I bought a house in October of 2013 and rented out my other house that I had lived in since 1994. I have taken a new job and need to move, so I am looking into how to sell both properties without paying the capital gains taxes. My main resisdance falls under moving for a new job and my rental property falls under the 2 of the past 5 years. ========>>For your rental pty, you are correct.
My question is, can I sell both and get both the breaks? I am married and both properties would be less then 500K.========>>I do not think so; You can only have one principal residence at a time. As you live in more than one place, as you have two homes, the property you use the majority of the time during the year will ordinarily be your principal residence for that year.As you have a second home / vacation home that has substantially appreciated in value since you bought it, you’ll be able to use the exclusion when you sell it if you use that home as your principal home for at least two years before the sale.
Which one is your primary home? To qualify for the $250K/$500k home sale exclusion, you must have used the home you sell as your principal residence for at least 2 of the 5 years prior to the sale.
Note; once you qualify for the exclusion, you may do anything you want with the tax-free proceeds from the sale; if you do buy another home, you can qualify for the exclusion again when you sell that house. Indeed, you can use the exclusion any number of times over your lifetime as long as you satisfy the requirements