A disastrous flood destroyed most of Winona, July 4, 1895. Eleven people were drowned, and most property on Front Street, along Pike Creek, was destroyed. The town was rebuilt on higher ground, and business places relocated around the present city square. In the early 1900's, Ozark Land and Lumber Company moved their operation elsewhere, resulting in a loss of population. Today, the population of Winona is again around 1,000.
Employment is more diversified, including manufacturing, farming, and timber related industries.
Several businesses serve the community needs in the food line, hardware, clothing, animal supplies, cafes, motels, and medicine. Winona has a new city facility which houses the City Police Department and the Fire Department. The water system and the electric system are owned by the city of Winona. Winona has a well staffed medical clinic. Winona is a friendly town, typical of the best traditions of Ozark hospitality.