Real Estate Tax Calc
The worked example: a business sells and leases back its headquarters
A manufacturing company owns its 20,000-square-foot production facility in Ohio. It purchased the building in 2010 for $1,200,000 (land: $200,000, building: $1,000,000). After 16 years of depreciation, the adjusted basis is:
Building basis after depreciation: $1,000,000 − ($1,000,000 ÷ 39 × 16 × depreciation factor) ≈ $1,000,000 − $410,256 = $589,744
Land basis: $200,000 (not depreciated)
Total adjusted basis: $789,744
The company sells the building to a real estate investor for $2,500,000 (land: $400,000, building: $2,100,000) on January 1, 2026, and simultaneously signs a 15-year NNN lease at $175,000/year.
Seller-tenant's tax at closing (2026):
- Amount realized: $2,500,000
- Adjusted basis: $789,744
- Total gain: $1,710,256
- Unrecaptured §1250 gain (depreciation taken on building, capped at 25% rate): $410,256
- §1231 gain above recapture (long-term capital gain rate): $1,710,256 − $410,256 = $1,300,000
Total federal tax at closing (illustrative, 20% LTCG + 3.8% NIIT on §1231 gain, 25% on recapture): ($1,300,000 × 23.8%) + ($410,256 × 25%) = $309,400 + $102,564 = $411,964.
The seller receives $2,500,000 cash, pays roughly $412,000 in federal tax, and nets ~$2,088,000 — plus the right to continue using the building for 15 years. Each year going forward, the $175,000 rent is fully deductible under §162, reducing the company's taxable income by $175,000/year. At a 25% marginal rate, that is $43,750/year in tax savings over 15 years = $656,250 in cumulative future tax savings, partially offsetting the $412K recognized at closing.
Buyer-landlord's tax picture:
- Depreciable basis: $2,100,000 (building only; land not depreciable)
- Annual straight-line depreciation (39 years, mid-month in year 1): ~$53,846/year at full years; ~$44,872 in year 1 (10.5/12 months)
- Annual rental income: $175,000
- Net income before deductions (year 1): $175,000 − $44,872 − other deductions
- Cost segregation potential: if a study identifies $400,000 in 5- and 15-year components, bonus depreciation (20% in 2026 on personal property; 100% available on §179 personal property) could add substantial first-year deductions
Under a true NNN lease, the tenant pays property taxes, insurance, and maintenance directly. The buyer reports only the $175,000 base rent and takes only depreciation and financing costs (if any) as deductions.
The seller's perspective: trading equity for rent deductions
The core appeal of a sale-leaseback for a business is converting a large, illiquid asset into working capital while retaining occupancy. From a tax perspective, the exchange is:
- Give up: depreciation on the building (since they no longer own it), and a lump-sum tax at closing on the accumulated gain.
- Get: full rent deductibility going forward — often significantly more valuable than the depreciation deduction that was replaced, because the seller deducts 100% of rent vs. the building's 1/39th annual depreciation fraction. On a $2.5M sale with $175K/year rent, the annual rent deduction is 7% of the sale price vs. the annual depreciation deduction before the sale of only 2.6% of the original cost.
This dynamic is why sale-leasebacks are especially attractive to businesses that have fully or largely depreciated their buildings. Once a building is depreciated down to zero basis, the owner captures no annual tax benefit from ownership and bears all the upside and downside of real estate appreciation. Selling crystallizes the gain, the rent is fully deductible, and the company redeploys the sale proceeds in its core business.
The buyer's perspective: NNN income plus depreciation
For the investor, a sale-leaseback acquisition is essentially the same as buying any NNN investment property — except the tenant is the previous owner, who typically has a strong economic incentive to maintain the property and honor the lease (they need the building to run their business). This creditworthiness dynamic often makes sale-leaseback properties more attractive than a typical NNN with a franchise tenant.
The buyer's tax treatment is straightforward:
- Purchase price allocates between land (not depreciable) and building (39-year MACRS, mid-month convention).
- A cost segregation study at acquisition can identify 5-, 7-, and 15-year components embedded in the purchase price — parking, specialized electrical, lighting, HVAC distribution, land improvements — and accelerate deductions. With bonus depreciation, significant first-year write-offs are possible.
- Annual rental income from the NNN lease is passive income (unless the buyer qualifies as a real estate professional).
- At eventual sale, the buyer faces the same gain-recognition and recapture mechanics as any commercial property sale — §1250 unrecaptured gain on building depreciation plus §1231 gain above that.
The buyer should also confirm that the lease term and structure survive a potential insolvency of the seller-tenant. A sale-leaseback where the seller-tenant later files bankruptcy can expose the landlord to lease rejection risk — a real concern for smaller businesses using the leaseback as emergency liquidity.
Can the seller use a 1031 exchange to defer the gain?
In a pure sale-leaseback, the seller receives cash — not real property — in exchange for the building. Because the seller does not acquire like-kind real property as replacement, there is no 1031 exchange on the sale itself. The gain is fully recognized at closing.
However, the seller can combine a sale-leaseback with a 1031 exchange if they simultaneously identify and acquire other like-kind real property with the sale proceeds. For example, a company that owns two buildings could sell both in a simultaneous transaction, leaseback one (needing the operational continuity), and use the other building's proceeds to acquire a 1031 replacement property. The gain on the leased-back building is recognized; the gain on the other building is deferred.
The buyer in a sale-leaseback transaction can also use the acquisition as 1031 replacement property, deferring gain from the sale of their prior property. From the buyer's perspective, a sale-leaseback target is simply a commercial property acquisition — a qualifying like-kind replacement.
State tax considerations
Most states follow federal treatment for gain recognition at sale and rent deductibility — but the allocation of the sale price between land and building, state depreciation conformity, and bonus depreciation addback rules vary. Several states do not conform to accelerated federal bonus depreciation and require the buyer to depreciate the full purchase price over 39 years at the state level, recovering the difference over time. Some states also impose a real estate transfer tax on the sale itself, which the parties should negotiate in the purchase contract (typically paid by seller, but negotiable).
For multi-state businesses, the sale of a building in State X while operating in State Y may apportion the gain under State X's nonresident rules. The rent deduction reduces apportioned income in both states proportionally. Work with a state-and-local tax advisor before closing on a sale-leaseback involving an out-of-state property.
Frequently asked questions
Does a sale-leaseback trigger a taxable gain?
Yes, in most cases. The seller recognizes gain (or loss) on the sale in the year of closing — it is a normal IRC §1001 disposition. The character of the gain depends on how long the building was held and how much depreciation was taken: depreciation is recaptured as unrecaptured §1250 gain (25% rate), and the balance is §1231 long-term capital gain.
Can a seller-tenant do a 1031 exchange to defer the gain?
Not on a pure sale-leaseback — the seller receives cash, not like-kind real property, so there is no exchange. The seller can combine the transaction with a simultaneous 1031 acquisition of other real property, deferring gain on that portion. The buyer can use the acquisition as 1031 replacement property.
How does the buyer-landlord depreciate a sale-leaseback property?
The buyer depreciates the building allocation of the purchase price over 39 years (nonresidential real property, mid-month convention). Basis equals the purchase price allocated to the building. A cost segregation study can reclassify shorter-life components for accelerated deductions.
Are the rent payments deductible for the seller-tenant?
Yes. Rent paid to use business property is deductible under IRC §162 as an ordinary and necessary business expense. The deduction is taken in full each year the rent is paid, with no spread over the lease term. Related-party and non-arm's-length transactions face scrutiny on whether the rent is at fair market value.
What are the tax risks if a sale-leaseback is recharacterized?
If the IRS determines the transaction is actually a financing arrangement, the seller loses the rent deduction, the sale is treated as a loan, and the gain is deferred while the seller retains beneficial ownership. Courts look at whether ownership risks transferred, whether the sale price was at fair market value, and whether the arrangement has economic substance beyond tax benefits.
Educational information and estimates only. Not tax advice. Tax rules change and vary by situation; consult a qualified tax professional before acting.