Everything the listing agent tells you at a showing is information you can use when structuring your offer. Most buyers treat showings as tours; experienced buyers treat them as intelligence-gathering sessions.
About the sellers' situation
Why are the sellers moving? The answer isn't always forthcoming, but it's worth asking. A job relocation or an estate sale signals a motivated seller. A vague answer ("they found their next home") often just confirms they're move-up buyers, which is neutral.
Where are the sellers going? If they've already bought and closed on their next home, they're carrying two mortgages and are more motivated to close quickly and at price. If they haven't found anything yet, they may want a longer closing or a leaseback arrangement.
Has the listing been reduced? This is visible on the listing history in TRREB data your agent can pull. Reductions signal that the original price was too aggressive or the property has been sitting. Either way, it gives you negotiating context.
About the property
How long has it been listed? Days on market (DOM) is publicly visible, but ask the agent for the full history including any re-listings. A property that was listed six months ago, withdrawn, and relisted as "new" has more market time than the current DOM shows.
Are there any known defects or material latent defects? In Ontario, sellers are required to disclose known material latent defects — problems not visible on a normal inspection that make the property unfit for habitation or unsafe. The listing agent should have a seller property information statement (SPIS) if one was prepared, though completion of a SPIS is voluntary. Ask directly. If the agent deflects, note that.
Has there ever been water in the basement? This is a specific follow-up worth asking separately from the general defects question. Water damage is one of the most common undisclosed issues in Toronto's older housing stock.
When were the major systems last updated? Furnace, roof, windows, electrical. If the agent doesn't know, that's an answer too — sellers who have recently invested in upgrades usually want buyers to know.
What's included in the sale? Appliances, light fixtures, window coverings, hot water tank (owned vs. rented), and any rental equipment (furnace, air conditioner, alarm system) should be confirmed. Rental equipment transfers with the property but carries its monthly obligation.
About the market context
Have there been any offers? If offers have been presented and rejected, ask what the disconnect was — price, conditions, closing date. This helps you calibrate whether the gap between expectations and market reality has already been established.
Is there an offer date? Many Toronto listings set a specific offer date to accumulate competing bids. If there is one, you need to be ready to submit by that deadline. If there isn't one, the seller is accepting offers as they come, which changes the dynamic entirely.
What closing date works for the sellers? Aligning with the sellers' preferred closing date can make an otherwise equal offer more attractive at no additional cost to you.
What you won't get answered — and why that's fine
The listing agent represents the sellers. They are not obligated to share negotiating strategy, the sellers' bottom-line price, or anything that would disadvantage their client. A good listing agent will answer factual questions about the property and be transparent about the process; they won't give you inside information. Treat what they tell you as useful input, not the full picture, and work with your own agent to fill the gaps.