Selling Real Estate: Comparing The Returns

Each structure has its own set of benefits and trade-offs when selling real estate, but taking advantage of the personal residence exemption is a no brainer if you are eligible

1031 exchanges and Opportunity Zones can make sense if you want to reinvest in real estate, you are okay with a concentrated investment in between 1 and 3 real estate properties, and the personal residence exemption doesn’t cover the majority of the gains

Charitable Remainder Trusts will be a good fit if you are interested in diversifying your investments and the personal residence exemption doesn’t cover the majority of the gains

We’ve had years of record growth, but the stock market swings wildly day to day and a bear market is on the horizon — or may already be here. Real estate, by contrast, hasn’t fallen much if at all. Given these macro conditions, we’ve heard from many investors and operators recently who are looking to take real estate gains off the table.

In our previous article, we told you about four solutions to the high capital gains taxes that accompany real estate sales: the personal residence exemption, Charitable Remainder Unitrusts (and in particular a version called a NIMCRUT), Opportunity Zones, and 1031 Exchanges. Today, we’ll compare these strategies across several useful metrics, including, most importantly, the bottom line: how much you’ll earn over your lifetime using each.

Before we begin, if you need a quick refresher on these structures you can read our previous article here.

Real Estate Tax Planning Strategies

 Personal     Residence   Exemption Charitable   Remainder     Trusts Opportunity     Zone 1031 Exchange
 When is this   used?After selling your personal  residenceBefore the property is  soldAfter an asset is sold  but within 180 days of  the saleImmediately after  selling your property
 Primary tax   benefitIndividuals can exclude up to $250,000 of capital  gains, while a married  couple can exclude up to  $500,000, provided that  they meet certain criteriaDefer federal and  state taxes on the  property saleDefer taxes on capital  gains income until  2027; avoid taxes on  further gains from OZ  investment (if held for  10+ years)Defer capital gains  taxes on property sale
 Liquidity100% up frontCan receive a % of  the trust assets every  year or defer the  distributionsTypically no liquidity for  at least 5 years and  potentially 10 yearsNo liquidity until the  sale of the second  property
 Common issuesIf your capital gains are  significantly larger than  your exemption, you can  still face a big tax billDon’t have access to  all the sale proceeds  upfrontYour investment is more volatile because it is concentrated in a single asset class and geography — and in a limited number of propertiesYour investment is more volatile because it is concentrated in a single property
Real Estate planning strategies

Comparing the return on investment (ROI) of each structure

Let’s start with our goal and a few baseline assumptions.

Goal: Evaluate each of these tax planning structures based on post-tax return on investment after 20 years.

Baseline Assumptions:

  • Bryan and Hannah are 35 years old, married, and based in California, and they are planning to sell a $5m property with a $1m cost basis.
  • They expect to be hit with a 37% tax rate (because all of their earnings will be long-term capital gains). As a result, they would owe around $1.5 million in state and federal taxes on their sale (37% of their $4 million capital gain).
  • They expect the stock market to grow 10.5% annually (based on historical S&P returns), while an opportunity zone investment and a 1031 investment might appreciate 9% annually (based on historical REIT returns).
  • This also assumes a base level of expenses for each strategy.


The returns from each strategy are relatively similar, which just means that your goals and assumptions about the future are critical to your choice. (We’ll articulate some of the reasons why you may choose one strategy over another below)

  • Unitrust (or CRUTs): $22.6 million (along with an additional $5m charitable donation that can go to your favorite charity or your own Donor Advised Fund or Foundation)
  • 1031 Exchange: $23.4 million
  • Opportunity Zone: $21.3 million
  • Personal Exemption: $20.4 million
  • No Structure: 19.4 million

When to use these different real estate tax planning strategies?

Personal residence exemption. This is the most straightforward tool. If your property qualifies and your gains are lower than the exemption, you can claim this deduction — it’s a no brainer. If the gain is significantly higher than your exemption (or your property does not qualify) then you should start to look at the other alternatives.

When looking at the other alternatives, the big questions are:

  • Do you want to reinvest exclusively in real estate (and, if so, do you want to manage the investment yourself)?
  • At what rate do you expect real estate to grow annually, as compared to other asset classes (like stocks)?

Other options. If you want to invest in non-real estate investments, expect other asset classes to outperform real estate or are charitably inclined you should look at Charitable Remainder Trusts. If, instead, you want to reinvest in real estate, two options that may make sense are Opportunity Zones or using a 1031 exchange. An Opportunity Zone may make sense if you do not want to choose and manage the real estate investment yourself while a 1031 exchange could be a fit if you want to choose and manage the real estate directly.

Next Steps

Real estate is rare among capital assets, in that there are a number of viable options for tax planning. Each strategy has merits and drawbacks, and each could be a fit for you depending on the asset’s past appreciation and your investment preferences and growth expectations. There’s no “one size fits all” solution, and the right choice will be depend on your personal preferences and tax position.

Schedule a time to chat with our team or get started setting up your trust (at no cost and with no commitment)

About Valur

We built a platform to give everyone access to the tax and wealth building tools of the ultra-rich like Mark Zuckerberg and Phil Knight. We make it simple and seamless for our customers to take advantage of these hard to access tax advantaged structures so you can build your wealth more efficiently at less than half the cost of competitors. From picking the best strategy to taking care of all the setup and ongoing overhead, we make it easy and have helped create more than $500m in wealth for our customers.