute was located here. It has moved to Oxford but it still has the name of this BR2 area.