Used 2021 Toyota Highlander for Sale nearKenosha, WI

How much does the 2021 Toyota Highlander cost?

Prices have softened 5.35% compared to this time last year, making it a favorable time to shop this model year.

There are 3,525 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 4.9/5 user rating and a 7.5/10 expert rating. The standout strength is Safety at 10/10. Owners consistently praise its comfort, reliability, and features, along with the smooth ride and high-quality interior. The Highlander also fits buyers who want a spacious, family-focused three-row SUV with strong safety credentials and easy day-to-day livability. Trade-offs include uninspired styling and an underwhelming base engine, and the technology is described as outdated. With 37.2% of listings marked as good or great deals, the market still offers some attractive opportunities.

Is the 2021 Toyota Highlander reliable?

Owners rate it 4.9/5, a strong signal of long-term satisfaction. Reviewers repeatedly describe it as reliable and praise its comfort, features, and smooth ride, while the expert review also points to a reputation for reliability and smooth, predictable operation. Toyota’s ownership experience is further supported by the model’s dependable, known-quantity V6 setup and its emphasis on trouble-free family use. For used buyers, the main long-term risk is less about core dependability and more about finding a well-kept example with the right maintenance history and condition.

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

Accident-free inventory is solid at 76.4% — always verify the vehicle history report.

You should still check the history report carefully, because accident-free status does not replace a full inspection. Pay close attention to interior condition, electronics, and how the third row and driver-assistance features operate in real use. If you’re comparing listings, prioritize examples that show consistent maintenance and clean wear patterns.

Key things to evaluate:

• Trim level: The XSE adds a more aggressive front end, 20-inch wheels with black accents, a unique front fascia, a lower spoiler, and some suspension tuning, while the Limited trim sits just below Platinum and brings a more upscale look and feel. Base trims miss some of the richer cabin presentation and larger-screen tech found higher up.
• 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 available front-wheel drive or all-wheel drive. It is tuned for smooth, predictable operation rather than quick acceleration.
• 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. The suite is standard across the lineup.
• Infotainment: Lower trims use an 8-inch touchscreen, while the Limited can get a 12.3-inch screen and the Platinum gets it standard. Android Auto and Apple CarPlay are standard, and the larger screen is bright and crisp.
• Fuel efficiency: The V6 is rated at 21 mpg city, 29 highway, and 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, so it makes sense if you want the Highlander’s core comfort, space, and safety without stretching the budget. It gives you the basics of the family-friendly formula, but you’ll miss some of the richer cabin and tech upgrades found higher up.
• XLE: This is the best-value choice for many shoppers because it adds meaningful equipment without jumping all the way to the pricier upper trims. It’s the trim to target if you want a more complete daily driver with a stronger mix of comfort and convenience.
• XSE: Choose this if you want the Highlander’s family practicality with a little more visual attitude and a slightly firmer setup. The sportier styling and suspension tuning make it the most distinctive choice, but it is still more about appearance and road feel than true performance.
• Limited: This is the trim that best matches the Highlander’s upscale side, with a more premium interior presentation and the option for the larger 12.3-inch touchscreen. If you care most about cabin quality and a more polished feel, this is the one to focus on.
• Platinum: Go here if you want the most fully equipped Highlander, including the standard 12.3-inch touchscreen. It is the top-tier choice for buyers who want the most features and the most upscale experience.
• Limited AWD: This is the right pick if you want the Limited’s upscale equipment with all-wheel drive already included. It suits buyers who want a more premium setup and prefer not to add AWD separately.

Toyota Safety Sense 2.5+ is standard across the lineup.

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

This is a moderate market for selective buyers, with enough inventory and deal activity to make shopping worthwhile.

• Deal availability: 37.2% of listings are priced as good or great deals.
• Inventory: There are 3,525 listings available.
• Price trend: Prices have softened 5.35% compared with last year.
• Clean inventory: 76.4% of listings are accident-free.

If you find a listing below $29,140, 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 $29,403 sits slightly below last year's $31,066.

That softer pricing can work in your favor if you buy now and plan to sell later, because you may be entering at a more favorable point in the cycle. If prices stabilize or recover, a well-kept Highlander could hold value better than a comparable vehicle bought at a higher point. Strong demand for family-friendly three-row SUVs also helps support future resale interest, especially for clean, well-equipped examples.

Vehicles with strong owner satisfaction ratings, like this model year's 4.9/5, 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+ 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 standard safety suite is a major strength across the lineup, and it helps explain why safety is such a central part of the Highlander’s appeal.

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:

• 37.2% of listings are priced as good or great deals.
• Accident-free inventory is solid at 76.4% — always verify the vehicle history report.
• Price trend: Prices have softened 5.35% compared with last year.
• Owners rate it 4.9/5 — a strong satisfaction signal.
• The 2021 adds Toyota Safety Sense 2.5+ as standard equipment.

Consider the 2020 if:

• At $27,363, the 2020 costs less than the current year's $29,403 average.
• It emphasizes comfort with a soft ride and a calm, premium feel.

Consider the 2022 if:

• At $32,056, the 2022 costs more than the current year's $29,403 average.
• It adds easy-to-use technology and keeps the family-focused formula strong.

The bottom line: If you want the best balance of price, safety, and family-friendly comfort, the 2021 is the smart default. If you’re especially price-sensitive, the 2020 is the value play; if you want a newer-feeling setup and can spend more, the 2022 is worth a look.

How does the 2021 Toyota Highlander compare to the 2021 Honda Pilot?

Expert Pros & Cons (per CarGurus review team)

2021 Toyota Highlander:

• Pros: Great ride quality, Comfortable, Spacious.
• Cons: Uninspired styling, Underwhelming base engine, Outdated technology.

2021 Honda Pilot:

• Pros: Spacious, Easy-to-use technology, Stylish design.
• Cons: Fairly pedestrian performance, Irritating transmission.

Our experts score the 2021 Toyota Highlander 7.5/10 and the 2021 Honda Pilot 7.2/10. The Highlander is the better pick if you care most about ride quality and comfort, while the Pilot has the edge in technology usability and styling. The Highlander’s weaker points are its base engine and outdated tech, while the Pilot’s drawbacks are more about performance feel and transmission behavior.

Read our full side-by-side expert comparison here.

These recommendations are based on CarGurus' proprietary market data from October 27, 2026, CarGurus experts' opinions, and generative AI.