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
Oak Hill (James Monroe house) to sell that property to pay debts he had incurred while serving as President. Monroe had put Oak Hill on the market in 1809, and placed an advertisement in "The Washingtonian" on December 23 of that year: He also attempted to sell the land in 1825, but failed to receive an acceptable bid both times. In 1822, Monroe began construction on the main house, a two-story brick mansion in the Federal style. He hired James Hoban, the designer of the White House, to serve as architect. Monroe's longtime friend and political mentor Thomas Jefferson offered many design suggestions. Monroe and