Used 2020 Toyota Highlander for Sale nearMilwaukee, WI

How much does the 2020 Toyota Highlander cost?

Prices have softened 4.28% compared to this time last year, making it a favorable time to shop this model year.

There are 3,445 listings available, which suggests solid inventory for used shoppers.

Is the 2020 Toyota Highlander a good car?

Yes — the 2020 Toyota Highlander earns a 4.6/5 user rating and a 7.7/10 expert rating. The model scores 9/10 across Form and function and Safety.

Owners consistently praise its smooth ride, advanced features, and spacious interior, and many call out the safety features and family-friendly practicality. The expert review also highlights its silent operation, soft ride, and cosseting cabin, with upper trims that feel close to a Lexus without the extra cost. The main trade-offs are poor handling and uninspired styling, so you should expect comfort and calm rather than sharp responses. For a midsize three-row SUV aimed at families and daily commuting, that balance makes sense. Good and great deals account for 36.8% of listings, which gives you some room to shop selectively.

Is the 2020 Toyota Highlander reliable?

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

User feedback points to a dependable, trouble-free ownership experience, with many drivers emphasizing the Highlander’s long-term appeal, smooth operation, and confidence-inspiring safety features. The expert review reinforces that sense of durability by describing the powertrain as smooth and practically silent at idle, with a calm, isolated driving character that suits long trips and everyday use. Toyota also includes two years of maintenance and roadside assistance, which helps reduce early ownership friction. For used buyers, the main long-term risk is that comfort-focused tuning and interior quality concerns may show up more clearly as mileage and age increase.

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

At 68.5% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should start with a vehicle history report and confirm whether any prior damage was repaired properly. A pre-purchase inspection should focus on the suspension, steering feel, interior wear, and the condition of the seats and cabin materials. Because this model is valued for comfort and family use, you should pay close attention to how well the cabin has held up and whether any accident history affected alignment, ride quality, or electronics.

Key things to evaluate:

• Trim level: Every trim except the base L has projector-beam LED headlights and fog lights, while the higher trims add prettier LED running lamps. The Limited and Platinum also get 20-inch wheels, and the Platinum adds diamond-quilted seat backrests.
• Powertrain: The Highlander uses a 3.5-liter V6 with front-wheel drive or all-wheel drive. It delivers brisk acceleration, smooth power delivery, and 295 horsepower, but the transmission can hesitate on kickdown.
• Safety package: Toyota Safety Sense 2.0 is standard and includes automatic emergency braking with pedestrian detection and cyclist detection, lane-keeping assist, adaptive cruise control, and automatic high beams. Blind-spot monitoring, parking sensors, and rear emergency braking are optional.
• Infotainment: An 8-inch touchscreen is standard, and a 12.3-inch touchscreen is available on higher trims. Apple CarPlay, Android Auto, and Amazon Alexa integration come standard, along with SiriusXM, HD radio, WiFi, and four USB-A ports.
• Fuel efficiency: The Highlander FWD is EPA rated at 21 mpg city, 29 mpg highway, and 24 mpg combined. With AWD, it is rated at 20 mpg city, 27 mpg highway, and 23 mpg 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 makes sense if you want the lowest starting price and standard safety tech without paying for extra appearance or convenience upgrades.
• LE: This is the best-value trim in the low $40,000 range, and it adds a stronger mix of everyday equipment while staying below the upper-trim pricing.
• XLE: This is the trim to target if you want a balanced mix of comfort, features, and value without jumping to luxury-like pricing.
• Limited: This trim brings the richer cabin treatment, the optional 12.3-inch touchscreen, and the more upscale feel that helps the Highlander stand out.
• Platinum: This is the top choice if you want the most premium Highlander experience, including the largest screen, the most upscale interior details, and the most fully equipped version of the model.

Toyota Safety Sense 2.0 is standard across the lineup, while blind-spot monitoring, parking sensors, and rear emergency braking remain optional.

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

This is a moderate market for selective buyers, so you can shop carefully and still find worthwhile listings.

• Deal availability: 36.8% of listings are priced as good or great deals.
• Inventory: There are 3,445 listings available.
• Price trend: Prices have softened 4.28% compared with last year.
• Clean inventory: 68.5% of listings are accident-free.

If you find a listing below $26,946, 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 $27,084 sits slightly below last year's $28,295.

That decline suggests the market has become a bit more favorable for buyers, but it also means future sellers may need to price competitively to move inventory. The Highlander’s strong comfort reputation and family appeal should help support demand, especially for cleaner examples with good equipment and no accident history. If you buy well now, you may have a better chance of preserving value later by choosing a trim and condition level that remain attractive to used shoppers.

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 Toyota Highlander earns a Top Safety Pick rating from IIHS.

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

Toyota Safety Sense 2.0 is standard and 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 cushion airbag for the front passenger are also standard. Blind-spot monitoring, parking sensors, and rear emergency braking are optional, so you should confirm whether a used example has the extra driver-assistance features 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:

• 36.8% of listings are priced as good or great deals.
• At 68.5% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 4.28% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• The 2020 redesign emphasizes comfort, a premium cabin, and Lexus-like refinement.

Consider the 2021 if:

• At $29,169, the 2021 costs more than the current year's $27,084 average.
• It adds more standard safety-feature technology.

The bottom line: Choose the 2020 if you want the better value and are focused on comfort, space, and a premium-feeling cabin. If you can stretch for the 2021, the added standard safety tech may be worth the extra cost for buyers who prioritize the newest equipment.

How does the 2020 Toyota Highlander compare to the 2020 Honda Pilot?

Expert Pros & Cons (per CarGurus review team)

2020 Toyota Highlander:

• Pros: Standard advanced safety features, Spacious.
• Cons: Poor handling, Uninspired styling.

2020 Honda Pilot:

• Pros: Powerful engine, Standard advanced safety features.
• Cons: Unintuitive technology, Interior materials feel cheap.

Our experts score the 2020 Toyota Highlander 7.7/10 and the 2020 Honda Pilot 8/10. The Highlander leans harder into comfort and a premium-feeling cabin, while the Pilot gets the edge on power. Both offer standard advanced safety features, but the Highlander’s poor handling and the Pilot’s unintuitive technology point to different compromises. If you care most about a relaxed ride and upscale feel, the Highlander makes sense; if you want stronger engine performance, the Pilot is the better fit.

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.