Used 2020 Toyota Highlander for Sale near Wisconsin

How much does the 2020 Toyota Highlander cost?

Prices have softened 4.39% compared to this time last year, making it a favorable time to shop this model year.

There are 3,320 listings available, which gives you a solid pool to compare prices and equipment.

Is the 2020 Toyota Highlander a good car?

Yes — the 2020 Toyota Highlander earns a 4.6/5 user rating and a 7.67/10 expert rating. The model scores 9/10 across Form and function and Safety.

Owners consistently praise the smooth ride, advanced features, and spacious interior, and many also highlight the safety equipment and overall family-friendly usefulness. The Highlander’s comfort-first character and quiet, relaxed driving feel come through clearly in both owner feedback and expert evaluation.

The trade-offs are just as clear: the styling is uninspired, handling is poor, and some owners mention front-seat comfort and interior materials as weak spots. Even so, the Highlander’s calm ride and roomy cabin make it a strong fit if you want a three-row SUV that prioritizes ease over excitement.

The model’s 35.5% good-or-great deal share suggests you can still find attractive listings if you shop carefully.

Is the 2020 Toyota Highlander reliable?

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

Owner feedback points to a dependable, trouble-free ownership experience, with many drivers describing the Highlander as a vehicle they can count on for family duty. The expert evaluation also emphasizes its calm, muted driving character and the sense that it’s built for long-term, low-stress use.

Toyota includes two years of maintenance and roadside assistance, which helps reduce early ownership friction. For used buyers, the main long-term risk is less about outright durability and more about finding a well-kept example with the right maintenance history and interior condition.

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

At 69.9% 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. Then prioritize a pre-purchase inspection, especially if you’re considering a higher-mileage example or one with visible wear inside the cabin. Because this model is valued for comfort and family use, condition matters a lot: pay close attention to seat wear, trim quality, and how well the electronics and safety systems work.

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; Limited and Platinum also get 20-inch wheels. The cabin quality is a highlight across the range, but the upper trims add the richest materials and the most upscale feel.
• Powertrain: You get a 3.5-liter V6 with either FWD or AWD, paired with an eight-speed automatic. It delivers smooth, brisk acceleration and very quiet operation, though 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 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: The standard touchscreen is 8 inches, and a 12.3-inch screen is optional on Limited and standard on Platinum. Apple CarPlay, Android Auto, and Amazon Alexa integration come standard, along with SiriusXM, HD radio, WiFi, and four USB-A ports.
• Fuel efficiency: The FWD model is rated at 21 mpg city, 29 mpg highway, and 24 mpg combined, while AWD returns 20/27/23.

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 comfort, space, and standard safety equipment at the lowest price. It makes sense if you want the cabin and ride quality without paying for extra luxury features.
• LE: This is the best-value trim. It sits in the low $40,000 range and is called out as the sweet spot for balancing equipment and price.
• XLE: This trim adds more comfort and convenience while staying below the luxury-focused upper trims, making it a smart choice if you want a better-equipped family SUV without stretching too far.
• Limited: This is where the Highlander starts to feel especially upscale, with richer interior details and more premium presentation. It suits you if you want the near-Lexus experience the Highlander is known for.
• Platinum: This is the most luxurious version, with the most advanced presentation and the biggest screen standard. It’s the right pick if you want the most fully loaded Highlander.

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, with enough inventory and deal activity to reward careful shopping.

• Deal availability: 35.5% of listings are priced as good or great deals.
• Inventory: There are 3,320 listings available.
• Price trend: Prices have softened 4.39% compared with last year.
• Clean inventory: 69.9% of listings are accident-free.

If you find a listing below $26,985, 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 $27,527 sits slightly below last year's $28,792.

That decline suggests the market has softened, which can work in your favor as a buyer but may trim upside if you plan to resell soon. If you buy at the right price and keep the vehicle in strong condition, you can help protect future value. The Highlander’s broad family appeal and comfort-first reputation should continue to support demand, especially for clean, well-maintained examples.

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 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 cushion airbag for the front passenger are also standard.

Blind-spot monitoring, parking sensors, and rear emergency braking are optional, so you’ll want to confirm whether a used listing has those extras if they matter to you. The main caveat is that some desirable safety equipment is not standard on every trim.

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:

• 35.5% of listings are priced as good or great deals.
• At 69.9% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 4.39% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• The 2020 redesign emphasizes comfort, quiet operation, and a more premium-feeling cabin.

Consider the 2021 if:

• At $29,775, the 2021 costs more than the current year's $27,527 average.
• It adds more standard safety-feature technology.

The bottom line: If you want the better value, the 2020 is the smarter buy because it combines a lower average price with strong owner satisfaction and a comfort-first driving experience. If you’re willing to pay more for added standard safety technology, the 2021 is the cleaner upgrade path.

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