We propose data-driven approaches to water content estimation and ripeness classification of the strawberry fruit. A narrowband hyperspectral spectroradiometer was used to collect reflectance signatures from 43 strawberry fruits at different ripeness levels. Then, the ground truth water content was obtained using the oven-dry method. To estimate the water content, 674 and 698 nm bands were selected to create a normalized difference strawberry water content index. The index was used as an input to a logarithmic model for estimating fruit water content. The model for water content estimation gave a correlation coefficient of 0.82 and Root Mean Squared Error (RMSE) of 0.0092 g/g. For ripeness classification, a Support Vector Machine (SVM) model using the full spectrum as input achieved over 98% accuracy. Our analysis further show that, in the absence of the full spectrum data, using our proposed water content index as input, which uses reflectance values from only two frequency bands, achieved 71% ripeness classification accuracy, which might be adequate for certain applications with limited sensing resources.