Used 2016 Toyota Highlander for Sale nearChicago, IL

How much does the 2016 Toyota Highlander cost?

Prices have softened 3.48% compared to this time last year, making it a favorable time to shop this model year.

There are 1,971 listings available, which gives you a solid pool of options to compare.

Is the 2016 Toyota Highlander a good car?

Yes — the 2016 Toyota Highlander earns a 4.9/5 user rating, which points to very strong owner satisfaction. Owners repeatedly praise its comfort, reliability, and abundance of features, and they also highlight the smooth ride and powerful V6 engine. For you, that makes it a strong fit if you want a practical midsize SUV that leans toward easy everyday use, family comfort, and versatility rather than sporty driving. With 32.2% of listings marked as good or great deals, there is still meaningful market opportunity if you shop carefully.

Is the 2016 Toyota Highlander reliable?

Owners rate it 4.9/5, a strong signal of long-term satisfaction.

The owner feedback also emphasizes reliability, dependability, and a trouble-free ownership experience, with many shoppers valuing it as a vehicle they can count on. That kind of reputation matters if you plan to keep the SUV for years and want fewer surprises from a used purchase. For long-term ownership, your biggest risk is buying a poorly maintained example, so condition and service history should carry extra weight.

What should I look for when buying a used 2016 Toyota Highlander?

At 58.4% 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 confirm accident records, title status, and ownership history before you commit. After that, prioritize a pre-purchase inspection, especially on the body, suspension, and any features that may have been repaired after a collision. Focus on overall condition and maintenance evidence, because a clean, well-kept example is the safest way to preserve the Highlander’s comfort and reliability advantages.

Is now a good time to buy a used 2016 Toyota Highlander?

This is a moderate market, so you can buy now if the right listing appears, but selective shoppers should still compare carefully.

• Deal availability: 32.2% of listings are priced as good or great deals.
• Inventory: There are 1,971 listings available.
• Price trend: Prices have softened 3.48% compared with last year.
• Clean inventory: 58.4% of listings are accident-free.

If you find a listing below $17,949, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2016 Toyota Highlander's resale value?

The current average of $17,957 sits slightly below last year's $18,605.

That softer pricing can help you buy more affordably today, but it also suggests resale values have eased compared with a year ago. If you plan to sell later, the current market points to steady rather than rising value retention, so condition and mileage will matter a lot when it is time to list. Well-kept examples should still appeal to family buyers who want comfort and practicality without paying new-SUV prices.

Vehicles with strong owner satisfaction ratings, like this model year's 4.9/5, tend to retain buyer demand, which supports resale value over time.

Should I buy a 2016 Toyota Highlander or consider a different year?

If you're weighing the 2016 against nearby model years, here's how to think about it:

Choose the 2016 if:

• 32.2% of listings are priced as good or great deals.
• At 58.4% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 3.48% compared with last year.
• Owners rate it 4.9/5 — a strong satisfaction signal.

Consider the 2017 if:

• At $19,845, the 2017 costs more than the current year's $17,957 average.
• It adds standard Safety Sense and refreshed styling for a more current feel.

The bottom line: Choose the 2016 if you want the better value and are comfortable shopping carefully for condition and history. If you want a newer-feeling Highlander with more standard safety equipment, the 2017 is the better secondary path, especially if you can stretch your budget.

How does the 2016 Toyota Highlander compare to the 2016 Honda Pilot?

These recommendations are based on CarGurus' proprietary market data from November 10, 2026, CarGurus experts' opinions, and generative AI.