Oakville neighbourhood guide

West Oak Trails

West Oak Trails is the belt of 1990s and early-2000s subdivisions between Upper Middle Road on the south and the newer Westmount streets to the north, built on former farmland west of Sixteen Mile Creek as Oakville expanded past Glen Abbey. Westoak Trails Boulevard, the curving collector the community takes its name from, ties together phases developed by several large builders from the mid-1990s through about 2005 (verify), with Fourteen Mile Creek and its tributaries left as wooded corridors between them. The result is a family suburb with detached two-storeys on modest lots, freehold townhouse rows, schools written into the plan and plenty of trail. Garth Webb Secondary School, opened in 2012 (verify), and the new Oakville hospital where Third Line meets Dundas Street, opened in December 2015 (verify), sit at the community's edges. Residents skew to young and established families, hospital and college staff, and commuters who drive to Bronte GO or take Bronte Road to the QEW and 407. It is not a walk-to-shops neighbourhood, but the plazas at Third Line and Dundas and along Bronte Road cover most weekly needs.

West Oak Trails homes by the numbers

Live from the MLS® feed · updated September 21, 2026

30 For sale now
22 New in 30 days
$1,299,500 Median asking price Middle half $1.0M to $1.5M
$665 Asking price per sq ft
12 days Median days listed
23% Listings with a price cut Median cut 4.1%

What is for sale: 18 detached homes · 9 townhouses · 2 semi-detached homes · 1 condos

Newest West Oak Trails homes for sale

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2257 Riverdale Place
2257 Riverdale Place — photo 2
1 / 19
New
For Sale
$1,598,000
5 bd · 4 ba
2257 Riverdale Place, Oakville
1 days on market
MLS® W13806850 · CENTURY 21 MYPRO REALTY
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Where West Oak Trails sits

West Oak Trails lies above Upper Middle Road West, between Bronte Road on the west and Third Line, extending east toward Fourth Line and the Sixteen Mile valley on some maps, with Westoak Trails Boulevard as the main internal street. Westmount takes over on the north side toward Dundas Street, and the line between the two communities is drawn differently by different sources. Fourteen Mile Creek winds through the western half.

The homes you will find

The first phases, closest to Upper Middle Road West and Third Line, went up from about 1995 to 2000: brick two-storey houses of three or four bedrooms with attached double garages, 36 to 45 foot frontages and modest yards, plus some links and semis. Phases from 2000 to 2006 toward Bronte Road and along Westoak Trails Boulevard added larger models, stone accents and nine-foot main floors, along with freehold townhouse rows near the collectors and a few blocks of stacked and condominium townhouses. Streets along Fourteen Mile Creek or the big Sixteen Mile ravine hold the premium lots. Mattamy, Fernbrook and Greenpark reportedly built phases here among others, though the builder of each phase should be confirmed (verify). Nearly every house has a finished or partly finished basement and many have a second kitchen. Roofs, furnaces and windows in the 1990s phases have reached replacement age, so check the invoices; on later phases inspect the stucco fronts and window flashing, and on any ravine lot ask for Conservation Halton's regulated area mapping.

Getting around

Most trips start by car. Bronte Road leads south to the QEW interchange and to the Bronte GO station on Wyecroft Road, roughly a ten-minute drive, while Third Line also has its own QEW interchange (verify). Northbound, Bronte Road and Neyagawa Boulevard reach Highway 407 interchanges above Dundas Street. Bronte GO, a Lakeshore West stop, sees weekday peak trains to Union and a thinner off-peak timetable than Oakville GO's (verify current pattern); some residents drive to Oakville GO instead for the 15-minute trains. Oakville Transit local routes on Westoak Trails Boulevard, Third Line and Bronte Road connect to Bronte GO and up to the Uptown Core terminal, and the Dundas Street route passes the hospital (verify route numbers). Walking and cycling are strong inside the community: the Fourteen Mile Creek trail and the Sixteen Mile Creek trail at Lions Valley Park link the subdivisions to Glen Abbey and north toward Dundas.

Schools

The public board, Halton District School Board, runs Garth Webb Secondary School, the Westoak Trails Boulevard high school opened in 2012 (verify), and elementary schools built inside the subdivisions, reportedly including Forest Trail, Pine Grove and West Oak public schools (verify names and boundaries), with French immersion at designated board sites. Catholic pupils are reportedly assigned to St. Gregory the Great or St. Mary, both elementary schools on or near Westoak Trails Boulevard (verify), and then to St. Ignatius of Loyola on Nottinghill Gate over in Glen Abbey (verify), all operated by Halton Catholic District School Board staff. French-language secondary students have Viamonde's Ecole secondaire Gaetan-Gervais, reportedly located on Westoak Trails Boulevard (verify), and MonAvenir runs Catholic French schools in town. School boundaries are drawn by the boards and revised as North Oakville grows, so ask each board which schools a particular house is assigned to.

Parks, shopping and daily life

Trails are the point of the name. Fourteen Mile Creek runs through the western half with a paved and gravel trail system, and the Sixteen Mile Creek valley at Lions Valley Park on the eastern edge offers longer walks along the river with a footbridge and picnic areas (verify access points). Neighbourhood parks with playgrounds, splash pads, soccer pitches and tennis courts are spaced through the phases, and the Pine Glen soccer fields off Third Line serve the leagues (verify). The Sixteen Mile Sports Complex at Neyagawa Boulevard and Dundas Street, a four-pad arena opened in 2010, and the Glen Abbey Community Centre and library branch to the south handle indoor recreation (verify). For errands, the plaza at Third Line and Dundas Street beside the hospital, the Bronte Road and Dundas plazas at Palermo and the Glen Abbey shops where Third Line crosses Upper Middle Road have supermarkets, pharmacies and takeout. Oakville Trafalgar Memorial Hospital is on the doorstep.

Who it suits

West Oak Trails is aimed at families who want a 1990s or 2000s house, a double garage and a trail a few doors down, schools within the phases, and a hospital and highway within minutes, at a size and finish level that is more modest than the newer estates in Westmount and Glenorchy. Hospital and Sheridan staff like the short commute. Buyers wanting a main street to walk to, a character house or a large lot will find it lacking, and the phases nearest Bronte Road and Dundas Street carry traffic sound. Anyone who needs the 15-minute GO trains daily will be driving to Oakville GO rather than Bronte.

Questions people ask about West Oak Trails

How do people in West Oak Trails get to the GO train?

Most drive: Bronte GO, down on Wyecroft Road, sits about ten minutes away via Bronte Road or Third Line, and Oakville GO, with more frequent trains, is roughly 15 minutes via Upper Middle Road. Oakville Transit routes along Westoak Trails Boulevard and Third Line reach Bronte GO for those without a car (verify routes).

Is the hospital a benefit or a nuisance?

Mostly a benefit. Oakville Trafalgar Memorial Hospital opened its Third Line and Dundas Street site in December 2015 (verify) with an emergency department and full services, and staff make up a real share of buyers. The nearest streets see ambulance and shift traffic, and the site is lit at night, so tour those blocks at different hours.

Are the creeks a flooding risk?

Fourteen Mile Creek and Sixteen Mile Creek are regulated by Conservation Halton, and the subdivisions were built with the valleys held as parkland and with stormwater ponds. Houses backing onto a ravine or pond should be checked against the regulated area mapping, and buyers should ask about basement water history and sump pump installation.

Are there townhouses and condos here?

Townhouses, yes: freehold rows in the 2000s phases plus a few condominium and stacked blocks near the collectors. Apartment condominiums are rare inside West Oak Trails; the nearest new mid-rise buildings are in Westmount near Dundas and in the North Oakville neighbourhoods across Dundas Street (verify).

What is Palermo?

Palermo is the old crossroads village where Bronte Road meets Dundas Street just north of the community, dating to the early 1800s with a few heritage buildings still standing. Today the name covers the plazas and new subdivisions around that intersection, and Palermo West is the Town's community north of Dundas and west of Bronte Road (verify).

Sources: oakville.ca · oakville.ca · oakville.ca · halton.ca · conservationhalton.ca · hdsb.ca