After the Sanibel lighthouse was completed in 1884, families started to arrive and by 1889, there were 21 houses, 40 families consisting of less than 100 people living in only 21 homes on Sanibel, that’s 2 families in most homes.

These rugged homesteaders included Anna and Sam Woodring (Woodring Point), The Nutt Family (Gray Gables) on what is now West Gulf Drive, The Rutland’s (The Rutland House is preserved in the Sanibel Historical Museum), and Capt. William Reed (First Post Office at Reeds Landing Tarpon Bay).

Back then, homestead rules mandated that you must stay 5 years and farm the land and never raise arms against the United States. Because many men had been confederates during the Civil War, this resulted in many homesteads registered in the wife’s name.

In 1894, a 21-year-old by the name of Frank Bailey moved to Sanibel to “seek his fortune”.

In October of 1886 Earnest and Frank Bailey paid a builder $500 to build their 4-bedroom home and for $15 more they could have a porch, but they opted to go without. The Bailey Homestead remains on Periwinkle Way as part of SCCF’s conservation efforts and can be visited by the public.

By 1896 Sanibel’s population topped 100 people and they built the first schoolhouse near the dock. The first teacher was Laticia Nutt (Gray Gables) and she received $2.50 per student per semester which totaled a whopping $50 a year. Her home Gray Gables was destroyed after Hurricane Ian in 2022 but the family cemetery survived.

Sanibel and Captiva Islands have a rich history, one that we can share with you visually, thanks to David E. Carter for digitizing images into the Sanibel Public Library's Pfeifer Vintage Photo Collection. It was a community effort to bring many of these images to Pfeifer Realty Group to be scanned and returned to the families. Thanks also to DigitalFGCU, Florida Gulf Coast University Library.