Sale-Leaseback: How It Works, Who It Fits, and the Catch

How a sale-leaseback works

A company (or its owner, through a real estate LLC) sells the building it uses to an investor. At closing, the seller signs a lease, usually triple net and often 10 to 25 years with renewal options, and keeps operating in the space. The investor buys a property with a tenant in place; the seller gets cash equal to the building's market value instead of a loan limited by a lender's loan-to-value rules.

Tax effects for the seller:

• Gain is recognized under IRC 1001 in the year of sale: unrecaptured Section 1250 gain on prior depreciation, capital gain on the rest, plus state tax.
• Rent is deductible under IRC 162(a)(3) as long as the business does not take title or equity in the property. That includes the land portion, which was never depreciable while owned.
• Depreciation shifts to the buyer. The seller gives up future depreciation on the building.
• Large leases with deferred or stepped rent can fall under IRC 467, which requires accrual of rent on a set schedule once total payments exceed $250,000, and can impose constant rental accrual on certain leasebacks with a tax-avoidance principal purpose.

Who it fits, and who it does not

Good fit:

• Owners who are selling the operating business: separating the real estate sale from the business sale can raise total value and give the business buyer a clean lease.
• Companies that need growth capital or want to retire expensive debt.
• Owners who want to stay at the location but stop being landlords to themselves.

Poor fit:

• Businesses whose cash flow cannot comfortably support market rent for the full term.
• Owners who expect the property to appreciate strongly and want to keep that upside.
• Owners hoping to avoid the tax on the sale. Without a 1031 or installment structure, the gain is due for the sale year.

Worked example (engine-computed)

Assumptions (labeled, not a client case): married filing jointly, 2026, $150,000 of other ordinary income. Their LLC sells a building to an investor for $4,000,000 and leases it back to their company. Original cost $2,500,000, depreciation taken $1,000,000, adjusted basis $1,500,000. Gain is $2,500,000: $1,000,000 of unrecaptured Section 1250 gain and $1,500,000 of other long-term gain.

Computed with the Big Sale Tax engine as the increase in 2026 tax. One adjustment the engine does not make: if the building was rented to a business in which the owners materially participate, the gain may be treated as nonpassive and excluded from the net investment income tax under Treas. Reg. 1.1411-4(g)(6)(ii), which would remove the $91,200 line. Ask your CPA to confirm the activity status.

IRS stance and audit risk

Sale-leasebacks are ordinary commercial transactions and are not listed transactions. The tax questions are about substance:

• Sale or loan? In Frank Lyon Co. v. United States, 435 U.S. 561 (1978), the Supreme Court respected a sale-leaseback where there was a genuine multiple-party transaction with economic substance, compelled by business or regulatory realities and not shaped solely by tax avoidance. Where the seller keeps the benefits and burdens of ownership, such as a repurchase option at a fixed below-market price, rent that simply amortizes the price like loan payments, or the buyer bearing no real estate risk, the IRS can treat the deal as a financing. Then there is no sale, the seller keeps depreciating, and part of each rent payment is principal, not deductible rent.
• The 30 year lease rule. Treas. Reg. 1.1031(a)-1(c) treats a leasehold of 30 years or more as like-kind to a fee interest. Courts split on what that means for a sale-leaseback at a loss: Century Electric Co. v. Commissioner, 192 F.2d 155 (8th Cir. 1951), treated one as an exchange and disallowed the loss, while Jordan Marsh Co. v. Commissioner, 269 F.2d 453 (2d Cir. 1959), and Leslie Co. v. Commissioner, 539 F.2d 943 (3d Cir. 1976), allowed losses where the price and rent were at market. Keep total lease terms, including renewals, in view.
• Related buyers. A sale to a controlled entity can turn gain on depreciable property into ordinary income under IRC 1239, and related-party sale rules can deny the installment method.
• Rent level. Rent above or below market between related parties invites reallocation.

Costs and fees

• Brokerage commission, legal fees for the purchase agreement and lease, title, escrow and transfer taxes.
• Prepayment penalties on existing mortgages.
• The economic cost: you pay rent at the investor's required yield for the life of the lease, and give up appreciation and depreciation.
• Lease obligations appear on the balance sheet under current lease accounting, which lenders and business buyers will review.

How it compares with a Section 453 installment sale

A sale-leaseback is about liquidity and keeping the location; by itself it does not defer tax. Two pairings can change that:

• Sale-leaseback with seller financing. If the investor pays part of the price with a note, the Section 453 installment method spreads the gain (other than any recapture income) as principal is paid. Your company is then both tenant and lender to the same owner, so set the note at or above the applicable federal rate and protect it with a down payment, a first-position deed of trust on the building, cross-default with the lease, and insurance requirements (see seller financing). If the buyer defaults, Section 1038 governs taking the property back.
• Sale-leaseback plus a 1031. The owner's LLC can exchange the sale proceeds into other investment real estate and defer the gain while the business still occupies the old building under its lease. A 1031 exchange keeps you invested in real estate.

The $5,000 Big Sale Tax Analysis compares a straight sale-leaseback, each pairing and a hold.

Frequently asked questions