As we move into January 2026, the Oakville real estate market is clearly shifting gears after a more measured close to 2025. Buyer demand normalized, pricing cooled from peak levels, and market conditions began to rebalance — which, from my perspective, is a healthy reset rather than a cause for concern.

By late 2025, Oakville’s MLS® HPI composite benchmark price sat around $1,054,500, down roughly 9% year-over-year, according to CREA. Average sale prices moved closer to $1.38M, days on market increased, and inventory expanded — giving buyers more negotiating room while sellers recalibrate strategy.

While 2025 ended softer than peak years, long-term demand in Oakville remains firmly anchored by location, lifestyle, and enduring desirability as we move into 2026.

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In case you haven’t heard, the show Stranger Things is very, very popular right now.

The season finale was just released last Wednesday on New Year’s Eve, so in the spirit of wrapping up the beloved show, we wanted to see what Oakville would look like if it was in the upside down…

Check it out.

p.s. make sure you follow us on Instagram for more cool stuff.👇

Ontario food fans will recognize Joseph DeBenedicts, one of the province’s most popular food creators with hundreds of thousands of followers across Instagram, TikTok, and Facebook. Known for touring standout and under-the-radar eats, Joseph recently released his Top 5 Meals in Ontario for 2025, and one Oakville spot made the cut.

This “secret spot” is called: The Chicken Cartel, a trailer-based operation at 2524 Royal Windsor Drive. The Chicken Cartel serves five signature chicken burgers year-round, alongside rotating limited-edition gourmet chicken sandwiches that often sell out within a week. One spicy option earned especially high praise: “If you can handle the OMG, it’s probably the spiciest, most delicious chicken thing I ever had.” They’re open Tuesday–Saturday, noon to 7:00 pm (sometimes 7:30 pm).

Two Burlington spots also made Joseph’s list: Dunky's Beach Shack and El Inka.

Oakville’s major 2025 stories showed strong themes of growth, infrastructure delays, and rising community debates. Projects like Midtown’s redevelopment, new community spaces, and major road upgrades progressed but faced pushback or schedule shifts. Several of these remain unresolved, setting the stage for continued discussion in 2026.

This year, those same themes are back, with added tension around housing, heritage, and policy. The Midtown plan is still contentious, a new stormwater fee is rolling out, and a municipal election looms. Overall, 2026 looks like a year of follow-through, where last year’s unfinished stories will shape the town’s next chapter.

Over 500 participants kicked off 2026 with a splash at Coronation Park, taking part in Oakville’s 41st annual Polar Bear Dip. The long-running New Year’s Day event, known for its wild costumes and spirited energy, continues to grow since its humble beginnings in 1986 as a family dare.

Beyond the fun, the dip has a purpose. This year’s plunge pushed the running total to nearly $2.5 million raised for World Vision Canada to support clean water initiatives.

Monday, January 5
🌨️ Yellow Warning - up to 15cm of snow expected
High: –0°C | Low: –6°C

Tuesday, January 6
☁️ Cloudy
High: 2°C | Low: –4°C

Wednesday, January 7
☁️ Cloudy
High: 2°C | Low: 1°C