The Simon Complex reflects a mid-19th century neighborhood pattern that combined courtyards, alley houses, first-floor shops, and second-floor apartments in areas crowded with immigrants. During the early and mid 19th century, builders adapted contemporary house designs for shops by enlarging doors for patrons and deliveries and expanding windows for displays on brick street-front buildings with simple brick cornices. The building at 1908-1914 Cherokee reflects this early local commercial architecture. Its gated passageway pierces the first floor and opens into a courtyard, and like many such buildings, the second-floor apartments were reached not from the street but by stairs from the courtyard. In 1890, a three-story alley house was built along the alley edge of the property, enclosing the yard. Although its mansard roof and facade faced the alley, the entrances to its two-room apartments came from porches, doors, and stairs opening onto the courtyard. Compton & Dry's Pictorial St. Louis from 1875 shows that the street-facing building originally extended several more units to the west, but that portion was razed in 1977. Architect and owner Ray Simon renovated the complex in 1988-90, converting the vacant lot into parking and a garden.
