As we saw in the section on his brother Isaac Mathews Sr., it is debatable as to who was born before the other, Charles or Isaac. Under the assumption that the order in which their father gave them land on 20 Jan 1741 represents their birth order then we go with Charles being born after Isaac, probably sometime around 1713. Like his father and his older brothers Charles would also move to North Carolina, but unlike them he returned to Virginia less than 10 years later where he would live for the rest of his life. As is the case with his brothers very little is known about Charles outside of land records.

In Brunswick County, Virginia Charles Mathews first obtained 235 acres given to him from his father on 20 Jan 1741. On the exact same day his brother Isaac Mathews Sr. had obtained a similar deed of gift from their father. Around this same time Charles's father, James Mathews Sr., was preparing to move to North Carolina or was already in the process of doing so. It would appear that James Sr. wanted to make sure his younger sons had some land of their own if they wished to remain in Virginia, however it would not be too many more years before Isaac and Charles followed their father to North Carolina.

After a brief interlude between approximately 1746 and 1753 when Charles lived in North Carolina he would go on to obtain several more parcels of land in Virginia. In 1761 Charles patented 404 acres in Lunenburg County on the waters of Stoney Creek just across the border from Brunswick County.104 In 1773 he purchased 293 acres from Robert and Mary Williams a little south of where his father had given him his 235 acres back in 1741.105

Charles is first mentioned in North Carolina records in a May 1746 Edgecombe County, NC deed where Nathaniel Hickman sold "Charles Matthews of Brunswick County Virginia" 100 acres on Conoway Creek (now called Little Fishing Creek) which is right where Charles's father and older brothers had settled.106 Charles would later buy another 150 acres in this same area from William Phillips in Jul 1752.107

For unknown reasons Charles apparently decided that he wanted to return to Brunswick County. In April 1753 he sold the 100 acres he had bought from Nathaniel Hickman and in the deed he was described as "Charles Matthis of Brunswick County Virginia".108 No record exists of him selling the 150 acres he got from William Phillips. It should be noted that while there is a Jan 1754 Edgecombe County deed where a Charles Matthis bought 50 acres from Edward Collins109 I believe that this Charles was the son of Thomas Mathews Sr. and not the Charles who was a brother of Thomas and son of James Mathews Sr.

We have to look to the will of Charles and the Chancery Causes (court of equity) of Brunswick County learn the names of his children. While no wife is mentioned in any of those records, thereby leading to the assumption that he was widowed at the time of his death, we do learn from Brunswick County Court Order records that he remarried at least once to Mrs. Elizabeth Hammond, widow of William Hammond, either in or shortly before 1756.110

Charles's will, recorded in Brunswick County 27 Nov 1780, mentions only his son Drury, grandsons John and Charles Conneley [Connally or phonetic equivalent], and son-in-law Matthew Bishop with his other children mentioned only indirectly.111 To find their names listed explicitly we have to look at a 1784 Chancery Cause where the siblings of Drury were sued by the estate for equitable distribution (a commonplace occurrence and not something that implied animosity between family members). The siblings of Drury (and the spouses of his sisters) are listed as: William, Luke, Matthew and Martha Bishop, Richard and Molly Hardy, and John and Lucretia Mathis (Lucretia had married an unrelated John Mathews).112