Capital Gains Tax is charged on the appreciation of capital assets and is commonly imposed only when the increase in value is realized through sale or exchange. The study aimed to determine how technology utilization affects the performance of Capital Gains Tax (CGT) in Kenya with specific focus in the West of Nairobi. The key source of CGT is mainly sale of movable and immovable properties; stocks, land and buildings respectively. Transfer of shares in the stock exchange is another source but not stocks and as ubiquitous in Africa as the later. The study was anchored on the theory of Technology Determinism. Descriptive research design was adopted in the study. The Target population was 8,800 land lords located in West of Nairobi. A simple random sampling method was adopted to arrive at a sample size 64 respondents. The study used primary data collected from the respondents, while secondary data was collected from existing literature on revenue reports and journals. Inferential statistics was analyzed through correlation analysis and regression analysis. The findings reveal that automation has significant positive correlation with CGT performance. The regression model further predicts that holding other factors constant, adequate use of technology increases the performance by 31.5%. The study thus recommends full adoption of systems automation, culminating in block chain management in order to optimize CGT and other property tax performance.