The property at 331 S. Main was originally occupied by two wooden buildings constructed in 1872 by early Carthage pioneer Timothy Regan. The north building housed the U.S. Post Office until 1895, while the south building was home to Dingle's Queens Ware* store, and later a variety of businesses, including a bookstore, cigar and news shop, shoe store, barbershop, and hardware store.

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In 1907, Regan’s son transformed the site by combining the two buildings into a single structure, extending its length, and remodeling the basement. The renovation introduced some of the Square's most distinctive architectural features, including the first curved display windows, prism glass transoms, and green marble panels. The project was heavily influenced by retail entrepreneur Samuel Kress, who believed his stores should enhance the appearance of their communities.

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That same year, the building became home to a Kress 5, 10 and 25 Cent Store, whose grand opening drew large crowds and community excitement. Kress remained in the building until 1973, followed by a Ben Franklin store, antique malls, and other retail businesses.

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Recent restoration efforts have carefully preserved its historic character, including the curved windows, prism glass, green marble detailing, and the original "Kress" name carved in marble at the entrances. More than a century after its transformation, it remains one of the Square's most distinctive and admired buildings.

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