The physical-geographical features of the mountainous area of Montenegro cause difficulties in farmers’ life and work. The organization of the agricultural production faces a number of problems that limit the overall development of rural areas. Some agricultural crops, such as raspberry, have found optimal growth conditions and produce appropriate yields associated with good fruit quality in such mountainous area. The Willamette variety dominates the production and has broadly expanded, as some new varieties, most notably, Tulameen, Fertȍdi Zamatos, and Glen Ample. The aim of this paper was to examine the biological and production characteristics of two raspberry varieties—one floricane (Tulameen) and one primocane (Polka)—grown in two localities. We confirmed the general rule that at lower altitudes, these varieties (570 m a.s.l, Bijelo Polje) are characterized by earlier vegetation, flowering, and fruit ripening in comparison to plants at higher altitude (1040 m a.s.l, Mojkovac). The Tulameen variety started flowering on 15 May in Bijelo Polje (the flowering phenophase lasted for 29 days, until 12 June) and on 25 May in Mojkovac (the flowering phenophase lasted for 27 days, until 20 June). That is a delay of 11 days in relation to different locations. The Polka variety started flowering on 25 June in Bijelo Polje (57 days, until 20 August) and on 1 July in Mojkovac (flowering for 67 days, until 5 September). That is a delay of 7 days. The Tulameen variety started maturation on 14 June in Bijelo Polje (maturation lasted for 27 days, until 10 July) and on 22 June in Mojkovac (26 days, until 17 July), with a delay of 9 days. The Polka variety started maturation on 23 July in Bijelo Polje (the maturation phenophase lasted for 55 days, until 15 September) and on 5 August in Mojkovac (52 days, until 25 September), with a delay of 14 days. The results showed that the Polka variety had significantly higher total phenol content than the Tulameen variety (4.43 and 4.03 mg, respectively). In terms of locality, the Mojkovac raspberries had higher total phenol content than the Bijelo Polje raspberries. Polka raspberries also had a higher content of total flavonoids than Tulameen, whereas differences between localities in regard to the content of total flavonoids in the fruit were not significant. The content of condensed tannins and gallotannins in the raspberry fruit was similar in relation to both varieties and localities. Finally, the total antioxidant capacity was significantly higher in the Polka compared to the Tulameen variety, whereas the differences between localities were not statistically significant.