Casey Key Where Relaxation is Priority 

Around 1840, US Army Captain John Casey was sent to oversee the removal of the Seminole Indians in the area, per the Congressional Removal Act of 1830, as well as do a detailed survey of the surrounding areas for future development.

Casey was well-esteemed by his peers, having graduated 11th in his class at West Point, along with future general Robert E. Lee, and was well-liked by both the army and the native tribesmen for his fairness and commitment to excellence.

So respected was his name that it is believed that the spirit and bond of trust he established allowed a fragile peace to exist and delayed the eruption of a third Seminole War for several years until his fragile health and Army transfer left both sides without a suitable advocate.

When he wasn’t maintaining relations between the natives and the US government, Casey, along with a few other conscripts, meticulously surveyed and laid out the Gulf Coast, Charlotte Harbor, and all the way down to Fort Myers. The work they did was utilized for maps for generations afterward, and in 1856, Lt. J.C. Ives made the decision to honor Casey by naming the small island after him.

In 1872, Zachariah M. Dryman visited the area and would return in 1909 to homestead more than 100 acres. In the meantime, Isaac Shumard brought his family, including 2 sons and 4 daughters, to Casey Key from Missouri, to make their fortunes. His eldest, Jesse, built his own home further to the north.

Sometime in the early 1910’s, Shumard sold all of his property save the 10 acre family homestead to the Sarasota-Venice Company, who planned to build a huge luxury hotel on the Southern tip of the key. Those plans were scrapped when the United States entered World War I.

Prior to the war, developers began marketing the Sarasota area as the “eternal garden,” hoping to bring even more visitors and residents to the area. One enterprising developer even attempted to rename the key Treasure Island and spread rumors of buried treasure to try and spur sales of his properties on Casey Key. The stories of buried pirate treasure outlived the temporary name change, lingering still today.

Shortly after Sarasota County was split off from Manatee, a bond was issued to create better roads and bridges in the new county, including one at either end of ‘Treasure Island.’ $4.8 million dollars was spent over the next 5 years making the area more drivable. Because of the development opportunities, Casey Key was given priority, and in 1925 the Champion Bridge Company began building a single lane “swing bridge” at the northernmost point of the island.

Blackburn Point Bridge (also sometimes called Treasure Island Bridge) was completed in December of 1926, just in time to see the real estate market crash, followed by the stock market 2 years later. The bridge itself is now a historical monument, one of the last remaining swing-style bridges built in that era, although it no longer moves.

After interning in Sarasota, Paul Rudolph started his own architecture firm with Ralph Twitchell and together they designed several iconic Sarasota homes, including three notable homes on Casey Key. The Joseph W. Lippincott House, designed for the publisher in 1935, the Miller House in 1948, and Rudolph’s own home: the Deering House. A fire in 2007 destroyed most of the Miller house, but Rudolph’s legacy lives on in the Yale Art and Architecture Building that he later designed.

Following World War II, a second Florida land boom erupted, doubling the state’s population in less than 10 years. However, the residents of Casey Key decided they’d rather preserve their land, and in 1950 formed the Casey Key Protective Association. The Association leapt into action – preventing further dredging of the bay, zoning the bulk of the island for residential use only and paving the one road that ran the length of the island, on the condition that its country road look would be preserved.

In 1951, the Sutcliffe House was built, including its own private lagoon. Sutcliffe was connected to several famous people, and hosted many of them in his home, including Cassius Clay, who would later become Muhammed Ali. It recently sold, reportedly for nearly $13-million.

Legendary film director Victor Nunez has a winter home on Casey Key, and in 1984 used the island to shoot the made-for-TV movie adaptation of John D MacDonald’s Flash of Green, starring Ed Harris.

Although it’s never been proven in a court of law, the largest estate on Casey Key is reputed to have a very interesting history. In 2001, in the midst of prosecuting Joe “the German” Watts, a legendary hit man and loan shark for the Gambino organized crime family, Casey Key took center stage. According to government lawyers, in 1996, Watts used his ill-gotten gains to purchase the land at 411 Casey Key Road and build a huge, walled estate compound for his retirement. All done through an energy drink shell company run by one “Tony Florida.”

Strangely enough, just prior to the trial, another home owned by Tony Florida was sold, for a record (at the time) $9-million dollars to best-selling author Stephen King & his wife Tabitha. They use the 6800 square foot house during the winter, and King used it and Casey Key as the inspiration for his novel Duma Key.

Today, fewer than 400 people live on the 8-mile stretch of Casey Key. It has been proposed several times to officially change the island’s name back to Chaise’s Key, but it is always rejected by the majority. There are no hotels or guest houses, although some residents do loan out their palatial homes. There are no traffic lights, no high-rise condo, no shopping, entertainment or night life. Although all are available just over either bridge, the residents prefer to keep things calm, quiet and isolated from the hustle and bustle of the ‘real world.’