Highland (James Monroe house) his house (the end of 1799) and dendrochronology which dates the existing structure as being made from trees harvested between 1815 and 1818. 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
James Monroe Gregory for six years. In 1887 he was a candidate to replace James Campbell Matthews as Washington, DC Recorder of Deeds, although the position went to William Monroe Trotter. Gregory was again a candidate for the position to succeed Trotter in late 1889, but the position went to Blanche Bruce. Gregory was president of the American Association of Educators of Colored Youth which was he founded in 1890 and led throughout its existence. He was a delegate to the 1892 Republican National Convention, and expressed interest in the Recorder of Deeds job again, which in 1893 went to C. H. J.