Highland (James Monroe house) Highland (James Monroe house) 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-four years. Personal debt forced Monroe to sell the plantation in 1825. Before and after selling Highland, Monroe spent much of his time living at Oak Hill. President Monroe simply called his home "Highland". It did not acquire the additional name of "Ash Lawn" until after his death. The
James Monroe of Virginia and rose to national prominence as a diplomat in France when he helped negotiate the Louisiana Purchase in 1803. During the War of 1812, Monroe served in critical roles as Secretary of State and the Secretary of War under President James Madison. Facing little opposition from the waning Federalist Party, Monroe was easily elected president in 1816, winning over eighty percent against Rufus King (who hadn't even been chosen by a convention since the Federalists were too weak to organize) of the electoral vote and becoming the last president during the First Party System era of American politics.