Sustainable infrastructure emerges when environmental, economic, and social factors find common ground during the infrastructure lifecycle, resulting in an efficient and accelerated construction without compromise in quality. Resilient infrastructure is able to recover to full designed functional capacity after extreme natural or man-made events. Optimum sustainability is achieved through (1) reduced wastage of global construction materials and (2) data-driven maintenance procedures based on need, instead of periodic maintenance based on past practice-there is a transformation from maintenance on a schedule to maintenance on demand. Can we measure resiliency and sustainability? The answer is yes. Are there case studies that show that resiliency and sustainability are achievable together and measurable in infrastructure? The answer again is yes, with the use of embedded sensors and wireless communications. Modern technologies such as embedded sensors and wireless communications have rapidly advanced, becoming ubiquitous in many a human endeavor. As these technologies mature, stakeholders are learning to apply them to bridge structures, creating smart transportation infrastructure. Data are collected wirelessly over an IoT-based cloud architecture to facilitate monitoring real-time and/or on as-need basis. This enables communications between various elements of smart infrastructure even beyond the transportation industry, enabling quantification of resiliency and sustainability. This paper discusses the concepts and a case study of recent deep foundation projects in Florida involving smart infrastructure that achieved resiliency and sustainability.