On 15 July 1811, pursuant to an order of court dated 19 March 1811, the slaves and lands belonging to the estate of John Croxton, Junior, were divided by Tho. Brockenbrough, Th: Jones, and Francis Smith, to Mrs. Milly Croxton (for her dower), Susanna Croxton, Catharine Croxton, and Mary Ann Bray. At court of 17 June 1817, these reports, made up in pursuance of a decree dated 19 March 1811 in a suit in chancery in which Winter Bray and Mary Ann his wife were plaintiffs, and Milly Croxton, and Catharine and Susanna Croxton, infants under the age of 21 by Milly Croxon their guardian, were defendants, were ordered recorded. [Essex County, Virginia, Will Book 18, pages 424–425.]

On 16 January 1815, Winter Bray and Thomas Pilcher were bound in the penalty of $2,000 for Winter Bray’s administration of the goods, chattels and credits of John Collins, deceased. [Essex County, Virginia, Will Book 18, page 91.]

On 21 February 1815, Winter Bray and Thomas Pilcher were bound in the penalty of $3,000 for Winter Bray’s administration of the goods, chattels and credits of Gabriel Purkins, deceased. [Essex County, Virginia, Will Book 18, pages 122–123.]

On 15 May 1815, Thomas M. Henley, Charles Hill and Winter Bray were bound in the penalty of $4,000 for Thomas M. Henley’s administration of the estate of William Purkins, deceased. [Essex County, Virginia, Will Book 18, page 162.]

The estate of Gabriel Purkins was in account with Winter Bray from 1815 to 1818. [Essex County, Virginia, Will Book 19, pages 57–58.] A dower payment to Susanna Gordon, widow of Gabriel, was made in 1819. [Essex County, Virginia, Will Book 19, page 58.]

On 28 December 1821, Winter Bray, Charles Bray, and P. J. Derieux agreed to a division of the dower slaves of Milly Croxton, widow of John Croxton Jr., deceased. Ordered recorded 21 March 1831. [Essex County, Virginia, Will Book 22, page 207.]

On 17 November 1823, Winter Bray, Thomas Pilcher and Charles Bray were bound in the penalty of $8,000 for Winter Bray’s administration of the estate of Edward Ware, deceased. [Essex County, Virginia, Will Book 19, pages 420–421.]

On 17 November 1823, Winter Bray, Thomas Pilcher and Charles Bray were bound in the penalty of $1,000 for Winter Bray’s executorship of the estate of Rachel Ware, deceased. [Essex County, Virginia, Will Book 19, page 421.]

On 18 March 1825, Lawrence Muse, commissioner, settled Winter Bray’s administration of the estate of Edward Ware, deceased. [Essex County, Virginia, Will Book 20, pages 163–166.]

On 13 and/or 14 November 1834, Winter Bray purchased property at the sale of the estate of Major Arthur L. Barnes. [Essex County, Virignia, Will Book 24, pages 12–20.]