Walter Chiles (died 1653) was a British merchant who emigrated to the Colony of Virginia where in addition to his business interests, he became a prominent planter, military officer and politician who at times represented Charles City County and James City County in the House of Burgesses, as well as briefly served on the Virginia Governor's Council and as Speaker of the House of Burgesses until removed by Governor WIlliam Berkeley because of a conflict of interest in ongoing litigation.
[2] Chiles moved to Virginia around 1638 and immediately invested in real estate, patenting 400 acres in Charles City County along the Appomattox River, using as headrights his wife Elizabeth , sons Walter and William, and four other people for whose passage he paid.
A March 23, 1649 document identifies Chiles as a merchant; it memorialized the sale to him by Governor William Berkeley of a lot in urban Jamestown (the seat of James City County and of the colony's government) with a brick house that had previously housed Secretary Richard Kemp and later Sir Francis Wyatt.
Richard Husband near Northumberland County, for having sailed from Rotterdam without a license (or for trading with the enemy during the periodic Anglo-Dutch wars).
His son and principal heir, Walter Chiles II also served as a burgess, representing James City County thrice beginning in 1659.