Westmount, Oakville: Neighbourhood Guide

TRREB counts Westmount as one of its Oakville communities, but its quarterly report doesn’t list boundary streets. A real estate team’s guide (not an official source) names Third Line, Bronte Road, Upper Middle Road and Dundas Street West as its edges, and a local real estate agent’s guide (also not official) maps the same block. A third description, on another real estate team’s website and written by a sponsor (also not official), uses Grand Oak Trail instead of Bronte Road as the western edge.

Some descriptions fold this land into West Oak Trails. A local real estate agent’s guide (not an official source) uses the name Westoak Trails for everything north of Upper Middle Road and south of Dundas Street between Bronte Creek and Sixteen Mile Creek, and Wikipedia’s summary of the Town’s planning communities places West Oak Trails on the north side of Upper Middle Road. TRREB reports Westmount and West Oak Trails as separate communities.

Real estate guides (not official sources) date the first construction to the mid or late 1990s, and one says most of the houses were built in the 2000s. They describe a mix of detached houses, semis and townhouses, and one adds stacked townhouses and condominiums.

Oakville Trafalgar Memorial Hospital, run by Halton Healthcare, is at 3001 Hospital Gate. According to Wikipedia, the hospital moved there, near Dundas Street and Third Line, on December 13, 2015, from its old site at 327 Reynolds Street.

Sales are spread across home types. In TRREB’s report for April to June 2026, 35 of Westmount’s 78 sales were detached houses, along with 17 attached or row townhouses, 10 condo townhouses, 8 semis and 8 condo apartments. Condo apartments were a bigger share of new listings than of sales: 47 of the quarter’s 216.

The gap between home types is wide: condo apartments had a median of about $497K and detached houses about $1,635K. The overall median of $1,195,000 says little about any single listing, so compare a home with recent sales of the same type. TRREB’s sales-to-new-listings ratio for the quarter was 73% for semis and 17% for condo apartments, and semis averaged 18 days on the market against 34 for condo apartments.

TRREB’s cover map for the quarter uses different district names from its community tables and doesn’t label Westmount, so the report doesn’t show exactly which streets these figures cover.

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.

Three HDSB schools are inside the Bronte Road to Third Line block: Captain R. Wilson Public School (2145 Grand Oak Trail), Emily Carr Public School (2255 Pine Glen Rd) and Garth Webb Secondary School (2820 Westoak Trails Blvd). Garth Webb’s website describes its namesake as a D-Day veteran who conceived the idea of the Juno Beach Centre in Normandy.

The HDSB has an elementary review open here. In June 2026, trustees restarted the Northwest Oakville Elementary Boundary Review, which looks at uneven enrolment in English and French Immersion among elementary schools south of Dundas Street and lists Captain R. Wilson PS and Emily Carr PS among the ten schools that may be affected. The board’s timeline, which it says may change, puts recommendations in late 2026 or early 2027, with any change taking effect as early as September 2027.

On the Catholic side, St. Ignatius of Loyola Catholic Secondary School is at 1550 Nottinghill Gate, south of Upper Middle Road, and its 2026–27 boundary map covers the whole block from Bronte Road to Third Line between Upper Middle Road and Dundas Street. Two schools in its family are inside the block: St. John Paul II Catholic Elementary School (2130 Kingsridge Dr) and St. Joan of Arc Catholic Elementary School (2912 Westoak Trails Blvd).

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.

West Oak Trails Community Park (2860 Westoak Trails Blvd) covers 6.5 hectares in the Town’s parks data. It has a splash pad, junior and senior playgrounds, a pickleball court, a lit softball diamond and two lit soccer fields. Smaller Town parks in the block include Grand Oak Park (2205 Grand Oak Trail), Millstone Park (2395 Pine Glen Rd), Greenwich Park (2410 Greenwich Dr) and Castlebrook Park (2207 Pine Glen Rd), which has a basketball court and a mini soccer field. Woodgate Woods (2088 Woodgate Dr) and Arbourview Woods (2201 Upper Middle Rd W) are listed as woodlots in the Town’s parks data.

Creek trails cross the area. The Town’s Fourteen Mile Creek Trail runs west of Third Line from the QEW to Dundas Street West, and north of Upper Middle Road West it splits into two sections, one of them east of Grand Oak Trail. The McCraney Creek Trail, which the Town lists as the trail access for Castlebrook Park, runs from Dundas Street West down to the Indian Ridge Trail at the QEW.

The Crosstown Trail follows the TransCanada/Enbridge pipeline corridor east and west across town and passes through the block. The Town awarded a contract to upgrade its stretch from Khalsa Gate to Sixteen Mile Creek into a four-metre-wide paved multi-use trail, with work scheduled to start in summer 2025 and finish by summer 2026.

In neighbouring Glen Abbey, Glen Abbey Community Centre (1415 Third Line) has a 25-metre leisure pool, a twin-pad arena, a fitness centre, squash courts, a double gym and the Glen Abbey branch of the Oakville Public Library. At Pine Glen Road and Third Line, the Town-owned Pine Glen Soccer Centre (1520 Pine Glen Rd) is an indoor soccer facility operated by the Oakville Soccer Club.

For everyday shopping, a local real estate agent’s guide (not an official source) points to Abbey Plaza in Glen Abbey, the Foxcreek plaza in West Oak Trails and the stores along Dundas Street.

Oakville Transit Route 13 Westoak Trails runs between Oakville GO and Bronte GO, with timed stops at Westoak and Upper Middle, Westoak and Third Line, and Westoak and Bronte. Route 3 runs north from Bronte GO along Third Line, stopping at Upper Middle and at Pine Glen, to the hospital. Route 5 runs along Dundas Street, with stops at the hospital’s west entrance and at Bronte, and Route 6 runs along Upper Middle Road, with stops at Bronte and at Third Line. On weekdays, Route 34 Pine Glen adds rush-hour trips from Bronte GO with stops at Pine Glen and Postmaster and at Westoak and Postmaster.

Bronte GO Station (2104 Wyecroft Rd) is on GO’s Lakeshore West line and has free parking in a main lot of 1,824 spaces and a south lot of 1,149. Oakville GO (214 Cross Ave), at the other end of Route 13, is on the same line, and VIA Rail trains stop there too.