Masefield was married to Jennifer Masefield, an orthopaedic nurse and physiotherapist who was active in charitable work during his governorship. The couple had three children: Nigel, Sally and Roger.[5] During their years in Bermuda, she served as patron of Pals, the island’s cancer charity, and the couple were known for their support of community and compassionate-care initiatives. In later life, she developed Alzheimer’s disease and died in April 2019 at the age of 79.[5]