1031 Exchange: How the Successful Navigate Capital Gains
Successful investors—from high-net-worth individuals to family offices and long-time CRE pros—know to use one of the most powerful tools in the IRS tax code: the 1031 exchange.
It’s not a loophole. It’s not a trick. It’s a well-established strategy that allows you to sell investment property, defer capital gains taxes, and reinvest your full equity into another deal. No tax bill, no reset. Just uninterrupted momentum for your portfolio.
And if done strategically, it’s how some investors go decades without paying capital gains—building cash flow, appreciation, and generational wealth along the way.
In this post, we’ll break down exactly how 1031 exchanges work, why they’re so valuable, and how the most successful real estate investors use them to scale their portfolios. Whether you’re looking to trade up into a triple net asset, diversify markets, or reposition your real estate for retirement or legacy, this is a strategy you need to understand—and use.
what is a 1031 exchange and how does it work?
If you’ve ever sold an investment property and felt the sting of capital gains taxes, you’re not alone. Between federal tax, state tax, and depreciation recapture, a significant chunk of your equity can evaporate the moment you close.
That’s where the 1031 exchange comes in—a tool that allows you to defer those taxes entirely, so you can reinvest 100% of your profits into a new property and keep your portfolio growing.
🔁 The Basics of a 1031 Exchange
A 1031 exchange—named after Section 1031 of the IRS Code—lets you sell a piece of real estate used for investment or business purposes and roll those proceeds into another “like-kind” property without triggering capital gains tax at the time of sale.
It’s a tax deferral, not a tax elimination —but if you structure your portfolio right, you can continue exchanging indefinitely. More on that later.
Here’s the key: you must reinvest into another qualifying property, and the IRS has strict timelines and rules to follow.
📋 Key Requirements to Qualify
Not every deal qualifies for a 1031. Here’s what you need:
Investment or business use
Both the property you’re selling and the one you’re buying must be held for business or investment purposes—not personal use.
Like-kind exchange
“Like-kind” doesn’t mean identical—it simply means both properties are real estate held for investment.
You can exchange a retail strip center for a flex industrial building, or a multifamily asset for a triple net lease.
Same taxpayer/entity
The same entity that sells the relinquished property must acquire the replacement.
Use a Qualified Intermediary (QI)
You cannot take possession of the funds. A QI must hold and transfer the proceeds on your behalf.
⏱️ The 1031 Timeline: Two Critical Deadlines
The IRS gives you two key timeframes to work within—and missing either one means your exchange will fail, and taxes will be due.
45 Days to Identify Replacement Property
From the day you close the sale of your relinquished property, you have 45 calendar days to identify (in writing) the potential replacement property or properties.180 Days to Close
From the same day of sale, you have 180 days total to close on the new property. The 45-day identification period is included in the 180-day window.
Pro tip: Start sourcing your replacement property before you sell—especially in tight markets. This is where experienced brokers and acquisition teams are invaluable.
🔒 Why the 1031 Is So Powerful
Most investors look at taxes as a cost of doing business. Smart investors look at taxes as something to manage with strategy.
When you use a 1031 exchange:
You defer your capital gains tax bill
You keep 100% of your equity working for you
You get to trade up into larger, more valuable, or better-positioned assets
You protect your buying power—and scale your portfolio faster
Used correctly, this isn’t just a tax tool. It’s a wealth multiplier.
Next, we’ll look at why this strategy is especially popular among high-net-worth investors and how they use it to grow their portfolios without interruption.
Why the wealthy love the 1031 exchange
The ultra-wealthy don’t just make money—they know how to keep it, reinvest it, and grow it tax-efficiently. That’s exactly why the 1031 exchange is a cornerstone in the playbook of savvy real estate investors, family offices, and institutional buyers.
This isn’t just about saving money on one deal. It’s about unlocking long-term, tax-deferred growth—the kind that compounds over decades and builds legacy wealth.
💰 More Buying Power
When you sell an investment property, you typically owe:
Federal capital gains tax (up to 20%)
State capital gains tax (varies)
Depreciation recapture tax (25% on prior write-offs)
Altogether, you could lose 25–35% of your gains just to taxes.
But when you use a 1031 exchange, none of that is due at closing. Instead, you roll the full proceeds into your next deal—giving you:
A larger down payment
More leverage with lenders
Stronger negotiating power with sellers
A faster path to higher-value assets
You’re putting the tax back to work.
📈 Scale Faster Without Shrinking Your Equity
Let’s say you sell a $2M property with $1M in equity and $400K in potential tax liability. Without a 1031, you’d only have $600K left to reinvest.
With a 1031, you keep the full $1M, which means:
You can acquire a larger asset with better income potential
You maintain momentum in your portfolio
You avoid the erosion of your purchasing power
Over time, repeating this process allows you to move from smaller, management-heavy properties to larger, more passive, higher-yield assets—without taking a tax hit every step of the way.
🔄 Upgrade, Consolidate, or Diversify—On Your Terms
The flexibility of a 1031 exchange makes it ideal for a range of investor strategies:
Trade up: Sell a small multifamily and move into a triple net lease with a corporate tenant.
Consolidate: Sell multiple smaller properties and exchange into a single, more efficient asset.
Diversify: Move capital into different markets or sectors (e.g., retail → flex, or one metro → multiple regions).
This is why so many seasoned investors use 1031s as part of their long-term portfolio design.
🧠 It’s Not Just a Tax Tool—It’s a Wealth Strategy
Here’s what sets the pros apart: they don’t just use 1031s to defer taxes—they use them to build leverage, simplify operations, reduce risk, and create intergenerational wealth.
And when structured properly, the benefits extend even beyond the investor’s lifetime (we’ll cover that in Section 4 with the “step-up in basis”).
For now, just know this: the 1031 isn’t just how the wealthy save—it’s how they scale.
The timeline and process and how to get it right
A 1031 exchange is one of the most powerful tax strategies available to real estate investors—but it’s also one of the most technical.
Miss a deadline or misstep in the process, and your exchange can fail—leaving you with a surprise tax bill you thought you’d deferred.
That’s why knowing the timeline, following the rules, and working with the right team is absolutely critical. Let’s walk through how to get it right, from sale to reinvestment.
⏱️ The Two Most Important Deadlines
The IRS gives you two time windows that must be followed exactly—no extensions, no do-overs.
📍 45-Day Identification Window
You have 45 calendar days from the closing date of your relinquished property to identify potential replacement properties.
Identification must be in writing, delivered to your Qualified Intermediary (QI).
You can use one of three identification rules:
3-Property Rule: Identify up to 3 potential properties—regardless of value.
200% Rule: Identify unlimited properties, as long as the total value doesn’t exceed 200% of the relinquished property’s sale price.
95% Rule: Identify any number of properties, but you must ultimately purchase 95% or more of the total identified value.
📍 180-Day Closing Window
From the date you close the sale of your relinquished property, you have 180 total calendar days to close on one or more of your identified replacement properties.
The 45-day identification period is included in this 180-day window.
Miss either deadline and the exchange is disqualified.
🧑💼 The Role of the Qualified Intermediary (QI)
A QI is a neutral third party required to handle the exchange. Their job is to:
Receive and hold the sale proceeds so you never take constructive receipt of the funds
Document the exchange paperwork and timelines
Ensure the transaction complies with IRS regulations
Important: You cannot act as your own intermediary, and your attorney, accountant, or real estate agent usually doesn’t qualify either. Work with a QI experienced specifically in 1031 exchanges.
🧾 Structuring the Exchange Correctly
Here are a few key rules and best practices that trip up inexperienced investors:
✅ Same Title, Same Taxpayer
The name on the relinquished property’s title must match the name on the replacement property’s title (or the tax entity).
If you sell in your personal name, you must buy in your personal name—unless you’ve structured a proper entity strategy.
✅ Equal or Greater Value
To defer all capital gains, your replacement property must be of equal or greater value than the one you sold.
You must also replace the same amount of debt (or inject cash to offset any reduction in leverage).
If you fail to meet those thresholds, you’ll pay taxes on the difference—called “boot.”
✅ Line Up Financing Early
Delays in financing can kill your 180-day timeline. Get pre-approved and underwrite your targets well in advance.
Many investors identify replacement properties before selling the relinquished asset to avoid timing issues.
💡 Pro Tip: Start Planning Before You Sell
Waiting until your property is under contract to think about a 1031 is often too late. Instead:
Talk to your QI, broker, and tax advisor before listing your property
Begin sourcing viable replacement properties early
Understand your financing needs and lender requirements upfront
This way, by the time you close your sale, you’re not scrambling—you’re executing.
Advanced Strategies the pros use
The standard 1031 exchange is already a powerful tool—but experienced investors and high-net-worth families know how to take it even further.
From solving timing issues to preparing for retirement and even wiping out capital gains altogether, these advanced tactics can help you maximize flexibility, preserve wealth, and simplify ownership.
Let’s walk through the moves that the pros use.
🔄 Reverse Exchanges: Buy First, Sell Later
In a hot market, finding a replacement property before you sell your current one can be a smart move. But under normal 1031 rules, you must sell first, then buy.
That’s where a reverse exchange comes in.
Here’s how it works:
Your Qualified Intermediary temporarily holds the title to your replacement property, while you prepare to sell your relinquished property.
Once the sale is complete (within 180 days), the new property is transferred to you, completing the exchange.
This structure is more complex and often more expensive, but it can be a game-changer if:
Inventory is tight
You’ve found a can’t-miss deal
You want to avoid sitting on cash or missing your 45-day window
🏢 Delaware Statutory Trusts (DSTs): The Passive 1031 Solution
For investors looking to step away from active property management—or who can’t find a suitable replacement—DSTs offer a powerful solution.
A DST allows you to:
Exchange into fractional ownership of large, institutional-grade properties
Receive passive monthly income with no management responsibility
Still satisfy 1031 exchange requirements
DSTs are often used by:
Retiring landlords who want mailbox money without selling outright
Family offices seeking portfolio diversification
Heirs inheriting 1031 assets who want out of day-to-day operations
Important: DSTs are illiquid and typically long-term holds, so they’re best for investors with a clear passive income goal.
🏛️ The Step-Up in Basis: The Ultimate Wealth Preservation Strategy
This is the part most investors miss—and where generational wealth gets protected.
If you hold your 1031-exchanged property until death, your heirs receive a step-up in basis to the property’s current market value.
That means:
All deferred capital gains are wiped out
Your heirs can sell the property with little or no tax liability
You’ve built a portfolio tax-deferred—and passed it on tax-free
This is why so many wealthy families continue to exchange for decades. It’s not about avoiding taxes forever—it’s about deferring until never.
Who They’re For and Why They Work
🔄 Reverse Exchange
Best for: Investors in fast-moving or inventory-constrained markets
Why it works: Lets you acquire the replacement property before selling your current one—avoiding rushed decisions or losing great deals due to timing constraints.
🏢 Delaware Statutory Trust (DST)
Best for: Investors looking for passive income or preparing to retire from active property management
Why it works: Allows you to reinvest 1031 proceeds into a fractional interest in large, professionally managed assets, while still meeting IRS requirements.
🏛️ Step-Up in Basis
Best for: Investors focused on generational wealth and estate planning
Why it works: When a 1031-held property is passed down to heirs, they receive a step-up in cost basis, effectively eliminating all deferred capital gains taxes.
Common mistakes and how to avoid them
The 1031 exchange can be one of the most effective tools in your real estate investing arsenal—but only if you execute it correctly.
The rules are rigid, the timelines are tight, and the IRS doesn’t allow for “close enough.” One small oversight can turn a tax-deferred transaction into a taxable event. Below are the most common mistakes investors make—and how you can avoid them to keep your portfolio moving forward, tax-efficient and intact.
❌ Mistake #1: Waiting Too Long to Identify a Replacement Property
Many investors make the mistake of listing their property without lining up the next acquisition. The result? Scrambling to find a deal during the 45-day identification window—and often settling for a poor fit or missing the deadline altogether.
How to avoid it:
Start sourcing potential replacement properties before you sell. Partner with an experienced broker or acquisition team who understands your criteria and can move quickly.
❌ Mistake #2: Mishandling the Exchange Funds
One of the quickest ways to invalidate a 1031 exchange is to touch the money. If you take receipt of the sale proceeds—even for a moment—you trigger a taxable event.
How to avoid it:
Use a Qualified Intermediary (QI)—a third-party professional who holds and transfers the funds for you. Don’t try to DIY this. Your QI must be in place before the first closing.
❌ Mistake #3: Not Matching Debt and Equity
Selling a property with $1M in value and $400K in debt? You’ll need to purchase a replacement property of equal or greater value and replace that debt—either by taking on new debt or injecting the same amount of equity.
If you don’t, the difference becomes boot, and you’ll pay taxes on it.
How to avoid it:
Work with your lender and QI to structure your financing in advance. Make sure you understand the total debt and equity required to fully defer your gain.
❌ Mistake #4: Choosing the Wrong Team
Not all intermediaries, attorneys, or brokers are well-versed in 1031 exchanges. Choosing the wrong advisor can lead to documentation issues, missed deadlines, or misinterpretation of the rules.
How to avoid it:
Only work with professionals who specialize in commercial real estate and have experience executing 1031 exchanges. Ask for examples of past transactions, timelines, and potential challenges up front.
❌ Mistake #5: Using the 1031 When You Shouldn’t
Not every sale warrants a 1031. If your gain is small, or if you’re planning to take the cash and sit on the sidelines for a while, trying to force an exchange can backfire.
How to avoid it:
Work with your tax advisor to calculate the true gain and determine whether deferring is worth the effort. Sometimes, paying a small capital gains bill now is better than rushing into a subpar deal just to avoid it.
The key takeaway?
The 1031 is a precision tool. Used correctly, it can help you grow your portfolio exponentially without triggering a tax event. Used sloppily, it can cost you time, money, and opportunity.
Conclusion
The most successful commercial real estate investors don’t just find great deals—they know how to keep their capital compounding and defer taxes with precision.
That’s the real power of the 1031 exchange.
Used strategically, it allows you to:
Reinvest 100% of your equity into bigger and better properties
Scale your portfolio without paying taxes at every step
Shift into more passive assets as your goals evolve
Create a legacy that can be passed down without a massive tax bill
This isn’t just about saving money—it’s about building momentum. And when you combine smart acquisitions with tax-efficient planning, your portfolio becomes a machine for long-term, generational wealth.
Ready to Put the 1031 Strategy to Work?
If you’re considering selling an investment property—or want help identifying your next acquisition—we’re here to help you navigate the process. Think long-term. Plan ahead. And keep more of what you earn working for you.
For those interested in delving deeper into commercial real estate investing, check out our course offerings. The courses provide in-depth insights, real-world case studies, and practical strategies to help you navigate the complexities of commercial real estate and achieve success in your ventures. Whether you're a seasoned investor or just starting in the world of commercial real estate, there's always more to learn. Equip yourself with the knowledge and tools you need to thrive in commercial real estate!
For the past decade, luxury apartments have dominated real estate headlines—and investor attention. Sleek downtown towers, rooftop pools, and Class A rents felt like the gold standard. But in 2025, the cracks are showing.
Across the country, we’re seeing rising vacancy rates, flatlining rents, and a flood of new high-end units hitting already saturated markets. Combine that with inflation, elevated interest rates, and construction costs that just won’t quit, and suddenly, that “can’t-miss” luxury multifamily project doesn’t pencil like it used to.
Meanwhile, the most seasoned investors—the ones focused on cash flow, downside protection, and essential demand—have already pivoted. They’re moving capital into real estate assets that don’t rely on trends or trophy aesthetics. Assets that deliver consistent occupancy, predictable income, and long-term tenant need.
In this post, we’re breaking down the asset classes that are taking over where luxury apartments are falling short—from flex space to medical offices—and why they’re attracting everyone from family offices to first-time CRE buyers.
If you’re thinking about what to buy next (or what to avoid), this is your roadmap.