Used 2016 Toyota Highlander for Sale nearChicago, IL

How much does the 2016 Toyota Highlander cost?

Prices have softened 3.60% compared to this time last year, making it a favorable time to shop this model year.

There are 1,878 listings available, which gives you a solid amount of inventory to compare before you buy.

Is the 2016 Toyota Highlander a good car?

Yes — the 4.93/5 user rating points to very strong owner satisfaction. Owners consistently praise its comfort, reliability, and abundance of features, and they also highlight the smooth ride and strong V6 power. For you, that makes it a sensible pick if you want a practical midsize SUV that prioritizes everyday usability, family comfort, and a well-equipped cabin over sporty driving feel. With 33.3% of listings marked as good or great deals, there is still room to shop selectively.

Is the 2016 Toyota Highlander reliable?

Owners rate it 4.93/5, a strong signal of long-term satisfaction.

The owner feedback also emphasizes reliability, dependable day-to-day use, and a trouble-free ownership experience. That kind of praise matters if you plan to keep the SUV for years, because it suggests the Highlander has earned trust from people who live with it every day. For used buyers, the main long-term ownership risk is less about the model’s reputation and more about the condition of the specific vehicle you choose.

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

At 59.3% 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 accident records. After that, prioritize a thorough pre-purchase inspection, especially on body panels, alignment, and signs of uneven wear that can point to past damage or poor repairs. Focus on overall condition and maintenance evidence, because a well-kept Highlander is the one most likely to deliver the comfort and reliability this model is known for.

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

This is a moderate buyer’s market, so you can shop carefully and still find worthwhile opportunities.

• Deal availability: 33.3% of listings are priced as good or great deals.
• Inventory: There are 1,878 listings available.
• Price trend: Prices have softened 3.60% compared with last year.
• Clean inventory: 59.3% of listings are accident-free.

If you find a listing below $17,931, 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 $18,194 sits slightly below last year's $18,873.

That softer pricing can help you buy more carefully now, but it also means future resale gains may be more gradual if the market stays steady. If you keep the vehicle in strong condition and maintain it well, you should be better positioned when it is time to sell. Demand should remain supported by the model’s strong owner satisfaction and practical family-SUV appeal.

Vehicles with strong owner satisfaction ratings, like this model year's 4.93/5, 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:

• 33.3% of listings are priced as good or great deals.
• At 59.3% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 3.60% compared with last year.
• Owners rate it 4.93/5 — a strong satisfaction signal.

Consider the 2017 if:

• At $20,153, the 2017 costs more than the current year's $18,194 average.
• It adds refreshed styling and standard safety updates.

The bottom line: You should lean toward the 2016 if you want the better value and are willing to shop carefully for condition and history. If you want a newer-feeling Highlander and can stretch your budget, the 2017 is the better secondary path.

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