Purchased in 1793, Monroe and his family permanently settled on the property in 1799 and lived at Highland for twenty-five years.

Before and after selling Highland, Monroe spent much of his time living at the plantation house at his large Oak Hill estate near Leesburg, Virginia.

Wooden Wing one storey high, 34 by 18 ft."[4] Over the next 16 years, Monroe continued to add onto his home, adding stone cellars and a second story to the building.

Quarters for field hands were at some distance from the main house, while the domestic slaves lived closer to their Monroe's home.

[5] Edward O. Goodwin purchased Highland from Monroe at twenty dollars an acre and often referred to the property as "North Blenheim."

[7] Highland was featured in Bob Vila's A&E Network production,[8] Guide to Historic Homes of America and in C-SPAN's Cities Tour, Charlottesville.

[10] Today, Highland is a 535-acre (2.2 km2) working farm, museum, and a performance site for arts, operated by the College of William and Mary.

[11][12] Additional evidence for the current residence being a guest house include construction techniques that post-date Monroe moving into his mansion at the end of 1799, and dendrochronology which dates the existing structure as being made from trees harvested between 1815 and 1818.