Used 2021 Toyota Highlander for Sale nearWindsor, ON

How much does the 2021 Toyota Highlander cost?

Prices have softened 10.10% compared to this time last year, making it a favourable time to shop this model year.

There are 262 listings available, which suggests you have a reasonable amount of inventory to compare.

Is the 2021 Toyota Highlander a good car?

Yes — the 2021 Toyota Highlander earns a 4.86/5 user rating and a 7.5/10 expert rating. The standout strength is Safety at 10/10.

Owners consistently praise its comfort, reliability, features, smooth ride, and high-quality interior. That lines up well with its role as a three-row family SUV, especially if you want something familiar, broadly appealing, and easy to live with. The Highlander also benefits from strong name recognition and added standard safety technology for this model year.

With 29.8% of listings marked as good or great deals, the market still offers some room to shop selectively.

Is the 2021 Toyota Highlander reliable?

Owners rate it 4.86/5, a strong signal of long-term satisfaction.

User feedback repeatedly points to reliability, comfort, and a smooth, trouble-free ownership experience. The expert assessment also highlights smooth, predictable operation and a reputation for reliability, which fits the Highlander’s family-first mission. Toyota’s added standard safety technology and the model’s established reputation should help reassure used buyers who want something they can count on.

For used shoppers, the main long-term ownership risk is not dependability so much as whether the fuel economy and feature configurability meet your expectations.

What should I look for when buying a used 2021 Toyota Highlander?

Key things to evaluate:

• Trim level: The Limited trim sits just below Platinum and brings a more upscale interior, while the XSE adds a more aggressive look with a little suspension tuning and an appearance package. Base trims are less lavish, so you should compare cabin materials and convenience features carefully.
• Powertrain: Every Highlander uses a 3.5-litre V6 with 295 horsepower and 263 pound-feet of torque, paired with an eight-speed automatic transmission and either front-wheel drive or all-wheel drive. It is tuned for smooth, predictable operation rather than excitement.
• Safety package: Toyota Safety Sense 2.5+ includes automatic emergency braking with pedestrian detection and intersection support, plus adaptive cruise control, lane-departure warning, lane-keeping assist, lane-tracing assist, and automatic high beams. Blind spot monitoring is also standard, and LED headlights are standard across the lineup.
• Infotainment: Trims below Platinum use an 8-inch touchscreen, while Platinum gets a 12.3-inch unit. Android Auto and Apple CarPlay are standard, and Bluetooth is included. Navigation is limited to Limited and above.
• Fuel efficiency: The V6 Highlander is rated at 10.3 L/100 km combined, with 11.9 L/100 km city and 8.3 L/100 km highway for front-wheel drive, or 11.8 L/100 km city and 8.6 L/100 km highway for all-wheel drive. In testing, it returned 11.5 L/100 km combined.

Which 2021 Toyota Highlander trim should I buy?

The 2021 Toyota Highlander is offered in 5 trim levels: L, LE, XLE, XSE, Limited.

Here's the short version:

• L: This is the entry point if you want the lowest starting price, but you should expect the fewest amenities. It makes sense if you mainly want the Highlander’s space, safety, and name recognition without paying for extras.
• LE: This is the best-value choice for many shoppers because it adds all-wheel drive and keeps the Highlander’s core family-friendly strengths intact. If you want a practical balance of equipment and price, start here.
• XLE: This trim is the step up if you want more comfort and convenience without jumping all the way to the pricier upper trims. It suits buyers who want a more polished daily driver.
• XSE: Choose this if you want the sportier look and slightly firmer suspension tuning. It is more about style and feel than outright performance.
• Limited: This is the luxury-leaning pick, with an upscale interior, navigation, and a JBL audio system. It is the right choice if you want the most premium Highlander experience.

Toyota Safety Sense 2.5+ is standard, and blind spot monitoring is also standard across the lineup.

Is now a good time to buy a used 2021 Toyota Highlander?

This looks like a moderate, selective buyer’s market, so you can shop with some leverage if you are patient.

• Deal availability: 29.8% of listings are priced as good or great deals.
• Inventory: There are 262 listings available.
• Price trend: Prices have softened 10.10% compared with last year.

If you find a listing below $38,445 CAD, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2021 Toyota Highlander's resale value?

The current average of $38,463 CAD sits slightly below last year's $42,784 CAD.

That softer pricing can be good news if you are buying now, but it also means future sellers may face a more competitive market if prices continue to normalise. The Highlander’s broad appeal, strong safety reputation, and family-friendly image should help support demand over time. Still, resale value will depend on how well the market continues to reward comfort, reliability, and standard safety equipment.

Vehicles with strong owner satisfaction ratings, like this model year's 4.86/5, tend to retain buyer demand, which supports resale value over time.

Is the 2021 Toyota Highlander safe?

The 2021 Toyota Highlander earns five-star ratings from NHTSA and a Top Safety Pick+ rating from IIHS.

It earns a 10/10 safety score from our experts.

Toyota Safety Sense 2.5+ is standard, and it includes automatic emergency braking with pedestrian detection and intersection support, adaptive cruise control, lane-departure warning, lane-keeping assist, lane-tracing assist, and automatic high beams. Blind spot monitoring is also standard, and LED headlights come standard as well.

Should I buy a 2021 Toyota Highlander or consider a different year?

If you're weighing the 2021 against nearby model years, here's how to think about it:

Choose the 2021 if:

• 29.8% of listings are priced as good or great deals.
• Price trend: Prices have softened 10.10% compared with last year.
• Owners rate it 4.86/5 — a strong satisfaction signal.
• Toyota added more standard safety-feature technology this year.

Consider the 2020 if:

• At $34,735 CAD, the 2020 costs less than the current year's $38,463 CAD average.
• It was all-new and prioritises comfort, quietness, and a cosseting ride.

Consider the 2022 if:

• At $41,642 CAD, the 2022 costs more than the current year's $38,463 CAD average.
• It adds family-focused versatility, easy-to-use tech, and a stout V6.

The bottom line: The 2021 is the best all-around pick if you want the Highlander’s strong safety, comfort, and broad appeal at a softened price. If you are more price-sensitive, the 2020 can save you money while still delivering the Highlander’s calm, family-friendly character.

These recommendations are based on CarGurus' proprietary market data from September 22, 2026, CarGurus experts' opinions, and generative AI.