In July 1603 Winwood married Elizabeth, daughter and coheiress of Nicholas Ball of Totnes, and stepdaughter of Sir Thomas Bodley, who had married the lady's mother in 1587. By patents dated in 1615 and 1617 he was granted by James I for himself and his heirs male the office of keeper of ‘the capital, messuage, and park of Ditton' in Buckinghamshire. On 24 Feb 1629-30 the widow Lady Winwood purchased a grant in fee of Ditton Park, and in 1632 her son Richard (1603-1688) bought Ditton Manor. Winwood left three sons and two daughters, all minors at the date of his death. The eldest surviving son, Richard, who became owner of Ditton Park and manor, was elected M.P. for New Windsor in 1641, April 1660, 1678-9, 1679, 1681. A daughter Anne married, in 1633, Edward Montagu, second baron Montagu. Her son, Ralph Montagu (afterwards first duke of Montagu) inherited her brother Richard's estate of Ditton on his death without issue in 1688.