Dempsey, Milton - July 2026 Real Estate Report

Dempsey, Milton: Prices Are Holding, But the Market Is Sending Signals You Should Not Ignore

If you own a home in Dempsey and you have been quietly wondering whether now is the time to make a move, here is the honest read on what is happening right now on your street.

The Vibe: What Is Actually Going On in Dempsey

Let us split this into two stories, because houses and condos are telling very different ones right now.

Houses in Dempsey

The house market here is steady, but it is not setting any records. The average sale price is sitting at $735,000, with listings averaging $739,000 this month. Buyers are paying 99.46% of list price - so yes, they are getting a small discount, but sellers are not giving the house away either. That is a stable, balanced dynamic.

• Average HonestDoor Price: $982,523 (down 0.57% from last period)
• Average sale price: $735,000
• Average list price this month: $739,000
• Price per square foot: $420
• Sale-to-list ratio: 99.46% - buyers are paying just below asking
• Average days on market: 21 days
• Predicted market value: $988,151
• 3-month moving average: $993,308 (values are dipping slightly)
• Estimated monthly rent: $4,190
• Rental yield: 4.70%
• Recent value change: -1.78%

The days-on-market rank is 5 out of 11 in Milton - so houses here are moving at a moderately fast pace compared to the rest of the city. That is actually a quiet strength for sellers. The tougher number is the growth rank: 22 out of 26 neighbourhoods in Milton. Dempsey houses are sitting near the bottom of the leaderboard when it comes to price appreciation right now. That does not mean panic - it means awareness.

On price rank, Dempsey sits at 11 out of 11 - the most affordable end of Milton for houses. For buyers, that is a genuine entry point. For sellers, it means you are competing on value, not prestige.

Condos in Dempsey

The condo picture has a bit more nuance. The HonestDoor Price has dropped 2.82% recently, landing at $535,351. That is a more noticeable dip. But here is the flip side - the predicted market value of $550,872 is actually trending up compared to the 3-month moving average of $547,944. So while the broader price has pulled back, the short-term momentum is quietly ticking upward.

• Average HonestDoor Price: $535,351 (down 2.82% from last period)
• Predicted market value: $550,872
• 3-month moving average: $547,944 (trending up)
• Estimated monthly rent: $2,741
• Rental yield: 3.74%
• Airbnb estimate: $133 per night
• Recent value change: +0.12%
• Growth rank: 17 out of 24 neighbourhoods in Milton

On the neighbourhood leaderboard, Dempsey condos rank 17 out of 24 in Milton for growth - below average, but not at the bottom. Nearby, Dorset Park condos are predicted at $652,792 and Clarke at $566,455, so Dempsey is the more affordable option in this pocket of Milton. For a buyer who wants in at a lower price point, that gap is worth paying attention to.

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 from the past. It does not know that house values in Dempsey have shifted by -1.78% recently. It does not know that condo prices have pulled back 2.82%. Your tax assessment is essentially a photo from a year or two ago, and the market has moved since then.

The HonestDoor Price is updated in real time. For houses, it is sitting at $982,523. For condos, it is $535,351. These numbers reflect what is actually happening on the ground today - not what a government office calculated before the market started taking a breather. If you are making any financial decision - refinancing, selling, or just figuring out your net worth - the HonestDoor Price is the number you want in your hand, not the assessment.

Think of it this way: your neighbour who sold last month did not use a two-year-old number to price their home. Neither should you.

The So What: Should You Sell in Dempsey This Summer?

If you own a house in Dempsey and are thinking about listing this summer, here is the straight talk. The market is stable, not hot. Buyers are engaged but they are not in a frenzy - they are paying just under asking, and they have 21 days on average to make up their minds. That means your pricing strategy has to be sharp from day one. Overpricing will cost you time, and time on market in a stable buyers market works against you.

The growth rank of 22 out of 26 tells us Dempsey is not leading the charge on appreciation right now. If you are waiting for a big run-up before selling, the data is not pointing that direction in the short term. Selling into a stable market with motivated buyers who are close to full asking price is actually a reasonable window - it just requires realistic expectations on price.

For condo owners, the slight uptick in predicted value is a small positive signal. But with a growth rank of 17 out of 24 and nearby neighbourhoods priced higher, the pressure to price competitively is real. A rental yield of 3.74% means holding as an investment is not a bad fallback if the sale price does not meet your number.

Bottom line - Dempsey is a solid, affordable corner of Milton. It is not the flashiest performer on the leaderboard right now, but it is not in freefall either. Know your real number, price it right, and move with confidence.

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.