Winkler County Courthouse was built in 1929-30 on the site of a 1910 courthouse after the discovery of oil in the county in 1926 created the need for a larger building. Designed by architect David Castle, the four-story Classical Revival/Beaux Arts courthouse features distinctive two-story classical columns, decorative double-door surrounds and transoms, and paired and triple windows on the second and third floors. A one-story addition was built in the 1950s.