Used 2019 Toyota Highlander for Sale nearMadison, WI

How much does the 2019 Toyota Highlander cost?

Prices have softened 5.04% compared to this time last year, making it a favorable time to shop this model year.

There are 2,933 listings available, which suggests you should have a solid range 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 they also value the safety features and engine performance. In practical terms, that makes it a strong fit if you want a family-focused midsize SUV for commuting, school runs, and everyday utility. With 36.8% of listings marked as good or great deals, there are still worthwhile opportunities in the market.

Is the 2019 Toyota Highlander reliable?

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

The review summary highlights reliability, comfort, and a trouble-free ownership experience as major strengths, which is exactly what many used-SUV shoppers want. Buyers also describe it as a vehicle they can count on for daily family duty, with long-term dependability standing out alongside safety and practicality. For used buyers, that usually means lower ownership anxiety if you choose a well-maintained example with a clean history.

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

At 64.5% 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, especially if the price looks unusually attractive. Put inspection priority on body condition, repair quality, and signs of past collision work, since those details can affect long-term value. It also makes sense to focus on overall maintenance records and interior wear so you can separate a clean, well-kept SUV from one that has simply been cleaned up for sale.

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

This is a moderate market for selective buyers, with enough inventory and deal activity to reward careful shopping.

• Deal availability: 36.8% of listings are priced as good or great deals.
• Inventory: There are 2,933 listings available.
• Price trend: Prices have softened 5.04% compared with last year.
• Clean inventory: 64.5% of listings are accident-free.

If you find a listing below $23,042, 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 $23,163 sits slightly below last year's $24,392.

That softer pricing can help you buy more value today, but it also means future resale gains may be more gradual if the market stays soft. For a seller, the upside is that the Highlander still benefits from strong family-SUV demand and a reputation for dependability, both of which help support buyer interest. If you keep mileage, condition, and maintenance records in good shape, you should be in a better position when it is time to sell.

Vehicles with strong owner satisfaction ratings, like this model year's 4.7/5, 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:

• 36.8% of listings are priced as good or great deals.
• At 64.5% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 5.04% compared with last year.
• Owners rate it 4.7/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $27,242, the 2020 costs more than the current year's $23,163 average.
• It brings a redesigned cabin with a more premium, comfort-first feel.

The bottom line: If you want the better value play, the 2019 is the stronger starting point because it combines a lower average price with solid owner satisfaction. If you are willing to spend more for a newer redesign and a more upscale comfort experience, the 2020 is the better upgrade path. Price-sensitive buyers should start with the 2019 and focus on clean-history examples.

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 November 3, 2026, CarGurus experts' opinions, and generative AI.