In the mid-Georgian period Wimbledon was a fashionable quarter of political activity. From 1783 to 1786 William Pitt the Younger (already Prime Minister at the age of 24) frequently rode down from London to stay with the philanthropist William Wilberforce at Lauriston House, and the following three years with his cousin the Hon. William Grenville (who became Speaker of the House of Commons) at Eagle House. In 1788 Pitt paid for the new copper spire for St Mary’s Church, then being built.

Between 1790 and 1794 Pitt frequently stayed with Henry Dundas, later Viscount Melville, at Cannizaro House. He recorded persuading Pitt to "shut himself up with me for 10 days at Wimbledon deciding how best to settle the affairs of Bengal". Whilst at Cannizaro House Pitt also met the future Prime Minister, George Canning, who dined there when he was staying with the Leveson Gowers at Wimbledon House. At this time the second Earl Spencer, at Wimbledon Park House, was First Lord of the Admiralty.

Next door to Dundas, at Chester House, lived the radical reformer John Horne Tooke, whose political pupil, Francis Burdett, was soon to take up residence at Wimbledon Villa on Southside. Pitt's immediate predecessor as Prime Minister, the Marquis of Rockingham, had lived in a house on the corner of Church Road until his death in 1782. The house was then occupied by Pitt's great political rival Charles James Fox.