[8] Winchester began as a residential community on 2,500 acres of land acquired by William D. Crews in 1959.

[12] According to the United States Census Bureau, the town has a total area of 4.5 square miles (11.7 km2), all land.

William D. Crews on behalf of the Green Country Racing Association applied to the Oklahoma Horse Racing Commission to build a $120 million pari-mutuel horse racetrack in the town, to be called Winchester Park, on December 16, 1983.

[14] However, that application was turned down twice, once in 1984 based on insufficient financing and unrealistic attendance and wagering projections, and finally in 1985 as incomplete.

[15] Winchester again made the news in March 1989 when the Institute for the Study of American Wars (ISAW), a Delaware-based nonprofit organization, chose Winchester over competing sites in Oklahoma, Arizona, Pennsylvania and New Mexico[16] for a proposed $150 million war museum complex.

[19] ISAW then selected the Phoenix area[19] and on July 17, 1989, announced the exact site as a donated 300 acres of a 7,500-acre cotton farm between Phoenix and Tucson once owned by movie star John Wayne, known as John Wayne's Red River Ranch, in Casa Grande, Arizona.

[20] In the end, the museum was never built in any location, and ISAW's entity status was voided effective March 1, 1998, by the Delaware Secretary of State.

[11] At least one lawsuit to enforce the ordinances and covenants against a homeowner placing a mobile home in an unauthorized location has been successfully prosecuted.