Winter Garden Downtown Historic District, Historic district in Winter Garden, Florida.

Winter Garden Downtown Historic District is a neighborhood area with historic buildings spread across multiple streets in central Florida. The district includes both residential and commercial properties displaying architecture from the early 1900s.

The district was listed on the U.S. National Register of Historic Places on August 1, 1996. It covers about 100 acres bounded by Woodland, Tremaine, Henderson and Lakeview Streets and holds 26 historic buildings. The oldest confirmed structures, the Dillard & Boyd Building and 36 W. Plant Street, date to 1912; some buildings may be older but their construction dates cannot be confirmed.

The district's 26 historic buildings include the Winter Garden Heritage Museum, the Garden Theatre, Tony's Liquors and the Dillard & Boyd Building. The Dillard & Boyd Building and 36 W. Plant Street are the oldest confirmed structures, both dating to 1912. The district was listed on the National Register of Historic Places on August 1, 1996.

The best way to explore the district is on foot, walking at a relaxed pace through the different streets. Most buildings are visible from the sidewalk, so you can get a good sense of the area without special planning or arrangements.

The district covers about 100 acres and holds 26 historic buildings, including the Winter Garden Heritage Museum, the Garden Theatre, Tony's Liquors and the Dillard & Boyd Building. The Dillard & Boyd Building and 36 W. Plant Street are the oldest confirmed structures, both dated to 1912. It was listed on the National Register of Historic Places on August 1, 1996.