Used 2019 Toyota Highlander for Sale nearFort Myers, FL

How much does the 2019 Toyota Highlander cost?

Prices have softened 4.38% compared to this time last year, making it a favorable time to shop this model year.

There are 2,741 listings available, which gives you a solid pool to compare prices and condition.

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. 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 33.2% of listings marked as good or great deals, you have a decent chance of finding a competitive offer.

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 over the long term. That kind of feedback matters most when you’re shopping used, because it suggests the Highlander has a reputation for holding up well with age. For you, the main long-term ownership risk is less about the model’s reputation and more about choosing a well-kept example with clean history and solid maintenance.

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

At 65.6% 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 those with accident records. 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 panel gaps, and any wear that suggests the SUV has had a harder life than the listing implies.

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

This looks like a moderate market, so you can shop selectively without expecting a deep bargain on every listing.

• Deal availability: 33.2% of listings are priced as good or great deals.
• Inventory: There are 2,741 listings available.
• Price trend: Prices have softened 4.38% compared with last year.
• Clean inventory: 65.6% 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 $23,796 sits slightly below last year's $24,887.

That softer pricing suggests the market has cooled a bit, which can help you buy more carefully now but may also limit short-term upside if you plan to resell soon. If you’re thinking ahead to resale, the good news is that the Highlander’s strong owner satisfaction should help keep demand steady. Well-kept examples with clean history and desirable equipment should remain easier to move than neglected ones.

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:

• 33.2% of listings are priced as good or great deals.
• At 65.6% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 4.38% compared with last year.
• Owners rate it 4.74/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $27,731, the 2020 costs more than the current year's $23,796 average.
• It was redesigned for 2020, with a quieter ride and a more premium-feeling cabin.

The bottom line: If you want the better value play, the 2019 is the smarter starting point because it combines a lower average price with strong owner satisfaction. If you’re willing to spend more for the redesigned feel and a more upscale comfort experience, the 2020 is the better secondary path.

These recommendations are based on CarGurus' proprietary market data from September 11, 2026, CarGurus experts' opinions, and generative AI.