The Winter Garden Downtown Historic District is a U.S. historic district in Winter Garden, Florida. It is bounded by Woodland, Tremaine, Henderson, and Lakeview Streets, encompasses approximately 100 acre, and contains 26 historic buildings. Among the 26 buildings are the Winter Garden Heritage Museum, Garden Theatre, Tony's Liquors, the Dillard & Boyd Building, and many more. The oldest confirmed of these are the Dillard & Boyd Building and 36 W. Plant Street, both dating to 1912 (there are some buildings which may be older, however sources cannot confirm their date of construction). On August 1, 1996, it was added to the U.S. National Register of Historic Places.