The homes in Southwest are incredible—big, custom-built places that come in all kinds of styles. You’ll see Victorian, Tudor Revival, modern designs, and tons of restored or renovated bungalows and 2-storey homes. Each one feels unique, which is part of the charm of this neighbourhood.
Southwest, like most of South Oakville, also has lakefront estates. These homes are some of the most expensive in Canada. But, we won’t go into much detail on these as you’re likely reading this guide trying to realistically determine what’s affordable in Southwest.
The good news?
Beyond these out-of-reach-for-anyone-but-pharma-CEOs lakefront estates, the majority of the neighbourhood is actually made up of smaller bungalows and 2-storey homes built between the 40s and 60s. These homes sit between Rebecca and Lakeshore Road.
However, most of these properties are being torn down or heavily gutted and restored/renovated. The Southwest area is a prime target not for flips but for people looking to build or renovate their dream homes.
Check out the home above. That’s a 1958 bungalow that sits on a 75ft x 160ft lot. That is absolutely prime real estate. Then check out all the other homes around it. You’ll see the custom-built properties that now dominate the neighbourhood.
There are still opportunities at reasonable prices, but they are becoming less common as the years go by. So, if you’re looking for that custom-home spot or want to take on a turnkey opportunity in the area, you still have a chance.
You can also find smaller pockets of detached 2-storey homes built in the 70s and 80s. These are typically larger and more expensive especially once upgraded. Head east past Fourth Line to find them.
Finally, if you are looking for 19th century homes, these will be tough to find. Most, if not all by this point, have been replaced but there is the odd one you can find that’s been structurally restored while retaining the original character. But, if you really want this, head over to Old Oakville for a much larger selection.
