Transformer lifetime assessments plays a vital role in reliable operation of power systems. In this paper, leveraging sensory data, an approach in estimating transformer lifetime is presented. The winding hottest-spot temperature, which is the pivotal driver that impacts transformer aging, is measured hourly via a temperature sensor, then transformer loss of life is calculated based on the IEEE Std. C57.91-2011. A Cumulative Moving Average (CMA) model is subsequently applied to the data stream of the transformer loss of life to provide hourly estimates until convergence. Numerical examples demonstrate the effectiveness of the proposed approach for the transformer lifetime estimation, and explores its efficiency and practical merits.