This is just what I interpret from ATO's website. You may also be taken to have received the market value if: you and the new owner were not dealing with each other at arm’s length in connection with the event, such as where property is transferred between family members. If that's the case, then it doesn't seem to make much sense to sell for below market value, yet pay tax as if you sold it for market value. Might as well sell it for market value then. In my particular case, my old man wants to sell an IP to his brother. However he doesn't want to pay extra tax on capital gains without actually getting the capital gains. Purchase price: $380,000 Intended sale price: $450,000 Market value: $550,000 - $650,000 (based on RP Data) Given the condition of the place, it's not a stretch to say the place might only be worth $500,000 - $600,000. If an independent valuation is done, does this prove to be dealing at arm's length? What can be done to reduce the value of the property or valuation? (Still tenanted, can't destroy stuff). Will a building and pest inspection, in conjunction with a valuation, highlighting any possible issues reduce the value of the property? If an independent valuation isn't done, will ATO do their own valuations? Am I correct in assuming that even buyer purchases in the name of a trust/company etc, as long as the buyer is the director of the company, a family link can be assumed, therefore not dealing at arm's length? Anything I might've missed?