Used 2016 Toyota Highlander for Sale nearMilwaukee, WI

How much does the 2016 Toyota Highlander cost?

Prices have softened 3.98% compared to this time last year, making it a favorable time to shop this model year.

There are 1,983 listings available, which gives you a solid pool of options to compare.

Is the 2016 Toyota Highlander a good car?

Yes — the 4.9/5 user rating points to strong owner satisfaction. Owners consistently praise its comfort, reliability, and feature content, and they also highlight the smooth ride and strong V6 performance. That fits especially well if you want a practical midsize SUV that is easy to live with for family use rather than something sporty. With 35.0% of listings marked as good or great deals, you have a decent chance of finding a competitive price.

Is the 2016 Toyota Highlander reliable?

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

Owners describe it as reliable, and they also emphasize its trouble-free ownership experience and dependable everyday use. The feedback suggests you can count on it for long-term family duty, especially if you prioritize comfort and consistency over excitement. For used buyers, the main risk is less about the model’s reputation and more about how well a specific example has been maintained over time.

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

At 59.6% 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 past damage. After that, prioritize a thorough pre-purchase inspection, especially on body panels, alignment, and signs of uneven wear that can point to prior repairs. Focus on overall condition and maintenance records, because a well-kept Highlander is likely to be a better long-term buy than a cheaper one with hidden issues.

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

This looks like a moderate, selective buyer’s market, so you can shop carefully without feeling rushed.

• Deal availability: 35.0% of listings are priced as good or great deals.
• Inventory: There are 1,983 listings available.
• Price trend: Prices have softened 3.98% compared with last year.
• Clean inventory: 59.6% 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 $17,973 sits slightly below last year's $18,717.

That softer pricing can help you buy more affordably now, but it also means future resale gains may be more limited if the market stays steady. If you plan to sell later, condition and maintenance history will matter a lot, because buyers tend to pay more for examples that look well cared for. Strong demand for a comfortable, practical SUV can still support value, especially when the vehicle has a clean history and solid ownership appeal.

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:

• 35.0% of listings are priced as good or great deals.
• At 59.6% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 3.98% compared with last year.
• Owners rate it 4.9/5 — a strong satisfaction signal.

Consider the 2017 if:

• At $20,013, the 2017 costs more than the current year's $17,973 average.
• It adds refreshed styling and standard Toyota Safety Sense.

The bottom line: You should lean toward the 2016 if you want the better value and are willing to shop carefully for condition. If you want the newer refresh and can stretch your budget, the 2017 is the cleaner upgrade path.

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

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