Used 2019 Toyota Highlander for Sale nearJanesville, WI

How much does the 2019 Toyota Highlander cost?

Prices have softened 4.43% compared to this time last year, making it a favorable time to shop this model year.

There are 2,709 listings available, which gives you a solid pool of options to compare.

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 they also like the safety features and engine performance. For you, that makes it a strong fit if you want a practical midsize SUV for commuting, errands, and family duty. With 35.1% of listings marked as good or great deals, there is still meaningful market opportunity if you shop carefully.

Is the 2019 Toyota Highlander reliable?

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

The review summary repeatedly highlights reliability, and it also points to a dependable, trouble-free ownership experience that many drivers feel confident counting on. That kind of feedback matters if you want a used SUV that should be easier to live with over time. For used buyers, the main long-term ownership risk is making sure a specific example has been maintained well and has a clean history.

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 so you can separate clean examples from ones with past damage. After that, prioritize a thorough pre-purchase inspection, especially if the listing price looks unusually attractive. Focus on overall condition, maintenance records, and signs of prior repair work rather than relying on mileage alone.

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

This is a moderate, selective buyer’s market, so you have room to shop carefully without expecting deep discounts everywhere.

• Deal availability: 35.1% of listings are priced as good or great deals.
• Inventory: There are 2,709 listings available.
• Price trend: Prices have softened 4.43% compared with last year.
• Clean inventory: 64.9% of listings are accident-free.

If you find a listing below $23,059, 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 $23,655 sits slightly below last year's $24,751.

That price movement suggests the market has cooled a bit, which can help you buy more confidently now but may also limit short-term upside if you plan to resell soon. Even so, the Highlander’s strong reputation for comfort and practicality should help it stay appealing to future shoppers. If you keep the vehicle in good condition and maintain it well, you should be in a better position when it is time to 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:

• 35.1% 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 4.43% compared with last year.
• Owners rate it 4.74/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $27,468, the 2020 costs more than the current year's $23,655 average.
• It adds a redesigned, quieter, more premium-feeling cabin.

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

These recommendations are based on CarGurus' proprietary market data from October 13, 2026, CarGurus experts' opinions, and generative AI.