Maintenance planning is crucial for efficient operation of wind turbines, particularly in harsh conditions where degradation of critical components, such as bearings, can lead to costly downtimes and safety threats. In this context, prognostics of degradation play a vital role, enabling timely interventions to prevent failures and optimize maintenance schedules. Learning systems-based vibration analysis of bearings stands out as one of the primary methods for assessing wind turbine health. However, data complexity and challenging conditions pose significant challenges to accurate degradation assessment. This paper proposes a novel approach, Uncertainty Bayesian-Optimized Extreme Recurrent EXpansion (UBO-EREX), which combines Extreme Learning Machines (ELM), a lightweight neural network, with Recurrent Expansion algorithms, a recently advanced representation learning technique. The UBO-EREX algorithm leverages Bayesian optimization to optimize its parameters, targeting uncertainty as an objective function to be minimized. We conducted a comprehensive study comparing UBO-EREX with basic ELM and a set of time-series adaptive deep learners, all optimized using Bayesian optimization with prediction errors as the main objective. Our results demonstrate the superior performance of UBO-EREX in terms of approximation and generalization. Specifically, UBO-EREX shows improvements of approximately 5.1460 ± 2.1338% in the coefficient of determination of generalization over deep learners and 5.7056% over ELM, respectively. Moreover, the objective search time is significantly reduced with UBO-EREX with 99.7884 ± 0.2404% over deep learners, highlighting its effectiveness in real-time degradation assessment of wind turbine bearings. Overall, our findings underscore the significance of incorporating uncertainty-aware UBO-EREX in predictive maintenance strategies for wind turbines, offering enhanced accuracy, efficiency, and robustness in degradation assessment.