Pettigrew Trail sits in the Dempsey neighbourhood of north Milton, a short residential lane that runs between Wettlaufer Terrace and Apple Terrace.
Pettigrew Trail sits in the Dempsey neighbourhood of north Milton, a short residential lane that runs between Wettlaufer Terrace and Apple Terrace. The street is quiet and family-oriented, framed by mature trees and well-kept lawns. It lies within walking distance of Chris Hadfield Public School, which anchors the immediate area. The broader Dempsey district is defined by its late-2000s and early-2010s construction, and Pettigrew Trail reflects that era with its consistent architectural character. The street is a cul-de-sac, which limits through traffic and reinforces a sense of enclosure. It is a few minutes by car from the Milton GO Station and Highway 401, making it practical for commuters.
Pettigrew Trail is composed entirely of semi-detached homes, a rarity in a neighbourhood where detached and townhouse forms are more common. The homes were built in the late 2000s and present a uniform two-storey profile with brick and stone facades. Each unit sits on a modest lot with a single-car garage and a small front yard. The semi-detached format here offers more square footage than a typical townhouse, with three bedrooms and approximately 1,500 to 1,800 square feet of living space.
The street's homes share a similar floor plan, with variations in exterior colour and trim. Most have been well maintained, with updated kitchens and finished basements appearing in several units. The semi-detached configuration provides a balance of privacy and affordability, appealing to families and first-time buyers. Across the Dempsey area, semi-detached homes typically trade around $897,000, placing Pettigrew Trail in a competitive segment of the local market.
Pettigrew Trail is within a five-minute drive of several grocery options, including Walmart, FreshCo, and Sobeys. Milton District Hospital is five minutes away by car. The street is also close to multiple parks: Coates Park and Velodrome Park are each a six-minute drive, while Milton Community Park is an eleven-minute walk. For outdoor recreation, Kelso Conservation Area is ten minutes away by car.
Several places of worship are nearby, including the Milton Muslim Community Centre (four minutes) and Guardian Angels Catholic Elementary School (four minutes). The Milton GO Station is a ten-minute drive, and Highway 401 is accessible in four minutes. The area is well served by public elementary schools, with Chris Hadfield Public School directly adjacent and Robert Baldwin Public School a four-minute walk.
Pettigrew Trail trades rarely, with only a handful of recorded transactions over the past year. The street's semi-detached housing stock attracts owner-occupants drawn to the Dempsey neighbourhood's proximity to Chris Hadfield PS and Milton Community Park, though the thinness of trade history makes broad pattern inference difficult. The one recent lease on record was a three-bedroom semi at approximately $2,900 per month, suggesting that owner-occupied units dominate the street's identity. Days on market have averaged around 71 days, a pace consistent with the broader neighbourhood, where comparable semi-detached homes have typically cleared in around 74 days. With only one active listing currently, supply is notably constrained.
The street's suitability is clearest when read against the neighbourhood comparable: across Dempsey, semi-detached homes typically trade around $897,000, and that band reflects the market where Pettigrew's own units sit. The neighbourhood has softened modestly year-over-year, with prices declining just over 5 percent from the prior year, though homes have held close to their ask price (sold-to-ask near 0.99), indicating minimal negotiation pressure despite the downward price movement. Buyers considering Pettigrew should recognize that the street's sparse transaction record means individual sales may move at their own pace; the neighbourhood's broader trade patterns and the proximity of adjacent streets like Wettlaufer (detached units trading around $1.8M) and Apple (mixed properties trading around $1.6M) provide better context for relative value.
Across Dempsey, comparable semi-detached homes typically trade around $897,000 based on a substantial sample of 149 sales over the past year. The neighbourhood has softened modestly through the period, with prices declining just over 5 percent year-over-year, yet homes have held very close to their ask price at approximately 99 percent sold-to-ask, suggesting that despite the directional price movement, buyer-seller balance remains measured and transactions close without significant discounting. Neighbourhood-wide pace matches the street's own rhythm, with comparable semi-detached homes typically clearing in around 74 days, consistent with Pettigrew's own 71-day average.
Pettigrew Trail sits in Dempsey, a pocket that trades proximity to the 401 for a quieter residential rhythm. The on-ramp at Regional Road 25 is a four-minute drive, making Mississauga a twenty-two-minute run and Pearson about half an hour. The Milton GO station is ten minutes by car; the full Toronto commute runs around seventy minutes door-to-door via the train. For daily errands, the grocery cluster at Walmart and FreshCo is four minutes away, and Milton District Hospital is five. The street itself sees little through-traffic, so the road network handles the load without the noise of a busier corridor.
Public elementary catchment falls to Chris Hadfield Public School, which sits directly on Pettigrew Trail itself — a walk of a few minutes for families at the street's north end. Robert Baldwin Public School is a four-minute drive south. Catholic elementary students draw to Guardian Angels Catholic Elementary School, four minutes away, or Our Lady of Fatima, five minutes. Secondary students attend St. Francis Xavier Catholic Secondary School, a six-minute drive. The concentration of schools within a short radius makes this stretch of Dempsey a natural fit for families routing multiple children through different boards.
Pettigrew Trail tends to suit buyers who want a newer semi-detached home in a quiet pocket without sacrificing highway access. The street's stock is almost entirely semis built in the early 2000s, which appeals to first-time buyers and young families looking for more space than a condo offers but at a lower entry point than detached homes in the area. The tradeoff is distance to the GO station — ten minutes by car rather than walking distance — so households that commute by rail will need a second car or a reliable drop-off routine. Rental activity here is light and almost entirely unfurnished, which signals long-term anchored tenants rather than transient demand.
If you're considering alternatives in similar pockets, Wettlaufer Terrace offers detached homes trading around $1.8M, a step up in price and space for buyers who want a freehold without leaving Dempsey. Apple Terrace mixes property types around $1.6M, which may suit those who want a broader range of lot sizes and eras within the same neighbourhood. Both streets share Pettigrew's highway proximity and school catchment but shift the price point and housing form. For buyers who prioritize walkability to the GO station, streets closer to Milton's core would be a better fit, though they trade off the quiet cul-de-sac feel that defines this part of Dempsey.
Semi inventory on Pettigrew Trail has seen 2 closed sales recently. Details below.
Sale activity on Pettigrew Trail in the recent period. Stats reflect closed transactions only.
Rental activity on Pettigrew Trail across recent months. Breakdown by bed count below.
| Date | Address | Beds | Sold | vs Ask | DOM | Listing brokerage |
|---|---|---|---|---|---|---|
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A thoughtful conversation grounded in every sale we have tracked on Pettigrew Trail.
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