Used 2020 Toyota Highlander for Sale nearWinnipeg, MB

How much does the 2020 Toyota Highlander cost?

Prices have softened 10.48% compared to this time last year, making it a favourable time to shop this model year.

There are 235 listings available, which suggests you should have a reasonable amount of inventory to compare.

Is the 2020 Toyota Highlander a good car?

Yes — it earns a 4.6/5 from owners and a 7.17/10 from experts. The model scores 9/10 across Form and function and Safety.

Owners consistently praise its smooth ride, advanced features, and spacious interior, and many say it is especially appealing for families. The review summary also points to strong safety features and confident handling as recurring positives.

On the downside, the expert assessment notes poor handling and uninspired styling, so this is not the SUV for you if sharp responses matter most. It fits best if you want a relaxed, family-friendly three-row SUV with a calm driving character and a premium-feeling cabin.

Only 28.5% of listings are priced as good or great deals, so the market is selective rather than flooded with bargains.

Is the 2020 Toyota Highlander reliable?

Owners rate it 4.6/5, a strong signal of long-term satisfaction.

The owner feedback highlights reliability, comfort, and a trouble-free ownership experience as part of the Highlander’s appeal. The expert assessment also describes it as smooth and practically silent at idle, which reinforces the sense of dependable, low-stress daily use.

Toyota’s maintenance coverage adds another ownership perk, with the first scheduled maintenance visit included. For used buyers, the main long-term risk is less about durability and more about whether the previous owner kept up with maintenance and avoided neglect.

What should I look for when buying a used 2020 Toyota Highlander?

Key things to evaluate:

• Trim level: The base L trim gets the essentials, but higher trims add more appealing lighting, larger wheels, richer interior materials, and a more upscale feel. If you want the best balance of equipment and value, the XLE is the standout choice.
• Powertrain: You get a 3.5-litre V6 with either FWD or AWD. It is smooth, quiet, and strong enough for brisk acceleration, but the chassis tuning is soft and the steering is loose at highway speeds.
• Safety package: Toyota Safety Sense 2.0 is standard, with automatic emergency braking with pedestrian detection and cyclist detection, lane-keeping assist, adaptive cruise control, and automatic high beams. Blind-spot monitoring, rear cross-traffic alert, parking sensors, and rear emergency braking are optional.
• Infotainment: The standard screen is 8 inches, while Platinum gets a 12.3-inch touchscreen. Apple CarPlay and Android Auto are standard, but the interface is dated and the screen and cameras are low-resolution.
• Fuel efficiency: The Highlander L FWD is rated at 11.9 L/100 km city, 8.3 highway, and 10.3 combined. With AWD, it is rated at 11.7 L/100 km city, 8.6 highway, and 10.3 combined.

Which 2020 Toyota Highlander trim should I buy?

The 2020 Toyota Highlander is offered in 5 trim levels: L, LE, XLE, Limited, Platinum.

Here's the short version:

• L: This is the entry point, and it gives you the Highlander’s core strengths without the higher price tag. It makes sense if you mainly want the roomy cabin, standard safety tech, and smooth V6 power.
• LE: This trim adds useful everyday equipment while staying close to the value end of the lineup. It is a sensible step up if you want a little more convenience without stretching too far.
• XLE: The XLE is the best-value trim. It is the sweet spot if you want the strongest mix of equipment, comfort, and price.
• Limited: This trim leans into the Highlander’s upscale side with richer materials and more premium-feeling features. It suits you if you want the near-luxury experience the Highlander is known for.
• Platinum: This is the most fully equipped version, with the largest touchscreen, head-up display, and the most advanced-feeling cabin presentation. Choose it if you want the most technology and the most upscale finish.

Toyota Safety Sense 2.0 is standard across the lineup, while some extra safety features remain optional.

Is now a good time to buy a used 2020 Toyota Highlander?

This is a moderate market for selective buyers, so it rewards comparison shopping.

• Deal availability: 28.5% of listings are priced as good or great deals.
• Inventory: There are 235 listings available.
• Price trend: Prices have softened 10.48% compared with last year.

If you find a listing below $34,043 CAD, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2020 Toyota Highlander's resale value?

The current average of $34,961 CAD sits slightly below last year's $39,055 CAD.

That softer pricing can help you buy more affordably now, but it also means future resale expectations should be more measured than they were a year ago. If you buy at the right price and keep the vehicle in strong condition, you can still protect value reasonably well. The Highlander’s broad family appeal and strong owner satisfaction should continue to support demand when it is time to sell.

Vehicles with strong owner satisfaction ratings, like this model year's 4.6/5, tend to retain buyer demand, which supports resale value over time.

Is the 2020 Toyota Highlander safe?

The 2020 Highlander earns a five-star overall safety rating from NHTSA and a 2020 Top Safety Pick from IIHS.

It earns a 9/10 safety score from our experts.

Toyota Safety Sense 2.0 is standard, and it includes automatic emergency braking with pedestrian detection and cyclist detection, lane-keeping assist, adaptive cruise control, and automatic high beams. A driver’s knee airbag and a special front-passenger cushion airbag are also standard.

Blind-spot monitoring, rear cross-traffic alert, parking sensors, and rear emergency braking are optional, so you should check whether a used example has the extra driver-assistance equipment you want.

Should I buy a 2020 Toyota Highlander or consider a different year?

If you're weighing the 2020 against nearby model years, here's how to think about it:

Choose the 2020 if:

• 28.5% of listings are priced as good or great deals.
• Price trend: Prices have softened 10.48% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• It delivers a calm, comfort-first redesign with a premium-feeling cabin.

Consider the 2021 if:

• At $38,485 CAD, the 2021 costs more than the current year's $34,961 CAD average.
• It adds more standard safety technology.

The bottom line: If you want the better buy today, the 2020 is the smarter starting point because pricing has eased and the core ownership experience is already strong. If you are willing to pay more for added standard safety tech, the 2021 is the better choice for you.

These recommendations are based on CarGurus' proprietary market data from September 29, 2026, CarGurus experts' opinions, and generative AI.