Many of the Overstreets found residing in Kenrucky were and are descendants of James Overstreet who moved to Kentucky from Virginia. Some of these hold to the theory that James Overstreet was an emigrant and mariner born in London, England, in 1736, and that he quit the sea and came to Virginia c 1759. Perhaps he was in the company of his brothers, John and Thomas. R. E. Overstreet of Canada has done much research into the records of England, and has failed to find a James Overstreet born in England in or about 1736. R. E. Overstreet does conclude that a possible birth place could have been Christchurch Parish, since their records weredestroyed. Some descendants and researchers believe that James Overstreet was born in Virginia, perhaps Hanover County, and that his father or an earlier ancestor came from England. Records do indicate that Overstreets were in the state of Virginia as early as 1650.
In a letter written in 1934, from Dr. Arthur Hieronymus of Oakland, California, to Edith O. Morris of Richmond, California, in which the following contents were found: "James Overstreet, the emigrant, was born in London in 1736. He was a mariner. He quit the sea and came to Virginia. In 1749, he married and settled in Culpeper Co. He became quite an extensive land owner and a man of considerable means. He married three times, first to Jenny ?; she was born in 1742, died in 1770, and married Dec. 6, 1759, had five children; second to Annie?; she died Oct 13, 1781, had five children; third to Nancy Davis, born in 1760, died Oct. 29, 1832, married July 25, 1783, had eleven children, two were born in VA, nine in Kentucky. In 1790, he sold his Virginia lands and moved to KY, with his slaves, horses, cattle and chattels. He trecked from Culpeper Co. to the Ohio River, then on a flat boat went down the Ohio to the mouth of the Kentucky River, then up this river to the great bend that formed the southern boundary of Fayette Co, the part now constituting Jessamine Co. He was accompanied by most of his children and their families. He took up 2000 acres of land and built a great log house. This house was still standing in 1907, and occupied by a Geroge Overstreet. James died there Feb. 28, 1817. His widow Nancy remained on the old place for a number of years. Her son Robert Dale lived with her. About 1828, he purchased land in Mercer Co.,KY, and moved there taking his mother with him. She died near Harrodsburg, KY, in 1832." [http://scribers.midwest.net/cbconly/over.htm]
James Overstreet may be the s/o Gabriel Overstreet.
Much of the early Overstreet material on James Overstreet and his first wife, Jennie, and their children is from the working papers of Scott G. Swanson of Butler University, 4600 Sunset Ave., Indianapolis, IN. 46208.
The 1783 Virginia Census shows James Overstreet residing in Hanover County. He is also listed on tax list in St. Martins Parish, Hanover Co., VA. in 1782,1783, and on 9 March 1784. His two oldest sons, Thomas and Henry, joined the Revolution War as soldiers in Hanover Co., VA in June 1780.
After the Revolutionary War was over James Overstreet and his many extensive family members including Thomas and Henry moved to Louisa County, Virginia, then moved in early 1789 to Kentucky. They came to Kentucky by way of the Ohio River on a flat-bottom boat eventually reaching Jessamine Count-, southwest of Lexington. They left the river at Limestone, Maysville, Kentucky, for Fayette County41 and then went to Jessamine County in 1791.
A family tradition reported by R. A. Hunt, Jr. in the Horine Family History has it that the large family travelling down the river drew fire from the Indians causing much excitement especially for James Overstreet who reminded someone later that he had three sets of children to look after. He took up 2000 acres of land and built a great log house. This house was reported still standing in 1907. It was then occupied by a George Overstreet.
James Overstreet had three wives and nineteen children. He died February 27, 1817 in Jessamine County, leaving no will. A record of the complicated estate settlement is in Jessamine County Will Book B (see Estate Papers -- dated: April 20, 1818).
James home was adjacent to the home sites of Charles and William Overstreet in the southwest portion of the county, just west of Phillips Road and south of Bethel Road.
