Tax Straddling – Pay Taxes in 2021 or 2022?

When a 1031 Exchange is opened in the latter part of the year, a seasonal treat worth mentioning is “tax-straddling”. If that exchange is successfully completed, those taxpayers defer taxes to receive the benefits of the 1031 Exchange. However, if that exchange fails and is not completed, taxes will be due. The treat for those taxpayers is that they may still qualify for a “mini-tax deferral” (via tax straddling) where they can report and pay their taxes on their 2021 tax returns instead of immediately on their 2020 tax returns.

Here is the technical explanation of how tax straddling works. Let’s assume a taxpayer attempts a 1031 Exchange at end of year with bona fide intent in the later part of 2020, but the exchange is not successful. Taxes on the gain from the sale will then need to be paid. If the monies being held by the 1031 intermediary are not returned to the taxpayer until after December 31st, the attempted exchange carries into 2020. This situation would create an Installment Sale under IRC Section 453 (and the 1031 regulations). With tax straddling, the taxpayer has two options:


  • The taxpayer can elect to report the taxable gain on the tax return for the year in which the property was sold (2018). Please refer to Publication 537 for election rules;      -OR-
  • The taxpayer can report the taxable gain on the tax return for the year in which the taxpayer came into possession of the sale proceeds (2019). By choosing option B, the taxpayer is granted with a de facto one-year tax deferral on the gains from the sale of the property. (See Section 453 of the Tax Code for details).

By choosing the second option, the taxpayer essentially receives a one-year tax deferral on the gains from the sale of the property. (See Section 453 of the Tax Code for details). Tax straddling simply provides an added incentive to investors selling investment property at the end of the year. Taxpayers will not be penalized by the IRS for attempting to complete a 1031 Exchange. Why not attempt to complete a 1031 Exchange with a one-year deferral as a back-up plan?

Taxpayers should consult with their tax advisors since tax straddling does not apply to all sales. Gain attributable to debt relief will be recognized in the year of sale. Please call us at IPX1031 to discuss tax straddling and other valuable tax deferral solutions. Consult with your tax and legal advisors to determine if you can take advantage of these valuable tax-deferral methods.


Previous tax straddling:
Tax Straddling – Pay Taxes in 2020 or 2021?
Tax Straddling – Pay Taxes in 2019 or 2020?
Tax Straddling for 2016-17
Tax Straddling for 2016
Tax Straddling for 2015
1031 Tax Straddling for 2014

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