Numerous studies have explored the challenge of optimizing maintenance grouping, aiming to efficiently manage maintenance resources and reduce costs associated with various maintenance opportunities. Maintenance grouping is even more important when the systems to maintain are geographically distributed because it significantly reduces travel costs. In this research, we tackle a novel problem that integrates condition-based maintenance with the selection of maintenance operations and technician routing. The problem involves the selection of machines requiring maintenance for each time period, determining the nature of required operations (based on the uncertain degradation state of the machines), selecting suitable technicians based on their skills and availability, and planning their routes. We formulate this problem as a mixed-integer program and propose a heuristic approach for its solution. Our method constructs a solution by iteratively adding maintenance operations to technician routes. To assess the method’s performance, we conduct experiments that evaluate both running times and solution quality.