Accurate and spatially explicit yield information is required to ensure farmers’ income and food security at local and national levels. Current approaches based on crop cutting experiments are expensive and usually too late for timely income stabilization measures like crop insurances. We, therefore, utilized a Gradient Boosted Regression (GBR), a machine learning technique, to estimate rice yields at ~500 m spatial resolution for rice-producing areas in India with potential application for near real-time estimates. We used resampled intermediate resolution (~5 km) images of the Moderate Resolution Imaging Spectroradiometer (MODIS) Leaf Area Index (LAI) and observed yields at the district level in India for calibrating GBR models. These GBRs were then used to downscale district yields to 500 m resolution. Downscaled yields were re-aggregated for validation against out-of-sample district yields not used for model training and an additional independent data set of block-level (below district-level) yields. Our downscaled and re-aggregated yields agree well with reported district-level observations from 2003 to 2015 (r = 0.85 & MAE = 0.15 t/ha). The model performance improved further when estimating separate models for different rice cropping densities (up to r = 0.93). An additional out-of-sample validation for the years 2016 and 2017, proved successful with r = 0.84 and r = 0.77, respectively. Simulated yield accuracy was higher in water-limited, rainfed agricultural systems. We conclude that this downscaling approach of rice yield estimation using GBR is feasible across India and may complement current approaches for timely rice yield estimation required by insurance companies and government agencies.