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Get your taxes done using TurboTax
it seems your talking about 4 homes
a) mountain home sold 5/28/21 owned and occupied for 2 out of 5 years before the sale. rented and used for a home office which means depreciation should have been taken
b) Hemlock sold 9/8/21 owned and occupied for 2 out of 5 years before the sale. Never rented
c) Curtis being rented
d) Carla primary residence
only one of the homes sold in 2021 can qualify for the exclusion. since the biggest gain seems to be on the mountain home that's the one I would choose. Note that since it was a rental and used as a home office before the exclusion applies you must recapture the depreciation allowed or allowable. if you did not depreciate it, turn to a pro because the law says even if you didn't take a tax deduction for depreciation on it upon sale you must recapture the depreciation you should have taken. since it seems your cost basis was less than the FMV, depreciation should have been computed using the cost basis after subtracting the value of the land when bought.