This question is academic until you find yourself seriously weighing options and contemplating change. If you started thinking about selling your house in 1995 and have spent the last 20 years dithering, you have done yourself a favour. However I wouldn’t bet heavily on there being much more time to procrastinate profitably.
Roughly speaking, in Toronto there have been 2 ½ boom/bust cycles in real estate since 1975. The first one was 1975 – 1985; the second took place between 1985 and 1995. Today, we are still on the ascendant of the third cycle which began in 1995. This means we have had a 20 year bull market.
If you want to put the equity tied up in your house to work, now is a good time to sell. Buyers are not afraid to take on whatever debt levels are needed to buy a home. Low interest rates are fuelling this willingness. If there is anything “different this time” about our booming Toronto market, it is the cost of borrowing. Lines of credit, which for many people started out as a solution to irregular cash flow, have morphed into vehicles that finance life styles. “In God we trust. Others pay cash.”
In conclusion, the time may be now to realize the most number of dollars for your real estate before the inevitable correction to the current boom occurs. On the other hand, there may be another 5 years left for the current bull to keep running. I do not have a crystal ball.