Wood, a time-honored construction material prized for its exceptional properties, has been in use for millennia. Its enduring popularity is attributed to its remarkable strength, aesthetic appeal, and favorable environmental footprint. However, wooden structures are susceptible to various defects and imperfections that pose threats to their structural integrity, durability, and safety. These issues encompass knots, cracks, warping, twisting, decay, insect infestations, and more, all of which, if left unaddressed, can culminate in structural failures. Thus, a comprehensive strategy involving inspection, maintenance, and remediation is indispensable for safeguarding wooden structures. Traditional manual inspections, while effective, are characterized by their resource-intensive nature, entailing significant time and cost investments. This study presents a pioneering approach that leverages Convolutional Neural Networks (CNNs) and Image Processing techniques to revolutionize the assessment of damage in wooden structures using digital imagery. Initially, CNNs are employed to categorize images into three fundamental classes: cracks, knots, and undamaged sections. Subsequently, Image Processing techniques are harnessed to compute precise characteristics of these defects, including parameters such as crack length, width, angle, and the extent of the defective area within knots. The Inception-ResNet-V2 pre-trained model is utilized, fine-tuned and validated with a robust dataset comprising 9000 wooden defect images, evenly distributed across the three aforementioned categories. A prudent division allocates 70% of the dataset for model training, with the remaining 30% reserved for validation. Following successful training, the model demonstrates an impressive overall accuracy of 92% when classifying an independent test set comprising 100 new images. To illustrate the model's performance, two images from each damage category are selected and tested to compute the characteristics of the defects. The quantification error for crack angle is only 0.15%, while it is 0.99% for crack length, and 2% for crack width, demonstrating the high performance of the model. The practical implications of this work are profound. By automating defect assessment in wooden structures, our approach offers significant advantages to industry professionals. It expedites inspections, reduces labor costs, and enhances the accuracy of defect quantification.