In the paper first was analyzed participation and trend of grapes production volume in Republic of Serbia within period 1998-2007. After that, using concrete technological, organizational and economic conditions for vineyards planting in one vineyard region of Republic of Serbia, have been formed investments models (taking into account different dynamics of vineyards planting). In the paper were used dynamical methods for investments evaluation (internal rate of return, net present value and payback period) as well as various variants of financial resources and financing conditions. The results indicated that it is more economically efficient and financially feasible to plant vineyard on the entire disposable area at the same time, than gradually in several phases. Applying appropriate mathematical and statistical methods, there was projected possible trend of grape production volume in following five years period. It was concluded that grape production would (in average) slightly grow comparing to former level. On the end there were deliberated possibilities for investments in development of vineyard production in republic of Serbia (starting from disposable natural, social and economical conditions, expected production trend, and needed investments for vineyard planting, as well as economical and financial evaluation of these investments).