Affordable housing contributes to the prosperity of any community. This study assesses housing challenges and enabling programs for affordable housing in the Kingdom of Saudi Arabia (KSA) within Vision 2030. A questionnaire of housing experts was undertaken, and responses were analyzed using the Relative Importance Index (RII) and Chi-Square. The findings show that the top-ranked challenges are the high price of residential land (RII = 0.89), high construction cost (RII = 0.87), and high urbanization rate (RII = 0.76). The study found that participants’ demographic factors led to significant differences in scores for six of the investigated challenges. In addition, the most effective enabling programs were the value-added tax (VAT) exemption program (RII = 0.82), followed by the developmental housing program (RII = 0.73), and ownership forms (RII = 0.73). Significant differences in scores for two of the enabling programs were found based on participants’ age and gender. The present study recommends that the government should review some of these programs and reassess the challenges of access to affordable housing.