You finally have the retirement date circled on the calendar, but there’s a five-figure home expense sitting over your head, literally. If your roof is already 20 years old, replacing it before retirement could consume money you’d rather save, while waiting could push the same major expense into years when you’re living on Social Security, a pension, or retirement withdrawals. The decision becomes more complicated because roof age alone doesn’t tell you whether replacement is immediately necessary. Condition, roofing material, insurance coverage, cash reserves, and how long you plan to remain in the house all matter when evaluating roof replacement before retirement. Instead of automatically replacing a roof because it reached a particular birthday, retirees should start with these questions.