Sir Roger Cholmeley (sometime around 1485 – June 21, 1565) was the founder of the Highgate Free Grammar School nearby, now Highgate School. He held the manor of Hampstead and served as Lord Chief Justice under Mary I. Most of his career as a lawyer was spent in the City of London. He was MP for Middlesex from 1554 to 1559. The school was demolished and rebuilt in 1866.