Quantitative assessment of real estate property is provided, wherein a qualitative assessment of a subject property as compared to a comparison property is obtained from a user. The qualitative assessment includes qualitative comparisons of the subject property to the comparison property across comparison criteria, and a qualitative assessment is determined based on the qualitative assessment, by translating the qualitative comparisons into quantitative comparisons of the subject property to the comparison property, to obtain at least one numerical value, and then determining an overall attractiveness score based on the obtained at least one numerical value. In further aspects, aggregate and predictive quantitative assessments of the subject property, as well as an estimated transaction value of the subject property, can be determined.