Toronto isn’t the city it used to be. I suppose I could say that for just about any city, but with Toronto, let’s not kid ourselves. The changes have been swift and visible all over the city. Just look at how many Blog TO posts pop up every few months to show a before photo of Toronto in the 70s, 80s or 90s and a photo from now with all the space of a given neighbourhood filled in with buildings. There’s a nostalgia for those earlier Toronto days. Not only because Toronto was simpler and easier to get around (though maybe less interesting), but also because it was a whole lot cheaper to buy real estate.

I can’t tell you how many times I have heard someone say something like this: “If only I had money in the 90s, I would have bought real estate then, and I’d be rich today.” And to those people I would say: “You would be right.” It’s not that you even had to be very smart about it back then. Any ‘ole house or condo would work. You could have bought almost anything, and it would very likely have appreciated in value by a lot. Of course, not all neighbourhoods were built the same, but in almost all neighbourhoods you were guaranteed to make money if you waited long enough to sell.

Plus, the mortgage rules were very different, particularly when lending institutions made it much easier to buy properties in the late 90s and early 2000s. I have an investor friend who bought eight properties back in the 90s for under $400K, and at times, even under $300K – all sprawling multiplexes in High Park. Houses he filled with tenants and created serious cash flow. Now, he’s wintering in Miami living off the income from all his properties. It was almost laughable by today’s standards.

Back then you could buy a detached house in decent shape as a starter home in the Annex or in High Park. Places like Leslieville still did not even have a name yet. Cabbagetown was for artists and media types, and the Junction was dry (re:no booze at any business). Condos were in the minority. They were set up as a kind of endless spa experience with tennis courts and swimming pools and a concierge who let you know when your pizza had arrived. Parking lots were all over the place. Yes, it was a different city back then. Perhaps you remember it. Perhaps, if you’re younger, you could imagine it. It feels like a golden age of real estate investment when you could buy a house for a song or buy a property and have instant income from the tenants.

I’m not reminding you of all this to make you feel bad or make you feel like you missed out. You’re no dope. You’re just like most people who just couldn’t buy then, didn’t want to buy then or were way too young or uninterested to even consider buying then. I am telling you this for a reason though. I’m telling you this because I do have this feeling sometimes when I walk through Hamilton. It’s a feeling that there is an opportunity here. I see it when I come out here with my buyer clients. I see beautiful Victorian and Edwardian homes for prices that you would have seen in Toronto decades ago. Some need a little love, and some of the neighbourhoods can be scrappy, but wow, it really reminds me of this Toronto’s 90s, a bygone era. There is just street after street of affordable historic homes. Even the conversion lofts are amazing with lots of space. You can drive by the warehouses of what would expect to be future conversion condos. It mimics Toronto’s houses of many decade ago. You could easily buy a house with a respectable income in the 275K to 400K range. Nicer neigbhourhoods will cost you more.

There is a lot of promise here. Many warehouses are currently being purchased by Toronto developers who do good things like the folks that brought us the 401 Richmond Street building in Toronto, an arts friendly building with some serious loft style. These developers know that the artists are heading to Hamilton in droves for cheap working spacs and to be around fellow artists. It’s the opposite of the canary in the coal mine. Artists are like the canaries who lead us to good investments. There’s no denying that Hamilton’s James Street is taking off as the hipster main street of Hamilton, but it doesn’t stop there. Ottawa Street is also taking off, and is even more affordble. I think Gage Park is amazing, though it still needs a good main street nearby. And there’s way more: portions of the waterfront, Hamilton’s Corktown, resemble the always pretty artsy town of Dundas.

If you’re an investor, Hamilton may sound like a great place to invest (and it is). But take extra precaution here. Renters in Toronto and renters in Hamilton are different animals. Renters in Hamilton can be scrappier and do pay less. Toronto renters, in most neighbourhoods are easy to find. Hamilton needs a bit more vetting. Make sure you check your tenants to make sure they will pay and have the ability to pay.

Of course, Hamilton may require things you are not willing to do like drive back and forth to Hamilton or take the GO train back and forth. Sadly, that is the price of much less expensive houses at this point in time.

If you are keen to stay in Toronto and would like to find a deal for house under $650K, then you may want to head for the next Leslieville with the Danforth Village. Still on the subway line and still affordable by Toronto standards. The closer you are to Vic Park, the more your price point will drop. Same goes for going north of the Danforth. If you’re looking for the next Little Italy, try Caledonia near St Clair and Dufferin and west of there. The Eglinton Crossway under construction to the north is going to be an excellent transit line, and the St. Clair streetcar has a streetcar only lane for getting around easily without the issue of being bunged up by cars and trucks. St. Clair is one of the most underrated main streets in the city. This part of St. Clair is mostly Portuguese working class. If you’re Portuguese, then it will be easy to fit in. If you’re not, be aware that many new buyers are from everywhere and the area is becoming quite mixed. Finally, if you’re looking for the next Junction, you want to look at Weston. Yes, there’s some grim, poorly maintained high rise rentals around Weston, but like the Junction, Weston started off as a small town. Many amazing houses sell for a fraction of the cost in the rest of Toronto. If you feel you are too isolated up at Weston and Lawrence, remember that the GO station is right there with the Union Pearson Line. With the stop at Weston, you could get to the airport quickly and you could get to the Bloor subway line in one stop and Union Station in two. And remember, prices just came down significantly on those train tickets. So, getting around with the Union-Pearson train is not just for traveling business folk. It’s for Toronto people too. Take advnantage!

In my lifetime, and probably yours too, there won’t be a time for buying real estate like the 90s in Toronto. We won’t be partying like it’s 1999 any more. It would be tough to recreate that again. But there are options. Good ones that will have people saying in 2036: “I wish I’d bought in Hamilton or Weston or Danforth Village or Caledonia back in 2016.”