Early Development on Fort Myers Beach

Opened in 1912, the Winkler Hotel was the first hotel on the island.

The early part of the 20th century brought more development as the first subdivisions were platted on Fort Myers Beach.  H.C. Case platted the first of these subdivisions in 1911.  Originally this was part of the Robert Gilbert homestead.  Starting at Connecticut Street, the subdivision extended about three quarters of a mile both north and south.

At this time,  Estero Boulevard was called Eucalyptus Avenue.  This was a north-south shell road that ended at Connecticut.  If you wanted to travel farther south, you would need to continue your journey on the beach.

Another five years passed before T.P. Hill subdivided a large tract started at Crescent Street and ending just south of Gulf Drive.  The lots that were on the beach side of Estero were normal sized lots.  However, the lots on the other side of the road were approximately 9-10 acres running from the street to the bay.

Land on the island in the 1900s was filled with brush and palmettos that were so thick no engineer would agree to complete an accurate survey because wading through the mangroves to accurately measure an acre of “cheap land” did not seem like a good idea.  

Three years later, Seagrape Subdivision was put on the market.  These lots were located on Mango and Avocado streets in 1919 (Avocado Street was renamed Chapel Street in 1952).

At this time, Crescent Beach (as it was called at that time) was becoming a popular destination for people living in town. In 1912 the Winkler Hotel was opened at the end of Pompano Street. At this time, the island was only accessible by boat. The guests would arrive by schooner and would dock at a pier on the gulf side in front of the hotel.

The Seminole Sands Casino was a popular destination on Fort Myers Beach.

In 1919, Captain Jack DeLysle arrived in Fort Myers and saw the potential in making Estero Island a tourist hot spot.   DeLysle opened the Seminole Sands Casino and dance pavilion on the beach at Connecticut Street.  The land boom of the 1920s had begun (stay tuned for more information on how this affected our island).

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