In the latest episode of the Ready to Real Estate podcast, host and TRREB Chief Information Officer Jason Mercer and licensed paralegal Bita Di Lisi discuss why selling or buying a tenanted property can look straightforward on paper, but is often more complex in practice.

Recorded in front of a live audience at TRREB REALTOR® QUEST 2026, the conversation explores legal and practical issues that can affect REALTORS®, buyers, sellers, landlords, and tenants. Di Lisi highlights why REALTORS® need to approach tenanted transactions with realistic expectations, legal awareness, and the right professional guidance.

“In transactions involving tenanted properties, informed guidance is essential,” says Di Lisi. “The best time to get legal advice is before the property is listed, not after a problem starts.”

With affordability pressures and rental challenges shaping the market, clients are asking more detailed questions about below-market rents, vacant possession, and long-term investment value. Sellers also need to understand an important point, listing or selling a property does not, on its own, end a tenancy.

“You can never guarantee vacant possession on a tenanted property,” explains Di Lisi. “When buyers purchase a tenanted property, they step into the shoes of the landlord.”

Ending a tenancy involves a specific legal framework, and misunderstandings can lead to delays, disputes, and added costs. REALTORS® can help clients by understanding the fundamentals, setting realistic expectations, and bringing in qualified legal professionals when needed.

Tenant rights are defined by law. Timelines matter, and outcomes may depend on notice requirements, negotiated agreements, or proceedings before the Landlord and Tenant Board. The same care applies to showings. While lawful notice may allow access, a respectful and well-managed process can help maintain cooperation throughout the transaction.

Bita also addressed personal-use notices and the risks that come with misusing them. Reclaiming a property for personal occupation is not the same as preparing it for sale or trying to secure a higher rent. If a notice is served in bad faith, former tenants may have grounds to seek compensation. For clients and REALTORS®, clear intent, careful communication, and compassion for the tenant matter.

“A tenant is not an obstacle to a sale – they are a person living in their home,” says Di Lisi.

A legal “cash for keys” agreement between the landlord and tenant may offer a practical path before listing the property or pursuing personal use. This type of legally binding agreement involves the landlord paying a mutually agreed-upon amount to the tenant, who, in return, voluntarily vacates the property. But Di Lisi warns that this approach is not automatic and is not appropriate in every situation.

“Cash for keys can be effective, but only when both sides truly agree,” she adds.

Find out more about buying and selling tenanted properties by listening to the full conversation between Jason and Bita.