Following the conflict, Winston once won election as one of Buckingham County's representatives in the Virginia House of Delegates, for the term beginning May 3, 1779, when he served alongside Joseph Curd, before voters elected two members of the prominent (and wealthy) Cabell family.Leonard p. 133 His father, also Anthony Winston, a longtime judge in the area, died in Buckingham County in 1783. In the 1787 Virginia tax census his estate owned nine adult slaves, one slave between 16 and 20 years old, as well as seven horses and 17 cattle, while this man (his son of the same name) did not reside in the county but owned six adult slaves, 11 slaves between 16 and 20 years old, six horses and a dozen cattle.Netti Schriener-Yantis and Florene Speakman Love, The 1787 Census of Virginia (Springfield, Virginia: Genealogical Books in Print 1987) p. 685
