Willoughby’s family held property in Oxfordshire, Warwickshire and Nottinghamshire, and was distantly related to the Lincolnshire magnates, the lords Willoughby of Eresby.
In his father’s will, Willoughby was bequeathed property in Nuneaton, Warwickshire, but the family’s main estate went to his elder brother, Gilbert.
Willoughby was resident at Seymours in 1602, when his property was valued at £40 in lands and goods, but later moved to Aston Rowant, purchasing the neighbouring manor of Kingston Blount from John Hungerford* for £8,200 in 1610. In the same year he also bought other lands later used to endow an annual £10 charity.
Returned to the Commons in 1614 for Wootton Bassett, Wiltshire, Willoughby had no personal links with his constituency, and was presumably nominated by John Hungerford, from whom he had earlier bought Kingston Blount manor and who owned property within the borough. Willoughby was named to a single committee, for the bill to ascertain fines for settling Sir John Fortescue’s* manor at Winslow, Buckinghamshire, on his recusant son (Sir) Francis† (12 May).
Willoughby sold various properties during his lifetime, including Easthampstead manor to Sir Richard Lovelace*.
