Charles Deering, son of William and Abbey Reed (Barbour) Deering, was born on July 31, 1852, in South Paris, Maine. His father was the founder of Deering, Miliken & Company, and later of Gammon & Deering, manufacturers of harvesters and the predecessor of the Deering Harvester Company, organized in 1880. This latter company merged with International Harvester Company in 1902.

Charles and his younger brother James (1859 - 1925) surrounded themselves with great art and ensued upon personal architectural projects. James's classical tastes are evident in the Italian Renaissance and Franco-European styled Viscaya estate, which he had built as his winter home in Miami circa 1910. Charles in turn gravitated toward Spanish and Dutch realism and supported the endeavors of talented artists at his home, the Deering estate. Among the painters and sculptors he counted among his friends were John Sargeant and Augustus St. Gaudens.