- Award-winning Winterset School District — high-achieving elementary and middle school, as well as the 2019 Iowa Superintendent of the Year.
- Winterset Courthouse Square Commercial Historic District, a very active retail and entertainment district.
- John Wayne Birthplace Museum.
- Municipal electric supply features a high percentage of non-emission energy.
- 310-acre greenfield development site on east side of Winterset. Currently undergoing site master planning with the possibility of becoming an Iowa Certified Site.
- 1.4-acre retail or multi-family housing redevelopment site on North John Wayne Drive.
- An expansion project has been planned and approved for Winterset Municipal Airport, adjacent to the Zone.