Look for condensation between the panes, drafts you can feel with a hand near the frame, and cracked or missing exterior caulking and flashing where the window meets the wall. In Saskatoon's climate, a poorly installed window shows up fastest as ice or frost forming on the inside of the glass in winter.
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A window that was installed correctly should have a continuous seal of flashing and caulking around the entire frame, tying into the home's weather barrier so water cannot get behind the siding or brick. When that seal fails or was never done properly, water finds its way into the wall cavity, and by the time you see a stain on the interior drywall the damage has often been building for a while, sometimes for more than one winter. Check the exterior first. Cracked, missing, or visibly aged caulking around the frame, and any gap where the frame meets the siding, are the first signs worth investigating further before you look inside.
Inside, run your hand around the frame on a cold day and feel for a draft, which usually means the installation gap between the window and the wall framing was not properly insulated and sealed, not that the window itself is defective. Condensation or frost forming between the two panes of a double-glazed window, rather than just on the inside surface of the glass, means the seal inside the unit itself has failed and the window needs replacing, not just re-caulking. Fogging that clears when you heat the room is normal humidity, fogging that stays between the panes is not, and it will not resolve on its own.
Saskatoon's winters put real stress on window seals through repeated freeze and thaw cycles, which is why a home built or renovated without proper flashing shows problems faster here than in a milder climate. A pre-purchase home inspection, typically $400 to $600, is the most reliable way to catch this before you buy, since an inspector checks both the visible exterior condition and the interior signs of moisture that a casual walkthrough misses entirely, including areas hidden behind trim and blinds that a buyer would not normally move during a showing.
Age alone is not a reliable indicator. A well installed window from decades ago can outperform a poorly installed newer one, so the installation quality matters more than the manufacture date when you are assessing a home's actual condition. Look at how the window was set into the opening, not just how new the glass looks.
If you are selling a home with older or DIY-installed windows, get an honest assessment of what condition they are actually in before you list, since this is exactly the kind of detail public records and online estimates never capture. A home inspection, which runs $400 to $600 in Saskatoon, will document what a walk-through misses, and CMHC publishes homeowner guidance on moisture and condensation that explains what those symptoms actually mean. Get your hand-reviewed valuation from Joel Dyck.