West Oak Trails, Oakville: Homes and Neighbourhood Guide

TRREB reports West Oak Trails and its neighbour Westmount as separate Oakville communities, but its quarterly report doesn’t list boundary streets. A local real estate agent’s neighbourhood maps (not an official source) draw the line between the two at Third Line: West Oak Trails runs from Third Line east to Sixteen Mile Creek, between Upper Middle Road and Dundas Street, and Westmount lies to the west.

Other sources draw it wider. Another agent’s guide (also not official) describes Westoak Trails as the land north of Upper Middle Road and south of Dundas Street, east of Bronte Creek and west of Sixteen Mile Creek, and HoodQ, a third-party data service, treats Westmount as part of West Oak Trails. Wikipedia’s summary of the Town’s planning communities places West Oak Trails on the north side of Upper Middle Road and calls it a newer development than the other communities.

HoodQ dates the start of development to the mid-1990s and describes the housing as mainly two-storey detached homes, with townhomes and some semi-detached homes. The first agent’s guide calls West Oak Trails a planned community that took shape from the late 1990s into the early 2000s.

Detached houses and townhouses made up most of the sales. In TRREB’s report for April to June 2026, 17 of West Oak Trails’ 34 sales were detached and 13 were attached or row townhouses, alongside 3 condo townhouses and 1 semi. TRREB recorded no condo apartment sales here in the quarter, and no condo apartments among its 77 new listings.

Townhouses sold at a median of about $950K and detached houses at about $1,615K, so the overall median of $1,217,500 says little about any single listing; compare a home with recent sales of the same type. With only three condo townhouse sales, their average (about $997K) and median (about $795K) sit far apart, and with 34 sales in all, treat the averages as a rough guide.

TRREB’s sales-to-new-listings ratio for the quarter was 43% for detached homes, 62% for attached or row townhouses and 50% for condo townhouses. Detached homes spent an average of 28 days on the market and townhouses 22.

Zoning changed in 2026. On June 15, Council adopted By-law 2026-088, which updates the low-density residential zones (RL1 to RL11) south of Dundas Street under the South Oakville zoning by-law (2014-014). If a purchase depends on adding on or rebuilding, confirm the current rules with the Town before you firm up.

School assignment goes by street address, and both boards are redrawing boundaries in parts of Oakville. Before you rely on any school below, check the exact address with the HDSB’s Find Local School tool and the HCDSB’s Find Your School tool.

Two public elementary schools are inside West Oak Trails as the agent’s map draws it: Forest Trail Public School (1406 Pine Glen Rd), which offers French Immersion from Grade 2 to Grade 8, and West Oak Public School (2071 Fourth Line). Garth Webb Secondary School is at 2820 Westoak Trails Blvd, on the west side of Third Line; it runs English and French Immersion programs and offers Environmental and Energy Specialist High Skills Major programs.

The HDSB has a boundary review open here. On June 2, 2026, trustees reinitiated the Northwest Oakville Elementary Boundary Review, which looks at the imbalance in enrolment among elementary schools south of Dundas Street and lists ten schools it may affect, including Forest Trail and West Oak. The board says a committee with parent representation will be formed in fall 2026, that it anticipates a final option being approved in winter 2026, and that changes could take effect as early as September 2027, possibly phased in over several years.

Separately, enrolment at Forest Trail has grown to the point that it has eight portables, and since February 1, 2026 the board has directed new registrations from the part of its boundary north of Dundas Street, between Neyagawa Boulevard and Sixth Line, to Sunningdale PS. New French Immersion registrations from south of Dundas Street continue at Forest Trail.

On the Catholic side, the 2026–27 boundary maps split the area between two schools in the St. Ignatius of Loyola family of schools. The map for St. Teresa of Calcutta Catholic Elementary School (1190 Westview Terrace) covers most of it, and the map for St. John Paul II Catholic Elementary School (2130 Kingsridge Dr, west of Third Line) takes in the north-west corner around Pine Glen Road, between Third Line, Dundas Street, Proudfoot Trail and Pinecliff Road. St. Ignatius of Loyola Catholic Secondary School is at 1550 Nottinghill Gate, south of Upper Middle Road, and its 2026–27 boundary map takes in the land between Upper Middle Road and Dundas Street west of Sixteen Mile Creek, which includes West Oak Trails.

HDSB secondary boundaries are changing too. In May 2026, trustees approved boundaries for the new Oakville NE #1 High School, which the board anticipates will open in September 2027, and the same decision adjusts the English and French Immersion programs at Garth Webb, T. A. Blakelock and White Oaks secondary schools. It is being phased in over three-plus years.

The Town’s Sixteen Mile Creek Heritage Trail is an asphalt multi-use trail built into the west embankment of the Sixteen Mile Creek valley. The section just south of Dundas Street and east of Fourth Line remains closed because of slope erosion, and the Town’s project page lists fall 2026 for finishing the repairs, so check it before you go.

The Crosstown Trail runs east and west across town along the TransCanada/Enbridge pipeline. The Town awarded a contract to upgrade the stretch from Khalsa Gate, west of Third Line, to Sixteen Mile Creek into a four-metre-wide asphalt multi-use trail, and its plan for that stretch shows the trail crossing Third Line, Proudfoot Trail and Fourth Line on the way to the creek. The project adds rest areas, bike racks and controlled pedestrian crossings at every road; work was scheduled from summer 2025 to summer 2026.

Pine Glen Park (1482–1520 Pine Glen Rd) and Sixteen Hollow Park (2140 Westoak Trails Blvd) have splash pads, and so does West Oak Trails Park (2860 Westoak Trails Blvd), on the west side of Third Line. Pine Glen Soccer Centre (1520 Pine Glen Rd) is an indoor soccer facility owned by the Town and operated by the Oakville Soccer Club.

A local real estate agent’s guide (not an official source) lists basketball and tennis courts, a soccer field and a playground at Bloomfield Park. For shopping, it points to Fox Creek Plaza, at Third Line and Dundas Street, for groceries, banking and restaurants, and to a couple of small plazas along Westoak Trails Boulevard.

Glen Abbey Community Centre (1415 Third Line), in neighbouring Glen Abbey, has a 25-metre leisure pool, a twin-pad arena and the Glen Abbey branch of the Oakville Public Library.

Oakville Transit Route 13, named Westoak Trails, runs seven days a week between Oakville GO and Bronte GO, with timed stops at Westoak and Upper Middle, Westoak and Third Line, and Westoak and Bronte. Route 34 Pine Glen runs only at weekday rush hours, from Bronte GO, with timed stops including Pine Glen and Proudfoot, and Oakville Transit supplements it with Ride On-Demand service for Palermo West and Bronte Creek.

Route 3 runs along Third Line between South Oakville Centre, Bronte GO and Oakville Trafalgar Memorial Hospital (3001 Hospital Gate), with timed stops at Third Line and Upper Middle and at Third Line and Pine Glen. Route 6 runs along Upper Middle Road and Route 5 along Dundas Street, where it stops at the hospital’s west entrance.

Both GO stations are on the Lakeshore West line. Bronte GO (2104 Wyecroft Rd) has a bus loop for Oakville Transit routes, and Oakville GO (214 Cross Ave) shares its platforms with VIA Rail’s Oakville station.