Used 2021 Toyota Highlander for Sale nearFort Myers, FL

How much does the 2021 Toyota Highlander cost?

Prices have softened 5.43% compared to this time last year, making it a favorable time to shop this model year.

There are 3,467 listings available, which suggests healthy inventory for shoppers comparing trims and prices.

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, spaciousness, and features, and they also highlight the smooth ride and high-quality interior. That lines up well with its role as a three-row family SUV that prioritizes comfort and everyday livability.

The trade-offs are clear: the styling is uninspired, the base engine is underwhelming, and the technology feels outdated. For you, that means the Highlander makes the most sense if you value a calm, practical family hauler over something more engaging or cutting-edge.

Good and great deals account for 33.8% of listings, so there is still room to shop selectively.

Is the 2021 Toyota Highlander reliable?

Owners rate it 4.9/5, a strong signal of long-term satisfaction.

User feedback repeatedly points to reliability, dependability, and trouble-free ownership, along with comfort and features that hold up well over time. The expert review also emphasizes smooth, predictable operation and a reputation for reliability, which reinforces the Highlander’s appeal as a long-term family vehicle.

Toyota’s safety and ownership focus adds to that impression, and the model’s standard equipment helps support confidence in daily use. For used buyers, the main long-term risk is less about core durability and more about finding one that has been maintained well and still feels fresh inside.

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

Accident-free inventory is solid at 76.8% — always verify the vehicle history report.

You should still check the vehicle history report carefully, because a clean title alone does not tell you how the SUV was maintained or repaired. Prioritize a thorough inspection of the cabin, electronics, and third-row operation, since owners mention limited configurability and some disappointment with certain settings. It also makes sense to focus on overall condition, because the Highlander’s value is tied closely to comfort, safety, and how well the interior has held up.

Key things to evaluate:

• Trim level: The lineup ranges from LE through Platinum, with the XSE adding a more aggressive front end, suspension tuning, and an appearance package. Base and lower trims use an 8-inch touchscreen, while the Limited can be optioned with a 12.3-inch screen and the Platinum gets it standard.
• Powertrain: Every Highlander uses a 3.5-liter V6 with 295 horsepower and an eight-speed automatic transmission, with front-wheel drive or all-wheel drive available. The setup is smooth and predictable rather than quick, and the soft suspension favors comfort over sharp handling.
• 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 expected across the lineup.
• Infotainment: Lower trims get an 8-inch touchscreen, while the Limited offers a 12.3-inch unit as an option and the Platinum makes it standard. Android Auto and Apple CarPlay are standard across the lineup, and the larger screen looks sharp even if some functions still feel constrained.
• Fuel efficiency: The V6 is rated at 21 mpg city and 29 mpg highway with front-wheel drive, or 20 mpg city and 27 mpg highway with all-wheel drive. In testing, the review observed 20.5 mpg combined in a Limited AWD.

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 trim.

Here's the short version:

• LE: This is the entry point, so it makes sense if you want the Highlander’s core comfort, safety, and space without paying for extras you may not need.
• XLE: This is the best-value trim for many shoppers because it adds meaningful equipment while staying below the more expensive appearance- and luxury-focused versions.
• XSE: Choose this if you want the sportier look and slightly firmer suspension tuning, but it is more about style and feel than true performance.
• Limited: This is the sweet spot if you want the upscale interior experience, and the review’s test vehicle showed how well this trim can deliver on comfort and finish.
• Platinum: Pick this if you want the most premium Highlander experience, including the standard 12.3-inch touchscreen.
• Limited trim: The review specifically notes a Limited-trim test vehicle sitting just below Platinum, with upscale exterior accents and a particularly strong interior presentation.

Toyota Safety Sense 2.5+ is standard, so even lower trims get the core driver-assistance suite.

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

This is a moderate, selective buyer’s market, so you can shop carefully and still find worthwhile listings.

• Deal availability: 33.8% of listings are priced as good or great deals.
• Inventory: There are 3,467 listings available.
• Price trend: Prices have softened 5.43% compared with last year.
• Clean inventory: 76.8% of listings are accident-free.

If you find a listing below $29,150, 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 $29,496 sits slightly below last year's $31,190.

That decline suggests the market has cooled a bit, which can help you as a buyer today but may also mean a future seller has less pricing power than before. Even so, the Highlander’s strong reputation for comfort, safety, and reliability should help it remain appealing to used shoppers.

Because demand tends to stay healthy for family SUVs with strong owner satisfaction, the Highlander should continue to hold interest better than many less desirable alternatives. Well-kept examples with clean history and desirable equipment should be easier to move later.

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+ 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 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 suite of driver-assistance features across the lineup.

The main safety caveat is not a crash-test weakness but the fact that some of the most advanced equipment is part of Toyota’s broader safety upgrade for this model year, so you should still confirm the exact feature set on the trim you’re considering.

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:

• 33.8% of listings are priced as good or great deals.
• Accident-free inventory is solid at 76.8% — always verify the vehicle history report.
• Price trend: Prices have softened 5.43% compared with last year.
• Owners rate it 4.9/5 — a strong satisfaction signal.
• It adds additional safety-feature technology as standard equipment.

Consider the 2020 if:

• At $27,370, the 2020 costs less than the current year's $29,496 average.
• It emphasizes comfort and a quiet, premium-feeling ride.

Consider the 2022 if:

• At $32,083, the 2022 costs more than the current year's $29,496 average.
• It keeps the family-focused formula while adding easy-to-use technology.

The bottom line: If you want the best balance of price, safety, and comfort, the 2021 is the primary pick. If you are especially price-sensitive, the 2020 is the cheaper path into the same comfort-first Highlander experience.

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 choice if you care most about ride quality and comfort, while the Pilot has the edge if you want easier technology and a more stylish look. The Highlander’s weaker points are its base engine and older-feeling tech, while the Pilot’s drawbacks are more about performance and transmission behavior.

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

These recommendations are based on CarGurus' proprietary market data from October 21, 2026, CarGurus experts' opinions, and generative AI.