The 'held for' test
Both the property you sell and the one you buy must be held for investment or productive use in a trade or business. Intent matters: the IRS looks at how you actually used and held the property.
What qualifies
Rentals, commercial buildings, raw land held for appreciation, and other income or investment real estate generally qualify.
What doesn't
Your primary residence, a second home used mainly personally, and property held primarily for resale (fix-and-flip inventory) generally don't qualify.
The 'held for' test is about intent
Section 1031 turns on whether the property is held for productive use in a trade or business or for investment. This is a facts-and-circumstances test, not a checkbox. The IRS and courts look at how long you held it, how you actually used it, whether you rented it, how you reported it on prior returns (Schedule E for a rental, for instance), and your documented intent. Two identical duplexes can get opposite answers: one bought to rent and hold qualifies; one bought to renovate and flip within months is inventory and doesn't.
Vacation and second homes: the safe harbor
A personal vacation home generally doesn't qualify, but one held for investment can. Revenue Procedure 2008-16 provides a safe harbor: for each of the two 12-month periods before the exchange (and, for the replacement, after it), you must rent the property at fair market value for at least 14 days and limit your own personal use to the greater of 14 days or 10% of the days it was rented. Meet those tests and the IRS won't challenge the held-for-investment character. Fall outside them and you're relying on the general facts-and-circumstances test.
Flips and dealer property
If you're a dealer — someone who holds real estate primarily for sale to customers — that property is inventory and never qualifies for a 1031, no matter how you'd like to characterize it. Frequent, rapid flips, extensive marketing, and treating gains as ordinary business income all point to dealer status. Investors who occasionally renovate and hold can qualify, but a genuine buy-fix-sell business cannot exchange its inventory. When in doubt, a longer hold and rental use strengthen the investment case.
Mixed-use and converting a residence
A property can be part personal, part investment — say a duplex where you live in one unit and rent the other. Only the investment portion qualifies for exchange treatment; the residence portion may instead use the Section 121 primary-residence exclusion. You can also convert property between categories over time: move out of a former home, rent it at fair value for a year or more to establish investment intent, and then exchange it. The reverse works too — replacement property from an exchange can later become a residence, subject to holding-period and recapture considerations.
Entities and ownership
The taxpayer who sells must be the taxpayer who buys. That means a property held by an LLC generally must be exchanged by that same LLC (a single-member LLC is disregarded, so the individual owner works). Partnership interests themselves are not like-kind property — you exchange the underlying real estate, not the partnership. When co-owners want to go separate ways, techniques like a drop-and-swap (distributing tenancy-in-common interests before the exchange) are used, though they carry their own holding-intent scrutiny.
How to document investment intent
Because intent decides these cases, build a paper trail: rent the property at fair market value and keep leases and rent records, report it on Schedule E, avoid excessive personal use, hold it long enough that a hold-and-invest intent is credible (there's no bright-line minimum, but many advisors suggest a year or more spanning two tax years), and keep records of why you acquired and disposed of it. Good documentation is what separates a defensible exchange from a disqualified one if the IRS ever asks.
Foreign property is a separate silo
Location matters for like-kind character. U.S. real property is not like-kind to foreign real property. You can exchange one U.S. investment property for another, or one foreign property for another foreign property, but you cannot exchange a U.S. rental for a property in Mexico or Portugal and defer the gain. Investors with overseas holdings sometimes overlook this and assume any investment real estate qualifies — it doesn't cross the U.S. border.
Raw land and development intent
Vacant land held for appreciation is classic investment property and qualifies. But land bought to subdivide, develop, and sell can tip into dealer (inventory) territory that doesn't qualify — the same resale problem that disqualifies flips. Undeveloped land you simply hold, lease for farming or parking, or intend to build a rental on generally keeps its investment character. As always, intent and use, documented over time, decide the question.
Business-use property counts too
The statute covers property held for productive use in a trade or business, not just passive investment. That means the building your own business operates from — a warehouse, a dental office, a restaurant you own the real estate for — can be exchanged for other business or investment real estate. The land and building qualify; the business's equipment, inventory, and goodwill do not, since personal property was removed from Section 1031 in 2018.
Related-party and identification limits
Even qualifying investment property has to clear the mechanical rules. You must identify replacement property within 45 days and close within 180 days, and identification is limited by the three-property rule (up to three, any value) or the 200% rule (any number, up to twice the relinquished value). Exchanging with a related party adds a two-year holding requirement. None of these change whether property is 'investment property,' but they'll sink an otherwise-qualifying exchange if ignored.
Practical takeaway
Ask three questions of any property: Is it real property (not equipment or a partnership interest)? Is it held for investment or business use rather than personal use or resale? Is it U.S.-situated (matching a U.S. relinquished property)? Three yeses put you in qualifying territory; a maybe on the 'held for' question is where most disputes arise, so lean on rental history, Schedule E reporting, and a genuine hold period to make your intent unambiguous.
Converting a primary residence to investment property
A home you've lived in doesn't qualify while it's your residence, but you can convert it. Move out, rent it at fair market value, report it on Schedule E, and after a credible hold (many advisors suggest a year or more spanning two tax years) it can be exchanged as investment property. There's an added wrinkle worth knowing: if you'd lived in it long enough to also claim part of the Section 121 exclusion, careful sequencing can let you combine some tax-free exclusion with a deferred exchange — but the rules are technical, so get advice before relying on it.
Converting exchange property into a residence later
The reverse conversion is also possible: property you acquired in a 1031 as a rental can later become your home. To respect the exchange, hold and rent it as investment property first — the IRS safe harbor in Revenue Procedure 2008-16 looks for at least 14 days of fair-market rental and limited personal use in each of the two years after the exchange. Only after establishing investment use should you move in. And if you eventually sell and claim the Section 121 exclusion, gain attributable to the earlier depreciation and to nonqualified use is still taxable.
Documentation beats good intentions
The recurring theme across all of these categories is that the IRS taxes facts, not labels. Calling a flip an 'investment,' or a vacation home a 'rental,' won't survive scrutiny without a paper trail: signed leases, rents deposited, Schedule E filings, a genuine hold period, and a business rationale for the transaction. When investment character is clear and documented, a 1031 exchange is straightforward; when it's borderline, the documentation is what turns a deferral into a defensible one.
Seller-financing and installment notes
If you sell on an installment note and want to do a 1031, be careful: the note itself is not like-kind property, and receiving payments personally is boot. The note generally must be assigned to your qualified intermediary and either paid off or bought so that only like-kind real property funds the replacement. This is a common trap — investors assume any investment real estate qualifies, then blow the exchange by taking back paper they didn't route through the intermediary. Plan the financing structure before closing the sale.
Combining the § 121 home-sale exclusion with a 1031
The most powerful planning move sits at the seam between investment and personal property. If you acquire a replacement property in a 1031 exchange and later convert it to your primary residence, you can eventually use the § 121 exclusion (up to $250,000 single / $500,000 married) on part of the gain — but § 121(d)(10) requires you to own the property for at least five years after the exchange before any exclusion is allowed. The exclusion also does not shelter the depreciation recapture you accumulated, and the portion of gain tied to nonqualified use (the years it was a rental) is not excludable.
The reverse pairing helps too: a former primary residence that you convert into a rental can be exchanged under § 1031 once it is genuinely held for investment, and in some cases you can layer a partial § 121 exclusion on the personal-use gain and defer the rest under § 1031 in the same transaction (Rev. Proc. 2005-14). These combinations are potent but detail-sensitive; the five-year rule, recapture, and nonqualified-use fractions all have to be computed, so run the numbers before assuming the residence conversion wipes out the tax.
Partnership interests and the 'drop and swap'
A partnership (or multi-member LLC taxed as a partnership) can do a 1031 at the entity level, but a partnership interest itself is explicitly excluded from § 1031. The problem arises when some partners want to exchange and others want cash. The common workaround is a drop and swap: shortly before the sale, the partnership distributes the real estate to the partners as tenants-in-common (the 'drop'), and each former partner then independently decides to exchange their undivided interest or cash out (the 'swap').
The catch is the 'held for investment' timing. The IRS can argue the TIC interest was held too briefly — that the partner held it for the exchange, not for investment — so practitioners prefer to complete the drop well before the sale, ideally in a prior tax year, and to have the TIC owners behave like real co-owners in the interim. A 'swap and drop' (exchange first, then dissolve) raises the same seasoning concern on the back end. These moves are routine but scrutinized; the more time and genuine investment conduct between the restructuring and the sale, the stronger the position.
Refinancing around an exchange without creating boot
Investors often want to pull cash out of a property they are about to exchange. Doing a cash-out refinance immediately before selling the relinquished property is risky: if the refinance is done in contemplation of the exchange purely to extract equity tax-free, the IRS can treat the loan proceeds as disguised boot. There is no bright-line waiting period, but a refinance driven by an independent business purpose and separated in time from the sale is far more defensible.
Refinancing the replacement property after the exchange closes is generally the cleaner path to access equity, because the exchange is already complete and the new loan is a separate transaction. Either way, remember that debt matters to the exchange math: to fully defer gain you must replace the debt you paid off (or add equivalent cash), so aggressive pre-sale cash-out can also leave you unable to match debt on the replacement side and create taxable boot that way too.
What the courts say about the 'held for' test
Because 'held for investment' turns on intent rather than a fixed holding period, the case law is the real guide. In Bolker v. Commissioner, the Ninth Circuit held that a taxpayer need only lack an intent to sell or use the property personally — not affirmatively intend to keep it long-term — for property to be 'held for' investment. In Reesink v. Commissioner, the Tax Court allowed an exchange even though the taxpayers moved into the replacement property after renting it for several months, because the facts showed a genuine initial rental intent that changed only after unforeseen circumstances.
The lesson from these cases is consistent: the IRS looks at your intent at the time of the exchange and the objective facts that corroborate it — did you actually rent it, advertise it, report it on Schedule E, and treat it as an investment? A later change of plans driven by real events (a job loss, a family need, an unsolicited offer) does not retroactively poison an exchange that was properly motivated when made. What sinks taxpayers is evidence the investment purpose was never real — an immediate move-in, a pre-arranged resale, or a property never offered for rent.
Frequently asked questions
Does raw land qualify for a 1031?
Yes, if held for investment or business use. Land bought to subdivide and sell can be dealer inventory, which doesn't qualify.
Can I exchange U.S. property for foreign property?
No. U.S. real property is only like-kind to other U.S. real property; foreign real estate is a separate category that can only be exchanged for other foreign real estate.
Does a rental property qualify for a 1031?
Yes, property held for investment or business use qualifies.
Can I 1031 a flip?
Generally no — property held primarily for resale is inventory, not investment property.
Can I 1031 a vacation home?
Only if it's held for investment. The Rev. Proc. 2008-16 safe harbor requires renting it at least 14 days a year and keeping personal use under the greater of 14 days or 10% of rental days.
Is there a minimum holding period for a 1031?
The code sets no bright-line minimum, but property must be genuinely held for investment. Many advisors suggest holding at least a year across two tax years to support that intent.
Can I exchange out of a property held in an LLC?
Yes, but the same taxpayer must complete the exchange. A single-member LLC is disregarded, so its owner can exchange; a multi-member partnership exchanges the underlying real estate, not the membership interests.
Can I move into a property I got through a 1031 exchange?
Yes, but not right away. To later claim the § 121 home-sale exclusion you must own the property at least five years after the exchange, and the exclusion won't cover depreciation recapture or the gain tied to the years it was a rental (nonqualified use). Moving in immediately undercuts the investment-intent requirement.
How do partners who disagree handle a 1031 on partnership property?
Often through a 'drop and swap': the partnership distributes the property to the partners as tenants-in-common before the sale, and each partner then independently exchanges or cashes out. Because a partnership interest itself can't be exchanged, timing matters — do the drop well before the sale to support that each partner held their interest for investment.
Can I refinance to pull cash out before a 1031 exchange?
It's risky right before the sale — the IRS may treat cash pulled out in contemplation of the exchange as taxable boot. Refinancing the replacement property after the exchange closes is generally the cleaner way to access equity, and remember you must replace the paid-off debt to keep the gain fully deferred.
Sources
Educational information and estimates only. Not tax advice. Tax rules change and vary by situation; consult a qualified tax professional before acting.
