Fitzgerald Crescent is a quiet residential loop in Milton's Dempsey neighbourhood, a pocket defined by its proximity to parks and schools.
Fitzgerald Crescent is a quiet residential loop in Milton's Dempsey neighbourhood, a pocket defined by its proximity to parks and schools. The street sits east of Regional Road 25, just north of Derry Road, in a part of town that developed steadily through the 2000s and 2010s. It is a short, inward-facing crescent with no through traffic, giving it a distinctly private feel. The surrounding blocks are largely residential, with Chris Hadfield Public School directly at the crescent's entrance. Fitzgerald is the kind of street where neighbours know each other by sight, and the pace of life is noticeably slower than on the main arteries nearby.
Fitzgerald Crescent carries a mix of semis and detached homes, all built in the early 2000s. The semis are two-storey units with attached garages, typically three bedrooms and two and a half bathrooms. The detached homes are slightly larger, with four bedrooms and brick-and-vinyl exteriors. Lots are narrow but deep, with modest front yards and fenced backyards. Driveways are standard for the era, accommodating two cars. The street's housing stock is consistent in age and material, with little variation in roofline or massing.
The homes here show good upkeep overall. Many have updated front doors, newer windows, and refreshed landscaping. The semis tend to have open-concept main floors with eat-in kitchens, while the detached homes offer separate living and family rooms. A few properties have added interlock walkways or stone veneer accents. The crescent's shape means most homes face inward toward a central green space, giving the street a cohesive, communal feel. Townhouses are absent from this street.
Fitzgerald Crescent sits within walking distance of several daily conveniences. Chris Hadfield Public School is at the crescent's entrance. A four-minute drive reaches Walmart, FreshCo, and the Milton Muslim Community Centre. Milton District Hospital is five minutes by car. The Milton GO Station is a ten-minute drive, and the on-ramp to Highway 401 at Regional Road 25 is four minutes away. For recreation, Coates Park and Velodrome Park are each six minutes away by car, while Milton Community Park is an eleven-minute walk.
The street is well served by public schools, with four elementary schools within a five-minute drive. Catholic options include Guardian Angels and Our Lady of Fatima, both four to five minutes away. St. Francis Xavier Catholic Secondary School is six minutes by car. The area has multiple grocery options within a five-minute radius, including Sobeys and Canadian Superstore. For longer commutes, driving to Mississauga takes about 22 minutes, to Oakville 24 minutes, and to downtown Toronto roughly 70 minutes via GO Transit.
Fitzgerald Crescent trades rarely, with only a handful of recorded transactions over the past year. The street accommodates a mix of housing forms: detached and semi-detached homes that reflect the broader Dempsey neighbourhood character. With just three active listings currently on the market, supply remains constrained. The one recorded sale took approximately 144 days to close, suggesting a measured pace where buyers and sellers allow time for proper matching rather than rush-driven activity. The single lease record on file captures a five-bedroom home at approximately $4,250 per month, which offers a data point for owner-occupancy benchmarking but is insufficient to draw yield conclusions across the street's broader inventory.
The neighbouring streets provide context for understanding Fitzgerald's position. Wettlaufer Terrace, immediately proximate, sees detached homes trading around $1.8M, while Apple Terrace captures mixed-type activity in the mid-range near $1.6M. These cross-street references frame the neighbourhood's overall price trajectory and suggest that Fitzgerald's own suitability and investment merit warrant evaluation against the broader Dempsey market performance and comparable home sales patterns in the immediate vicinity rather than in isolation.
Across 1029 - DE Dempsey, comparable semi-detached homes have sold at broadly consistent levels over the measurement window. The typical sold price for semi-detached homes in the neighbourhood settles around $897,000, drawn from a robust sample of 149 recent transactions. This neighbourhood price has softened modestly year-over-year, reflecting the broader regional trend, while sold-to-ask ratio sits near 0.99, indicating that buyers are closing near asking price with minimal negotiation room. Neighbourhood-wide pace runs noticeably faster than Fitzgerald's own DOM, with comparable semi-detached homes typically clearing in approximately 74 days, a full 70-day gap from the crescent's slower recent transaction. This pace differential suggests that while Fitzgerald Crescent's specific homes may require longer marketing windows, the semi-detached form itself moves efficiently once positioned correctly in the broader neighbourhood context.
Fitzgerald Crescent sits in Dempsey, a pocket that trades convenience for quiet. The 401 on-ramp at Regional Road 25 is a four-minute drive, making Mississauga a 22-minute run and Pearson reachable in just over half an hour. The GO station is further out at ten minutes by car, so the realistic Toronto commute runs around 70 minutes door-to-door via train and TTC. For those who drive into the city, the highway access is the daily handle; for transit commuters, the drive to the station is a necessary first leg. The street itself sees no through traffic, which is the point.
Public elementary catchment draws to Chris Hadfield Public School, which sits directly on the crescent — a walkable option for families with young children. Robert Baldwin Public School and Anne J. MacArthur Public School are within a five-minute drive, offering alternative catchment boundaries. Catholic elementary students attend Guardian Angels Catholic Elementary School, a four-minute drive, or Our Lady of Fatima at five minutes. Secondary students in the Catholic system draw to St. Francis Xavier Catholic Secondary School, a six-minute drive. The proximity of multiple elementary options gives families some flexibility within the public board.
Fitzgerald Crescent suits buyers who want a quiet crescent in a built-out neighbourhood without paying a premium for a newer subdivision. The stock is a mix of semis and detached homes from the early 2000s, which appeals to families who value lot size over square footage and prefer established landscaping over builder-grade finishes. The street's position near the 401 but away from its noise works for commuters who drive regularly. Renters on the crescent tend to be longer-term anchored households, given the unfurnished lease profile and the single recent lease record that took 144 days to move — a signal that tenants here are selective and stay put.
If you're considering alternatives in similar pockets, Wettlaufer Terrace offers detached homes trading around $1.8M, a step up in price and lot presence for buyers who want more space without leaving Dempsey. Apple Terrace mixes property types around $1.6M, which may suit those who want a wider range of options within the same neighbourhood feel. Both streets share Fitzgerald's quiet character and proximity to the 401, so the choice comes down to budget and whether a detached footprint matters more than the specific crescent setting.
Detached inventory on Fitzgerald Crescent is currently active but has thin recent sale history.
Semi inventory on Fitzgerald Crescent has seen 1 closed sales recently. Details below.
Townhouse inventory on Fitzgerald Crescent is currently active but has thin recent sale history.
No closed sales on record for Fitzgerald Crescent in the recent period.
Rental activity on Fitzgerald 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 Fitzgerald Crescent.
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