Optimal sensor placement (OSP) is essential for effective structural health monitoring (SHM). More recently, deep learning algorithms have shown great potential in sensor-based SHM. However, existing optimization frameworks, such as population-based algorithms, are often not suited for data-driven SHM. Evaluating a number of sensor layouts includes training on large datasets, which is computationally expensive. This paper proposes deep generative Bayesian optimization (DGBO) as a solution for a parallel optimization of black-box/expensive OSP objective functions. Conditional variational autoencoders are leveraged as generative models that transform the OSP problem into a lower-dimensional latent space. Additionally, DGBO utilizes a surrogate neural network to capture the probability distribution of the objective function space. The proposed method is validated on two case studies on a nine-story reinforced concrete moment frame. The first one serves as a proof of concept to show that DGBO can find the global optimum configuration. The second case study aims to maximize the semantic damage segmentation (SDS) accuracy using a fully convolutional neural network. Transfer learning is proposed in training the vibration-based SDS model, which reduces the evaluation times by more than 50%. Without compromising the performance, the number of accelerometers can be reduced by 52% and 43%, respectively, for damage location and severity predictions. It is also shown that DGBO can outperform genetic algorithm with the same number of function evaluations. DGBO can serve as a scalable solution to address the high-dimensionality challenge in OSP for large-scale civil infrastructure.