Used 2019 Toyota Highlander for Sale nearNew Haven, CT

How much does the 2019 Toyota Highlander cost?

Prices have softened 4.54% compared to this time last year, making it a favorable time to shop this model year.

There are 2,728 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. If you want a practical, comfort-focused midsize SUV for family use, it fits that role well, even if some shoppers wish for more rear-seat space. With 34.8% of listings marked as good or great deals, you have room to shop selectively.

Is the 2019 Toyota Highlander reliable?

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

User feedback highlights reliability, dependability, and a trouble-free ownership experience, with many drivers saying they feel confident counting on it over time. That kind of praise matters if you plan to keep the SUV for the long haul and want something that should age well with routine maintenance. For used buyers, the main ownership risk is less about the model’s reputation and more about finding one with a clean, well-documented 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.

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 so you can avoid paying strong money for a compromised example.

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

This is a moderate market, so you can be selective without expecting deep discounts on every listing.

• Deal availability: 34.8% of listings are priced as good or great deals.
• Inventory: There are 2,728 listings available.
• Price trend: Prices have softened 4.54% compared with last year.
• Clean inventory: 64.5% of listings are accident-free.

If you find a listing below $23,059, 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 $23,684 sits slightly below last year's $24,810.

That softer pricing suggests the market has eased, which can help you buy at a better entry point today. For a future seller, it also means resale value may depend more on condition, mileage, and documentation than on broad market momentum. Well-kept examples 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:

• 34.8% 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 4.54% compared with last year.
• Owners rate it 4.74/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $27,527, the 2020 costs more than the current year's $23,684 average.
• The redesign brings a quieter ride and a more premium-feeling cabin.

The bottom line: Choose the 2019 if you want the better value and are comfortable shopping carefully for condition and history. If you can stretch your budget and want the newer redesign's calmer, more upscale feel, the 2020 is the stronger upgrade path. For price-sensitive buyers, the 2019 remains the smarter buy as long as you verify the vehicle's background and inspect it closely.

These recommendations are based on CarGurus' proprietary market data from September 29, 2026, CarGurus experts' opinions, and generative AI.