Charles, Jacob and John Winfree (sometimes spelled Winfrey) were living in New Kent Co., Va., in 1688. These are the earliest mentioned Winfrees that have been found in Va., and the Winfrees of Chesterfield and nearby counties are descended from them. The Reg of St Peter's Parish, New Kent Co., has records of two Jacobs, two Johns and two Charles Winfrees, evidently the children of the first three named, but it is impossible to say definetly which ones were their fathers. Charles WInfree's land in CHesterfield Co., processin 1739 seems to be the first Winfree mentioned in Chesterfield Co. Henry WInfrey acquired land in that county in 1745 and Valentine Winfree I acquired land in the county in 1746. Who their father was\has not been determined but they came from New Kent CO. From Valentine Winfree I's wil (Will Book 4, p. 465) filed in 1795, it is easy to trace his descendants. His wife was Martha Graves WInfree, daughter of WIlliam Graves and wife Sarah Cox Graves. She was the daughter of Henry Cox (Deed Book 3, p. 94) Valentine WInfree I's mother was probably a Major of the New Kent County family. Valentine Winfree I d. 1795 and Martha Winfree d. 1814. They had the following children:

1. Valentine WInfree II
2. Major Winfree
3. James Winfree
4. Reuben Winfree
5. John Winfree
6. Henry Winfree
7. William Winfree
8. Mary WInfree (Mrs D Oliver), who was the great grandmother of US Senator Benjamin (Pitchfork) Tillman of SC.

Valentine Winfree II was born June 15, 1762, d. Apr 8, 1824. He married Lucy Cheatham, great granddaughter of immigrant ancestor Thomas Cheatham. She was born Mar 26, 1764, m. Jan 3, 1783, d. 1836. She was also a direct descendant in the sixth generation of immigrant ancestor Christopher Branch I, thru his daughter Obedience Branch Cheatham. (See allied families Branch).

Valentine Winfree II and wife Lucy Cheatham Winfree were the parents of Martha Johnson Winfree. She was born Feb 11, 1790, and married John La Fon of Chesterfield Co., Nov 3, 1817. They were the parents of: Lucy Catherine La Fon, who married Dr. William Epes Ellery, MD., July 13, 1847. They were the parents of Martha Winfree Ellery, born in 1856, who married 8 John Goode Farmer II in 1878, and of Dr. William Ellery, MD who married Cora Snapp, granddaughter of 7 John G Farmer I.

One of Valentine Winfree II's sons, Valentine III, married Delilah La Fon, sister of John La Fon, mentioned above. Their daughter Lucy Catherine Winfree married W Tilghman Cogbill, who fell in the battle of Gettysburg in Pickett's charge. He left four children, among them Hon. Phillip V Cogbill, a former Virginia State Senator, and for many years county clerk of Chesterfield County.

Valentine Winfree II's will was probated in April 1824, Will Book 10, p. 248. Valentine Winfree II was one of the wealthy and prominent citizens of Chesterfield County. He was the owner of the land on which Chesterfield courthouse stands and built the fine old residence across the street from it. It is still lived in by a member of the family (Winfree of Virginia compiled by Mrs. William C Stubbs, Audubon Park, New Orleans, LA) (Winfree records compiled by Mrs. AVD Pierrepont, professional genealogist).

Valentine Winfeee II and wife, Lucy C Winfree, were the parents of 11 children as follows, according to his family Bible: (Photostatic plates are in the Va. State Lib).

1. Nelson Winfree, b. 1783, d. 1813, m. Frances Vaden
2. Christopher Winfree, b. 1785, d. 1858, m. first Mary Warwick, d. 1815; second, Cornelia M Tilden, m 1817; Children by first marriage, Louisa Ann, b. 1809; Lucy Adelaide, b. 1811; Martha, b. 1813; children by second marriage, Mary, b. 1817
3. Valentine Winfree III, b. Oct 27, 1789, d. 1851, m. Delilah La Fon 1826. He was Sheriff of Chesterfield Co. Their daughter Lucy Catherine, m. W Tilghman Cogbill
4. Martha Johnson Winfree, b. Oct 11, 1790, d. 1875, m. John La Fon of Chesterfield Co., Nov 3, 1817. Their children are listed under the La Fon family.
5. Lucy Hobson Winfree, b. Dec 18, 1791, d. Dec 3, 1814, m. William Spencer Dance
6. Polly Cheatham Winfree, b. Jan 1794, d. 1825, m. William Winfree (1824), her cousin, son of Reuben Winfree.
7. Thomas Winfree, b. 1796, d. July 9, 1809
8. Margaret Winfree, b. Mar 1798, d July 1820.
9. Robert Burton Winfree, b. March 2, 1800, m. Amanda Hatcher, daughter of Archibald Hatcher, Jan 12, 1825.
10. Elizabeth Owens Winfree, B. Jan 1803, m. John W Dance, son of Ezekiel Dance, Jan 27, 1821.
11. William Washington Winfree, b. 1806, d. 1807.