He hired New York residential and landscape architect Bryant Fleming to design the house and gardens, and gave him full control over every detail of the project, including interior furnishings.

Recently, the Museum has pursued a consciously focused acquisition process, having added paintings by James Hamilton, William Bradford, and new contemporary sculpture for the Trail.

A year-long renovation, completed in June 2017, restored much of the original building, which revealed authentic features (wood and marble floors that had been carpeted), and conserved historical architectural motifs, such as the illusionist murals that line the main corridor.

The Contemporary Art collection, housed in the galleries created out of the estate's original garage and stables, is small but of high quality, including paintings by Larry Rivers, Andy Warhol, Robert Ryman, Red Grooms, and Marylyn Dintenfass.

Extending across the grounds from the Museum of Art, the Botanical Garden encompasses the entire 55-acre (22 ha) site with an emphasis on display, education, and study.

The plant collections include boxwood, conifer, crape myrtle, daffodil, daylily, dogwood, fern, herb, holly, hosta, hydrangea, Japanese maple, magnolia, Southeastern US natives, redbud, and trillium.

[6] In addition to the Museum and the Botanical Garden, Cheekwood operates two gift shops, and a restaurant called the Cafe 1929 which is located in the Frist Learning Center.