do i have to pay capital gains tax?

Question

if i sell three rentals can i put the proceeds into my owner occupied duplex without paying capital gains?

Answer 1

No, you'll still have to pay it.

Answer 2

I would say no. Your three rentals are considered investment property under the tax code. Investment property is defined as property that you do not occupy more than two weeks of the year. You can roll over proceeds without paying tax through the mechanism of a 1031 exchange as long as you put the money back into property also considered investment property. Since you occupy the property you are considering putting the money into, it would not be considered investment property and would trigger the tax. You might be able to improve the side of the duplex you do not occupy and not have to pay. You might also be able to partition the duplex into two seperate parcels and refinance any debt into two seperate mortgages and pay off the debt relevant to the parcel you do not occupy without triggering the tax. I would research the rules governing section 1031 exchanges thoroughly before acting.