Colonel Robert Preston was born in Londonderry, Ireland in 1753. He immigrated to Virginia in 1770 and apprenticed to become a surveyor under his first cousin, Colonel William Preston of Smithfield Plantation, in what is now Montgomery County, Virginia. William Preston was active in politics in colonial Virginia. He was a member of the House of Burgesses and a friend and colleague of Thomas Jefferson. In building his house at Smithfield, William Preston was influenced by the Tidewater architecture of Williamsburg. As well as learning the surveying profession, it is evident that Robert Preston was influenced by his cousin in architecture because the detailing found in Walnut Grove is very similar to the detailing found at Smithfield.
In 1779, Robert Preston moved to what is now Washington County. Soon after his arrival in February of 1780, he surveyed the lots for the new county seat of Washington County, Abingdon, Virginia. On April 19, 1780 he submitted twenty thousand pounds to the Commonwealth of Virginia and was granted a surveyor's bond signed by Governor Thomas Jefferson. Later that summer Robert married his second cousin, Jenny Preston of Smithfield Plantation in Montgomery County, and acquired seven hundred acres of what is now part of Bristol, Virginia. Legend has it that he and Sarah were on their honeymoon when Evan Shelby and William Campbell mobilized their men and marched to Kings Mountain, South Carolina to defeat the British army in the pivotal Battle of Kings Mountain. Later that year he would increase his Walnut Grove plantation by purchasing two hundred and twenty acres from Robert Timble.
After the American Revolution, Preston would have two sons, John and Alexander, and one daughter, Sarah. In 1803, he was commissioned a captain in the Light Infantry Battalion of the 105th Regiment of Virginia. At this time of his death in 1832, Robert Preston had amassed a sizable estate. Walnut Grove was a plantation of almost one thousand acres. Preston had seventy-four head of cattle, twelve horses, sixty-two breeding hogs, twenty-seven hogs for pork, sixty-four head of sheep and twelve casks of brandy. He also had twenty-nine slaves named Charlotte, Lewis, Scotty, Cuppy, Aggey, Margaret, Nancy, Susy, Ned, his wife Ellen, Fanny, Bob, Tom, Harriet, Kate, Billy, Moses, Jack, Mary, Joe, Jim, Adam, Henry, Aleck, Sondson, Ann, Sarah, Eliza and Mary Ann.
His wealth was also reflected in his furnishing he imported from his native Ireland. He furnished his home with eighteen chairs, two cupboards, eight beds, one bed stand, a desk, a bureau, and a chamber chair. He also had door hardware such as box locks imported from Londonderry. His cousin John worked as his agent and often advised him on items to purchase while also stating his disdain for King George III, which was apparently a popular topic for their correspondence, which was found in his papers at the College of William and Mary.
In 1889, Robert F Preston died and gave the house, the farmland, and an inventory of livestock, equipment and furniture valued at one hundred and sixty-two dollars to his daughter Mary Preston Winston and her children. As the nineteenth century came to a close, the fortunes of the Preston family were waning. In 1900, Mary Preston Winston died and gave the farmland and the house to her nephew F Robert Sheffey. Her furniture and belongings were valued to be $58.45. - NRHP, 1 July 2004