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 Gregory James Monroe Gregory James Monroe Gregory (January 23, 1849 – December 17, 1915) was a Professor of Latin and Dean at Howard University. During the American Civil War, he worked in Cleveland for the education and aid of escaped slaves. He initially attended Oberlin University. He transferred to Howard and was the valedictorian of Howard's first graduating class in 1872. He then became a member of faculty, where he served until the late 1880s. During that time he was active in civil rights, particularly related to the education of African American children. He fought to desegregate Washington D.C. schools in