This paper presents a novel evaluation framework to assess the effectiveness of city transformation projects related to energy efficiency and sustainable mobility actions. The evaluation framework is part of an Urban Regeneration Model designed to accelerate the urban transformation toward the smart city concept, taking into account all aspects of sustainability. This model has been developed and validated in the three EU cities (Valladolid, Spain; Nottingham, United Kingdom; and Tepebaşı, Turkey) where interventions in the energy, mobility, and ICT fields have been deployed. This model relies on an Evaluation Framework to support its main phases considering two levels of evaluation: city level, to assess globally the smartness and sustainability of the city, and project level, to support the decision-making and assess the impacts of specific implementations. This paper is focused on the second level and its application through the evaluation-supporting tool STILE in the assessment of the energy efficiency and sustainable urban mobility actions implemented in the city of Valladolid. The assessment analysis has allowed assessing how the energy efficiency interventions carried out in the Valladolid district have reduced the energy consumption, increased the use of renewable energies, and reduced the CO2 emissions. In addition, it has allowed evaluating other aspects such as the air quality, thermal comfort, and energy bill, which have been also improved for the residents. Considering the analysis of the sustainable mobility interventions, the evaluation framework supports the assessment of the reduction of emissions and air pollutants and how the actions have converted electro-mobility into a real option for citizens. The evaluation of results after the implementation of this kind of actions is key to ensuring that successful actions can be replicated in other places achieving smarter and more sustainable cities.