The present study used surveys of the cattle sector over the period of 2009–2015 to develop a typology of cattle farms to evaluate their evolution over time and to identify variables that may be associated with systems’ adaptive changes and continuance. Four groups of farms were defined using multivariate analyses as follows: Group I are small calf-cow operations using non-specialized beef breeds; Group II is similar to Group I but employs specialized beef breeds; Group III is dedicated to finishing cattle, and Group IV are larger farms (>1000 animals) with a complete cycle of breeding and fattening. In general, beef cattle production in the temperate—Mediterranean Southern Zone of Chile is declining in response to the opening up of the economy that allows for ample imports, the high opportunity cost of land, and recurrent droughts associated with climate change. Current policies and regulations have modified farms’ businesses models depending on their ease of access to markets, farm size and financial capacity. The defined groups require different development paths and strategies. Sustainable intensification is an alternative strategy for farms in Group I and II, particularly if they were to contract the finishing stage of their cattle with Group III farms. In contrast, it is suggested that Group IV farms concentrate on pastoral production using low external inputs to enhance the production of “natural” beef for high-value niche markets, with positive externalities.