Used 2016 Toyota Highlander for Sale nearWindsor, ON

How much does the 2016 Toyota Highlander cost?

Prices have softened 4.49% compared to this time last year, making it a favourable time to shop this model year.

There are 91 listings available, which gives you a modest amount of choice in the used market.

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 consistently praise its comfort, reliability, and the abundance of features it offers, and they also highlight the smooth ride and powerful V6 engine. That makes it a strong fit if you want a practical midsize SUV for family use, daily commuting, and longer trips. With 26.4% of listings marked as good or great deals, you still have some room to shop carefully.

Is the 2016 Toyota Highlander reliable?

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

The user feedback also points to reliability, dependability, and a trouble-free ownership experience, which is exactly what many used-SUV shoppers want from a family vehicle. The Highlander’s reputation for long-term durability helps support confidence if you plan to keep it for years. For used buyers, the main long-term ownership risk is less about the core vehicle and more about finding one that has been maintained properly.

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

This looks like a moderate market, so you can be selective without expecting a deep bargain on every listing.

• Deal availability: 26.4% of listings are priced as good or great deals.
• Inventory: There are 91 listings available.
• Price trend: Prices have softened 4.49% compared with last year.

If you find a listing below $22,098 CAD, 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 $22,956 CAD sits slightly below last year's $24,035 CAD.

That softer pricing suggests the market has become a bit more buyer-friendly, which can affect what you recover later if you sell. If you buy at the right price now, you may have a better chance of limiting depreciation pressure over your ownership period. The Highlander’s strong reputation and steady demand should help support future resale interest, especially among shoppers looking for a dependable family SUV.

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:

• 26.4% of listings are priced as good or great deals.
• Price trend: Prices have softened 4.49% compared with last year.
• Owners rate it 4.9/5 — a strong satisfaction signal.

The bottom line: You should lean toward the 2016 if you want a well-liked, comfort-focused midsize SUV with strong owner approval and a market that still offers some deal potential. If you are especially price-sensitive, it can also make sense to compare nearby model years and focus on whichever one gives you the best combination of condition, mileage, and asking price.

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.