Used 2020 Toyota Highlander for Sale nearMilwaukee, WI

How much does the 2020 Toyota Highlander cost?

Prices have softened 4.51% compared to this time last year, making it a favorable time to shop this model year.

There are 3,178 listings available, which suggests you have a solid pool of used Highlanders to compare.

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 its smooth ride, advanced features, and spacious interior, and many also highlight its safety features and overall family-friendly usefulness. The trade-offs are its uninspired styling and poor handling, which make it better suited to calm commuting and family duty than spirited driving. In other words, if you want a comfortable three-row SUV that prioritizes ease and refinement, this year’s Highlander fits that brief well. With 35.0% of listings marked as good or great deals, there is still room to shop selectively.

Is the 2020 Toyota Highlander reliable?

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

Reviewers describe it as smooth, dependable, and a vehicle they can count on, especially for family use and everyday driving. The expert evaluation also emphasizes its calm, quiet character and its ability to deliver an effortless, low-stress driving experience over long trips. Toyota includes two years of maintenance and roadside assistance, which adds a helpful ownership perk early on.

For used buyers, the main long-term risk is less about outright durability and more about finding one that has been cared for properly, since comfort and technology can vary with condition and trim.

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 then prioritize a careful inspection of bodywork, interior condition, and any signs of prior repair quality. Because this model is valued for comfort and technology, it makes sense to pay close attention to seat wear, cabin materials, and whether the electronics and driver-assistance features work as intended. If a listing has accident history, condition and repair quality matter even more.

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 major strength, and the upper trims add richer materials and more upscale presentation.
• Powertrain: The Highlander uses a 3.5-liter V6 with front-wheel drive or all-wheel drive. It delivers brisk acceleration, smooth operation, and quiet idle behavior, though the transmission can be slow to kick down.
• 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: Apple CarPlay, Android Auto, and Amazon Alexa integration come standard. The system uses an 8-inch touchscreen, while a 12.3-inch screen is optional on Limited and standard on Platinum; the larger display still does not fully expand usable map or vehicle-control space.
• Fuel efficiency: The Highlander FWD is rated at 21 mpg city, 29 mpg highway, and 24 mpg combined. AWD models are 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, but it still gives you the Highlander’s core comfort and safety appeal. It makes sense if you want the lowest starting price and can live without the extra lighting and upscale touches found higher up.
• LE: This is the best-value trim. The cost-effectiveness commentary points to the XLE as the best value in the low $40,000 range, but among the named trims here, the LE is the sensible step up if you want more equipment without chasing luxury pricing.
• XLE: This is the trim to target if you want the strongest balance of equipment and price. It sits in the sweet spot for shoppers who want a well-equipped family SUV without paying for the top-end luxury features.
• Limited: This trim is for you if you want the Highlander to feel closest to a Lexus. It adds a more premium cabin presentation and can be paired with the larger touchscreen, making it the right choice if comfort and upscale feel matter most.
• Platinum: This is the top trim for shoppers who want the most upscale Highlander experience. It gets the standard 12.3-inch touchscreen and the richest feature set, but it is best for buyers who are willing to pay for the full luxury-like treatment.

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, selective buyer’s market, so you can shop with some leverage if you stay patient.

• Deal availability: 35.0% of listings are priced as good or great deals.
• Inventory: There are 3,178 listings available.
• Price trend: Prices have softened 4.51% compared with last year.
• Clean inventory: 69.9% of listings are accident-free.

If you find a listing below $26,981, 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 $27,605 sits slightly below last year's $28,908.

That softer pricing suggests the market has already adjusted downward, which can help you buy more confidently now. For a future seller, it also means resale value may depend heavily on condition, mileage, and trim, since the market is rewarding clean examples more than average ones. Well-kept Highlanders should still draw interest because they remain popular family SUVs with strong comfort and safety appeal.

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. Blind-spot monitoring, parking sensors, and rear emergency braking are optional, so you may want to confirm which driver-assistance features are fitted on any used example you consider.

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:

• 35.0% 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 4.51% 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 cabin feel.

Consider the 2021 if:

• At $29,852, the 2021 costs more than the current year's $27,605 average.
• It adds more standard safety-feature technology.

The bottom line: If you want the better value, the 2020 is the smarter starting point because it already delivers the comfort-first character and strong safety reputation that define the Highlander. If you are willing to pay more for additional standard safety technology, the 2021 is the cleaner upgrade path.

These recommendations are based on CarGurus' proprietary market data from September 22, 2026, CarGurus experts' opinions, and generative AI.