Home of the Nelsons and Pages since 1812, Oakland was built by Captain Thomas Nelson, son of Colonel Hugh Nelson of Yorktown, on a portion of General Thomas Nelson's land. Oakland then passed to Colonel William Nelson, who led Nelson's Artillery in the Civil War.

The Reverend Robert Nelson was a missionary to China and father of Ruth Nelson who became the wife of Rosewell Page. His brother, Thomas Nelson Page was a lawyer, diplomat and author, who captured the romance of the old South in his stories. In Two Little Confederates, Page describes Oakland, which had been enlarged several times, as having �"as many wings as Ezekiel.�"

When the house burned in 1899, Thomas Nelson Page had it rebuilt along similar lines using the original foundations and chimneys. The east wing would later become a single large room. The �"old parlour�" was described by Rosewell Page Jr. in his newspaper column, Voice of the Native, as having been "built for the comfort and convenience of a great Virginia lady, her family and friends.�"