Founded in 1825, Pine Apple became a regional commercial center because of its strategic position as the end of the Selma to Pensacola Railroad line from 1871 to the 1890s. Its progressive spirit during the centennial period 1850 to 1950 is reflected in its historic commercial, residential, civic, educational, and religious architecture, including the Bank of Pine Apple building, Pine Apple Water Tower and Waterworks building, Moore Academy, Matheson Community Library, Pine Apple Methodist Church, and Friendship Baptist Church. Its residential architecture ranges from 19th century cottages and early 20th century bungalows to more academic applications of the Greek Revival, Queen Anne, and Colonial Revival styles. In contrast to surrounding relics of a sleepy antebellum plantation South, Pine Apple's historic buildings evoke a bustling Deep South mercantile and educational center at the turn of the 20th century. The district includes 73 properties dating from the mid-19th to the mid-20th century and was entered into the National Register of Historic Places on February 26, 1999.