Used 2023 Toyota Highlander for Sale nearWindsor, ON

How much does the 2023 Toyota Highlander cost?

Prices have softened 10.28% compared to this time last year, making it a favourable time to shop this model year.

There are 213 listings available, which suggests a healthy amount of inventory for you to compare.

Is the 2023 Toyota Highlander a good car?

Yes — 4.75/5 is a strong user rating for the 2023 Toyota Highlander, and it fits a practical, comfort-focused midsize SUV role well. The Highlander gives you a roomy cabin, up to 2,387 litres of cargo space with the seats folded down, and standard tech such as an 8-inch touchscreen, USB inputs, Apple CarPlay, and Android Auto. It also suits you if you want a family hauler that prioritises comfort, safety, and everyday usefulness over driving excitement. With 28.2% of listings marked as good or great deals, there is still meaningful market choice for you.

Is the 2023 Toyota Highlander reliable?

Owners rate it 4.75/5, a strong signal of long-term satisfaction.

The 2023 Toyota Highlander is described as having a strong reputation for reliability and safety, with Toyota Safety Sense standard and top safety recognition from the IIHS. That combination makes it appealing if you want a used SUV that is built around dependable daily use rather than novelty. For used buyers, the main long-term ownership risk is less about outright dependability and more about whether the small third row and comfort-first tuning match your needs over time.

Is now a good time to buy a used 2023 Toyota Highlander?

This looks like a moderate, selective buyer’s market, so you can shop carefully without feeling rushed.

• Deal availability: 28.2% of listings are priced as good or great deals.
• Inventory: There are 213 listings available.
• Price trend: Prices have softened 10.28% compared with last year.

If you find a listing below $43,559 CAD, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2023 Toyota Highlander's resale value?

The current average of $43,844 CAD sits slightly below last year's $48,865 CAD.

That price movement suggests the market has cooled, which can improve your buying position now but may also mean less upside if you plan to resell soon. If you buy at the right price, you reduce the risk of taking an immediate depreciation hit. The Highlander’s practical appeal and strong reputation should help it stay relevant with used shoppers, especially those prioritising comfort and safety.

Vehicles with strong owner satisfaction ratings, like this model year's 4.75/5, tend to retain buyer demand, which supports resale value over time.

Should I buy a 2023 Toyota Highlander or consider a different year?

If you're weighing the 2023 against nearby model years, here's how to think about it:

Choose the 2023 if:

• 28.2% of listings are priced as good or great deals.
• Price trend: Prices have softened 10.28% compared with last year.
• Owners rate it 4.75/5 — a strong satisfaction signal.

Consider the 2022 if:

• At $41,543 CAD, the 2022 costs less than the current year's $43,844 CAD average.
• It focuses on the basics families need: space, versatility, technology, and safety.

The bottom line: Choose the 2023 if you want the newer pricing context and a well-equipped, comfort-first SUV with strong satisfaction. If you are more price-sensitive, the 2022 is the better value path because it costs less while still covering the Highlander’s core family-hauling strengths.

These recommendations are based on CarGurus' proprietary market data from October 13, 2026, CarGurus experts' opinions, and generative AI.