A Justice of the Peace, he lived at Coleshill Park, Warwickshire, and Sherborne Castle, Dorset, another family seat.
[1] On 13 December 1883 Wingfield Digby married firstly Georgiana Rosamund Hewitt, a daughter of James Hewitt, 4th Viscount Lifford, and Lydia Lucy Wingfield Digby, in County Donegal.
On 12 December 1888, his father died, and he inherited landed properties.
[1] With his first wife, Wingfield Digby had three children, Lydia Mary (1884–1887), Frederick James Bosworth (born 1885) and Georgina Rosamund Lettice (1887–1888).
With his second wife, he had a further five children, Kenelm Essex Digby Bosworth (1891–1972), Kathleen Venetia (1892–1982), Dorothy Charlotte Edith (1894–1918), John Reginald (1896–1988), and Robert Almarus Wingfield Digby (1901–1974).