Grape maturity estimation is vital in precise agriculture as it enables informed decision making for disease control, harvest timing, grape quality, and quantity assurance. Despite its importance, there are few large publicly available datasets that can be used to train accurate and robust grape segmentation and maturity estimation algorithms. To this end, this work proposes the CERTH grape dataset, a new sizeable dataset that is designed explicitly for evaluating deep learning algorithms in grape segmentation and maturity estimation. The proposed dataset is one of the largest currently available grape datasets in the literature, consisting of around 2500 images and almost 10 k grape bunches, annotated with masks and maturity levels. The images in the dataset were captured under various illumination conditions and viewing angles and with significant occlusions between grape bunches and leaves, making it a valuable resource for the research community. Thorough experiments were conducted using a plethora of general object detection methods to provide a baseline for the future development of accurate and robust grape segmentation and maturity estimation algorithms that can significantly advance research in the field of viticulture.