I sold a house in Feb of 2016 and a condo in June of 2016.

I meet the 2/5 rule for both of them. I have lived in both for 2 out of the last 5 years.

Lived in House from July 2009 to May 2014 (I bought in 2009)
Lived in Condo from June 2014 to June 2016 (I bought in 2012)

Neither was a rental property. I just bought the condo when it was offered too me by a family friend....it stayed vacant for a couple years.

Bought the house for $228K, sold for $280K
Bought the condo for $25K, sold for $70K

So combined I didn't come close to making $250K in profit.

The house was bought via a traditional mortgage and the condo I originally bought with cash (no mortgage).

My question is, do I need to pay taxes on either property since I sold 2 within the same year? Do I pick which one to pay taxes on?

Let me know if any additional information is needed. I really appreciate any help you can provide. Oh, and I live in Georgia (if that makes a difference).

My question is, do I need to pay taxes on either property since I sold 2 within the same year? =====>>Yes; To qualify for the exclusion, you must have used the home you sell as your principal residence for at least2 of the5 years prior to the sale. Your principal residence is the place where you and your spouse if you're filing jointly and claiming the $500k exclusion for couples live.you can not have two primary homes at the same time you neeed to choose one of them as your primary home.

Do I pick which one to pay taxes on?=======>Remember; UNLESS your marginal tax rate is higher than 15%, you donot need to pay Long term capital gain tax on the gain on the disposition of the home; aslongas your marginal tax rate is higher than 15% then you ?d pay tax on the condo whose capital gain is $45K as $45K<$52K to save your capital gain tax .

Thank you for the information Wnhough. It's been difficult locating information for my specific situation.

I am single and both places that I sold were my primary residence for 2 out of the past 5 years. I lived in the house as my primary, then moved into condo which was my primary.

I've always done my own taxes, but I supposed I should hire a tax expert this year with my unusual situation.

as mentioned previously yopu simulataneously can not claim 2 primary homes but you must choose only oneo f the two homes as your primary home.A primary residence is defined as where you spend the majority of 365 days each year. Therefore, you cannot have two primary residences at the same time

also aslongas your ordinary tax rate is either 10~15 % then your long term capital gain tax rate is 0% if your ordinary tax rate is between 25~35%, then your long term capital giantax rate'd be 15%.
you need to contact an Enrolled Agent or a CPA doing taxes in your local area for professional help.