Dempsey, Milton - October 2026 Real Estate Report
Dempsey, Milton: Your Neighbour Just Got a Reality Check on Their Home Value
If you own a home in Dempsey and you're still relying on your last property tax assessment to know what your place is worth - stop. That number is already old news. Here's what's actually happening on our streets right now.
The Vibe: Houses vs. Condos in Dempsey
We're seeing two pretty different stories play out depending on what you own here.
On the house side, things are holding steady. The average sale price sits at $735,000, and homes are selling at 99.46% of list price. That means buyers are paying just a hair under asking - not the wild overbidding we saw a couple of years ago, but sellers aren't getting lowballed either. One property sold last month, spending about 21 days on the market before finding a buyer. That's a reasonable pace. The HonestDoor Price for houses is averaging $1,014,151, which is down a slim 0.73% from last period - basically a blip, not a trend. The predicted market value is actually sitting at $1,021,597, up from the 3-month moving average of $997,630, so the forward-looking signal is positive.
On the condo side, we need to be honest with each other. The HonestDoor Price for condos is $518,888 - up a modest 0.49% - but the predicted market value of $516,370 is trending below the 3-month moving average of $533,330. Condo values have shifted -5.82% recently, and Dempsey condos rank 14 out of 24 neighbourhoods in Milton for growth. That puts us in below-average territory for condos right now. Clarke, Dorset Park, and Timberlea condos are all priced higher than ours, which tells you something about where demand is sitting.
- House HonestDoor Price: $1,014,151 (down 0.73%)
- House predicted market value: $1,021,597
- House average sale price: $735,000
- House price per square foot: $420
- House sale-to-list ratio: 99.46%
- House average days on market: 21
- House rental yield: 4.65% - estimated rent $4,278/month
- Condo HonestDoor Price: $518,888 (up 0.49%)
- Condo predicted market value: $516,370
- Condo recent value change: -5.82%
- Condo rental yield: 3.81% - estimated rent $2,598/month
The Neighbourhood Leaderboard
Here's how Dempsey stacks up against the rest of Milton right now - think of it as our local rankings board.
For houses, we rank 12 out of 26 neighbourhoods for growth - that's above average, which is a decent spot to be. Our days-on-market rank is 4 out of 12, meaning houses here sell moderately fast compared to other Milton neighbourhoods. The one number worth watching: our price rank is 14 out of 14, making Dempsey houses among the most affordable in Milton. Depending on your perspective, that's either a buying opportunity or a signal that demand hasn't fully caught up yet.
For condos, the growth rank of 14 out of 24 puts us just below the midpoint. Not a crisis, but not a bragging right either.
The Secret Sauce: Why Your HonestDoor Price Matters More Than Your Tax Assessment
Your city assessment is a snapshot from the past. It doesn't know what happened on your street last month, and it definitely doesn't know that house values in Dempsey are trending toward $1,021,597 right now. The HonestDoor Price updates in real time using actual market activity - sales, listings, price shifts in nearby neighbourhoods like Timberlea (where houses are averaging $1,030,644) and Clarke ($1,002,214).
If you're a house owner in Dempsey, your HonestDoor Price is likely sitting above your last tax assessment. That gap is money you might be leaving on the table if you price based on old data. Check it now, not when you're already mid-negotiation with a buyer.
Condo owners - same advice, different reason. With values shifting, you want a current number, not a stale one that makes you think you have more cushion than you do.
The So What - Thinking About Selling This Summer?
For house sellers, the window looks reasonable. Buyers are active enough to close at 99.46% of list price, and 21 days on market means you're not sitting forever waiting for an offer. The market isn't on fire, but it's not frozen either - call it a stable, workable environment. Price it right from day one and you'll find a buyer. Overprice it and you'll feel those 21 days stretch into 60.
The rental angle is worth knowing too. At $4,278 per month in estimated rent and a 4.65% yield, Dempsey houses are genuinely attractive to investors - which means your buyer pool isn't just families, it includes people running the numbers on income properties. That's a wider net for you as a seller.
For condo sellers, this summer calls for a sharper strategy. With values trending down recently and nearby neighbourhoods priced higher, buyers have options. You need to come in priced competitively and in good condition. The good news - if you're a condo buyer, Dempsey is one of the more affordable entry points in Milton right now, and a 3.81% rental yield still makes the math work for investors.
Bottom line: get your HonestDoor Price updated before you make any move. It's the real-world number - not the government's best guess from two years ago.
dempsey | milton | october 2026This 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.