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How to Sell Rental Property as a 1031 Exchange

Can you sell your rental property as a 1031 exchange? It depends. Toby Mathis and Jeff Webb of Anderson Advisors answer your tax questions (Selling Rental Property as a 1031 Exchange). Submit your tax question to taxtuesday@andersonadvisors.


  • Can I offer my condo as a rent-to-own rental for six months and sell it as a 1031 exchange? If you’re offering the condo as rent-to-own, you’re contemplating the sale of that property, so it becomes a sale property, not a rental property, and taxed differently
  • Should I invest into limited partnership (LP) multifamily syndications with the same LLC as I have active personal rentals? Ideally, everything should be in its own LLC or you may be at risk for outside liability
  • I am a co-founder of a startup (C Corp). Can I establish a self-directed Roth IRA and put my company share in it? Yes, you can, but it depends on how you go about doing it – Rollover as Business Start-ups (ROBS)

For all questions/answers discussed, sign up to be a Platinum member to view the replay!

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Infinity Investing: How The Rich Get Richer And How You Can Do The Same by Toby Mathis

1031 Exchange

IRS – Section 168

IRS – Section 179

Bonus Depreciation

Depreciation Recapture

Entity Formation

Cost Segregation Authority

Real Estate Professional Requirements


Retirement Plans

Wills and Trusts

Tax Reform Act of 1986

Self-Employment Tax

Old Age, Survivors, and Disability Insurance (OASDI)

Capital Gains and Losses

Section 121 – Capital Gains Exclusion

Step-Up in Basis

Fannie Mae

Freddie Mac

Schedule A

Schedule C

Schedule E

Schedule K-1

Unrelated Business Income Tax (UBIT)

Unrelated Debt-Financed Income (UDFI)

Rollover as Business Start-ups (ROBS)

IRC 469(c)7

Secure Act

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Full Episode Transcript:

Toby: Hey, guys. You’re watching Tax Tuesday, or listening to Tax Tuesday—whichever you may be doing—or both. My name is Toby Mathis.

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