Set on the historic Wooster Pike, 529 South Court Street stands the test of time due to its geographical importance. Built in 1838, this house is the oldest standing home on South Court Street and one of the oldest in Medina. Throughout the 1800s, the Wooster Pike was the main vein connecting Cleveland to southern suburbs. The solitary nature of the street made it an extended hub of commerce. With American expansionism just beginning, it was the perfect time to strike out and live along this road. Barney Prentice (or Prentiss), one of the very first pioneers of Wooster Pike, realized that it was a spot with substantial potential for a small business operation within prosperous Medina. In the spirit of economic proliferation, Prentice sought to enrich both his wallet and family through business ventures on the Square. Unfortunately, his attempts in acquiring a portion of the legendary American prosperity ended in catastrophic failure. Despite this failure, 529 South Court Street, or the Prentice-Kauffman House, can be seen as an example of the entrepreneurial spirit of Medina. It was in this spirit that many people after him took the same risky step toward business. Alan Wainwright seized the entrepreneurial opportunity and converted the building into an antique shop in the 1970s. "Alan H. Wainwright Antiques" exemplified the lucrative potential of the Prentice-Kauffman house, successfully running for almost a decade. Beyond business, the house also became an example for other historic homes within Medina. These other houses made Medina their city, populating Medina with families and diversifying the town with their unique styles and architecture in the process. The Prentice-Kauffman house is an integral part of this illustrious history. This Federal style home fits in with the other historic homes on South Court Street as well as the Gazebo fits in with Medina's beloved Square. The Prentice-Kaufman house is a monument to the character and unique history of a prosperous Medina. Its value and beauty have drawn families into its historical walls for generations, and it will continue to flourish in the hands of our posterity.