Used 2019 Toyota Highlander for Sale near Connecticut

How much does the 2019 Toyota Highlander cost?

Prices have softened 5.32% compared to this time last year, making it a favorable time to shop this model year.

There are 2,912 listings available, which gives you a solid pool of options 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 they also value the safety features and engine performance. In practical terms, that makes it a strong fit if you want a family-focused midsize SUV for commuting, school runs, and everyday utility. With 35.6% of listings marked as good or great deals, you have a meaningful chance to find a competitive offer.

Is the 2019 Toyota Highlander reliable?

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

The user feedback highlights reliability, and drivers also describe the Highlander as dependable and trouble-free in everyday use. That lines up well with its reputation for long-term ownership appeal, especially if you want a used SUV you can count on for family duty. For used buyers, the main long-term risk is less about the model’s core durability and more about finding one that has been maintained well and not worn down by heavy use.

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

At 62.8% 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 accident records. Then prioritize a pre-purchase inspection, especially if the listing has higher mileage or incomplete service documentation. You should also pay close attention to interior condition, rear-seat wear, and signs of family use, since those areas often reveal how carefully 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 patiently but should move quickly on strong listings.

• Deal availability: 35.6% of listings are priced as good or great deals.
• Inventory: There are 2,912 listings available.
• Price trend: Prices have softened 5.32% compared with last year.
• Clean inventory: 62.8% of listings are accident-free.

If you find a listing below $23,023, 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 $23,023 sits slightly below last year's $24,316.

That softer pricing suggests the market has become a bit more favorable for buyers, which can put some pressure on future resale expectations if you sell soon. Even so, the Highlander’s steady demand and family-friendly reputation help support value retention better than many alternatives. If you keep mileage reasonable and maintenance records organized, you should be in a stronger position when it’s time to sell.

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:

• 35.6% of listings are priced as good or great deals.
• At 62.8% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 5.32% compared with last year.
• Owners rate it 4.7/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $27,084, the 2020 costs more than the current year's $23,023 average.
• It brings a redesigned cabin with a quieter, more premium-feeling ride.

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 comfort and premium feel, the 2020 is the better upgrade path. For price-sensitive buyers, the 2019 offers the more compelling balance of cost and appeal.

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 November 10, 2026, CarGurus experts' opinions, and generative AI.