Used 2019 Toyota Highlander for Sale near Massachusetts

How much does the 2019 Toyota Highlander cost?

Prices have softened 4.97% compared to this time last year, making it a favorable time to shop this model year.

There are 2,888 listings available, which gives you a solid amount of inventory to compare.

Is the 2019 Toyota Highlander a good car?

Yes — the 4.7/5 user rating points to strong owner satisfaction. Drivers consistently praise its comfort, spaciousness, and reliability, and many also appreciate the safety features and overall practicality. For you, that makes it a strong fit if you want a family-friendly midsize SUV with everyday usefulness and a comfortable, easygoing character. With 35.4% of listings marked as good or great deals, there is still meaningful market opportunity if you shop carefully.

Is the 2019 Toyota Highlander reliable?

Owners rate it 4.7/5, a strong signal of long-term satisfaction.

The user review summary highlights reliability, and drivers also describe the Highlander as dependable and comfortable over time. That combination matters if you want a used SUV you can count on for regular commuting, errands, and family duty. For used buyers, the main long-term ownership 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 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 those with prior 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 past repairs, since those details matter more when you are choosing among many similar family SUVs.

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 with some leverage if you stay disciplined.

• Deal availability: 35.4% of listings are priced as good or great deals.
• Inventory: There are 2,888 listings available.
• Price trend: Prices have softened 4.97% compared with last year.
• Clean inventory: 65.2% of listings are accident-free.

If you find a listing below $23,049, 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 $23,277 sits slightly below last year's $24,495.

That price movement suggests the market has cooled a bit, which can help you buy more favorably now but may also limit short-term upside if you plan to resell soon. Even so, the Highlander’s strong owner satisfaction and practical appeal should help it stay in demand with used SUV shoppers. If you keep mileage, condition, and maintenance history in good shape, you should have a better chance of protecting value over time.

Vehicles with strong owner satisfaction ratings, like this model year's 4.7/5, 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:

• 35.4% 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 4.97% compared with last year.
• Owners rate it 4.7/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $27,363, the 2020 costs more than the current year's $23,277 average.
• It adds a quieter, more upscale-feeling cabin with a stronger premium comfort focus.

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 a more refined, comfort-first experience, the 2020 is the better upgrade path.

How does the 2019 Toyota Highlander compare to the 2019 Honda Pilot?

Read our full side-by-side expert comparison here.

These recommendations are based on CarGurus' proprietary market data from October 27, 2026, CarGurus experts' opinions, and generative AI.