James Monroe bought one thousand acres adjacent to Thomas Jefferson's Monticello in 1793 for one thousand pounds, purchasing the land from the Carter family. The parcel had once belonged to the nearly 10,000-acre land grant of Secretary John Carter. Jefferson encouraged the purchase; the two men were close friends and political allies, and Jefferson wanted Monroe nearby. Six years after buying the land, Monroe moved his family onto the plantation in 1799. He named it Highland. Monroe described his home that year as "one wooden dwelling house, the walls filled with brick, one story high, 40 by 30 feet" with a wooden wing measuring 34 by 18 feet. It was a working plantation with stables, two barns with a threshing machine, a grist mill, and a sawmill. Monroe and his family lived at Highland for 25 years.

The archaeological discovery in 2015 rewrote Highland's story. Excavators unearthed nails, fragments of home furnishings, and a significant amount of bottle glass and ceramic pieces dating from the late 18th and early 19th centuries -- the Monroe era. The foundation they uncovered was far larger than the standing building, matching the dimensions Monroe himself had described. Dendrochronology confirmed the twist: the trees used to build the surviving structure were harvested between 1815 and 1818, well after Monroe moved into his mansion at the end of 1799. Construction techniques in the standing building also post-date Monroe's arrival. The smaller house was likely a guest house, built around 1818 by carpenters on the plantation. For generations, the guest quarters had been mistaken for the president's home.

Public service cost Monroe dearly. Years of diplomatic postings, a governorship, and the presidency itself drained his personal finances. By 1825, personal debt forced him to sell Highland. Edward O. Goodwin purchased the property at twenty dollars an acre and renamed it "North Blenheim." Monroe spent his remaining years between his larger Oak Hill estate near Leesburg, Virginia, and eventually New York City, where he died in 1831. The Highland property changed hands and names multiple times. For decades it was known as Ash Lawn-Highland, a name that obscured Monroe's connection. In 2016, the estate was officially redesignated "James Monroe's Highland" to restore the link to its most famous resident.

Today Highland is a 535-acre working farm, museum, and performing arts venue operated by Monroe's alma mater, the College of William and Mary. The property was added to the National Register of Historic Places in 1973. Visitors walk the grounds year-round, though hours are limited from October through March. The site sits just down the road from Monticello, making it part of a remarkable corridor of presidential homes in the Virginia Piedmont. Jefferson, Monroe, and Madison all built within a few miles of one another, drawn by the same fertile soil, temperate climate, and Blue Ridge views. Highland's ongoing archaeological work continues to reveal new details about Monroe's life, his enslaved workers, and the daily operations of a Virginia plantation in the early republic.