Winchcombe's last will was written on 2 December 1557.

[33] He died soon after, and he was buried in

St. Nicolas [sic] Church in Newbury on 8 December. This was the church which was rebuilt in the
1520s and 1530s, and his merchant's mark (a capital 'I’ with a lower-case sigma across the centre)
appears regularly among the roof bosses in the nave. In this church, he and his son took part in
hearings which condemned three Protestants to be burnt to death during Queen Mary's reign. His
will was proved on 23 May 1558. In spite of his importance, no memorial to him has survived in the
church, although there is a brass to his father.
He had been married at least three times, and he was survived by his children John, Thomas, Henry
and Anne.[34] His eldest son, the third John Winchcombe, also served as a Member of Parliament in
the 1550s and 1570s.