Should the Real Estate Be Part of the Deal?

When an owner owns both the school operation and the underlying real estate, the question of whether to sell them together is one of the first we work through. There is no universally correct answer — but there are clearly better and worse paths for any given owner.

Selling them together simplifies the transaction and often produces a higher headline price. It also concentrates the tax event into a single year and removes optionality.

Retaining the real estate and leasing it to the buyer preserves a long-term income stream and allows for a smaller, simpler transaction now. It also requires being a landlord — sometimes for decades — and ties your retirement income to the operational health of a business you no longer control.

We have helped owners do both. The right answer depends on your tax situation, your appetite for ongoing involvement, and what you intend to do with the proceeds.