The midfielder has agreed on terms with the Lilywhites after leaving Newmarket Town.
Previously with Ely City and Great Shelford, Whitehead found the net 34 times for the Jockeys during the 2016/17 season and last year scored 10 goals in 25 appearances.
Robbie Nightingale, manager of Cambridge City, told their official website: "I am really pleased to bring Lewis to the club. I believe he will be an exciting player for us and has the talent to really succeed at this level".
Hartley Wintney: Exclusive Manager Interview
The Evo-Stik League South have interviewed Daniel Turkington, Hartley Wintney’s joint first team manager, on how he feels the club have prepared for their first season in the Evo-Stik League Premier South.