Used 2019 Toyota Highlander for Sale nearWinnipeg, MB

How much does the 2019 Toyota Highlander cost?

Prices have softened 13.31% compared to this time last year, making it a favourable time to shop this model year.

There are 183 listings available, which gives you a modest amount of choice when comparing trims, mileage, and condition.

Is the 2019 Toyota Highlander a good car?

Yes — the 4.74/5 user rating 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 for family use. With 26.2% 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 review summary highlights reliability, and drivers also describe it as dependable and trouble-free in everyday use. That kind of feedback matters if you want a used SUV you can count on for long-term ownership.

For used buyers, the main ownership risk is paying too much for a well-kept example, so condition and maintenance history still matter.

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 without expecting every listing to be a bargain.

• Deal availability: 26.2% of listings are priced as good or great deals.
• Inventory: There are 183 listings available.
• Price trend: Prices have softened 13.31% compared with last year.

If you find a listing below $29,371 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 $29,371 CAD sits slightly below last year's $33,881 CAD.

That price movement suggests the market has cooled, which can help you buy more affordably now but may also limit upside if you plan to resell soon. If you purchase at the current average, your future resale value will depend heavily on mileage, condition, and how well the vehicle has been maintained. Strong demand for practical family SUVs can still support values, especially for clean examples.

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:

• 26.2% of listings are priced as good or great deals.
• Price trend: Prices have softened 13.31% compared with last year.
• Owners rate it 4.74/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $34,961 CAD, the 2020 costs more than the current year's $29,371 CAD average.
• It brings a quieter ride and a more upscale-feeling cabin.

The bottom line:
Choose the 2019 if you want the better value and are comfortable with a proven, family-friendly package. If you can stretch your budget and want a more refined driving experience, the 2020 is the better upgrade; if price matters most, the 2019 is the smarter buy.

These recommendations are based on CarGurus' proprietary market data from September 29, 2026, CarGurus experts' opinions, and generative AI.