No. Rolling the proceeds into another home has not sheltered the gain since 1997. The old rollover rule that let you defer taxes by reinvesting in a replacement home went away with the Taxpayer Relief Act of 1997. What replaced it is the Section 121 primary-residence exclusion: if you owned and lived in the home as your primary residence for at least two of the last five years, you can exclude up to $250,000 of gain filing single, or up to $500,000 married filing jointly (confirm the current figures with a CPA, since tax rules change). Anything above the exclusion is taxable whether or not you buy again. One point trips people up constantly: your gain is your sale price minus your cost basis, and basis is what you paid plus documented improvements plus selling costs like commissions. Your remaining mortgage balance has nothing to do with it. A well-kept file of receipts for capital improvements can meaningfully shrink the taxable number. If you sell before the two-year mark, you may still qualify for a partial exclusion when the move is driven by a job relocation, health, or certain unforeseen circumstances. This is your money and your tax return, so run your specific situation past a CPA or tax professional before you sell.