Pineland's importance to Pine Island is twofold: (1) historical - there is evidence that the Calusa Indians lived here from 2000 B.C. until sometime in the eighteenth century; (2) geographical - it boasts the highest point of land in Lee County.

Originally, it was known as Batty's Landing, named for William Batty who bought 142 acres there in 1885. At that time the Calusa mounds were sixty feet high instead of the present thirty feet and the cross-island canal built by the Calusa was still quite visible. Renowned archeologist Frank Hamilton Cushing found this place to be one of the most extensive mound sites he visited in 1885, indicating that it may have been the central city of the Calusa culture. Pineland is now home to the Randell Research Center, established in 1994 as a center of research and education of Florida's heritage and environment.

When the post office was established in 1902, the name was changed to Pineland, but the sleepy character of this small settlement has changed little through the years. United Mineworkers Union president John L. Lewis, spent his winters enjoying the seclusion of this area until his death in 1963.

Pineland still has some of the most valued home sites on the island. A large marina, Alden Pines Country Club and Golf Course Community, as well as the historic mounds and buildings make it a desirable place to live.