Used 2019 Toyota Highlander for Sale nearBoston, MA

How much does the 2019 Toyota Highlander cost?

Prices have softened 4.69% compared to this time last year, making it a favorable time to shop this model year.

There are 2,731 listings available, which gives you a solid pool of options to compare.

Is the 2019 Toyota Highlander a good car?

Yes — the 2019 Toyota Highlander earns a 4.74/5 user rating, which 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, it fits well if you want a family-friendly midsize SUV that emphasizes everyday usefulness, comfort, and affordability over excitement. With 37.0% 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.

User feedback repeatedly highlights reliability, and drivers also describe it as dependable and trouble-free for everyday use. That kind of owner confidence matters if you plan to keep the vehicle for the long haul, because it suggests fewer surprises and steadier ownership satisfaction. For used buyers, the main risk is less about the model’s reputation and more about how well a specific example has been maintained.

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

At 65% 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 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, since those details matter more when you are comparing used examples.

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 opportunities.

• Deal availability: 37.0% of listings are priced as good or great deals.
• Inventory: There are 2,731 listings available.
• Price trend: Prices have softened 4.69% compared with last year.
• Clean inventory: 65.0% of listings are accident-free.

If you find a listing below $23,055, 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 $23,685 sits slightly below last year's $24,849.

That softer pricing can help you buy more carefully now, but it also means future resale will depend heavily on how well you preserve the vehicle’s condition. If you keep mileage reasonable, maintain service records, and avoid accident history, you should be in a better position when it is time to sell. The current market also suggests that clean, well-kept examples should remain easier to move than rougher 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:

• 37.0% of listings are priced as good or great deals.
• At 65% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 4.69% compared with last year.
• Owners rate it 4.74/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $27,507, the 2020 costs more than the current year's $23,685 average.
• Redesigned for 2020, it emphasizes a quieter, more premium-feeling ride.

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 and a meaningful share of deal-priced listings. If you are willing to spend more for a newer redesign and a more upscale comfort focus, the 2020 is the better secondary path.

These recommendations are based on CarGurus' proprietary market data from October 6, 2026, CarGurus experts' opinions, and generative AI.