[1] In 1581, his father inherited Gosfield Hall, Essex from his relative Ann, Lady Maltravers.
[1] He succeeded to his father's estates in 1588 before being appointed High Sheriff of Essex in 1592, and serving until 1593.
He was a Member of the Parliament of England for Essex in 1597 and for Wootton Bassett, presumably due to the influence of his wife's uncle, the Earl of Hertford, in 1601.
He was succeeded in the family estates, that "splendid inheritance", by his eldest son Sir John Wentworth, 1st Baronet, who dissipated the wealth accumulated by his father.
[1] Through his daughter Cicely, he was a grandfather of four grandchildren, including Heneage Finch, 3rd Earl of Winchilsea.