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The grandest part of the area called the Highlands, Cherokee Triangle was developed in the late 19th and early 20th centuries. Its tree lined streets - where F. Scott Fitzgerald's Gatsby courted Daisy Fay - lead between Bardstown Road, the city's Restaurant Row and Bohemian headquarters, and Cherokee Park, the second-largest of the city's Olmstead parks. Cherokee Triangle properties are architecturally distinguished, with a solid mix of single-family homes and large houses that have been turned into apartments.

