If you are financially able, do it. I fear prices for freehold won't get any better. A new standard/pricing has been established thanks to covid and even right now, homes are fetching top dollar prices.

We were in the same predicament and bit the bullet in late July. We both wfh, have a toddler and 1+1 wasn't working for us anymore. However, we bought our next home before selling our condo. And we thought we wouldn't be able to sell our condo given the low traffic but luckily we received an offer in 2 days! Other units in our building had been listed anywhere from 7 days to 30+ days!

Honestly w condo sales, they are a dime a dozen, if buyers miss one, they'll just wait for another to pop up. And I imagine in September with increased inventory, prices for condos may also flatten a bit.

If I had to do it again, I'd still buy and sell just because so many have sold their homes only to be priced out or out bid. It's not a good feeling I bet. You can always try listing it to test the market but ultimately it boils down to what will work for your family.