Dempsey is one of Milton's established central pockets, a neighbourhood where the city's growth story meets a quieter, more settled rhythm.
Dempsey is one of Milton's established central pockets, a neighbourhood where the city's growth story meets a quieter, more settled rhythm. Its streets carry a sense of continuity, shaped by decades of family life and a steady hum of daily activity. Here, the pace is unhurried, yet the pulse of Milton's wider energy is never far away.
Positioned within the city's core, Dempsey offers a balance of proximity and retreat. It is a place that feels both central and self-contained, a neighbourhood that has grown into its character over time.
Currently, 39 homes are listed for sale in Dempsey. With typical days on market at 80, the pace reads as balanced. Condos and townhouses make up the largest share of active listings, while detached homes and semis are fewer in number.
Everyday errands sit close at hand in Dempsey, with a network of local shops and services woven into the fabric of the neighbourhood. Parks and green spaces are a defining feature, offering room for quiet walks, weekend play, and a connection to the outdoors. The streets are lined with mature trees, and the sense of a community that looks after its own is tangible. It is a place where the daily rhythm feels both convenient and calm.
Dempsey is a natural fit for buyers who want the reassurance of an established neighbourhood without sacrificing access to the city's amenities. It suits families looking for room to grow, as well as those who value a slower pace and a strong sense of place. The trade-off is a quieter lifestyle, one that rewards those who appreciate continuity over constant change.
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Dempsey's market is defined by its mix of property types and a broad price range. Over the past year, the typical home traded around $800,000, with sales spanning from roughly $400,000 to $1,550,000. Condos averaged near $550,000, while detached homes settled around $1,140,000. Semis and townhouses clustered near $915,000 and $765,000, respectively. The average days on market reached 80, suggesting a measured pace.
Quarterly trends show some fluctuation. The typical price rose from about $775,000 in Q2 2024 to $890,000 in Q3 2024, then eased to $830,000 in Q4 2024. It held near $825,000 in Q1 2025 before climbing to $865,000 in Q2 2025. A slight dip to $855,000 in Q3 2025 was followed by a decline to $820,000 in Q4 2025. In Q1 2026, the typical price was around $815,000, then dropped to $690,000 in Q2 2026. The overall trend has been uneven, with a softening in recent quarters.
Dempsey's typical sale price of approximately $800,000 sits below the Milton-wide typical of about $1,025,000, placing it on the more affordable side of the city. Homes in Dempsey also tend to sell slightly faster, with a median of 80 days on market compared to 87 days across Milton. This combination of lower entry points and a quicker pace suggests a neighbourhood that turns over efficiently, appealing to buyers seeking value without extended wait times.