Martha “Patsy” Jefferson Randolph (1772–1836), the eldest child of TJ and Martha Wayles Skelton Jefferson, was a lifelong friend and confidante of her father. Having been educated in Philadelphia and Paris during the 1780s, she married her third cousin and childhood friend Thomas Mann Randolph (1768–1828) in 1790. They had seven daughters (one of whom died in infancy) and five sons. Martha Randolph acted as TJ’s hostess for extended periods during his presidency and resided primarily at Monticello following his retirement from public office. Financial difficulties and Thomas Mann Randolph’s increasingly erratic behavior contributed to the couple’s estrangement, but Martha Randolph reconciled with her husband shortly before his death. After the sale of Monticello in 1829, she lived with her children in Boston, Washington, D.C., and at her eldest son’s Edgehill estate in Albemarle County. Randolph was buried alongside her husband and father at Monticello (ANB description begins John A. Garraty and Mark C. Carnes, eds., American National Biography, 1999, 24 vols. description ends ; William H. Gaines Jr., Thomas Mann Randolph: Jefferson’s Son-In-Law [1966], 28–30, 104–5, 185–6; PTJ description begins Julian P. Boyd, Charles T. Cullen, John Catanzariti, Barbara B. Oberg, and others, eds., The Papers of Thomas Jefferson, 1950– , 31 vols. description ends , 6:359–61; Shackelford, Descendants description begins George Green Shackelford, ed., Collected Papers to Commemorate Fifty Years of the Monticello Association of the Descendants of Thomas Jefferson, 1965 description ends , 1:47, 50, 252; Washington Daily National Intelligencer, 17 Oct. 1836).

At least four John Watsons were living in Albemarle County in 1810, but the likeliest prospective purchaser was John Watson (ca. 1760–1841), a successful merchant in Milton who moved there from Amherst County by the mid-1790s. He served as a factor for McLure, Brydie & Company, operated a tavern, and conducted business with TJ for more than twenty-five years. Watson was Milton’s postmaster, 1798–99, a justice of the peace starting in 1800, and sheriff of Albemarle County in 1825. In 1813 he moved his family to Forest Hill, a plantation of more than one thousand acres below Milton that he purchased from Brown, Rives & Company (Woods, Albemarle description begins Edgar Woods, Albemarle County in Virginia, 1901 description ends , 339; Axelson, Virginia Postmasters description begins Edith F. Axelson, Virginia Postmasters and Post Offices, 1789–1832, 1991 description ends , 5; MB description begins James A. Bear Jr. and Lucia C. Stanton, eds., Jefferson’s Memorandum Books: Accounts, with Legal Records and Miscellany, 1767–1826, 1997, The Papers of Thomas Jefferson, Second Series description ends , esp. 2:915, 1281, 1372; PTJ description begins Julian P. Boyd, Charles T. Cullen, John Catanzariti, Barbara B. Oberg, and others, eds., The Papers of Thomas Jefferson, 1950– , 31 vols. description ends , 30:56, 626–7; Richmond Whig & Public Advertiser, 14 May 1841).

TJ deeded the Randolphs roughly one thousand acres adjoining Poplar Forest as a wedding gift on 21 Feb. 1790 (PTJ description begins Julian P. Boyd, Charles T. Cullen, John Catanzariti, Barbara B. Oberg, and others, eds., The Papers of Thomas Jefferson, 1950– , 31 vols. description ends , 16:189–91). The sale detailed above was never carried out, but on 19 Feb. 1810 the Randolphs sold 840 acres to Anne Moseley (“lately” of Powhatan County) for $8,400, a transaction witnessed by TJ and seven others, proved on 26 Mar., and recorded at the Bedford County courthouse on 28 May 1810. The tract sold to Moseley lay “west of a marked line begining at a red oak in Colonel John Wattses boundary & runing North 24 East 146 poles to another red oak in the same & of another line runing from the last tree along the North east side of a dry valley or sunken ground, making a run from near the said red oak toward the wolf branch or creek to the said creek and of the said creek as it meanders untill it leaves the aforesd tract and enters the land of Bartlet Ballard being the same part of the said Tract which was leased by the said Thomas Mann to Joseph Slaughter on the 28th day of September 1806 Containing by a survey made on the 28th day of February 1810 by Wm Callaway Surveyor of Bedford County Eight hundred & forty acres bounded as followetth to wit Begining at Earleys & Watts’s corner white oak thence along Watts’s line No 24 E 150 poles to his corner red oak thence a new line through the old field No 14 W 30 poles to two maples on wolf branch thence down the branch as it meanders No 43 E being the general course 350 poles to Ballards line, thence along Ballards and Hobsons line No 60 West 284 poles to Hobsons corner white oak near the mill pond, thence along his & Burtons line S 45 W through a small part of the mill pond 304 poles to a small white oak in Mrs Moseleys line, thence along hers & Earleys lines S 1. W 290 poles to Earleys corner pointers, thence along his line East 80 poles to his corner white oak & thence S. 51. E 95 poles to the first station.” On 29 Oct. 1810 the Randolphs sold the residue of their Bedford County estate to their son-in-law Charles L. Bankhead for five shillings, an agreement recorded on 24 Apr. 1811 (Bedford Co. Deed Book, 13:487, 586 [Vi microfilm]).