Used 2019 Toyota Highlander for Sale nearKenosha, WI

How much does the 2019 Toyota Highlander cost?

Prices have softened 4.36% compared to this time last year, making it a favorable time to shop this model year.

There are 2,644 listings available, which suggests solid inventory for comparison shopping.

If you find a listing below $23,067.06, that's toward the low end of the year-round range and worth acting on quickly.

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 appreciate the safety features and engine performance. That lines up well with its family-focused, practical role as a roomy midsize SUV that prioritizes everyday usefulness over flash. If you want a calm, comfortable three-row SUV with broad appeal, this model year fits that use case well.

28.7% of listings are priced as good or great deals, so you still have 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 repeatedly points to reliability, and drivers also describe the Highlander as comfortable and dependable. That combination matters if you want a used SUV you can count on for daily family duty and longer ownership. For used buyers, the main long-term risk is less about the model’s reputation and more about choosing a well-kept example with clean history and consistent maintenance.

What should I look for when buying a used 2019 Toyota Highlander?

At 64.9% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should start with a vehicle history report and confirm whether any prior damage was repaired properly. Put inspection priority on body condition, panel alignment, and signs of uneven wear, since those can reveal past issues that matter later. Focus on overall condition and maintenance records so you can separate a clean, well-kept SUV from one that only looks good online.

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 rushing.

• Deal availability: 28.7% of listings are priced as good or great deals.
• Inventory: There are 2,644 listings available.
• Price trend: Prices have softened 4.36% compared with last year.
• Clean inventory: 64.9% of listings are accident-free.

If you find a listing below $23,067.06, 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 $24,034 sits slightly below last year's $25,129.

That softer pricing can help you buy at a more favorable point in the cycle, but it also means future resale gains may be more limited if the market stays cool. For a seller, the upside is that the Highlander still benefits from strong family-SUV demand and a reputation that tends to support buyer interest. If you keep mileage reasonable and maintenance documented, you improve your odds of holding value better than average.

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:

• 28.7% of listings are priced as good or great deals.
• At 64.9% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 4.36% compared with last year.
• Owners rate it 4.74/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $27,779, the 2020 costs more than the current year's $24,034 average.
• It was redesigned for a quieter ride, softer feel, and more upscale cabin.

The bottom line: Choose the 2019 if you want the better value and are comfortable shopping carefully for condition and history. Consider the 2020 if you’re willing to pay more for a more refined, comfort-first driving experience; price-sensitive buyers should stay with the 2019 and target the best-maintained listings.

These recommendations are based on CarGurus' proprietary market data from August 28, 2026, CarGurus experts' opinions, and generative AI.