Can I roll over the profits from my second home straight to building our new primary residence without paying capital gains.
Simple answer is NO. Period. End of story. The ability to do that expired 10-20 years ago. It was commonly referred to back then as a capital gains deferment.
If the property you sold was your *PRIMARY* residence for at least 731 days of the last 1,826 days you owned it, counting backwards from the closing date of the sale, then you could qualify for the capital gains tax exclusion of $250K if single, or $500K if married filing joint and you were both listed as owners on the deed. Note that the days it was your primary residence do NOT have to be consecutive either.
But since you specifically and explicitly state it was your "SECOND" home, if that's true for the last 5 years, you do not qualify for any exclusion.
If the property was a rental property for "ANY" period of time while you owned it, then you have depreciation recapture to deal with. If you don't know what you're doing, that *WILL* complicate matters for you. (But TurboTax can handle it just fine *if* you know what you're doing.)
For a 1031 exchange you are required by federal law to complete the transaction with a 3rd party professional qualified to complete such exchanges. There are time limits also, between the time of disposing of the old property, and acquiring the new property. But I don't see a 1031 exchange as even a possibility here, since your purchase was for land only. You specifically and explicitely state that you are "building our new primary residence" which indicates you sold real estate with a structure on it, and purchase real estate without a structure on it - raw land. I just don't see any possibility of getting a house built with a CO issued within the 1031 exchange time frame required by law.
