Capital Gain


Taxable profit on the sale of an appreciated asset.

Flipping and Capital Gains

A common dilemma for real estate investors is the issue of flipping and taxes. In this article, we look specifically at the tax issues associated with flipping and capital gains.

In recent years, people have been looking at the real estate market as they once looked at the stock market, eyes filled with dollar signs. Flipping became a popular real estate investment strategy to make fast cash. However, one thing that people forgot in their haste to play the game was to be properly prepared with the knowledge to avoid paying high taxes on their profits. Towards that end, here's some noteworthy information about taxes as you think about your flipping strategy.

First, in order to avoid overly onerous "ordinary income taxes" on flipping properties you must have the property treated as a capital gain. Most often, if you sell the property in less than a year, you will be taxed at the ordinary income tax rate, which can be in excess of 35 %. Only when you've held the property for more than a year, does the long-term capital gains tax of 15 % (for most tax payers) come into play. In order to have the property treated as a capital gain you must show that you had no intention of flipping that property. Ironically, this could entail holding the property for this extended period of time which counteracts the whole point of flipping - which is to make money fast.

Also, it's not only about "when" you flip, but about "how often" you flip. If you flip too often, the IRS may view that this strategy is your "trade or business" and therefore the profits you make are subject to ordinary income and self-employment taxes. And you don't want that.

Secondly, if you want to employ other strategies to avoid big taxes like installment or structured sales or private annuity treatment while flipping, you can't. Spreading tax out doesn't work because the property is not labeled investment property. This again goes back to issue of holding periods and intention of sale.

If you are hoping to use the 1031 exchange strategy as the approach for flipping and capital gains, again you will find yourself between a rock and a hard place. 1031 exchanges are reserved for investment properties only and if you can prove, through holding periods and intention, that the property is a capital gain or investment property, you will not be eligible. The IRS supports investors and savers, not speculators and gamblers.

Once most of your tax deferral options are exhausted, your last resort for flipping and capital gains may be to have that property re-characterized to a capital gain property by moving in to it and treating it as your personal residence. It may work, but holding even longer holding periods apply.

In conclusion, flipping can be an exciting and fast way to make money. But when it comes to taxes it is hard to make flipping and capital gains work together.


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