Tax Loss Selling in the stock market has been common place over the years. People, who have made profits selling stocks over the year, often sell stocks they know will never make money at year end and use the losses from these sales to offset the profits and taxes payable from the winners. Revenue Canada has recently ruled that anyone that makes a profit from selling a condo Assignment or even a resale without holding it for a reasonable length of time (?) will have the profits taxed as income and NOT capital gains. So if these gains are to be treated as income, then any losses from these same types of sales must also be treated as an offset to your income (and not as a capital loss which cannot be offset against your income). Ideally the best time to sell these condos that will lose you money would be at year end. But if you have substantial income from work or profits from other condo sales, then taking a loss this year could be a good strategy. We can already think of some projects that will lose investors’ money as they come to registration. Besides the obvious Trump Tower, some investors in the Shangri La, Cinema Tower Condos, and soon to be occupied Ice Condos will find out that they will be losing money on closing or registration of their units. Obviously, some investors will choose to wait and hope that prices in the condo market will continue to rise over time to recoup their losses. How long is this wait? Ask the experts – some of which see a flat market over the next two years. Or you can look at your total income and decide that a Tax Loss Selling Strategy is not the worst option. We would talk to someone who knows the Assignment Market for a reading on your investment unit.