A massive fire in 1815 that engulfed much of downtown Petersburg destroyed about five hundred of its buildings. Virtually overnight, the old wooden downtown was rebuilt into what is still the brick core of the city. Most of the resulting three-story Federal commercial buildings on N. Sycamore have gable roofs and stone windowsills and lintels. Several have Italianate veneers from post–Civil War remodeling and some are new Italianate buildings. A series of smaller fires south of N. Sycamore's intersection with Tabb Street resulted in reconstruction from the mid-nineteenth century to the early twentieth century.
Department stores and ready-to-wear ap-parel shops began appearing in the early twentieth century in Petersburg. Following the city's tradition of reusing its large commercial spaces, the former Lavenstein's (112–114 N. Sycamore) remodeled an 1850s four-story building, cladding the upper stories in white glazed terra-cotta and installing Chicago windows. At N. Sycamore and Tabb streets are three classically inspired banks. The former Virginia National Bank (now General District Court Annex; 144 N. Sycamore) of 1911 by Huggins and Bates received an addition c. 1980. Huggins also designed the National Bank (1906; 147 N. Sycamore) and Pebbles and Sharp of Norfolk designed the former Petersburg Savings and Insurance Company (c. 1888) at 150 N. Sycamore. These substantial classical buildings designed by leading Virginia architects were conceived as visual reminders to investors and depositors that the city was in sound financial condition. The dark-red brick Odd Fellows Building (1880s, Harrison Waite) at 133 N. Sycamore is one of the largest late-nineteenth-century buildings in the city despite having its third floor destroyed by fire. Like many fraternal organizations, the Odd Fellows leased the first stories to commercial tenants and used the upper levels for their offices and lodge rooms.