The number of XLPE cables being used near or beyond their designed lifespan is increasing. The importance of timely cable replacement is increasing. Therefore, research is actively being conducted using VLF Tan δ diagnostic technology to assess the insulation condition of cables. There is a lack of studies measuring and analyzing VLF Tan δ of service aged XLPE cables. Additionally, there is a lack of research considering the operating environment. Therefore, research is needed to diagnose and analyze the insulation condition of the same serviced aged cable when it is operated in a different environment. This paper evaluates and analyzes the insulation condition of cables installed in the BFP, cooling tower, and deaerator booster pump of a combined heat and power plant. Each cable was analyzed by measuring VLF Tan δ, dielectric breakdown test of the cable, and tensile strength, elongation at break, crystallinity, and dielectric strength of XLPE specimens. Additionally, the correlation between VLF Tan δ and other characteristics was also analyzed. It was found that degradation progressed in the order of BFP, cooling tower, and deaerator booster pump. Therefore, it was confirmed that even for the same cable, deterioration varies depending on the installation location.