George Washington gave this part of Mount Vernon to his nephew and step-granddaughter, Lawrence and Eleanor Lewis, in 1799. Dr. William Thornton, architect of the U.S. Capitol, designed Woodlawn. Construction of the Federal-style houses occurred between 1800 and 1805. The Lewises relied on the labor of at least 90 enslaved workers to farm Woodlawn's 2,000 acres.
In 1846, the Lewises' son sold the property to two northern families; members of The Society of Friends (Quakers). Ethically opposed to slavery, the Friends and like-minded Baptists established a free-labor colony, successfully demonstrating that profitable farms did not require slave labor. Many members of this free community were descendants of Mount Vernon slaves. During this period, Woodlawn served as a place of worship, a school, and the focal point of the diverse community.
By 1900, the house was abandoned and dilapidated. Twentieth century owners, playwright Paul Kester, heiress Elizabeth Sharpe, and U.S. Senator Oscar Underwood, endeavored to restore the mansion to its early grandeur. These early preservation efforts add to Woodlawn's historic significance. The National Trust for Historic Preservation made Woodlawn its first historic site in 1951.