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This study attempts to establish the need for a framework to assess the impact of connected buildings in a smart community. The contribution is a software framework designed to optimize buildings and grids at a district level. The following research products are developed: (1) An innovative method to model a cluster of buildings—with people’s behavior embedded in the cluster’s dynamics—and their controls so that they can be integrated with grid operation and services; (2) a novel optimization framework to solve complex, centralized control problems for large-scale systems, leveraging convex programming approaches; and (3) a methodology to assess the impacts of connected buildings in terms of (a) the grid’s operational stability and safety and (b) buildings’ optimized energy consumption. To test the proposed framework, a large-scale simulation of a subtransmission network with three power generating stations and serving over 300 artificial buildings is conducted.