Dills Crescent is a quiet residential loop in Milton's Dempsey neighbourhood, a pocket of the city defined by family-oriented streets and proximity to schools.
Dills Crescent is a quiet residential loop in Milton's Dempsey neighbourhood, a pocket of the city defined by family-oriented streets and proximity to schools. The crescent sits south of Derry Road and west of Thompson Road, placing it within a grid of similar crescents and cul-de-sacs. Its immediate context is suburban and orderly: sidewalks line both sides, street trees are young but established, and traffic is local only. The street is bookended by Chris Hadfield Public School at its northern edge and a small parkette near the southern turn. Dills does not carry through traffic, which gives it a contained, private character. It is the kind of street where children walk to school and neighbours recognize one another by sight.
Dills Crescent is a single-type street. Every residence is a semi-detached home, built in a consistent architectural vernacular that suggests a single development phase. The homes are two-storey, three-bedroom units with attached single-car garages. Brick and vinyl siding are the dominant exterior materials, with colour palettes ranging from beige to grey. Lot widths are modest, typically in the low 30-foot range, and driveways are shared between adjoining units. The street's uniformity is its defining trait: rooflines, window placements, and front-door styles repeat with minor variations.
Inside, floor plans follow a standard two-storey layout: main floor with living, dining, and kitchen; upper floor with three bedrooms and a main bath. Basements are unfinished in most cases, offering expansion potential. The homes were built in the early 2000s and show their age in cosmetic details rather than structural ones. Many have updated flooring and kitchens; a few retain original finishes. The street's semi-detached format appeals to buyers seeking ground-floor space without the premium of a detached home. Townhomes and detached houses are absent, giving Dills a focused, predictable stock.
Dills Crescent sits within walking distance of several daily anchors. Chris Hadfield Public School is at the crescent's northern edge, a literal two-minute walk for most residents. Grocery options are a short drive: Walmart and FreshCo are four minutes away, Sobeys five. Milton District Hospital is five minutes by car. For recreation, Coates Park and Velodrome Park are each six minutes away by car; Milton Community Park is an 11-minute walk. The Milton Muslim Community Centre is four minutes driving, and the Islamic Community Centre of Milton is nine minutes.
The street is well positioned for commuters. Highway 401 at Regional Road 25 is four minutes from the crescent. Milton GO Station is a 10-minute drive, with trains to Toronto Union in about 70 minutes via GO and TTC. Driving to Mississauga takes 22 minutes, to Oakville 24, to Burlington 20, and to Pearson International Airport 32 minutes. The street's location in Dempsey places it near the edge of Milton's developed area, with conservation land and the Niagara Escarpment within a 10-minute drive.
Dills Crescent trades rarely. The street's recorded activity consists of a single lease transaction over the measurement window, with no completed sales to establish a price point. Two listings are currently active on the crescent, suggesting modest supply momentum but insufficient transaction depth to extract a meaningful price range or days-on-market pattern at the street level. The lean trade record reflects the crescent's profile as a modest-sized street in the Dempsey neighbourhood, drawing a narrow resident base and infrequent inventory turnover.
The property mix skews toward semi-detached homes, a form that anchors the Dempsey neighbourhood's character. Context for prospective buyers and owners emerges most clearly when read against the neighbourhood comparable. Across Dempsey, semi-detached homes typically trade around $897,000, with year-over-year pricing softening modestly and sold-to-ask ratios hovering near 0.99, indicating minimal negotiation friction at the neighbourhood level. The single recorded lease on Dills Crescent, a three-bedroom unit at approximately $2,700 per month, aligns with typical rental patterns for comparable semis in the area. Because Dills itself has generated no recent sales, suitability assessment depends on neighbourhood context and the crescent's street-level amenity read rather than its own transaction history.
Across Dempsey, comparable semi-detached homes typically trade around $897,000. The neighbourhood sample of 151 transactions over the past year reflects a mature, active market for this housing form. Year-over-year pricing has softened modestly, with the typical sale price declining approximately 4.5% from the prior-year window, suggesting a measured ease in buyer competition. Sold-to-ask ratios near 0.99 indicate that buyers are negotiating from a position of modest strength but not forcing material discounts; most homes clear near or slightly below listing price. Days on market for comparable semis across Dempsey average around 74, a pace that reflects stable, unhurried turnover. For renters, three-bedroom semis in the neighbourhood area have been leasing in the $2,600 to $2,800 band, implying gross yields in the 3.5% to 3.7% range against comparable sale prices, a pattern consistent with the broader GTA semi-detached rental-to-sale dynamic.
Dills Crescent sits in Dempsey, a neighbourhood that puts the 401 ramp at Regional Road 25 within a four-minute drive. That on-ramp is the daily handle for commuters heading to Mississauga, a 22-minute run, or to Pearson in just over half an hour. The Milton GO station is ten minutes by car, making the downtown Toronto commute a realistic 70 minutes door to door via the train. The street itself is a quiet crescent, so the road network handles the load without through-traffic noise. For those working in Oakville or Burlington, the drive runs 20 to 24 minutes, a tradeoff that many Dempsey residents accept for the relative calm of the street.
Public elementary catchment falls to Chris Hadfield Public School, located directly on the crescent itself — walkable from every doorstep. Robert Baldwin Public School is a four-minute drive, and Anne J. MacArthur Public School is five minutes away. Catholic students attend Guardian Angels Catholic Elementary School, four minutes by car, or Our Lady of Fatima Catholic Elementary School, five minutes away. For secondary, Catholic students draw to St. Francis Xavier Catholic Secondary School, a six-minute drive. The proximity of multiple elementary options makes Dills a street where families can match catchment to preference without a long commute.
Dills Crescent tends to suit families who want a quiet crescent with immediate access to a public elementary school. The stock is semi-detached, which keeps entry prices lower than the detached homes that dominate much of Dempsey. Buyers here accept a tighter floor plan in exchange for a walkable school catchment and a short drive to the 401. The rental market is thin but anchored: the single recent lease was a three-bedroom unit that rented quickly, suggesting demand from young families who are testing the neighbourhood before buying. For those who prioritize a short commute to Mississauga or Pearson over a large lot, Dills offers a practical tradeoff.
If you're considering alternatives in similar pockets, homes built in the early 2000s on crescents with larger lots may suit buyers who want more outdoor space. For those who prefer a newer subdivision with more uniform architecture, the southern part of Dempsey offers homes from the late 2010s. Buyers who need a shorter walk to the GO station might look closer to Milton's core, where the tradeoff is more street noise and tighter frontage. The key difference is lot size and build era: Dills Crescent's semi-detached stock from the early 2000s sits at a different price point than the newer detached homes nearby.
Detached inventory on Dills Crescent is currently active but has thin recent sale history.
No closed sales on record for Dills Crescent in the recent period.
Rental activity on Dills Crescent across recent months. Breakdown by bed count below.
| Date | Address | Beds | Sold | vs Ask | DOM | Listing brokerage |
|---|---|---|---|---|---|---|
| Loading sold records… | ||||||
A thoughtful conversation grounded in every sale we have tracked on Dills Crescent.
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