Urban areas often face versatile stressors (e.g., food security, congestion, energy shortage, water pollution, water scarcity, waste management, and storm and flooding), requiring better resilient and sustainable infrastructure systems. A system dynamics model (SDM), explored for the urban region of Orlando, Florida, acts as a multi-agent model for portraying material and energy flows across the food, energy, water, and waste (FEWW) sectors to account for urban sustainability transitions. The interlinkages between the FEWW sectors in the SDM are formulated with multiple layers of dependencies and interconnections of the available resources and their external climatic, environmental, and socioeconomic drivers through four case studies (scenarios). The vital components in the integrated FEWW infrastructure system include urban agriculture associated with the East End Market Urban Farm; energy from the fuel-diverse Curtis H. Stanton Energy Center; reclaimed wastewater treated by the Eastern Water Reclamation Facility, the Water Conserv II Water Reclamation Facility, and stormwater reuse; and solid waste management and biogas generation from the Orange County Landfill. The four scenarios evaluated climate change impacts, policy instruments, and land use teleconnection for waste management in the FEWW nexus, demonstrating regional synergies among these components. The use of multicriteria decision-making coupled with cost-benefit-risk tradeoff analysis supported the selection of case 4 as the most appropriate option as it provided greater renewable energy production and stormwater reuse. The SDM graphic user interface aids in the visualization of the dynamics of the FEWW nexus framework, demonstrating the specific role of renewable energy harvesting for sustainably transitioning Orlando into a circular economy.