Chesterton attended RMC Sandhurst, before being commissioned in the Irish Guards. He served with distinction during World War II and was decorated with the Military Cross.
After military service, he returned to the family business where his market knowledge was much in demand, not least as a long-serving Commissioner of the Crown Estates.
From 1962, he was a director of The Woolwich, which was in the process of expanding from its south London origins, by a series of acquisitions of smaller societies, to become one of Britain's leading mortgage lenders.
Chesterton was chairman of the Woolwich Equitable from 1976 to 1983, often acting as spokesman for the building society sector as a whole at a time of high interest rates, restricted mortgage availability and, towards the end of his tenure, rapidly rising house prices.
Chesterton's family had been engaged as land agents in Kensington since the end of the eighteenth century.[2] One of his uncles was the celebrated writer and poet, G. K. Chesterton.[3]
He married, in 1944, Violet Ethel Jameson, who died in 2004. They had two sons and a daughter.[4]
