Used 2019 Toyota Highlander for Sale nearWindsor, ON

How much does the 2019 Toyota Highlander cost?

Prices have softened 11.03% compared to this time last year, making it a favourable time to shop this model year.

There are 179 listings available, which gives you a solid amount of inventory to compare.

Is the 2019 Toyota Highlander a good car?

Yes — the 2019 Toyota Highlander earns a 4.7/5 user rating, which points to strong owner satisfaction.

Drivers consistently praise its comfort, spaciousness, and reliability, and many also appreciate the safety features and engine performance. That lines up well with its family-friendly focus: you get a practical midsize SUV with a smooth ride, useful technology, and enough versatility for daily errands, road trips, and hauling gear.

With 34.6% of listings marked as good or great deals, you have a decent chance of finding a competitive example.

Is the 2019 Toyota Highlander reliable?

Owners rate it 4.7/5, 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 kind of praise matters if you want a used SUV you can count on for regular family duty rather than something that feels fragile or high-maintenance.

For used buyers, the main long-term ownership risk is finding an example that has been neglected, since condition and maintenance history matter more as these vehicles age.

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 carefully without feeling rushed.

• Deal availability: 34.6% of listings are priced as good or great deals.
• Inventory: There are 179 listings available.
• Price trend: Prices have softened 11.03% compared with last year.

If you find a listing below $29,402 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 $30,054 CAD sits slightly below last year's $33,780 CAD.

That softer pricing suggests the market has become more favourable for buyers, but it also means future sellers may need to be realistic about expectations. If you buy now, the lower entry price can help cushion depreciation compared with a stronger market. The Highlander’s broad appeal should still support demand, especially among shoppers who value comfort and practicality.

Vehicles with strong owner satisfaction ratings, like this model year's 4.7/5, 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:

• 34.6% of listings are priced as good or great deals.
• Price trend: Prices have softened 11.03% compared with last year.
• Owners rate it 4.7/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $35,086 CAD, the 2020 costs more than the current year's $30,054 CAD average.
• It shifts toward a quieter, more premium-feeling ride.

The bottom line:
Choose the 2019 if you want the better value and are comfortable with its practical, comfort-first personality. If you can stretch your budget and want a more refined-feeling Highlander, the 2020 is the stronger upgrade; if price matters most, the 2019 is the smarter buy.

How does the 2019 Toyota Highlander compare to the 2019 Honda Pilot?

Read our full side-by-side expert comparison here.

These recommendations are based on CarGurus' proprietary market data from November 10, 2026, CarGurus experts' opinions, and generative AI.