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 5 August 1831, a deed of trust was executed between George Taylor of the first part, James R Micou Jr of the second part, and Winter Bray & Co. of the third part, all of the County of Essex. Whereas the said Taylor in indebted to the said Bray for $420.15 by bond bearing date of the same day with this indenture and is anxious to secure to Bray the said sum of money, Taylor sells for $1 to James R Micou Jr all his right title and interest in negroes Peggy Lucinda and Edward. Nevertheless if George Taylor shall pay unto the waid Winter Bray & Co. the $420.15 with costs by the 5th day of August next, then this deed to be void, otherwise the said Micou shall sell the said negroes to the highest bidder to satsify the debt, with the balance to be paid to the said George Taylor. Signed Geo Taylor, James Roy Micou Jr, W. Bray & Co. No witnesses. On 16 August 1831 ordered recorded. [Essex County, Virginia, Deed Book 43, pages 432–433.]

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.]