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I wish I had bought

  • Shawn Lackie
  • Jul 9
  • 2 min read
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by Shawn Lackie


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 Iceland, Estonia, New Zealand, Turkey and Canada are countries which 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 known as, Leslieville, in East Toronto. It was a four bedroom semi, on the cusp of the Beaches neighbourhood which needed a lot of work, but at $58,000 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. However, in 1987, when we went to sell our home we had three offers on it and it sold for $131,000 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 which required a lot of time, he would pretty much clear around 10K in overtime pay. So, he would take that extra cash and buy another house in the Beaches, Cabbagetown and Riverdale. He’d buy three or four bedroom semis and then rent them out and had at least 12 of them, at last count. 

For his tenants, he had three simple rules:

1. Don’t burn the place down. 2. Make sure the rent is paid on time. 3. Don’t call me over little things, fix it yourself. In other words, he was the perfect landlord.

A few of his co-workers would get on his case about wasting his money. However, 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. The thing which makes me laugh the most is, the place we bought in Port Perry 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.” That's pretty much the same message as the meme. I guess the proof really IS in the pudding.

1 Comment


Aubin Houde
Aubin Houde
Jul 14

That meme really captures the timeless truth about real estate. It actually reminds me of book marketing too authors often ask, “When’s the best time to promote?” and the answer is also “Yesterday.” Especially for non-fiction books, early and consistent non fiction book marketing strategy makes all the difference!

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