This paper explores the use of a cyber-physical systems (CPS) "loop-in-the-model" approach to optimally design the envelope and structural system of low-rise buildings subject to wind loads. Both the components and cladding (C&C) and the main wind force resisting system (MWFRS) are considered through multi-objective optimization. The CPS approach combines the physical accuracy of wind tunnel testing and efficiency of numerical optimization algorithms to obtain an optimal design. The approach is autonomous: experiments are executed in a boundary layer wind tunnel (BLWT), sensor feedback is monitored and analyzed by a computer, and optimization algorithms dictate physical changes to the structural model in the BLWT through actuators. To explore a CPS approach to multi-objective optimization, a low-rise building with a parapet wall of variable height is considered. In the BLWT, servo-motors are used to adjust the parapet to a particular height. Parapet walls alter the location of the roof corner vortices, reducing suction loads on the windward facing roof corners and edges, a C&C design load. At the same time, parapet walls increase the surface area of the building, leading to an increase in demand on the MWFRS. A combination of non-stochastic and stochastic optimization algorithms were implemented to minimize the magnitude of suction and positive pressures on the roof of a low-rise building model, followed by stochastic multiobjective optimization to simultaneously minimize the magnitude of suction pressures and base shear. Experiments were conducted at the University of Florida Experimental Facility (UFEF) of the National Science Foundation's (NSF) Natural Hazard Engineering Research Infrastructure (NHERI) program.