Dempsey, Milton - September 2026 Real Estate Report

Dempsey, Milton: Your Neighbour Just Asked If Now Is a Good Time to Sell - Here Is the Honest Answer

If you own a home in Dempsey and you have been quietly wondering what it is actually worth right now, you are not alone. The market here is doing some interesting things depending on whether you own a house or a condo - and the gap between those two stories is worth paying attention to.

The Vibe: Houses vs. Condos in Dempsey

Houses - Holding Steady With Some Muscle

We are seeing houses in Dempsey hold their ground. The average HonestDoor Price sits at $1,021,597 - up 3.32% from the previous period. That is not a headline-grabbing spike, but it is real, positive movement. For context, the predicted market value for houses here is $988,770, which is ticking up from the 3-month moving average of $986,481. The direction is right.

• Average HonestDoor Price: $1,021,597 (up 3.32%)
• Average sale price this period: $735,000
• Current average listing price: $739,000
• Price per square foot: $420
• Homes sold for 99.46% of list price - buyers are paying close to asking, but just under
• Average days on market: 21 days
• Estimated monthly rent: $4,186 with a rental yield of 4.70%
• Airbnb income potential: approximately $208 per month

One thing worth noting - only 1 house sold in the tracked period. That is a thin sample, so treat the sale price data as a directional signal, not a definitive verdict. The HonestDoor Price, which pulls from a much broader data set, gives us a more reliable picture of where values actually sit.

On the neighbourhood leaderboard, Dempsey houses rank 12 out of 26 neighbourhoods in Milton for growth - that puts us in the above-average tier. Days on market rank is 4 out of 12, meaning homes here move moderately fast compared to the rest of Milton. The one number to watch: price rank is 13 out of 13, making Dempsey the most affordable option among comparable Milton neighbourhoods. That is either a buying opportunity or a ceiling question, depending on which side of the transaction you are on.

Condos - Taking a Breather

The condo story in Dempsey is a different conversation. The average HonestDoor Price dropped 5.82% to $516,370. That is a real pullback. Every nearby neighbourhood - Clarke at $534,658, Dorset Park at $590,939, and Timberlea at $586,463 - is pricing higher than us right now. If you own a condo here, that context matters.

• Average HonestDoor Price: $516,370 (down 5.82%)
• Predicted market value: $548,271 (up from 3-month average of $544,831)
• Estimated monthly rent: $2,731 with a rental yield of 3.74%
• Airbnb income potential: approximately $136 per month
• Recent value change: up 2.41%
• Growth rank: 18 out of 24 neighbourhoods in Milton - below average

The short-term predicted value is showing a small recovery - $548,271 versus a 3-month average of $544,831 - so the floor may be in. But we are sitting below Clarke at $567,010 and well below Dorset Park at $624,790 on predicted values. Condo owners here need to watch this gap carefully.

The Secret Sauce: Why Your HonestDoor Price Matters More Than Your Tax Assessment Right Now

Here is the thing about your city assessment - it is a snapshot taken in the past, updated on a schedule that has nothing to do with what the market is doing today. If your assessment was set when the market looked different, it could be telling you a number that is thousands of dollars off from reality - in either direction.

The HonestDoor Price is a real-time estimate. It is recalculated continuously using current sales data, market trends, and comparable properties. For Dempsey house owners, that means the $1,021,597 average reflects what is happening now - not what happened 12 or 18 months ago. For condo owners, it is flagging the 5.82% dip in real time, so you are not caught off guard.

Think of it this way: your tax assessment tells you what the city thinks your home was worth. The HonestDoor Price tells you what a buyer would likely pay for it this week. Those two numbers are not always the same - and the difference can change your entire strategy.

The "So What?" - Thinking About Selling This Summer?

If you own a house in Dempsey and are thinking about listing this summer, the timing is not bad. Values are up 3.32%, homes are selling at 99.46% of list price, and the 21-day average market time means you are not sitting on the market forever. The fact that Dempsey ranks as the most affordable in Milton could actually work in your favour - buyers who have been priced out of Timberlea or other nearby neighbourhoods are going to be looking here.

If you own a condo, the honest advice is to get your HonestDoor Price updated before you make any decisions. The 5.82% drop is a signal to understand, not panic over - but you want to price strategically from the start. Sitting above market in a below-average growth neighbourhood is how listings go stale.

Either way, the smartest first move is the same: check your HonestDoor Price at HonestDoor.com. It is free, it is current, and it gives you the real-world number - not the government's best guess from last year.

This information is all based on our opinions based on the information available to us. Everyone's situation may be different and you should reach out to us for more personalized information.