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Established in 1886 on a dairy farm amidst rolling terrain, meandering creeks, and granite outcroppings, this 100-acre property was developed by James and Sallie Dooley as their private estate. Situated on a high precipice overlooking the James River, architect Edgerton Rogers designed the Gilded Age home, completed in 1893. Though they had no master plan for the property, the Dooleys established expansive lawns punctuated with statuary, garden ornaments, and gazebos. Specimen trees were imported from exotic locations and an extensive arboretum was slowly developed. Between 1904 and 1911 local architects Noland and Baskervill designed a Normandy-style carriage house and accompanying water tower, a three-story brick and granite barn, a balustraded fountain, and a terraced Italian garden. Accessed via a flower-lined promenade that passes under a stone arch, this formal garden is comprised of a Venetian wrought iron-domed gazebo, a pergola supported on rusticated stone columns, a secret garden, and an ornamental cascade that lies in counterbalance to a nearby naturalistic (though manmade) 45-foot waterfall. Continuing the Italian theme, a grotto was added to the hillside. In 1912, Japanese garden master Y. Muto and his partner Zuki created a garden with the waterfall as the backdrop, an earthen bridge, rock groupings, stone lanterns, and traditional pavilions.

Bequeathed to the City of Richmond, Maymont opened to the public in 1926 as a park and museum. In the 1930s, the Civilian Conservation Corps constructed a workshop and laid granite walls. Over the years, a wildlife exhibit was added to the grounds. The Maymont Foundation, established in 1975, commissioned Barry Starke of Earth Design to develop a master plan. Starke recommended a renovation of the Japanese Garden, completed in 1981, and a restoration of the Italian Garden, which is ongoing.  Maymont was added to the National Register of Historic Places in 1971.