Used 2019 Toyota Highlander for Sale nearMilwaukee, WI

How much does the 2019 Toyota Highlander cost?

Prices have softened 4.68% compared to this time last year, making it a favorable time to shop this model year.

There are 2,634 listings available, which gives you a solid amount of inventory 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 many also like the safety features and engine performance. For you, that makes it a strong fit if you want a practical, comfort-focused midsize SUV for family use, especially if you value everyday usefulness over sporty driving. With 34.7% of listings marked as good or great deals, there is still some room to shop selectively.

Is the 2019 Toyota Highlander reliable?

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

The user feedback also emphasizes reliability, along with a trouble-free ownership experience and confidence in the vehicle over the long term. That combination suggests the Highlander is the kind of used SUV you can count on if you want something built for steady daily use. For used buyers, the main long-term risk is less about the model’s reputation and more about finding one with clean history and consistent maintenance.

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 start with a vehicle history report so you can separate clean examples from ones with past damage. After that, prioritize a pre-purchase inspection, especially if the listing price looks unusually attractive. Focus your condition check on signs of prior repair quality, wear consistency, and whether the SUV still feels tight and well maintained.

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

This is a moderate buyer’s market, so you can shop selectively and still find worthwhile options.

• Deal availability: 34.7% of listings are priced as good or great deals.
• Inventory: There are 2,634 listings available.
• Price trend: Prices have softened 4.68% compared with last year.
• Clean inventory: 64.5% of listings are accident-free.

If you find a listing below $23,070, 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 $23,668 sits slightly below last year's $24,829.

That softer pricing can help you buy at a more favorable entry point, but it also means future resale gains may be more limited if the market stays soft. If you plan to sell later, a well-kept example with clean history should hold up better than one with accident history or visible wear. Strong demand for this model’s comfort and reliability should continue to support used-market interest.

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:

• 34.7% 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 4.68% compared with last year.
• Owners rate it 4.74/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $27,605, the 2020 costs more than the current year's $23,668 average.
• The redesign brings a quieter ride and a more upscale, Lexus-like feel.

The bottom line: You should lean toward the 2019 if you want the better value and are comfortable shopping carefully for condition and history. If you want the newer redesign and are willing to pay more for a quieter, more premium-feeling SUV, the 2020 is the stronger upgrade path. For price-sensitive buyers, the 2019 is the smarter buy as long as you verify the vehicle’s past and inspect it closely.

These recommendations are based on CarGurus' proprietary market data from September 22, 2026, CarGurus experts' opinions, and generative AI.