This study evaluated the effect of grape sour rot on wine fermentation and characterized the chemical composition and the sensory changes in wines produced from rotten musts. Microvinifications were performed during two vintages using healthy Trincadeira and Cabernet Sauvignon red grape varieties to which were added grapes affected by sour rot. Increasing sour rot percentages, up to 50%, contributed to a clear decrease in free run must and final wine yields and induced significant changes in grape must chemical composition expressed by the increase in sugar content, total acidity, volatile acidity, anthocyanins, total phenols, and color intensity. After malolactic fermentation, wines from rotten grapes showed higher values of alcohol content, dry extract, reducing sugar content, total and volatile acidity, anthocyanins, total phenols, and color intensity. Despite the higher levels of reducing sugars, the microbial stability was similar to that of healthy wines. The sensorial evaluation, after malolactic fermentation, showed that both types of wine were not statistically different regarding color, aroma, taste, and overall quality. During 6–8 month storage, wines from rotten grapes showed a significant higher percentage of color loss, suggesting that sour rot is responsible for the decrease in color stability. Nevertheless, the results of sensorial analysis demonstrated that the fermentation of grape musts containing up to 30% sour rot yields wines with similar or even higher-quality scores than wines made with healthy grapes.