The Winchester surname is of Anglo-Saxon origin. The first record of the name was found in Hampshire, England. It is believed that a Saxon Lord was displaced in Hampshire in 1066 and moved north to Scotland where he acquired lands in the county of Ayrshire and Lanarkshire.

The surname Winchester has included the spellings Winchester and Wincester, and these variations in spelling frequently occurred even between father and son.

Thomas Winchester along with John and Henry of Lanarkshire rendered homage to King Edward I of England on his brief conquest of Scotland in 1296. Later in 1495, William Winchester was Vicar of Grantully, and Andrew Winchester was Minister at Fishwick. The family flourished and was found at Ardtrailye, Aberchirder, St. Andrews, Artrelle, Spymie, Glasgow, Banff and Canongate. In Ireland the family settled in Ulster. In later years the family name branched south to Malden in Surrey, and Henry Winchester was Sheriff of Londres in 1826. Distinguished members of the family at this time included Sir Thomas de Winchester.

Migrants to America bearing the Winchester surname o a variable spelling include John Winchester who settled in Virginia in 1636; Andrew Winchester, with his wife and child, who settled in Virginia in 1639; William Winchester who arrived in Maryland in 1732; William Winchester, Sr. who arrived in Maryland in 1790; and Samuel Winchester who arrived in Baltimore in 1822.

Willobye Winchester, born 1696 in London, went to America with his two sons, Willoughby and William, and settled in South Carolina and died in Craven County in 1768.