Old Oakville: Neighbourhood Guide

Wikipedia’s summary of the Town’s planning communities puts Old Oakville between Sixteen Mile Creek and Oakville Harbour on the west and Chartwell Road on the east, with Cornwall Road to the north and Lake Ontario to the south. A local real estate agent’s guide (not an official source) uses the same lines, and TRREB reports Old Oakville as one of its Oakville communities.

HoodQ, a third-party data service, calls it the area of Oakville’s original settlement, in 1827. According to Wikipedia, William Chisholm bought 390 hectares around the creeks at auction in 1827, land the Mississaugas had ceded to the Crown, and he also started a shipbuilding business at Navy Street and Sixteen Mile Creek.

Downtown runs along Lakeshore Road East. The Downtown Oakville BIA, a non-profit that markets and looks after the district, has more than 500 business members.

Detached houses lead, but the market is thin. In TRREB’s report for April to June 2026, 21 of Old Oakville’s 33 sales were detached, along with 6 condo apartments, 4 attached or row townhouses, 1 condo townhouse and 1 other. Homes spent an average of 50 days on the market and went for an average of 94% of their list price.

With only 33 sales, one or two large or unusual properties can move the averages, so treat them as a rough guide. The detached median was about $2,800K.

The Town has four heritage conservation districts here. The Old Oakville district, established in 1981, was Oakville’s first and one of the first in Ontario; it runs south of Robinson Street to the lake, from Sixteen Mile Creek east to Allan Street. The First and Second Street district, designated in 1989, sits between Lakeshore Road East and the lake from Allan Street to Second Street. The Trafalgar Road district, from 1994, covers early homes on both sides of Trafalgar Road, many built before 1860. The Downtown Oakville district took effect on March 9, 2013 and runs roughly from just west of Navy Street to Dunn Street.

Changes to a designated property, including one designated as part of a district, need a heritage permit; properties that are only listed on the Town’s Heritage Register don’t. The Town suggests booking a consultation with one of its heritage planners before you start, and its online Heritage Register lets you look up any address.

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. The same review looked separately at zoning in the Old Oakville, First and Second Street and Trafalgar Road districts, with an open house on May 14, 2025.

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.

On the public side, New Central Public School is at 133 Balsam Dr.

On the Catholic side, the 2026–27 boundary map for St. Vincent Catholic Elementary School (1280 Braeside Dr) covers the lakeshore from Sixteen Mile Creek east to the Mississauga border, between the lake and the rail corridor, which includes Old Oakville. St. Vincent is in the St. Thomas Aquinas family of schools, and the 2026–27 map for St. Thomas Aquinas Catholic Secondary School (124 Dorval Dr) covers Oakville south of the QEW from the Burlington boundary to the Mississauga border.

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.

Lakeside Park (144 Front St) sits on the lake downtown, with a bandstand, a playground and two historic buildings, the Old Post Office and the Thomas House. Across the street, the Erchless Estate grounds (8 Navy St) have been restored to their early-1900s look from period photographs, and the Oakville Museum is on the property. The Town also names Dingle Park as one of the Old Oakville district’s two waterfront parks.

Oakville Harbour (99 Forsythe St) has about 200 boat slips and a launch ramp. On Navy Street, the Central branch of the Oakville Public Library is at 120 and the Oakville Centre for the Performing Arts is at 130.

Oakville Trafalgar Community Centre (325 Reynolds St), built in partnership with Oakville Hydro as a LEED-certified building, has a 25-metre lap pool, a warm-water pool, a fitness centre with an indoor track, a double gym and a splash pad. Post Park (512 Macdonald Rd) has a leash-free dog park.

Oakville GO Station (214 Cross Ave) is on GO’s Lakeshore West line, and VIA Rail trains stop there too. It has free parking in a main lot of 2,712 spaces, a 1,398-space garage and a south lot of 291.

Oakville Transit Route 14 leaves Oakville GO with a timed stop at Reynolds and Church, then heads west along Lakeshore Road toward Bronte and Appleby GO. Route 1 Trafalgar starts at Church and Dunn and runs to Oakville GO and then north along Trafalgar Road. Route 4 runs along Cornwall Road, with timed stops at Cornwall and Chartwell, on its way to Clarkson GO.