South Main Street
Two unidentified men walk south on Main Street, past the South Apopka Supply Company at 32 South Main Street. The building was erected ca.1915, standing directly south of the 1912 Dillard and Boyd building. At one time, Earl W. Ewing’s Real Estate and Insurance business was located here. Signs on the building advertise shoes and furniture upstairs. Seen in the distance, on the northwest corner of Plant and Main Streets, is the J. L. Dillard-constructed Shelby Hotel. Today, the South Apopka Supply building is the home of R.C. Stevens Construction Company upstairs and leased office space on the first floor. The building’s almost completely faded painted sign can still be seen on the brickwork above the current awning.
The building above was located at 31 South Main Street and constructed by J.L. Dillard in 1922. The Mann and Mills Dry Goods store occupied the bottom floor and upstairs featured the Lafayette Apartments, named for James Lafayette Dillard. When merchants Thomas Franklin Mann and Willie Mills arrived in Winter Garden in 1912, they opened their original store in the Dillard and Boyd building at the corner of Plant and Main Streets, later moving to this newer building. The building was also the site of a shoe store owned by J.L. Dillard’s son-in-law, Lee Grimes. During World War II Collie Biggers opened the Gem Theatre here, to handle the overflow crowds at the Garden Theatre. Seen in the photo are (L to R): Thomas F. Mann, his daughter Blanche and 3 unknown people.