: Diabetic Retinopathy (DR) is an eye disease associated with chronic diabetes. DR is the leading cause of blindness among working aged adults around the world and estimated it may affect more than 93 million people. Progression to vision impairment can be slowed or controlled if DR is detected in time, however this can be difficult as the disease often shows few symptoms until it is too late to provide effective treatment. Currently, detecting DR is a time-consuming and manual process, which requires an ophthalmologist or trained clinician to examine and evaluate digital color fundus photographs of the retina, to identify DR by the presence of lesions associated with the vascular abnormalities caused by the disease. The automated method of DR screening will speed up the detection and decision-making process, which will help to control or manage DR progression. This paper presents an automated classification system, in which it analyzes fundus images with varying illumination and fields of view and generates a severity grade for diabetic retinopathy (DR) using machine learning models such as CNN, VGG16 and VGG-19.This system achieves 80% sensitivity, 82% accuracy, 82% specificity, and 0.904 AUC for classifying images into 5 categories ranging from 0 to 4, where 0 is no DR and 4 is proliferative DR.