Used 2019 Toyota Highlander for Sale nearKenosha, WI

How much does the 2019 Toyota Highlander cost?

Prices have softened 4.69% compared to this time last year, making it a favorable time to shop this model year.

There are 2,776 listings available, which suggests solid inventory for shoppers comparing prices and trims.

If you find a listing below $23,062, 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 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 strong fit if you want a family-focused midsize SUV that prioritizes comfort, practicality, and everyday usefulness over excitement. With 32.1% of listings marked as good or great deals, you have a meaningful chance to find a competitive offer.

Is the 2019 Toyota Highlander reliable?

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

User feedback repeatedly highlights reliability, along with comfort and a trouble-free ownership experience. That kind of pattern matters if you want a used SUV you can count on for long-term family duty. 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 65.8% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should start with a vehicle history report so you can screen for accidents, title issues, and ownership patterns before you go any further. After that, prioritize a pre-purchase inspection, especially if the listing price looks unusually attractive. Focus your condition check on signs of prior bodywork, uneven wear, and anything that suggests the SUV has been used harder than the listing implies.

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 expecting every listing to be a bargain.

• Deal availability: 32.1% of listings are priced as good or great deals.
• Inventory: There are 2,776 listings available.
• Price trend: Prices have softened 4.69% compared with last year.
• Clean inventory: 65.8% of listings are accident-free.

If you find a listing below $23,062, 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 $23,878 sits slightly below last year's $25,051.

That price movement suggests the market has cooled a bit, which can help you buy more selectively now but may also mean slower appreciation if you plan to sell soon. For a future seller, the good news is that this model still benefits from strong demand tied to its family-friendly reputation and broad appeal. If you keep mileage reasonable and maintenance records organized, you should be in a better position to protect value when it’s time to trade or sell.

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:

• 32.1% of listings are priced as good or great deals.
• At 65.8% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 4.69% compared with last year.
• Owners rate it 4.74/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $27,677, the 2020 costs more than the current year's $23,878 average.
• The redesign brings a quieter, more upscale cabin with a more premium feel.

The bottom line: If you want the better value play, the 2019 is the smarter starting point because it combines strong owner satisfaction with a lower average price. If you’re willing to pay more for a newer redesign and a more premium-feeling cabin, the 2020 is the better secondary path.

These recommendations are based on CarGurus' proprietary market data from September 4, 2026, CarGurus experts' opinions, and generative AI.