Pleasantville was surveyed and established as a town on August 1, 1849 on land then owned by William Wesley Jordan. Previous to the ownership of Mr. Jordan, the land comprising the original town plot of Pleasantville changed hands for one horse and $30.
A petition for incorporation was filed in District Court on June 11, 1872 with an election subsequently held in which there were 46 votes in favor and 16 votes against.
The completion of the Chicago, Burlington, and Quincy Railroad Line through Pleasantville in 1879 caused an increase in development and Pleasantville became one of the active business centers in Marion County and the principal shipping point between Knoxville and Des Moines.
The earliest population figures available begin in 1900 with 738 residents.
The first school was built in the fall of 1847, and in 1868, the school district joined with the Masonic Lodge in building a three story brick building that remained a school facility until 1992. Today, the Pleasantville School district consists of three buildings, an elementary, a middle school, and a high school.