Highland, formerly Ash Lawn–Highland, located near Charlottesville, Virginia, United States, and adjacent to Thomas Jefferson's Monticello, was the estate of James Monroe, fifth President of the United States. Purchased in 1793, Monroe and his family permanently settled on the property in 1799 and lived at Highland for twenty-five years. Personal debt forced Monroe to sell the plantation in 1825. Before and after selling Highland, Monroe spent much of his time living at the plantation house at his large Oak Hill estate near Leesburg, Virginia.