Englewood was settled in the late 1800's by pioneers like William Goff, who opened a trail from El Jobean to Vineyard, and Lorin Ainger, who set up a store to serve area fishermen. In 1884, Herbert Nicholas, of Englewood, Ill., and his two brothers came to the area to create a business growing lemons, a cure for the scurvy, which were in high demand throughout the world. Following two hard freezes in 1894 and 1895, most of the lemon trees were destroyed and the brothers had to find and alternative use for their land. They advertised Englewood as a fine place to raise families, or retire, with an easy lifestyle pace and excellent fishing and hunting.

The lumber industry came to the area at the turn of the century, providing jobs and a boost to the economy of Englewood. But this too, would eventually falter as railroad ties, booming construction and turpentine stripped the area of trees. Reforestation was not a common practice in those days, hence, when the trees were gone, so were the jobs. The promoters once again resorted to advertising Englewood as a tourist attraction and a fine place to retire in an easy-going lifestyle and a wonderful place to raise children.

In 1927 a bridge was built across Lemon Bay, joining Manasota Key and the Gulf beaches with the mainland, with a toll of 50 cents. This bridge has been rebuilt twice, once in 1950 and again in 1964. A part of the old wooden bridge is now the Bill Ainger fishing pier. Alexander Graham Bell's invention, the telephone, finally arrived in remote Englewood in 1948 and a Venice phone book listed 46 phone numbers for Englewood. In 1956, the Sarasota side of Englewood had only a part-time sheriff, who worked full-time as a carpenter. He was to be available 24 hours a day, use his own automobile and provide his own gas for the sum of $200 per month.