Used 2021 Toyota Highlander for Sale nearWindsor, ON

How much does the 2021 Toyota Highlander cost?

Prices have softened 8.89% compared to this time last year, making it a favourable time to shop this model year.

There are 265 listings available, which suggests you should have a reasonable amount of inventory to compare.

Is the 2021 Toyota Highlander a good car?

Yes — the 2021 Toyota Highlander earns a 4.9/5 user rating and a 7.5/10 expert rating. The standout strength is Safety at 10/10.

You’ll also see recurring praise for comfort, reliability, a smooth ride, and a high-quality interior. For a mainstream three-row SUV aimed at family duty, that mix of spaciousness, safety features, and everyday ease makes it especially appealing. There are also plenty of listings, and 32.1% are priced as good or great deals, which helps the market look workable for shoppers.

Is the 2021 Toyota Highlander reliable?

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

Drivers consistently describe it as reliable and dependable, with many saying it feels like a vehicle you can count on. The expert assessment also points to smooth, predictable operation and a reputation for reliability, which reinforces that impression. Toyota’s first scheduled maintenance visit is on the house, which helps early ownership costs.

For used buyers, the main long-term ownership risk is less about durability and more about living with the Highlander’s compromises if you value fuel economy or flexible cabin settings.

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

Key things to evaluate:

• Trim level: The XSE adds a more aggressive look, a little suspension tuning, and an appearance package, while Limited and Platinum bring a more upscale feel. Base trims miss some of the richer cabin touches and higher-end equipment that make the Highlander feel especially polished.
• Powertrain: Every Highlander uses a 3.5-litre V6 with 295 horsepower and an eight-speed automatic. It’s smooth and predictable rather than exciting, so you should focus on whether that calm, family-friendly character suits you.
• Safety package: Toyota Safety Sense 2.5+ 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, while LED fog lights are available from the XLE grade up.
• Infotainment: Lower trims use an 8-inch touchscreen, while Platinum gets a 12.3-inch unit. Android Auto and Apple CarPlay are standard, and the larger screen is bright and crisp, though navigation and app layout can be less flexible than you might expect.
• Fuel efficiency: The V6 is rated at 10.3 L/100 km combined, with 11.9 L/100 km city and 8.3 highway for front-wheel drive, or 11.8 city and 8.6 highway for all-wheel drive.

Which 2021 Toyota Highlander trim should I buy?

The 2021 Toyota Highlander is offered in 6 trim levels: L, LE, XLE, XSE, Limited, Platinum.

Here's the short version:

• L: This is the entry point if you want the lowest starting price, but it’s the most basic way into the lineup and leaves you with fewer comfort and convenience features than the higher trims.
• LE: This is the best-value trim for many shoppers because it adds all-wheel drive and keeps the Highlander’s core family-friendly strengths intact without pushing the price as high as the upper trims.
• XLE: Choose this if you want a more upscale daily driver, since it builds on the LE with more equipment and sits in the middle of the range without jumping straight to luxury pricing.
• XSE: Pick this if you want the sportier-looking Highlander. It adds the more aggressive styling, a bit of suspension tuning, and a sharper presence, but it’s more about appearance and feel than true performance.
• Limited: This is the sweet spot if you want the Highlander to feel genuinely premium. It brings the upscale interior treatment, navigation, and a JBL audio system, making it a strong choice for comfort-focused buyers.
• Platinum: Go here if you want the most fully equipped Highlander, including the 12.3-inch infotainment screen and the highest trim presentation.

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

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 carefully without expecting a fire sale.

• Deal availability: 32.1% of listings are priced as good or great deals.
• Inventory: There are 265 listings available.
• Price trend: Prices have softened 8.89% compared with last year.

If you find a listing below $38,462 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 $38,558 CAD sits slightly below last year's $42,318 CAD.

That softer pricing suggests the market has become more favourable for buyers, but it also means a future seller may need to be realistic about expectations. If you buy at today’s average and later resell into a similar market, you may not recover as much as owners did when prices were higher a year ago. Strong demand for a well-known three-row SUV should still help support values, especially for well-kept examples with desirable equipment.

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.

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+ 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, which strengthens the Highlander’s family-focused safety story. The main caveat is that LED fog lights are only available from the XLE grade up.

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:

• 32.1% of listings are priced as good or great deals.
• Price trend: Prices have softened 8.89% compared with last year.
• Owners rate it 4.9/5 — a strong satisfaction signal.
• Toyota added more standard safety technology this year.

Consider the 2020 if:

• At $35,086 CAD, the 2020 costs less than the current year's $38,558 CAD average.
• It prioritises comfort, a soft ride, and a calm, premium-feeling cabin.

Consider the 2022 if:

• At $41,345 CAD, the 2022 costs more than the current year's $38,558 CAD average.
• It adds versatility, a stout V6, and standard safety features for family use.

The bottom line: The 2021 is the best all-around pick if you want the newer safety focus and a still-reasonable used price. If you’re more price-sensitive, the 2020 can be a smart way to save money while keeping the Highlander’s comfort-first character.

How does the 2021 Toyota Highlander compare to the 2021 Honda Pilot?

Our experts score the 2021 Toyota Highlander 7.5/10 and the 2021 Honda Pilot 7.2/10.

The Highlander has the edge in expert scoring, while the Pilot is cheaper on the used market. The Highlander also brings a stronger safety story and a slightly better highway fuel figure, which may matter more if you prioritise family duty and peace of mind. The Pilot counters with a lower average used price and similar city fuel consumption, so it can make sense if value is your top priority.

Read our full side-by-side expert comparison here.

These recommendations are based on CarGurus' proprietary market data from November 10, 2026, CarGurus experts' opinions, and generative AI.