The Legare Waring House began as a modest overseer's dwelling, constructed in the mid-19th century, when the property was part of Old Town, a sea-island cotton plantation. The exact date of its construction remains unknown, but evidence suggests it was built about 1840. Jonathan Lucas III acquired Old Town in 1835 and commissioned a plat of the plantation the following year. The plat depicts the Horry-Lucas House (built around 1775) but fails to show a building at the site of the present-day Legare Waring House.
Jonathan Lucas' primary residence was the "Brick House" in downtown Charleston, and he visited Old Town chiefly for recreation. Lucas died in 1848, and the plantation was put up for sale the following year. After the main house (now the Horry-Lucas ruins) burned during the Civil War, the overseer's dwelling became the primary residence. The property came to the Legare family in 1878, when Julia Thomas Graves gave it to her daughter Katherine Malcomson Graves, wife of Edward T. Legare.
When Edward died in 1924, he left 1,000 acres of Old Town, including the house, to his grandson William Legare. William died in 1930, and his brother-in-law employed a "caretaker" to manage the property. The caretaker proved to be highly incompetent, and on his watch, rats gnawed through the dining-room floorboards of the overseer's house to get to the corn that he was storing inside. During this time, even goats took up residence in the house.
Following the death of William Legare, his older sister Ferdinanda Backer, affectionately known as "Ferdi," inherited a portion of Old Town, including the house. By this time, the house had fallen into disrepair, and the surrounding landscape was a tangle of vines and weeds. Consequently, Ferdi made reclaiming Old Town one of her life's ambitions. Beginning in the mid 1930s, she initiated a major redesign project that would continue for decades.
In the late 1940s, Ferdi and her second husband, Dr. Joseph I. Waring, enlarged and remodeled the old overseer's house in the Colonial Revival style. Harking back to the Georgian tastes of the 18th century, the Colonial Revival style embraces an appreciation for symmetry and classical architectural elements, such as the Legare Waring House's Doric porch columns and the dentil-work molding on the cornice below the roof, in addition to the cross-gabled pediment and fanlight above the front door. As for the surrounding grounds, Ferdi not only installed the formal live-oak avenue leading up to the house but also planted thousands of azaleas and camellias. Ultimately, she established 80 acres of picturesque gardens, including the freshwater lagoons behind the house today.