The Wagner House is the centerpiece historical structure at Winedale. The Wagner House and the Four-Square Barn are the only two nineteenth-century structures at Winedale which are located on their original sites. The house is now named for the Wagner family who lived in it for eighty years beginning in 1882, but it was built by Samuel K. Lewis, a local surveyor and cotton farmer, after he acquired the property in 1848.
The Lauderdale House was built about 1858 by James Shelby Lauderdale (1812-1908) when he settled near Long Point in Washington County. The house's imposing pediment porch reflected the filtering of Classical Revival architecture into the area. Ima Hogg purchased the house in 1963 and moved it to Winedale before its original location was flooded to create Lake Somerville. The Lauderdale House served as a residence for visiting artists and scholars until it was destroyed by an electrical fire in 1981. Debris from the fire was buried in a mound between the two chimneys.