Fleming was living on the Isle of Wight in 1609, probably as lessee of his father’s house in Newport.
In June 1625 Fleming informed the 1st Viscount Conway (Sir Edward Conway I*), the newly appointed captain of the Isle of Wight, that its castles were in poor repair.
On 17 Feb. 1628 Sir John Oglander* reported to Conway that Fleming was in demand as a candidate at Yarmouth, but he was again returned for Newport.
