This paper presents SmartSPEC, an approach to generate customizable smart space datasets with information about sensorized spaces in which people and events are em- bedded. Smart space datasets are critical to design, deploy and evaluate robust systems and applications to ensure cost-effective operation and safety/comfort/convenience of the space occupants. Often, real-world data is difficult to obtain due to the lack of fine-grained sensing; privacy/security concerns prevent the release and sharing of individual and spatial data. SmartSPEC is a smart space simulator and data generator that can create a digital representation (twin) of a smart space and its activities. SmartSPEC uses a semantic model and ML-based approaches to characterize and learn attributes in a sensorized space, and applies an event-driven simulation strategy to generate realistic simulated data about the space (events, trajectories, sensor datasets, etc). To evaluate the realism of the data generated by SmartSPEC, we develop a structured methodology and metrics to assess various aspects of smart space datasets, including trajectories of people and occupancy of spaces. Our experimental study looks at two real-world settings/datasets: an instrumented smart campus building and a city-wide GPS dataset. Our results demonstrate the accuracy of techniques within SmartSPEC in synthesizing smart space data.