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The Intricate Dance Between REITs and 1031 Exchanges: Is It Possible?

Published on: September 28, 2023

One question that often arises among savvy real estate investors nearing retirement is: “Can I exchange my property for shares in a REIT (Real Estate Investment Trust) using a 1031 Exchange?” While the straightforward answer is no, there’s a nuanced strategy involving 1031 and 721 exchanges, also known as UPREITs, that can allow for such a transition. If you’re tired of actively managing your properties and are looking at REITs as a simpler path to passive income, this information will be a game-changer for you.

Key Advantages of REITs

Before venturing further into the complicated world of 1031 and 721 exchanges, it’s essential to understand the inherent advantages that REITs offer:

  • Diversification: Investing in a portfolio of properties.
  • Professional Management: Experts handle the property management.
  • Transparency: Publicly available financial records.
  • Liquidity: Especially true for publicly traded REITs.

Delaware Statutory Trusts: A Stepping Stone

Back in 2004, the IRS ruled that a Delaware Statutory Trust (DST) could qualify as a like-kind investment under a 1031 exchange (Revenue Ruling 2004-86). This allows investors to sell one property and invest in a DST, serving as a midway point towards a REIT exit. Essentially, this becomes a two-step strategy:

  1. Step One: Gain beneficial interest in real estate through a DST, thereby meeting 1031 exchange requirements.
  2. Step Two: At the liquidation of DST investments, engage in a 721 exchange or UPREIT, converting your ownership into shares of a REIT.

Strategic Exits and Tax Implications

When crafted meticulously, this complex exchange can defer your capital gains tax from your initial property to a DST and, eventually, to a REIT. Be aware, though, that the sale of REIT shares will trigger a taxable event. On the upside, owning liquid shares allows you to better manage tax implications, offering flexibility that’s particularly beneficial for estate planning.

Points to Consider

Investors must be prudent and consult with legal and tax advisors, weighing the risks and benefits of each step in this complicated transaction. Due diligence includes thoroughly reading the memorandum or prospectus associated with the REIT and DST investments.

Next Steps: Consult, Plan, and Act

The combination of REITs and 1031 Exchanges is a nuanced process that offers remarkable benefits for the right investor. It may seem intricate, but with professional guidance and advanced planning, transitioning your active real estate investments into a REIT can be a rewarding move.

  • Consult: Talk to tax and legal advisors familiar with 1031 and 721 exchanges.
  • Plan: Review the risk-to-reward ratio and evaluate whether this strategy aligns with your financial goals.
  • Act: If this aligns with your strategy, consider making the first move to invest in a DST as the gateway to a REIT investment.

Don’t miss the chance to navigate the complex yet rewarding path from property ownership to REIT investment. Reach out to our 1031 exchange investment experts to guide you through each step, ensuring a seamless and tax-efficient transition.


Authored By:

1031 Investment Advisor

Nate oversees the daily operations, business development, and strategy for 1031 Exchange Place. He became interested in real estate from a young age due to his father's influence. After earning his real estate license at 18, Nate worked in the 1031 industry, focusing on business development through a unique white-labeling model. Following a religious mission in Taiwan, he continued in the industry until the 2008/2009 real estate crash. During the downturn, Nate pursued entrepreneurship and marketing, working with startups and outdoor companies. As the 1031 market recovered, he returned to work with his father, aiming to provide a more personalized experience for clients. Nate is passionate about outdoor activities and spends his free time with his wife and four sons, enjoying fly fishing, skiing, backpacking, rock climbing, and riding dirt bikes.