Cuffawa, built in 1838, is one of the oldest houses in Holly Springs, with the original dog-trot log cabin still located at the heart of the house.
Dunvegan, a raised basement Greek Revival cottage built in 1845, was the home of the late artist S. Vadah Cochran Jr., whose beautiful murals can still be found on the walls inside the house.
Greystone is a Greek Revival cottage built in 1839 with a Georgian addition from the 1920s.
Hamner House is a Greek Revival house built by Morris Hamner in 1852.
Wakefield, built in 1858 by the Wynne family, was the site of a scandalous affair during the Civil War.
The Levy-Gresham House, one of the earliest examples of the Craftsman style in Holly Springs, was built by Henry Levy and has been owned by the Greshams for over 50 years.
White Pillars, originally built in 1838 but significantly altered since then, was owned by the famous Falconer family for nearly 50 years.
Sutherland is a Greek Revival, raised basement house built in 1839.
Finley Place, a Greek Revival home built in 1859, was the headquarters of the Audubon Society for several years before again becoming a private residence in 2016.
The Wells-Greer House, built in 1909, is a great example of a late Queen Anne Victorian house with early Colonial Revival elements.