In 1909, the residential section of Winona was formed on thirty-one of the original fifty acres. It is north of Lafayette Residence Park, east of the Lafayette River, and bounded by Huntington Crescent. In 1924, the city platted the eastern and southern boundaries of the suburb, expanding it eastwards to Cottage Toll Road and Tidewater Drive. The residential area's well-built single-family homes are of moderate size and set on narrow lots with a significant amount of green space. It has achieved significance as an artistic and historic product of its time period.
The Winona neighborhood, including the downtown district, was intended to be a residential area, but was not improved until 1923. The Second building period continued until the start of World War II, when only twenty-two houses were completed. As a result, there were more than 235 people living in the city during the 1920 census. During this period, the residential area of Winona reached a high of 235 people.
Despite its residential development, Winona was largely untouched by commercial intrusion. Its small-scale, dead-end streets and residential-style buildings were preserved. Despite its rural setting, Winona benefits from convenient access to downtown, medical areas, and interstate highways. Its location near the city's largest thoroughfare, Tidewater Drive, makes it easy to commute north or south.