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How to Avoid Capital Gains Tax on Sale of Commercial Property

July 31, 2023

When you're at the stage of considering the sale of a commercial property, one question might loom large: "How can I avoid capital gains tax?" Capital gains tax can indeed pose a serious financial burden, potentially diminishing a substantial part of the profit you've painstakingly built up. In fact, with strategic planning, there are legitimate ways to reduce this burdensome tax. In this article, we will explore the concept of capital gains tax, the reasons for its avoidance, and various strategies to legally minimize its impact.

What is Capital Gains Tax?

To navigate through the labyrinth of tax avoidance strategies, it is first crucial to understand what capital gains tax actually is. It is essentially a tax that you have to pay on the profit that you earn from selling an asset - for instance, a commercial property. Importantly, this tax does not apply to the entire sale price of the property. Instead, it is only charged on the difference between the price at which you bought the property and the price at which you sell it. This difference is often referred to as 'capital gain,' hence the term capital gains tax.

Capital Gains Tax on Commercial Property

When it comes to commercial properties, the capital gains tax can be particularly significant. This is especially the case if the value of your property has risen markedly since you purchased it. Given the potential financial impact, it is understandable why many property owners seek strategies to avoid this tax. We will explore some of these strategies in detail later in the article.

Why Should You Avoid Capital Gains Tax?

From a financial perspective, it makes perfect sense to minimize the capital gains tax as much as legally possible. This tax can take a significant bite out of your profits, and if you can reduce it, you will have more capital to reinvest or to utilize in other ways.

The Financial Impact

The financial impact of capital gains tax can be substantial. It directly reduces the return on your investment - the profit you make after accounting for all expenses, including taxes. By minimizing or even avoiding this tax, you increase your return on investment.

Long-term Investment Strategies

Beyond immediate financial gains, there's another compelling reason to avoid capital gains tax. Strategically planning to bypass capital gains tax can foster smarter and more profitable long-term investment decisions. This could involve selecting the right properties to invest in, timing your investments wisely, or leveraging tax avoidance strategies to make your money work harder for you.

How to Avoid Capital Gains Tax on Sale of Commercial Property

The complexity of the tax code, while often daunting, also provides opportunities. There are multiple strategies that you can use to legally avoid or minimize capital gains tax. Here are a few of the most effective ones.

1031 Exchange

One of the most well-known methods is the 1031 exchange, named after Section 1031 of the Internal Revenue Code. This method allows you to defer the payment of capital gains taxes by reinvesting the proceeds from your property sale into another property of a similar kind. This new property is often referred to as a 'like-kind' property, but it doesn't have to be identical to the original one. It just needs to be similar in nature or character. For instance, you could sell an office building and invest in a retail complex under a 1031 exchange.

Installment Sales

Another strategy is the use of installment sales. In this approach, you, as the seller, finance a part of the property's purchase price for the buyer. Instead of receiving the full payment at once, you receive it over several years. The advantage of this strategy is that it spreads out your capital gains income over several years, thereby potentially reducing your overall tax liability.

Tax Opportunity Zones

Then, there are tax opportunity zones. These are designated underprivileged areas where investments can lead to capital gains tax reductions and deferrals. By investing in these areas, you not only get the chance to minimize your taxes but also contribute to the economic development of these communities.

Charitable Remainder Trusts

A charitable remainder trust (CRT) is another strategic option. This involves donating your property to a charitable organization while retaining an income stream from it. You typically place your property in a trust, which then sells it and invests the proceeds. You receive income from the trust for a certain period, after which the remainder goes to the charity. This strategy can result in significant tax deductions and can be a win-win situation for both you and the charity.

Owner Financing

Owner financing, also known as seller financing, is a real estate transaction where the seller provides credit to the buyer for the purchase. Like installment sales, this method can spread out your capital gains tax liability over time, potentially reducing the total tax you need to pay.

Tips for Successful Tax Planning

Successful tax planning isn't just about knowing and implementing the right strategies. It also requires understanding the nuances of these strategies, staying updated on changes in tax laws, and seeking professional advice. Consulting with a tax professional or a real estate attorney can be invaluable. They can help you understand the implications of different strategies, guide you in timing your investments, and assist you in executing your plans effectively.

Risks and Considerations

While the strategies discussed above can help reduce or eliminate capital gains tax, they all come with their own sets of risks and considerations. For instance, a 1031 exchange requires meeting specific deadlines, and failing to meet them could negate the tax benefits. Similarly, investing in opportunity zones might involve risks related to the local economic conditions. Therefore, it is critical to take these factors into account and get professional advice before implementing any tax avoidance strategy.


In conclusion, while the capital gains tax on the sale of a commercial property can be significant, there are several strategies available that can help you avoid or defer this tax, thereby maximizing your profits. These strategies range from 1031 exchanges and installment sales to investments in opportunity zones and charitable remainder trusts. Each of these strategies requires careful planning, professional advice, and informed decision-making. With the right approach, you can not only save on taxes but also make smarter investment decisions, helping you grow your wealth over the long term.


1. What is capital gains tax? Capital gains tax is a levy you pay on the profit earned from the sale of an asset, such as commercial property.

2. What is a 1031 exchange? A 1031 exchange is a method that allows you to defer paying capital gains taxes by reinvesting the proceeds from the sale into a 'like-kind' property.

3. What are tax opportunity zones? Tax opportunity zones are designated underprivileged areas. Investing in these zones can lead to capital gains tax reductions and deferrals.

4. What is a charitable remainder trust? A charitable remainder trust involves donating your property to a charitable organization while retaining an income stream. This can result in significant tax deductions.

5. What is owner financing? Owner financing, also known as seller financing, is a real estate transaction where the seller provides credit to the buyer for the purchase. This can help spread out your tax liability

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