This paper investigates the privacy and usability of AI-enabled smart devices commonly used by youth, focusing on Google Home Mini, Amazon Alexa, and Apple Siri. While these devices provide convenience and efficiency, they also raise privacy and transparency concerns due to their always-listening design and complex data management processes. The study proposes and applies a combined framework of Heuristic Evaluation, Personal Information Protection and Electronic Documents Act (PIPEDA) Compliance Assessment, and Youth-Centered Usability Testing to assess whether these devices align with Privacy-by-Design principles and support meaningful user control. Results show that Google Home achieved the highest usability score, while Siri scored highest in regulatory compliance, indicating a trade-off between user convenience and privacy protection. Alexa demonstrated clearer task navigation but weaker transparency in data retention. Findings suggest that although youth may feel capable of managing their data, their privacy self-efficacy remains limited by technical design, complex settings, and unclear data policies. The paper concludes that enhancing transparency, embedding privacy guidance during onboarding, and improving policy alignment are critical steps toward ensuring that smart devices are both usable and compliant with privacy standards that protect young users.