Here's what I have concerning Philip P. Winn (1773-1843): He was adult head of household on Hanover co. VA Tax List, 1798. He married 1) Martha Patsy Duke c1797; she died 1805. He married 2) Jennie Sims in 1807; she died. He married 3) Elizabeth Bacon Journey. Philip Winn & wife Jennie Sims relocated from Hanover Co. to Maury Co. TN in 1808, moving in the company of Jennie's father's family -the Col. William Sims.

For those interested in source information for parents of Philip P. Pledger, here are my abstracts of several Louisa Co. VA Chancery suits [Library of Virginia]:

Louisa County, VA, Chancery Causes, John Harris vs. Ann Winn et al, 1796. Suit over division of estate of Richard Winn, dec’d.; mentions Richard Winn’s widow Ann and their three children as follows: son Philip P. Winn; daughter Elizabeth, now wife of John Harris; and son John Winn, dec’d. Suit also mentions Polly and Cuzy Winn, the two surviving heirs of John Winn dec’d.

Louisa County, VA, Chancery Causes, Polley Winn vs. Philip P. Winn et al, 1802. Lewis Johnson, guardian for Polley and Keziah Winn, infant daughters of John Winn, dec’d., filed complaint that they did not receive their father’s share from the estate of their grandparents, Richard Winn and Ann Winn; Court orders division from estate of Richard Winn, dec’d., to be made agreeable to a deed from Richard Winn to his children. Suit mentions Frances Winn, widow of John Winn, dec’d., married Lewis Johnson in 1796 in Louisa Co. VA.

Louisa County, Va. Chancery Causes, Alexander Kersey vs. Phillip P. Winn, 1799. The bill entered states that Philip P. Winn secured a debt to Alex. Kersey by a deed of sale of fifty acres in Louisa Co., dated 22 Feb. 1796; deed was exhibited, which deed states the fifty acres adjoined “John Winn’s orfins and the land of James Burnley.”

Louisa County, VA, Chancery Causes, David Johnson vs. Wm. Dickenson et al, 1810. Suit mentions a judgment against Philip P. Winn in Goochland County, Virginia, and “that the said Philip P. Winn has removed out of this state.”

Richard & Ann Winn (parents of Philip P. Winn) lived in Hanover Co. VA 1782-1784 and moved to Louisa Co. VA some time after buying land there in 1786. I have no proof of Richard Winn's parents. It's possible Richard may have been a son of John Winn b. 1706 & wife Mary Pledger. Here are some records of Richard Winn & his wife Ann:

Hanover County Virginia Tax List 1782-1784 – Richard Winn

Hanover County Virginia Deeds 1783-1792 by Rosalie Edith Davis, pp. 35-36. Deed, 10 May 1784; Richard Winn and wife Ann to Joseph Cross 422 acres in St. Paul’s Parish S side of S fork of Pamonkey River.

Hanover County Virginia Deeds 1783-1792 by Rosalie Edith Davis, p. 74. Dower release for deed to Joseph Cross, 422 acres. “We did this day go to Mrs. Ann wife of Richard Winn and she did freely relinquish her right of dower, 14 Feb. 1785”

William & Mary Quarterly Vol. 22, No. 2, p. 126. Hanover County Virginia Deed, 21 May 1784; Minor Mead to Stephen Haynes, 350 acres on Stag Creek, adjacent to Richd. Winn, Cornelius Toler, Jno. Hicks & Jno. Mead.

Louisa County Virginia Deed Book F, 1784-1790, pp. 83-86. Deed, 3 Feb. 1786; Nelson Anderson to Richd Wine, 250 acres bounded by James Burnley, the widow Hamilton.

Louisa County, VA, Personal Property Tax 1787, List B – Ann Winn

Louisa Co. VA Deed Book F, pp 525-527. Deed, 4 Dec. 1789; David Hambleton to Richard Richardson, 100 acres on Branches of Henson’s Creek, lines between Kersey and land belonging to Estate of Richard Winn, dec’d. ...to James Burnley’s line to line of Richard Winn dec’d.

I concur with Connie Cole that y-DNA from a descendant of Philip P. Winn is a match to FTDNA Winn Group K. Other Group K matches include a kit from a descendant of Hezekiah Winn/Christiana Bowles, son of John Winn/Mary Pledger, Hanover Co. VA; and two kits from descendants of John Winn/Susanna, son of Richard Winn/Pledger, Hanover Co. VA. Group K matches also include kits from descendants of Daniel Winn (1715-1789), Lunenburg VA; John Winn/Ann Stone, Lunenburg VA; and Minor Winn/Margaret Connor, Fauquier VA.

FTDNA Winn Group M is a different y-DNA, and the paper trails show this group is comprised of descendants of Robert Wynne, Canterbury. Even though Daniel Winn resided in Prince George Co. VA for ten years before moving to Lunenburg Co. VA in 1755, his descendants do not match the Prince George Co. Wynne group on the y-DNA. Daniel Winn is closely related to the Winn groups in Lunenburg & Hanover Cos. VA. Oral tradition of these groups say their ancestry is in Wales. We should eventually be able to pinpoint our Welsh ancestry through DNA testing in Wales.

Sorry this is long, but these different bits of information may be helpful to some.

Stephanie Winn Miller