Used 2019 Toyota Highlander for Sale nearWindsor, ON

How much does the 2019 Toyota Highlander cost?

Prices have softened 11.66% compared to this time last year, making it a favourable time to shop this model year.

There are 167 listings available, which gives you a modest amount of choice in the used market.

Is the 2019 Toyota Highlander a good car?

Yes — the 2019 Toyota Highlander earns a 4.74/5 user rating, which points to strong owner satisfaction. Drivers consistently praise its comfort, spaciousness, and reliability, and many also like the safety features and engine performance. For you, that makes it a sensible fit if you want a practical, comfort-focused midsize SUV with a family-friendly layout and broad usefulness. With 31.7% of listings marked as good or great deals, there is still some room to shop selectively.

Is the 2019 Toyota Highlander reliable?

Owners rate it 4.74/5, a strong signal of long-term satisfaction.

The user feedback highlights reliability, and drivers also describe it as dependable and comfortable for everyday use. That combination matters if you want a used SUV you can count on over the long term, especially for family duty and regular commuting. For used buyers, the main ownership risk is paying too much for a well-liked model when condition and maintenance history vary from one listing to the next.

Is now a good time to buy a used 2019 Toyota Highlander?

This looks like a moderate, selective buyer’s market, so you can shop patiently and still find worthwhile listings.

• Deal availability: 31.7% of listings are priced as good or great deals.
• Inventory: There are 167 listings available.
• Price trend: Prices have softened 11.66% compared with last year.

If you find a listing below $29,805 CAD, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2019 Toyota Highlander's resale value?

The current average of $29,853 CAD sits slightly below last year's $33,794 CAD.

That price movement suggests the market has cooled, which can make the Highlander easier to buy now but may also cap upside for a future seller. If you own one, strong condition and a clean history matter more when the broader market is already softer. The model’s reputation for comfort and reliability should still help support demand, especially among shoppers looking for a practical family SUV.

Vehicles with strong owner satisfaction ratings, like this model year's 4.74/5, tend to retain buyer demand, which supports resale value over time.

Should I buy a 2019 Toyota Highlander or consider a different year?

If you're weighing the 2019 against nearby model years, here's how to think about it:

Choose the 2019 if:

• 31.7% of listings are priced as good or great deals.
• Price trend: Prices have softened 11.66% compared with last year.
• Owners rate it 4.74/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $34,735 CAD, the 2020 costs more than the current year's $29,853 CAD average.
• It brings a quieter ride and a more upscale, Lexus-like feel.

The bottom line: If you want the better value today, the 2019 is the stronger starting point because it combines a lower average price with solid owner satisfaction and decent deal availability. If you are willing to spend more for a newer redesign and a calmer, more premium-feeling drive, the 2020 is the better alternative. For price-sensitive buyers, the 2019 is the smarter buy; for shoppers prioritising refinement over value, the 2020 deserves a look.

These recommendations are based on CarGurus' proprietary market data from September 22, 2026, CarGurus experts' opinions, and generative AI.