The buildings were constructed from the 1850s through the 1870s. The Italianate style North House was built in the 1850s and was the home of the Joseph S. Winter family. The Second Empire style South House was built in the 1870s and was the home of Winter's daughter, Sally Gindrat Winter Thorington, and her husband, Robert D. Thorington. Joseph S. Winter's first house in Montgomery was designed by Samuel Sloan in 1851 and it is believed by architectural historians that Sloan designed Winter Place as well. Following several decades of neglect, the property was placed on the Alabama Historical Commission's Places in Peril list in 2004. It was purchased in 2006 by Craig Drescher, who attempted to stabilize and restore the structures. The complex was added to the Alabama Register of Landmarks and Heritage on September 29, 2005, and to the National Register of Historic Places on May 31, 2006.
