John George was listed on 18 Jun 1724 in Essex Co, VA Court records.
On 18 Nov 1729, Robert George Sr of Middlesex Co, VA gave his son (so named in the deed) John George of Essex Co, VA, 270 acres in Essex Co, VA. (Essex Co, VA Deed book 19 page 66).
John George apparently lived in Essex Co, VA from ca 1724 until 1735, though he appeared in Caroline Co, VA records by 1734. Since Caroline bordered Essex (and was formed from part of Essex), his land may have been near the border.
John George was named in the Will of his father Robert George written in 1733 in Middlesex. He was also one of the Executors of the Will.
On 9 May 1734, John George was listed in Caroline Co, VA Court when William and Mary Dillen acknowledge a deed to John George. This doesn't mean that John lived there then, but had purchased land there by then. Caroline Co, VA Deeds were lost, so the court orders regarding these early deeds are all we have. (Caroline Co, VA Order Book 1732-1740 pg 140).
On 21 Feb 1735 John George "of Essex" sold 373 acres of land in Essex Co, VA to Francis Smith. This is probably when John moved to Caroline Co, VA. (Essex Co, VA Deed book 20page 156).
On 13 Jun 1735 Robert George acknowledged his deed of land to John George. This probably is the land John lived on. (Caroline Co, VA Order Book 1732-1740 pg 297).
John George's name appears in the Caroline Co, VA Order books many times over the next several decades, often on Juries, and as witnesses to deeds or wills. Quite often his name was on the same records with his brothers Robert George and Richard George, his brother-in-law Robert Williamson, and his nephew Robert Mickleborough. John Dudley often appears on the same records as well. He may be the father of Ursula Dudley, John George's 2nd wife.

John George made his Will on 7 Feb 1784. This Will was found in the Fredericksburg District Court records. In the Will he names his son Reuben George; son John George; son James George; daughter Ann Woolfolk and he mentions Robert Woolfolk (her husband, though that relationship is not stated); daughter Elizabeth Baber; grandchildren Mary Isbell, Daniel Isbell, Nancy Isbell, John G. Graves, Benjamin Graves and Frances Graves. He also mentions their mother, though doesn’t give her name, and mentions Beverly Graves (who is his son-in-law, though that relationship was not stated in the Will); daughter Sarah George; daughter Mary Mackhaney (McHaney); and daughter Catey Brown (Catherine Brown). Son Reuben George is made sole executor. Witnesses were James Yarbrough, Gilly Yarbrough, and William Brown. He signed the Will as “John George Senr” and the Will was proven in Caroline County Court in May 1784.
John George died between 7 Feb 1784 and 22 Apr 1784 for on that latter date his son Reuben George wrote a letter to brother-in-law Cornelius McHaney informing him of the death of John George Sr.