Is there a "best" time of year to do this?
There is no best time of the year to do windows.
If a professional installs the windows level and plumb, caulks them in one straight line and foams evenly around the frame, then the windows should turn out perfect.
The time of the year is only changes the way of installing windows.
In summer they all come out in the same time, in winter they get replaced one by one so the house does not frieze.
If you go with a window company that knows how to work in winter you should be O.K.
I completely agree with the other two responses. We have replaced windows at all times of the year and had no issues. Like Harry said, just make sure to do them 1 at a time! The one important thing I would like to mention though to avoid condensation issues is to make sure the foam is installed correctly. It should be installed from the inside and fill the "cold zone" of the space between the exterior side of the window. All you need to do is push the foam gun right inside and fill about half way. I have seen a ton of people only fill the gap near the inside wall. This is incorrect.
Hopefully that made sense!
The best time is when it is not raining or snowing. If it is too cold then the caulking and capping of the windows could be an issue although it could be done when the weather is conducive to completing the installation provided that the installation is weather tight.
Windows are normally removed and replaced one or two at a time depending upon the circumstances.
Buy them from a manufacturer in the winter. And have them install durring the early part of the summer. That way you get the best price on the purchase. And have the work done durring a comfortable part of the year.
In addition, at this time of year if problems are found such as mold, insulation issues etc, no one is rushing. And they can be dealt with properly.
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