This building, originally built by Dr. Whipple as a residence in 1841, has been home to several influential families. The second owner of the house, Dr. Abiel DeWolf, added the second floor and Italianate features to the original structure in 1856. Dr. DeWolf took over Dr. Whipple's medical practice and for the next 40 years could be seen traveling throughout Kane and DuPage counties via horseback or buggy.

H.T. Rockwell, who served as mayor (1885-89), postmaster, alderman, and a representative of the Kane County Congressional Committee, later resided here. Rockwell, a native of New York, came to St. Charles in 1863. During his term as mayor, a stage line was established between Geneva and St. Charles and citizens moved to create provisions for city fire protection.

Colonel Edward Baker's house once stood next to the Whipple House, on the site of what is now the parking lot for Yurs Funeral Home. Baker's house was moved to State Avenue in 1985.