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During the Civil War, raids made life too hazardous and the Whitakers moved northward to Manatee where they stayed until the war ended.

The decade and a half between 1868 and 1883, resulted in the initial "large scale" discovery by outsiders of the richness of the Sarasota area. Acreage was cleared by early settlers, orange groves and gardens planted, and herds of cattle joined the Whitaker herd on the rich grazing plains.

John Webb moved to the area during this period and opened the first "manufacturing plant" to refine sugar and to produce syrup. Webb also built the first Winter resort with individual guest cottages - advertised in northern newspapers as a special paradise - Webb's Winter Resort on Little Sarasota Bay.

A small community grew up in Webb's neighborhood and in 1884, he applied for a post office. The community was named Osprey in accordance with his wishes.

The Jesse Knight family settled further down the bay in the area that eventually became the sister communities of Venice and Nokomis.

Isaac A. Redd, who had lived in the area in 1857 prior to the war, returned 10 years later to become the founder of Bee Ridge. In 1876, Redd led a movement to establish a missionary BaptIT church, which became the first church built in what was to become Sarasota County.