President Monroe spent much of time at his estate, Oak Hill. He spent a great deal of time with his friend James Madison. He also spent a great deal of time reading in his library, which contained more than three thousand books. Unfortunately, Monroe’s financial situation had deteriorated over the years and he had to sell off some of his land to pay off debts. He applied to recover monies from the federal government for his years of service, finally receiving a congressional grant of $30,000—less than half the sum recommended by a congressional committee.

President Monroe also provided service to the University of Virginia, where he worked with Presidents Jefferson and Madison. He committed himself to writing, including The Political Writings of James Monroe.