Milk is one of the most valuable products in the food industry with most milk production throughout the world being carried out using conventional management, which includes intensive and traditional systems. The intensive use of fertilizers, antibiotics, pesticides and concerns regarding animal health and the environment have given increasing importance to organic dairy and dairy products in the last two decades. This review aims to compare the production, nutritional, and compositional properties of milk produced by conventional and organic dairy management systems. We also shed light on the health benefits of milk and the worldwide scenario of the organic dairy production system. Most reports suggest milk has beneficial health effects with very few, if any, adverse effects reported. Organic milk is reported to confer additional benefits due to its lower omega-6–omega-3 ratio, which is due to the difference in feeding practices, with organic cows predominantly pasture fed. Despite the testified animal, host, and environmental benefits, organic milk production is difficult in several regions due to the cost-intensive process and geographical conditions. Finally, we offer perspectives for a better future and highlight knowledge gaps in the organic dairy management system.