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I WISH I HAD BOUGHT

  • Sep 13, 2025
  • 3 min read


I saw a pretty funny meme on a Real Estate website the other day. It said “In 2025 – I wish I had bought 5 years ago” and then “In 2030 – I wish I had bought 5 years ago”. Which, as funny as it sounds, pretty much sums up the market for Real Estate in Canada over the last 50 years. If you were to google countries where house prices rise every year, the result is pretty interesting. It shows that Iceland, Estonia, New Zealand, Turkey and Canada are countries that show house price increases year after year. That shouldn’t come as a surprise to anyone living in this country. I almost gag on some of the prices I see these days for modest homes in nice areas. I always tell my buyers the first house we bought in 1983 was in what’s now know as Leslieville in East Toronto. On the cusp of the Beaches neighbourhood it was a 4 bedroom semi that need a pantload of work. But at $58,000.00 you couldn’t beat the price. Even back then there were bidding wars. A lot of people seem to think that practice has only come about in the last decade or so, but in 1987 when we went to sell our home we had 3 offers on it and it sold for $131,000.00 which, at the time, was a sizeable increase. I check on the place from time to time just to see where prices have headed. The last time it sold the home at 9 Connaught went for a cool $1.2 million. It seems just about every area of Toronto has been gentrified and given some kind of funky name. We just knew it as the Canada Metal neighbourhood back in the day. At that time you could pretty much find great prices in most areas. I worked with a cameraman at the CBC, who had a hobby of buying houses. Every time we would come back from some special event that required a lot of time worked he would pretty much clear around 10K in overtime pay. So he would take that extra cash and buy another house. He had at least 12 of them at last count. And he was buying in the Beaches, Cabbagetown and Riverdale. He’d buy 3 or 4 bedroom semis and then rent them out. For his tenants he had 3 simple rules. Don’t burn the place down. Make sure the rent is paid on time. And don’t call me over little things – fix it yourself. In other words, the perfect landlord. A few of his co-workers would get on his case about wasting his money but my question would be – who’s laughing now? We ended up riding the equity wave right out to Whitby and then ended up in Port Perry in 2007. Thing that makes me laugh the most is that the place we bought in Port was the most expensive home we bought over the course of 40 plus years. Which is funny because what we paid for it would barely constitute a healthy down payment in today’s market. Buyers always ask “When is the best time to buy?” My answer is always “Yesterday” Pretty much the same message as the meme. Guess the proof really IS in the pudding.

 
 
 

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© 2025 by Shawn Lackie.

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