Used 2021 Toyota Highlander for Sale nearKenosha, WI

How much does the 2021 Toyota Highlander cost?

Prices have softened 5.73% compared to this time last year, making it a favorable time to shop this model year.

There are 3,240 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 4.86/5 user rating and a 7.5/10 expert rating. The standout strength is Safety at 10/10.

Drivers consistently praise its comfort, reliability, and features, and many also highlight the smooth ride, high-quality interior, spaciousness, and safety features. That lines up with the overview: you get a family-focused three-row SUV that emphasizes comfort and practicality, especially if you want a roomy cabin and a calm ride.

The trade-offs are clear too: the base engine is underwhelming, the styling is uninspired, and the technology is dated. Even so, if you want a straightforward family hauler rather than something sporty, the Highlander fits that brief well.

With 33.1% of listings marked as good or great deals, the market gives you some room to shop selectively.

Is the 2021 Toyota Highlander reliable?

Owners rate it 4.86/5, a strong signal of long-term satisfaction.

User feedback points to reliability, dependability, and trouble-free ownership, with many drivers saying they feel confident counting on it over time. The expert review also emphasizes smooth, predictable operation and a reputation for reliability, which reinforces that impression.

Toyota’s safety and comfort focus also supports the ownership experience, and the model’s standard equipment helps it feel well covered from the start. For used buyers, the main long-term risk is less about durability and more about whether the vehicle’s condition and maintenance history match its reputation.

What should I look for when buying a used 2021 Toyota Highlander?

Accident-free inventory is solid at 76.5% — always verify the vehicle history report.

You should still check the report carefully, because a clean listing percentage does not replace a proper history review. Prioritize a pre-purchase inspection, especially if you’re considering a higher-mileage example or one with incomplete service records. Focus on overall condition, interior wear, and whether the vehicle’s features and controls work as expected.

Key things to evaluate:

• Trim level: The lineup starts with an 8-inch touchscreen on trims below Limited, while Limited can be optioned with a 12.3-inch screen and Platinum gets it standard. The XSE adds a more aggressive appearance package and some suspension tuning, while Limited leans more upscale inside.
• Powertrain: Every Highlander uses a 3.5-liter V6 with 295 horsepower and 263 pound-feet of torque, paired with an eight-speed automatic transmission and front-wheel drive or all-wheel drive. It is smooth and predictable, but not especially quick.
• Safety package: Toyota Safety Sense 2.5+ includes automatic emergency braking with pedestrian detection and intersection support, plus road-sign assist, adaptive cruise control, lane-departure warning, lane-keeping assist, lane-tracing assist, and automatic high beams. These features are standard across the lineup.
• Infotainment: Lower trims use an 8-inch touchscreen. A 12.3-inch screen is available on Limited and standard on Platinum. Android Auto and Apple CarPlay are standard, but navigation is optional.
• Fuel efficiency: The V6 returns 21 mpg city, 29 highway, 24 combined with front-wheel drive, or 20/27/23 with all-wheel drive.

Which 2021 Toyota Highlander trim should I buy?

The 2021 Toyota Highlander is offered in 6 trim levels: LE, XLE, XSE, Limited, Platinum, and Limited AWD.

Here's the short version:

• LE: This is the entry point, and it gives you the Highlander’s core family-hauling strengths without pushing the price too high. It makes sense if you want the basics and value standard safety equipment.
• XLE: This is the best-value trim for many shoppers because it adds more comfort and convenience without jumping into luxury pricing. If you want a well-rounded Highlander, this is the one to focus on first.
• XSE: Choose this if you want the sportier look and slightly firmer tuning. It adds a more aggressive front end, unique styling, and suspension changes, but it is more about attitude than real performance.
• Limited: This is the trim that best matches the Highlander’s upscale side. It brings a more premium cabin feel, and the available 12.3-inch touchscreen makes it especially appealing if you want a more polished daily driver.
• Platinum: Pick this if you want the most fully equipped version, including the standard 12.3-inch touchscreen. It is the top choice for shoppers who want the most features and are willing to pay for them.
• Limited AWD: This is the same upscale direction as Limited, but with all-wheel drive for added traction. It suits you if you want the Limited experience and live where AWD matters.

Toyota Safety Sense 2.5+ is standard, so every trim starts with a strong safety foundation.

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

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

• Deal availability: 33.1% of listings are priced as good or great deals.
• Inventory: There are 3,240 listings available.
• Price trend: Prices have softened 5.73% compared with last year.
• Clean inventory: 76.5% of listings are accident-free.

If you find a listing below $29,154, 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 $29,947 sits slightly below last year's $31,768.

That price movement suggests the market has cooled a bit, which can help you buy more confidently now. For a future seller, it also means you should expect resale value to depend heavily on condition, mileage, and how well the vehicle is equipped.

The Highlander’s broad appeal helps support demand, especially because it remains a popular family SUV with strong safety and comfort credentials. If you keep it clean, well maintained, and accident-free, you should have a better shot at holding value than a less in-demand three-row SUV.

Vehicles with strong owner satisfaction ratings, like this model year's 4.86/5, 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 five-star ratings from NHTSA.

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

Toyota Safety Sense 2.5+ is standard, and it includes automatic emergency braking with pedestrian detection and intersection support, road-sign assist, adaptive cruise control, lane-departure warning, lane-keeping assist, lane-tracing assist, and automatic high beams. That gives you a broad set of driver-assistance features right from the start.

The main safety takeaway is that the Highlander is built to give you a strong baseline of protection and active safety tech across the lineup. That makes it especially appealing if safety is one of your top priorities in a used three-row SUV.

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:

• 33.1% of listings are priced as good or great deals.
• Accident-free inventory is solid at 76.5% — always verify the vehicle history report.
• Price trend: Prices have softened 5.73% compared with last year.
• Owners rate it 4.86/5 — a strong satisfaction signal.
• It adds more standard safety technology while keeping the Highlander’s comfort-first character.

Consider the 2020 if:

• At $27,731, the 2020 costs less than the current year's $29,947 average.
• It emphasizes comfort, quiet operation, and a cosseting interior.

Consider the 2022 if:

• At $32,559, the 2022 costs more than the current year's $29,947 average.
• It adds versatility, a stout V6, and standard safety features buyers want.

The bottom line: If you want the best balance of price, safety, and family-friendly comfort, the 2021 is the sweet spot. If your budget is tighter, the 2020 can save you money while staying close in character. If you want to spend more for a newer model-year alternative, the 2022 is worth a look, but you’ll pay a premium for it.

These recommendations are based on CarGurus' proprietary market data from September 11, 2026, CarGurus experts' opinions, and generative AI.