Used 2019 Toyota Highlander for Sale nearChicago, IL

How much does the 2019 Toyota Highlander cost?

Prices have softened 4.49% compared to this time last year, making it a favorable time to shop this model year.

There are 2,694 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 they also like the safety features and engine performance. In practical terms, that makes it a strong fit if you want a comfort-focused midsize SUV for family use, especially if you value everyday usefulness over sporty driving. With 34.5% of listings marked as good or great deals, you have 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 highlights reliability, dependability, and a trouble-free ownership experience, along with confidence in the vehicle’s long-term durability. That kind of feedback matters if you want a used SUV you can count on for years rather than one that feels risky to own.

For used buyers, the main long-term ownership risk is less about the model’s reputation and more about finding one that has been maintained well and not worn down by prior use.

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 start with a vehicle history report so you can separate clean examples from ones with accident records. After that, prioritize a thorough inspection of body panels, alignment, and signs of uneven wear, since condition matters more when you’re shopping a model with mixed listing history. It also helps to focus on maintenance records and overall interior condition, because those are strong clues to how the SUV was treated.

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 and still find worthwhile options.

• Deal availability: 34.5% of listings are priced as good or great deals.
• Inventory: There are 2,694 listings available.
• Price trend: Prices have softened 4.49% compared with last year.
• Clean inventory: 65.2% of listings are accident-free.

If you find a listing below $23,064, 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 $23,725 sits slightly below last year's $24,841.

That price movement suggests the market has cooled a bit, which can make the vehicle easier to buy now but may also limit short-term appreciation for a future seller. If you plan to resell later, the current trend points to steady demand rather than a strong upward pricing surge. Even so, a well-kept example should still hold appeal because shoppers continue to value this model’s comfort and practicality.

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:

• 34.5% 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 4.49% compared with last year.
• Owners rate it 4.74/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $27,701, the 2020 costs more than the current year's $23,725 average.
• The redesign brings a quieter ride and a more luxurious-feeling cabin.

The bottom line: If you want the better value play, the 2019 is the stronger starting point because pricing has softened and inventory is broad enough to shop selectively. If you’re willing to pay more for the redesigned 2020’s calmer, more upscale feel, that newer year is the better secondary path for buyers who prioritize comfort over price.

These recommendations are based on CarGurus' proprietary market data from September 15, 2026, CarGurus experts' opinions, and generative AI.