Kennedy Circle West

Kennedy Circle West at a glance

Kennedy Circle West traces a quiet arc through the Cobban, Coates, and Beaty neighbourhoods of north Milton. The street is a loop, not a through road, which keeps traffic local and the pace unhurried. It sits between Martin Street and Millside Drive, a short drive from the escarpment's conservation lands. The area was developed in the early 2000s, part of Milton's steady expansion north of the 401. Mature trees line many lots now, giving the circle a settled feel. It is a street where children walk to school and neighbours recognize one another by sight.

The homes here

Detached houses dominate Kennedy Circle West, with a handful of townhomes near the circle's edges. Most detached homes sit on standard 35- to 40-foot lots and offer between 1,500 and 2,500 square feet of living space. Two-storey plans are the norm, with brick and stone facades and attached two-car garages. The builder is not attributed with high confidence, but the consistent rooflines and window patterns suggest a single development phase. Townhomes are fewer and appear in short rows near the street's entrance.

Interiors typically feature open main floors with hardwood or laminate, gas fireplaces, and kitchens with granite or quartz counters. Upstairs, four bedrooms are standard, with the primary suite occupying the front corner. Basements are often unfinished, left for future expansion. Exterior colours lean toward neutral beiges and greys, with occasional red brick accents. The street shows good upkeep; roofs and driveways are mostly original but well maintained. Detached homes here trade in the low-$1Ms to mid-$1.4Ms, reflecting their size and the neighbourhood's stability.

What's nearby

Daily errands are a short drive from Kennedy Circle West. Walmart, FreshCo, and Sobeys cluster along Main Street East, about seven minutes by car. Milton District Hospital is also seven minutes away, and the Milton GO Station is nine minutes south, offering a 69-minute commute to downtown Toronto. For recreation, Kelso Conservation Area is five minutes north, with hiking and skiing in season. Coates Park and Rotary Park are within a ten-minute drive, providing sports fields and playgrounds.

Several public elementary schools serve the area, including E.W. Foster PS and Sam Sherratt PS, both within a ten-minute walk for some parts of the circle. Catholic families have Guardian Angels and Our Lady of Fatima nearby. The Milton Muslim Community Centre is seven minutes away. Highway 401 access at Regional Road 25 is seven minutes south, linking to Mississauga in 22 minutes and Pearson in 32. The street's position balances suburban quiet with reasonable access to the region's major arteries.

The market right now

Kennedy Circle West has traded across a wide band over the past year, with the typical sale settling near $1.15M and the full range running from around $710,000 at the entry end to approximately $1.45M at the top. Detached homes, which dominate the street's resale activity, cluster meaningfully higher: the typical detached trade lands near $1.25M, with the band running from $1.1M to around $1.45M. The quarterly read shows a non-linear arc. The typical price climbed from around $1.05M in Q4 2024 to roughly $1.275M in Q2 2025, held near $1.3M in Q3 2025, then softened from $1.25M in Q1 2026 to near $1M in Q2 2026, suggesting the strongest pricing landed mid-cycle rather than at the most recent window. Days on market average around 103, a pace that points to deliberate buyers rather than urgent ones, and the two active listings currently posted sit within a thin pipeline that tends to reward sellers who price to the band rather than above it. The lease ledger adds a useful counterweight: nine leases against thirteen sales over the period, with four-bedroom detached homes leasing in the $3,350 to $3,700 range against sale prices in the $1.1M to $1.45M band. That math implies gross yields in the 3.0 to 3.7 percent range, modest by investor standards, which is consistent with a street where owner-occupiers, not yield buyers, set the price.

Comparable homes nearby

Across the Cobban neighbourhood, comparable detached homes typically trade around $1.3M, drawn from a deep pool of sales that gives the figure real weight. Year-over-year movement has been essentially flat, with values holding steady within roughly a percentage point of where they sat a year earlier, a read that points to a market in equilibrium rather than one in transition. The sold-to-ask ratio sits near 0.98, indicating modest negotiation room without meaningful discounting, and consistent with buyers and sellers meeting close to list rather than at the extremes. Neighbourhood-wide pace runs slightly faster than the street's own DOM, with comparable detached homes typically clearing in around 96 days, a small but useful tell that the wider Cobban pool moves with marginally more conviction than Kennedy Circle West itself.

Getting around

Kennedy Circle West sits in Milton's northeast, a position that makes the GO line the realistic Toronto commute. A nine-minute drive to Milton GO Station puts Union under 70 minutes total, a rhythm that suits riders who value the train over the 401 crawl. For those working in Mississauga, the drive runs around 22 minutes via Regional Road 25; Pearson is roughly 32 minutes by car. The circle itself is quiet, with no through-traffic, so the road network handles the load without the noise that defines busier corridors.

Schools and catchment

Public elementary catchment draws to E.W. Foster Public School, a five-minute drive, and Sam Sherratt Public School, six minutes away. Catholic elementary students attend Guardian Angels Catholic Elementary School, seven minutes by car. For secondary, public students typically attend W.I. Dick Middle School for grades 6-8, while Catholic secondary draws to St. Francis Xavier Catholic Secondary School, six minutes away. The mix of nearby schools gives families options within a short drive, though none are walkable from the circle itself.

Who this street suits

Kennedy Circle West tends to suit families who want a detached home in a quiet pocket without sacrificing highway access. The stock is almost entirely detached, with typical prices in the mid-$1.2Ms, which positions it for buyers who need space and a yard but aren't chasing new construction. The rental side is dominated by unfurnished detached homes on 12-month leases, signalling long-term anchored tenants rather than transient demand. Lease velocity is moderate; homes typically find tenants within a month or two. The tradeoff is that you trade walkability to schools and shops for a quieter street and a larger lot.

If different priorities matter more

If you're considering alternatives in similar pockets, the nearby Martin area trades around $310K, a different price tier that reflects a mix of housing types and a more urban feel. Millside, another nearby street, sees condo trading around $490K, which suits buyers prioritizing lower entry price and less maintenance. For those who want newer construction or a more walkable setting, streets in the Coates or Beaty neighbourhoods may offer a different balance of lot size and proximity to amenities.