Used 2016 Toyota Highlander for Sale nearMilwaukee, WI

How much does the 2016 Toyota Highlander cost?

Prices have softened 4.36% compared to this time last year, making it a favorable time to shop this model year.

There are 1,848 listings available, which gives you a solid amount of inventory to compare.

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 feature content, and they also highlight the smooth ride and strong V6 performance. That lines up well with the Highlander’s role as a practical family SUV that prioritizes everyday usability, space, and comfort over flash. With 33.9% of listings marked as good or great deals, you have a meaningful chance to find a competitive listing.

Is the 2016 Toyota Highlander reliable?

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

Owners describe it as reliable and appreciate that it feels dependable for daily use, with a reputation that supports trouble-free ownership over the long term. The strong satisfaction from current owners suggests you can count on it as a family vehicle if it has been maintained well. For used buyers, the main long-term ownership risk is buying a poorly documented example, so condition and maintenance history matter.

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

At 57.8% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should start with a vehicle history report and confirm whether any prior damage was minor or structural. Then prioritize a thorough pre-purchase inspection, especially for signs of uneven wear, repair quality, or neglected maintenance. Focus on overall condition and documentation, since a clean, well-kept example is the safest path in this market.

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 expecting every listing to be a bargain.

• Deal availability: 33.9% of listings are priced as good or great deals.
• Inventory: There are 1,848 listings available.
• Price trend: Prices have softened 4.36% compared with last year.
• Clean inventory: 57.8% of listings are accident-free.

If you find a listing below $17,938, 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 $18,133 sits slightly below last year's $18,959.

That softer pricing suggests the market has become a bit more favorable for buyers, but it also means future sellers may face some pressure if prices continue to ease. If you buy well and keep the vehicle in strong condition, you can help protect your exit value later. 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:

• 33.9% of listings are priced as good or great deals.
• At 57.8% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 4.36% compared with last year.
• Owners rate it 4.93/5 — a strong satisfaction signal.

Consider the 2017 if:

• At $20,233, the 2017 costs more than the current year's $18,133 average.
• It adds refreshed styling, an updated engine, and standard safety equipment.

The bottom line: If you want the better value play, the 2016 is the stronger starting point because it combines a lower average price with strong owner satisfaction. If you’re willing to pay more for a fresher feel and updated equipment, the 2017 is the better secondary path.

These recommendations are based on CarGurus' proprietary market data from September 15, 2026, CarGurus experts' opinions, and generative AI.