Winterset Courthouse Square Commercial Historic District is a nationally recognized historic district located in Winterset, Iowa, United States.

The Madison County Courthouse (1878) is a Renaissance Revival structure designed by Alfred H. Piquenard.

The stone buildings include the courthouse, the White, Munger and Company Store (1861), and the Sprague, Brown, and Knowlton Store (1866), all of which are individually listed on the National Register.

Unlike many historic downtowns in Iowa, Winterset replaced its initial frame buildings with masonry buildings because of economic prosperity, and not because of fires.

Foster (Madisonian Building, 1872; City Hall Block/Jones & Tidrick, 1875), Joseph S. Blake (Firemen's Hall/City Hall/Light Plant, 1888, 1889, 1923), Frank E. Wetherell (Bevington Building/Masonic Temple, 1914 remodel), and Louis A. Simon (U.S. Post Office, 1935).