Prestwood’s family traced their roots to fifteenth-century Worcestershire. His grandfather Thomas, a successful merchant, settled at Exeter, serving twice as mayor, and representing the city in Parliament from 1549 to 1552. A staunch Protestant, he invested in ex-monastic property, and built up a moderate landed estate.
Prestwood replaced Champernowne as a Totnes MP in 1628, but made no recorded contribution to the Commons’ proceedings. Most unusually, while still a serving Member, he was elected mayor of Totnes in September 1628. Although not debarred from resuming his seat when Parliament reassembled in the following January, his local responsibilities must have made it difficult for him to do so, and it is therefore questionable whether he attended the 1629 session.
Prestwood’s problems with the town mills worsened in 1629, when another local landowner, the 5th marquess of Winchester (Lord John Paulet*), complained that the weir had caused flooding on his property. Forced to compensate the marquess, Prestwood sought to offset his financial losses against his rent, but Totnes’ corporation refused to endorse this arrangement, and in 1633 successfully sued him for payment of his arrears. Prestwood, who asserted that he had agreed Winchester’s compensation deal in consultation with the corporation, denounced this apparent betrayal by close associates such as Walter Dottyn*, Christopher Brooking* and Lawrence Adams*, which he regarded as a scant reward for his former services to the town, not least as its MP.
