Whitby is a move-up market, which makes it a two-closing-dates market
Whitby — Brooklin especially — draws buyers trading an entry condo or townhome elsewhere in Durham for detached family space. That makes the defining local problem a sequencing problem rather than a qualifying one. When the purchase closes before the sale, the down payment is tied up in a property you still own on the day the lender needs the money. Lenders solve this with bridge financing: short-term, interest-bearing money covering the days or weeks between the two closings, secured against the departing home. It works well and it has firm conditions — most lenders require the sale to be firm, not conditional, before they will bridge against it, and it carries its own setup and legal costs. The alternative, closing the purchase with no sale in place, means qualifying while carrying both mortgages at once, with the debt-service ratios tested at the stress-test rate on both. Some households can absorb that; many discover late that they cannot. The third route — selling first and renting in between — is the cheapest financially and the most disruptive practically. None of the three is universally right. What is universally right is choosing between them before the offer goes in, because the choice determines what closing dates you can safely accept.