Used 2019 Toyota Highlander for Sale nearKenosha, WI

How much does the 2019 Toyota Highlander cost?

Prices have softened 4.85% compared to this time last year, making it a favorable time to shop this model year.

There are 2,760 listings available, which gives you a solid pool of options to compare.

Is the 2019 Toyota Highlander a good car?

Yes — the 4.7/5 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. In practical terms, that makes it a strong fit if you want a family-friendly midsize SUV with an easygoing character and broad everyday usefulness. With 33.4% of listings marked as good or great deals, you have a meaningful chance to find a competitive price.

Is the 2019 Toyota Highlander reliable?

Owners rate it 4.7/5, a strong signal of long-term satisfaction.

The user feedback repeatedly highlights reliability, and drivers also describe it as dependable and trouble-free in day-to-day use. That kind of owner sentiment matters if you want a used SUV you can count on for long-term ownership. For used buyers, the main risk is less about the model’s reputation and more about finding one that has been maintained well and hasn’t accumulated hidden wear.

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

At 65.2% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should run a vehicle history report before you commit, then prioritize a pre-purchase inspection from a trusted mechanic. Focus on overall condition, signs of prior bodywork, and whether the cabin, suspension, and electronics show wear that matches the mileage. If a listing looks especially clean and well cared for, that can matter more than chasing the lowest sticker price.

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

This is a moderate, selective buyer’s market, so you can shop patiently but should move quickly on the best listings.

• Deal availability: 33.4% of listings are priced as good or great deals.
• Inventory: There are 2,760 listings available.
• Price trend: Prices have softened 4.85% compared with last year.
• Clean inventory: 65.2% of listings are accident-free.

If you find a listing below $23,054, 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 $23,382 sits slightly below last year's $24,573.

That softer pricing suggests the market has already adjusted downward, which can help you buy at a more favorable entry point. For a future seller, that also means resale value will depend heavily on condition, mileage, and how well the vehicle has been maintained. A clean history and strong presentation should matter more if you want to protect value later.

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:

• 33.4% of listings are priced as good or great deals.
• At 65.2% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 4.85% compared with last year.
• Owners rate it 4.7/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $27,370, the 2020 costs more than the current year's $23,382 average.
• Redesigned styling and a quieter, more premium-feeling cabin improve comfort.

The bottom line: If you want the better value today, the 2019 is the smarter starting point because it combines a lower average price with strong owner satisfaction. If you can stretch your budget and want the more refined redesign, the 2020 is the better upgrade path; if price matters most, the 2019 remains the more accessible 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 October 21, 2026, CarGurus experts' opinions, and generative AI.