The purpose of the study is to investigate the challenges of Taxation on Commercial property investment in Obio/Akpor L. G. A, Rivers State of Nigeria. Open ended questionaires, structured on the 2-point yes /no was used because of flexibility and simplicity benefits in data interpretation. A total of 102 questionaires were administered to commercial property investors, Estate Surveyor and Valuers and staffs of Rivers State Board of Internal Revenue (Estate and Tax department) and of these number 92 questionaires were completed and returned representing a response rate of 90.2%. The Data collected was analyzed using the SPSS package of descriptive frequency and mean. Results revealed that the forms of property tax in the study area include stamp duty, consent fees, title registration, capital gain tax, withholding tax, and inheritance/gift tax, betterment tax, planning rate, tenement rate, land use changes, development levy, operational permit and signage levy; the forms of commercial property investments include office buildings, retail outlets, multifamily buildings, land and non-residential properties such as hotels, hospitality, and medical and self-storage development; the challenges to commercial property taxes includes assessment and valuation inconsistencies, illiteracy and ignorance, illegal documents, attitude of the tax payer and taxing authority and defective policies. Based on the findings, the need for relevant stakeholders in tax administration to formulate or modify existing tax policies to fit effectively into different business sectors including the commercial property sector was recommended.