The building sector accounts for approximately 30% of global energy use. The demand for energy-efficient, high-performance buildings is increasing given the increasing awareness of the climate crisis. The building envelope greatly influences overall building energy performance. Considering the broad shift from passive to adaptive systems, smart window technologies are attracting attention. Despite their potential, few scholars have examined occupant comfort in spaces with smart windows. This gap is addressed herein by comparatively analyzing occupants’ responses to thermal and visual environments in a room with a smart window (RoomSW) and a room with a conventional window (RoomCW) in a residential building in winter. The smart window is operated via a glare-prevention tint control strategy, whereby the tint level is adjusted stepwise when glare occurs. The results reveal that under thermal conditions comparable to those in an actual dwelling, winter-time smart window tinting for glare prevention does not decrease occupants’ thermal sensation or satisfaction. Regarding visual comfort, the conditions in both the RoomSW and RoomCW satisfy the minimum indoor illuminance requirements, but glare occurs in the RoomCW. The questionnaire results indicate greater satisfaction with the luminous environment in the RoomSW relative to the RoomCW. This difference is statistically significant (p < 0.05).