Beneath today's Oak Hill are the remains of Surruque el Viejo, an Indian village that was first noted on the LeMoyne map of 1564. The first English settlers arrived late in the 1700's but didn't stay long. The area was named Oak Hill by a group of northern tree loggers who were killed here by the Seminoles in 1836. By Civil War times, there was a salt works in operation, several mercantiles and the first orange groves were being planted. After the war ended is when settlement really began to happen with folks coming in from everywhere.

The first real schoolhouse was built in the early 1890's, and it was for whites only. The first school for African Americans wasn't built until 1927, the same year the City of Oak Hill was first chartered. Then the Great Depression hit and the city was disbanded in 1930. The city re-incorporated in 1962 and the first mayor elected was Clarence Goodrich. He served as the mayor until 1988, the longest any mayor has ever served in Florida.

In 2011, two new city commissioners somehow got the city commission to violate Florida's "sunshine law" and meet in private. In that meeting, they voted to disband the city's police department and turn all law enforcement duties over to the Volusia County Sheriff's Department.

The population of Oak Hill has risen by 30% since 2000.