Can I sell the rental property and use the proceeds to pay off the mortgage on my primary residence without paying capital gains tax?

[what-the-hello]

Property was converted from my primary residence to rental 5yrs ago and I have owned the property for 20 yrs.....I estimate the gains from the sale would be $75,000.

[kruno]

You will have to report the Capital gain - to qualify for a residential deduction you have to reside in your home for 2 years out of the last 5. The proceeds from the sale can be used to pay of the mortgage - but the occupancy rule applies.

[Hal_Al · Accepted solution]

No. The two events are not related. 

There are some quirks in the tax system, that you may have heard of, but they don't apply to your situation.

The old rule about selling a house and using the proceeds to buy a new house to avoid capital gains was eliminated many years ago. Even then it would not have applied to paying off a mortgage.

"Like kind exchange" doesn't apply either.

There is a capital gain exclusion for selling your principal residence. But you don't qualify because the house sold was not your principal residence for 2 of the 5 years before it was sold. 

[DoninGA]

No.  Paying off the mortgage on your personal residence is not reported on a federal tax return.