Overseas Highway: The Impact of Roads on Real Estate in the Florida Keys, Part 1 of 5

The development of Florida Keys real estate is directly linked to the creation of roadways in the islands. Before the chain was connected to the mainland of Florida, homes in the Florida Keys were sparsely inhabited by the early pioneers making a living primarily by growing crops like pineapples and limes. Most of the land was either undeveloped, or used as working farmland. The revolution in Florida Keys real estate began in 1912 when Henry Flagler completed his Overseas Railway.


Flagler’s vision was to extend his Florida East Coast Railway that he previously had built to connect his business ventures throughout Florida, all the way down to Key West. Flagler recognized the new business and trading opportunities that were opening up at the time because of the construction of the Panama Canal. Flagler was looking to capitalize on trade with South America as well as with the American West, and needed the deep water harbor at Key West in order to do that.

He spent the next several years seeing his vision become a reality. By 1912, the railroad stretched all the way down to Key West, and the Keys became easily accessible. With the railroad came an influx of goods and people into the Florida Keys. Post offices were established first, and people began to move into the area as new jobs became available. One of the most important events in the history of the regions real estate was the Labor Day Hurricane of 1935.

The hurricane completely leveled much of the Keys, including Flagler’s Overseas Railway. When Flagler’s company went bankrupt after his death, they lacked the funds necessary to rebuild the railroad. Left with no other option, the railroad was sold to the State of Florida. Florida government officials had their sights set on transforming the railroad into a highway. Since the railroad had brought larger numbers of residents to Florida Keys real estate, it seemed only natural to facilitate even more movement throughout the area. Additionally, the hurricane brought in a new wave of real estate in the Florida Keys, with homes needing to be rebuilt. Visit our Florida Keys Real Estate resource center for additional information about topics that affect the real estate in that region.


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