Various Lutteral/Litteral/etc/ families from the Cumberland County, Kentucky, area relocated to Lawrence County, Indiana, around the same time that Winnie's daughter Mary Chandler married Josiah Thomas there (1824).
The Winfred Chandler who married Benjamin Chesnut is Lawrence County (7 July 1827), and the Winney Chesnut who married Doyle Bowden in the same county (25 November 1830) may be the same person as Winnie Litteral who had been married to John Chandler.
Note that on page 108 of the 1830 census for Lawrence County, "Wineford Chesnut" - born between 1780-1790 - is enumerated next to John Luttrell with Uriah Luttrell a little further down the page. The female age 15-20 may be daughter Betsey Chandler and the two males may be sons Thomas and Elzey, although the age of one of the children suggests that he was born after John Chandler's death and may be a child of Benjamin Chesnut.
Kentucky, Probate Records, 1792-1977. Cumberland County. Will records, 1815-1831, Vol. B. Images 102-103; 138. Pages 197-198; 266-267. Inventory and Settlement of John Chandler's estate. Image of original documents hosted at FamilySearch.org.
Probate Court Records: Cumberland County, Kentucky. As cited by user georgedl1 on Ancestry.com: "Probate Court Records made Winnifred Chandler Guardian of the five minor children of John Chandler, deceased. The children were Polly Chandler, Cinthia Chandler, Betsey Chandler, Thomas Chandler and Elzey Chandler." http://trees.ancestry.com/tree/161119/person/-1479462092
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It may be possible to confirm family relationships with Winnifred by comparing test results with other carriers of her mitochondrial DNA.
However, there are no known mtDNA test-takers in her direct maternal line.
It is likely that these autosomal DNA test-takers will share some percentage of DNA with Winnifred: