Set on 8 acres (3.2 ha) overlooking Lick Creek to the north and west, its main feature is a group of six log buildings.

It is built in an oversized version of the traditional dogtrot house, with two separate white oak log structures joined via a central enclosed space under a common roof.

[4] The main building was built in 1828 by A. R. Wynne, William Cage, and Stephen Roberts, to serve as a stagecoach inn for travelers between Nashville and Knoxville, and for people taking the waters of the nearby sulphur springs.

In 1834, Wynne purchased his partners' shares in the property and moved into the inn with his family, where he resided until his death in 1893.

On February 5, 2008, during the 2008 Super Tuesday tornado outbreak, Wynnewood suffered major damage to much of the second story, roof, and trees on the property.