Enterprise remained the county seat until 1888 when the growing population in DeLand voted to make that town the new seat. The old Enterprise courthouse had been sold in 1891 to the Board of Instruction for a Normal School. It continued to be used as a school until torn down in 1917 for a new school on the site. The present two-story structure (the second oldest building) was built in 1936 for the older grades. In 1964 a fire started by lightning completely destroyed the older building.
But the courthouse building was not the oldest school in Enterprise. That honor goes to a freedmen’s school formed by Charles Chipman in 1869. “I am now teaching about fifteen scholars by the light of pine knots in front of my shanty, after working through the day trying to get a potato crop growing.” Chipman asked the freedmen’s bureau to build a schoolhouse for students here and for the 25 waiting for a teacher at Sauls, but the bureau ceased operation, and his request went unfilled.