This data release consists of four datasets that were used for evaluating winter drawdown patterns in 166 Massachusetts lakes greater than 0.3 km2 surface area. The first dataset (“Water area and level.csv”) provides water area and water level time series data of 166 lakes from 2016 to 2021. Water area and water level time-series data were derived from European Space Agency’s Sentinel 1 synthetic aperture radar satellite sensor using the JavaScript code in Google Earth Engine platform. Details of this code were described in the software release (https://doi.org/10.5066/P9ZA5I1U). The second dataset (“Water area interpolated.csv”) is the linearly-interpolated daily water area time series data of the 166 lakes from the first dataset that were used in winter drawdown classification model as input files. The third dataset (“Winter drawdown classification.csv”) is the winter drawdown classification model derived binary classification (1 for winter drawdown and 0 for non-winter drawdown) of 166 lakes for 5 years (2016–2021). The fourth dataset (“Winter drawdown metrics_2016.csv”, “Winter drawdown metrics_2017.csv”, “Winter drawdown metrics_2018.csv”, (“Winter drawdown metrics_2019.csv”, and “Winter drawdown metrics_2020.csv”) are the winter drawdown metrics such as timing, duration, and magnitude of drawdown derived for the winter drawdown lakes from the water area time series (second dataset) for 5 years. The codes used for the classification model and drawdown metrics are also available in the software release (https://doi.org/10.5066/P9ZA5I1U).