Used 2021 Toyota Highlander for Sale nearWinnipeg, MB

How much does the 2021 Toyota Highlander cost?

Prices have softened 8.85% compared to this time last year, making it a favourable time to shop this model year.

There are 270 listings available, which suggests you have a healthy 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.

Owners consistently praise its comfort, reliability, smooth ride, high-quality interior, spaciousness, and safety features. That lines up well with its family-focused role as a three-row SUV, especially if you want a mainstream model with strong name recognition and an easy-to-trust reputation.

Only 31.9% of listings are priced as good or great deals, so the market is somewhat selective even if the model is broadly appealing.

Is the 2021 Toyota Highlander reliable?

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

User feedback repeatedly points to reliability, comfort, and a trouble-free ownership experience, with many drivers saying they feel confident counting on it day to day. The expert review also frames the Highlander as a smooth, predictable SUV with a reputation for reliability, which supports its appeal for long-term use.

Toyota’s ownership story is helped by its family-friendly mission and standard safety focus, and that can make it feel like a sensible used buy if you want something dependable. For used buyers, the main long-term risk is that higher-mileage examples may still show the usual wear from family duty, so condition matters.

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, suspension tuning, and an appearance package, while Limited trim brings a more upscale interior feel and sits just below Platinum. Base trims are less richly equipped, so you should compare comfort and convenience features carefully.
• Powertrain: Every Highlander uses a 3.5-litre V6 with 295 horsepower and an eight-speed automatic, with front-wheel drive or all-wheel drive depending on trim. The setup is smooth and predictable rather than sporty.
• 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 across the lineup, and navigation is only equipped from the Limited grade.
• Fuel efficiency: The V6 is rated at 10.3 L/100 km combined. Front-wheel drive is rated at 11.9 L/100 km city and 8.3 highway, while all-wheel drive is rated at 11.8 city and 8.6 highway.

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, and it makes sense if you want the Highlander name and core safety tech at the lowest starting price, but you should expect the fewest comfort and convenience features.
• LE: This is the best-value trim for many shoppers because it adds all-wheel drive and keeps the Highlander’s practical family focus intact without pushing too far up the price ladder.
• 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.
• XSE: Pick this if you want the sportier-looking Highlander, with its unique front end, suspension tuning, and appearance package.
• Limited: This is the trim for you if you want the more premium-feeling cabin, plus navigation and the JBL audio system.
• Platinum: Go here if you want the most luxurious and most fully equipped Highlander, including the 12.3-inch infotainment screen.

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

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

This is a moderate market for selective buyers, with enough inventory to shop carefully and enough price movement to create opportunities.

• Deal availability: 31.9% of listings are priced as good or great deals.
• Inventory: There are 270 listings available.
• Price trend: Prices have softened 8.85% compared with last year.

If you find a listing below $38,461 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 $38,586 CAD sits slightly below last year's $42,334 CAD.

That price decline suggests the market has become more favourable for buyers, which can make resale a little tougher for current owners than it was a year ago. If you plan to sell later, you should expect value to depend heavily on condition, mileage, and trim, especially because higher trims can be expensive when new.

At the same time, the Highlander’s strong reputation and broad appeal help support demand in the used market. 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 a Top Safety Pick+ rating from IIHS and a five-star overall rating from NHTSA.

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

Toyota Safety Sense 2.5+ is standard and 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-friendly safety package.

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:

• 31.9% of listings are priced as good or great deals.
• Price trend: Prices have softened 8.85% 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 $35,016 CAD, the 2020 costs less than the current year's $38,586 CAD average.
• It prioritises comfort, a soft ride, and a calm, premium-feeling cabin.

Consider the 2022 if:

• At $41,149 CAD, the 2022 costs more than the current year's $38,586 CAD average.
• It adds more family-focused versatility and keeps the easy-to-use tech and safety strengths.

The bottom line: If you want the best balance of price movement, safety, and broad appeal, the 2021 is the strongest all-around pick. If you’re more price-sensitive, the 2020 can be a smart value play, while the 2022 makes sense if you want to spend more for a newer model-year alternative.

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 edges ahead on expert scoring and safety emphasis, while the Pilot undercuts it on average used price. The Highlander also has the stronger deal share and slightly better highway fuel consumption, which may matter if you want a more efficient family SUV. The Pilot remains the lower-cost choice if your priority is stretching your budget.

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

These recommendations are based on CarGurus' proprietary market data from November 4, 2026, CarGurus experts' opinions, and generative AI.