The Estero Island Historic Society cottage is open to visitors on Saturdays from 10 a.m. to noon, October through May.


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Early Settlers on Estero Island

March 11, 2024

For many years, Estero Island was home to Calusa Indians, Cuban Fishermen, Spanish Missionaries, and some say, pirates. It was not until the mid-1870s that the first family settled on Fort Myers Beach.


Sam Ellis, his wife, and his son, George Underhill, settled at the end of Connecticut Street where the Mound House now sits. Although Ellis and his family ended up moving to Sanibel where they homesteaded a track of land near Tarpon Bay, George’s son (also named George) returned to Fort Myers Beach where he raised his family.



The Homestead At of 1862 brought new settlers to the island. Intrigued by the idea of getting free land, the settlers came from all over the United States and Europe hoping to prove their claim by living on the land for five years, clearing it, farming it, and improving it. 

When the first settlers came to Estero Island in the mid-1850s much of the island was a mangrove jungle filled with dense foliage.


Unfortunately, life on the island in those days was difficult, and many of these early settlers did not stay long enough to claim their land. Frank Johnson, however, managed to receive a patent including all of Mound Key issued in 1891. Three years later, Robert Gilbert received a patent on 171 acres starting near Bay Street and going to Bayland Ave. This area was located in the central part of the island and included the shell mound at the end of Connecticut where the Mound House now sits.



The second patent on the island was granted to James Bratt in 1895. Prior to 1895, the area presently known as Bowditch Point was called the government lighthouse reservation. Bratt was a doctor from New York who was one of the few settlers who decided to set up his homestead at the south end of the island where he attempted to farm 150 acres at Bowditch Point.

Robert Gilbert filed his claim in 1898 and built his home at the end of Connecticut Street. Today, the Mound House is the oldest remaining structure on the island known today. Gilbert built the original home as a Tudor home with dock and cistern in 1906, and it was known as the “Mound Villa”. In 1909, the home was known as the “Bungalow by the Banyan” when the brick structure was added.


Bratt wanted to grow tomatoes on his land, and he had a successful first harvest. However, in mid-February 1895, a cold wave blew into south Florida with temperatures of 38 degrees recorded, damaging much of Bratt’s tomato crop. Bratt did not give up and continued to farm until 1899 when another deep freeze hit the area, killing all Bratt’s crop of tomatoes. After this loss, Bratt gave up on farming and focused on placing a lighthouse at the tip of Bowditch Point. Unfortunately, Bratt died in 1899 before he could get permission from the government to construct the lighthouse. His 150 acres was then granted to Ambrose McGregor.


Hugh McPhie homesteaded 112 acres running from Flamingo Street to Fairview Isles in 1899. McPhie’s old homestead was built in a coconut grove just south of what is now the Outrigger Hotel.  The house was destroyed by a storm in 1947.


Six years went by before George McAuley received a patent on 72 acres which began near Tropical Shores and ran to Donora Street. The next year, 1907, McPhie created McPhie Park which ran from Aberdeen Street to Avenida Pescadora and to the end of Seminole Way.


In 1914, Albert Austin homesteaded a triangular piece of land starting at Aberdeen Street and going north to Williams Drive. This was a little over 24 acres.

The Koreshans played a major role in the history of Estero Island. Leroy Lemoreaux was a member of the Koreshan Unity when he left Estero and homesteaded property on the island.


The last of the homesteaders was Leroy Lemoreaux who was a member of the Koreshan Unity. He came to Estero when he was fourteen years old in 1894. In 1918 Lemoreaux homesteaded 65 acres between the two tracks owned by McPhie. This is the property where the Church of the Ascension is now located. Lemoreaux sold the property to the church.


In A Short History of Fort Myers Beach, Barrett and Adelaide Brown report that during the boom of the 1920s, McPhie was offered half a million dollars for his property. He turned down the offer; however, eventually he subdivided his property into McPhie Park and sold about forty lots in the park, earning about $40,000.

March 11, 2024
Although the story of Anne Bonny and Calico Jack honeymooning on Estero Island may be less fact than fiction, it is a refreshing part of the history of Estero Island. According to Jack Beater’s book, Pirates and Buried Treasure on Florida Islands, Anne Bonny was the daughter of a wealthy lawyer who lived in North Carolina.
March 11, 2024
Opened in 1912, the Winkler Hotel was the first hotel on the island. The early part of the 20 th 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.
March 11, 2024
Yesterday I was surfing the Internet, and I came across an article about haunted restaurants. This article mentioned the Whale (formerly the Beached Whale and before that the Mermaid Club) as being haunted by the ghosts of Jim and Mary Galloway (I covered their murder in an earlier posting). Suddenly, I remembered reading about another haunted restaurant on the island: the Holmes House. This led me down a rabbit hole as I got caught up in trying to learn more about the ghost that was supposed to be the daughter of the restaurant owner who had died (I can’t remember how she was supposed to have died). Unfortunately, I came up empty on the ghost story, but I did learn some interesting facts about this lost icon of Fort Myers Beach.
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