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Work on the overseas extension began in 1905. It was operational from 1912 until the Labor Day Hurricane of 1935. Financially unable to rebuild, the Florida East Coast Railway sold the roadbed and remaining bridges to the State of Florida, which built the Overseas Highway to Key West, using much of the remaining railway infrastructure. The extension was later added to the National Register of Historic Places in 1979 as Overseas Highway and Railway Bridges.

Accompanying note: "On September 2, 1935 Flagler's 'Overseas Railroad' was 'killed' by the worst hurricane ever to hit this hemisphere - barometer 26.35. The last rescue train was trapped on the Matacumbe (Kill Man) Keys. 577 bodies were found; many more were not. Only the 106-ton Schenectady-built 4-8-2 locomotive, 'Old 447,' remained on the tracks. Today the Overseas Highway crosses the viaducts and bridges which survived the great storm. Photos from The Railroad that Died at Sea: The Florida East Coast's Key West Extension, by Pat Parks."