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Today, good food criteria also include healthy capacity. So, the wine on our table should not only have good organoleptic qualities, but should be characterized by a high healthy potential. For the first time, extensive research was conducted on commercial red wine grape varieties cultivated in different Bulgarian regions in two consecutive years. Antioxidants, including trans-resveratrol, quercetin, and total phenolic content and antioxidant potential in wine grapes and wines were determined by HPLC, UV, and NIR methods. The results obtained showed similar concentration levels compared to the same varieties, produced in other countries. Trans-resveratrol showed the greatest contribution to the radical scavenging capacity. The factor with largest impact on the content of the tested substances was definitely the variety. Among agro-meteorological condition, temperature amplitude, rain fall, and UV irradiation before ripening had strong influences. Maintaining the balance between the level of synthesized and degraded and captured antioxidants during the wine making process was crucial to preserving the antioxidant properties of the final wine product. NIR spectroscopy showed very good accuracy of determination of trans-resveratrol, quercetin, total phenolic content, and the antioxidant activity of tested grape varieties and red wines. It could be a promising technique in the quantification of their antioxidant parameters.