Courtland S. Winn was born in Lawrenceville, Georgia, while the American Civil War raged. His father, Judge Samuel J. Winn, was then acting Colonel of the 13th regiment of Georgia Cavalry riding with Morgan's Raiders in Northeast Georgia and East Tennessee. His mother Sara Simmons was at home in Lawrenceville looking after her first-born. Both parents were from pioneer Gwinnett County families, Elisha Winn (1777–1842) and Adam Q. Simmons (1786–1863).