The surface pressure-area (pi-A) isotherms of DMPC, DPPC, and DSPC/cholesterol binary monolayers were systematically measured with great care to gain insight into the lateral molecular packing in these binary monolayer systems. The average molecular area A and the area elastic modulus C-s(-1) at a given surface pressure were calculated as a function of cholesterol mole fraction x(chol). As a result, data reliable enough for the analysis of detailed phase behavior were obtained. We identified several characteristic phase regions and assigned the phase state in each region on the basis of the deviation of A(x(chol)) and C-s(-1)(x(chol)) from ideal additivity. We also estimated the partial molecular areas of DMPC, DPPC, DSPC, and cholesterol in the single-phase regions, where C-s(-1)(x(chol)) values fell on an ideal additivity curve. We found that the addition of cholesterol induces the formation of a highly condensed phase where the diacylphosphatidylcholine (diacyl PC) molecule has a surface area even smaller than that in the solid phase, irrespective of the surface pressure and the chain length of diacyl PC. Here, we call the cholesterol-induced condensed phase the CC phase. Furthermore, we demonstrated that the basic features of A(x(chol)) and C-s(-1)(x(chol)) profiles can be explained semiquantitatively by assuming the state of vicinity lipids surrounding sparsely distributed cholesterol molecules in the low x(chol) region as a third state of the diacyl PC molecule in addition to the states in the pure diacyl PC monolayer and in the CC phase.