Patrick Conlin built a house on a well-drained region of what would become Lake Forest, Illinois in 1856.

The Vine–Oakwood–Green Bay Road community was first planned at this point as part of a simple grid system west of the Chicago and North Western Railways tracks.

Eastern Lake Forest gradually became known as a retreat for the wealthy citizens of Chicago, who built estates on the curving, tree-lined streets.

Early settler John J. McIntyre built a house in 1884 after selling his farm and retiring.

Wallis Simpson, the future Duchess of Windsor, rented a house for about a year at 494 Oakwood Avenue.