The objective of this study is to assess the effect of legal pluralism practices on perceived transaction failure risk within Unguja's prevailing social structure. A descriptive research design was applied, using mixed methods, with interviews and surveys administered to a sample of 290 respondents. These instruments were used to describe the risks associated with property transactions in a legal pluralism environment. Simple linear regression analysis was further carries out to assess the probability of real transaction failure. These allowed the researcher to analyse, test for statistical significance, describe the direct and indirect effect, and relationships that result from the transaction dilemma. Findings reveal that legal pluralism practices have a significant effect on all stages of real property transactions. The study further confirms that legal pluralism-related practices pose substantial risks to property transactions, including legal and development risks, land title risks, and financial risks. The results indicate that LPPs have a positive unstandardized coefficient of 0.267 (p-value = 0.000<0.05), which suggests the existence of significant LPPs transaction risk escalation effect thus increasing the chances for the occurrence of TFRs across case study areas. The study further identify Multiple ownership Structure (MOS), Multiple Institutional Structure (MIS) and land tenure types as potential TFRs’ escalators by causing transaction delay of between 8 – 20 percent. To overcome institutional power dilemma and limited protection of title deed holder, it is recommended that the land policy be modernised to strengthen and integrate all land transactions into an effective land management system using low-cost technology.