Individual Details

Parents of Ursula?
https://www.genealogy.com/forum/surnames/topics/fleming/5512/

I would be glad to know if you have found any documentation to support the idea that the Flemings of Virginia are connected to the Earls of Wigton. In the meantime I am repeating a message I first posted in 2001 with the results of a careful examination of existing records in both Virginia and Scotland.
The early Flemings in Virginia are very confusing and there is scant documentation to help. Sir Thomas didn't exist, Capt. Alexander may or may not have been the second son of the Earl of Wigton, John may have been kin to Alexander, and Charles was probably kin to John but we don't know what the relationship was.
The legend of Sir Thomas Fleming in Virginia was started by R. A. Brock in a column he wrote for the Richmond Standard 7 Feb 1880. Brock's misinformation was debunked as early as 1902 in the William and Mary Quarterly. Unfortunately, the same misinformation continues to be repeated with no evidence to support it. There is no record of a Thomas Fleming in Virginia.
The second son of John, 7th Lord Fleming and 2nd Earl of Wigton, and his wife, Margaret Livingston, was Alexander. According to the Scots Peerage, Alexander was born about 1612.
A marriage contract was signed between Alexander Fleming and Elspet Anderson 6 Dec 1643. The baptisms of three daughters of this couple are recorded in Scotland's Old Parish Registers: Margaret 13 Sept 1644, Elspet 4 Sep 1645, Mareone (Marion) 20 Feb 1648.
Alexander is often said to be the same person as Capt. Alexander Fleming of Old Rappahannock County, Virginia although I have never found anything to verify that. There is no mention whatsoever of Elspet or the three daughters in Virginia records.

Capt. Alexander married three times in Virginia and had a daughter with each wife. First Ursula, widow of John Brown(e), with whom he had Ursula, born about 1657. Next he married Elizabeth Madestard, widow of both Epaphroditus Lawson and William Clapham. They had Alexia born about 1663. Last he married Joyce Jones, widow of Anthony Hoskins. They had Elizabeth, born 1668. Extensive details of these marriages is in an article by Lenora Higginbotham Sweeny titled "Captain Alexander Fleming and Joyce, His Wife" (Vol. XXXIII, No. 3, July, 1939, of Americana, The Quarterly Historical Magazine).
Capt. Alexander died by 13 Mar 1668 when his will was probated in Old Rappahannock County (the will does not survive). He did leave many records but there is never any mention of a son.

John Fleming appears when he was granted a patent on 28 Feb 1658 for 250 acres in New Kent County (Patent Book 4, p. 254). Although there are exceptions, a man had to be 21 in order to take out a patent. If John was in fact 21, he must have been born before 1637 or at least six years before the marriage contract between Alexander Fleming and Elspet Anderson.
The baptisms of two of John's children are recorded in Charles Parish, York County. They are Lidia, daughter by Mercy bap. 30 Oct 1679 and John, son by Mary bap. 14 April 1683. There is nothing to tell us whether or not Mercy and Mary were the same person.

An interesting question is what went on in John's life between 1658 and 1679? Did he have other wives and children?

Charles Fleming was very probably related to John Fleming but we don't know if he was a son, brother, nephew or some other relation. Charles is usually said to be John's son. They lived on adjacent land and Charles took up a patent which had first been granted to John.

Spouse	Capt. GEORGE Keeling ( - )
Child	MARY Keeling (1684 - )
Child	Ursula Keeling ( - 1696)
Child	George Keeling ( - )