Charles Walter Redding arrived in Biloxi shortly after the Civil War. He was born and raised nearby in Bay St. Louis, so settling in Biloxi was like coming home. Until 1905, his business and family residence were combined on the upper floors of what is today, Spanish Trail Book, 781 Vieux Marche Mall. By 1907, all of Mr. Redding's business ventures were thriving, including his primary business Ship's Chandlery. He embraced the opportunity to expand the company headquarters of his business, and decided to relocate his growing family in a more spacious and prestigious estate. After a hurricane in 1898, Mrs. Nancy "Annie" Pittman Redding had vetoed property that Charles had scouted on the beach for the new family homestead. They eventually agreed that the Jackson Street location was far enough from the shoreline and would avoid any potential damage or harm during the course of any significant storms. Mr. Redding engaged renowned local architect Mr. Harkness to design and build an estate, reflective of his prominence and position in Biloxi. Mr. Harkness brought forth many renderings in a variety of styles including Queen Anne with towers and turrets, Italianate, Gothic Revival and Colonial Revival. His choice was clearly Colonial Revival. The estate remains the most stunning example of this architectural style in all of Southern Mississippi.