[2] His grandfather, sea Captain Isaac Winston and his wife, the former Sarah Jennings, had settled near the falls of the James River and what became Richmond, Virginia.
Around 1765, the Winston family obtained a five-year old orphaned Portuguese boy, Peter Francisco, who had been found on the docks at City Point, Virginia and taken to the Prince George County Poorhouse.
At some point well before the conflict, while a young man, the elder Anthony Winston moved his family to Buckingham County and became its sheriff and later justice of the peace and eventually judge before dying in 1783.
Voters in Buckingham County elected Winston to what would be the final session Virginia House of Burgesses, where he served alongside fellow patriot and later prominent lawyer John Nicholas.
His second son, John Jones Winston (1785–1850) would continue the family's military tradition during the War of 1812, as well as became a friend of future U.S. President Andrew Jackson, who danced at his wedding.