An experimental study was conducted to quantify the characteristics of a tornado-like vortex and to reveal the dynamics of the flow-structure interactions between a low-rise, gable-roof building model and swirling, turbulent tornado-like winds. The experimental work was conducted by using a large-scale tornado simulator located in the Aerospace Engineering Department of Iowa State University. In addition to measuring the pressure distributions and resultant wind loads acting on the building model, a digital Particle Image Velocimetry system was used to conduct detailed flow field measurements to quantify the evolution of the unsteady vortices and turbulent flow structures around the gable-roof building model in tornado-like winds. The effects of important parameters, such as the distance between the centers of the tornado-like vortex and the test model and the orientation angles of the building model related to the tornado-like vortex, on the evolutions of the wake vortices and turbulent flow structures around the gable-roof building model as well as the wind loads induced by the tornado-like vortex were assessed quantitatively. The detailed flow field measurements were correlated with the surface pressure and wind load measurements to elucidate the underlying physics to gain further insight into flow-structure interactions between the gable-roof building model and tornado-like winds in order to provide more accurate prediction of wind damage potential to built structures.