John Boswell I was born in 1665 in Ware Neck, Virginia, and was united in marriage to Phebe Colegate Iverson Boswell in Gloucester, Virginia in 1688. They are the parents of John Boswell II, Joseph Boswell, Robert Boswell,, Mary Boswell and Diana Boswell. The children born of this union were reared in Ware Parish, an area called Ware Neck just outside Gloucester, Virginia. No other information is recorded concerning John I until he engages in land agreements with his brother, Joseph Boswell, and Thomas Booth.

In 1696 John Boswell I deeded to Joseph Boswell, his brother, 220 acres in Ware Parish.

In 1705 a deed from John Boswell I to Thomas Booth is recorded for 207 acres in Ware Parish.

John Boswell I of Parish Ware bonded to Thomas Booth, a Country Gent of Ware Parish, in the sum of 240 pounds, conditions; John Boswell II (Jr. age 13) performs the covenants in one pair of indentures bearing date of 14 April 1705. Witnesses: Thomas Coleman and John Robins.