In late December 1871, surveyor J.O. Fries rode a lumber wagon pulled by a horse and a mule between Sanford and Orlando. He noted a lone house along the entire road and one small store in Maitland. The only inhabitants of what would be Longwood were the Hartley family, which had a homestead on Fairy Lake. Today, the city's historic district includes includes 24 homes and businesses built during the late 1800s and early 1900s.