This study investigates the effects of the Olympic announcement and the actual event on property values in the host region using the case of the 2018 PyeongChang Winter Olympic Games. We collected Korean government-issued apartment transaction data in the host city, Gangneung, and other cities. We performed propensity score matching to generate a suitable control group compared to units in Gangneung and exploited difference-in-difference analyses to test the impact of the announcement and the actual event separately. The results show that the Olympic announcement increased property values in Gangneung by 5.5% compared to propensity-matched units, and the effects are mostly shown in units in downtown Gangneung. Units close to the KTX station and the Olympic arena observed additional increases in housing prices. During the actual Olympic event, property values in Gangneung increased by 8.3% after the KTX station opened, but the actual event period and Athletes’ Village opening did not generate additional effects. The additional increases in housing prices close to the opening of the KTX station were found for units close to the KTX station, the Olympic arena, and Athletes’ Village.