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 Jefferson continued to serve as a mentor to Monroe, and, at Jefferson's prompting, he befriended another prominent Virginian, James Madison. Monroe resigned from Congress in 1786 to focus on his legal career, and he became an attorney for the state. In 1787, Monroe won election to another term in the Virginia House of Delegates. Though he had become outspoken in his desire to reform the Articles, he was unable to attend the Philadelphia Convention due to his work obligations. In 1788, Monroe became a delegate to the Virginia Ratifying Convention. In Virginia, the struggle over the ratification of the proposed