Used 2021 Toyota Highlander for Sale nearMilwaukee, WI

How much does the 2021 Toyota Highlander cost?

Prices have softened 5.76% compared to this time last year, making it a favorable time to shop this model year.

There are 3,228 listings available, which suggests solid inventory for shoppers comparing trims and prices.

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.

Owners consistently praise its comfort, reliability, and features, and they also highlight the smooth ride, high-quality interior, spaciousness, and safety features. That lines up with the overview’s family-focused use case: you’re looking at a three-row SUV built to prioritize comfort and practicality over flash.

The trade-offs are clear too: the base engine is underwhelming, the styling is uninspired, and the technology feels dated. Even so, if you want a roomy, easygoing family hauler with a strong reputation, the Highlander fits that brief well.

Only 35.4% of listings are priced as good or great deals, so the market still rewards careful comparison shopping.

Is the 2021 Toyota Highlander reliable?

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

User feedback points to reliability, comfort, and a trouble-free ownership experience, 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 from a shopper’s perspective.

Toyota’s first scheduled maintenance visit is on the house, which helps soften early ownership costs. For used buyers, the main long-term risk is less about headline reliability and more about finding a well-kept example with consistent maintenance and no hidden wear.

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

Accident-free inventory is solid at 76.1% — always verify the vehicle history report.

You should still run a history report on any candidate, because accident-free status is only a starting point. Prioritize a pre-purchase inspection that checks the cabin electronics, seat and trim condition, and how well the vehicle’s comfort and safety systems operate. Since this model is often bought as a family hauler, pay close attention to signs of heavy interior use, especially in the second and third rows.

Key things to evaluate:

• Trim level: The lineup starts with an 8-inch touchscreen on trims below Limited, while Limited adds an available 12.3-inch screen and Platinum makes it standard. The Limited trim also stands out for its upscale interior presentation, while the XSE adds a more aggressive look and a bit of suspension tuning rather than a true performance transformation.
• Powertrain: Every Highlander uses a 3.5-liter V6 with 295 horsepower and 263 pound-feet of torque, paired with an eight-speed automatic and either front-wheel drive or all-wheel drive. It’s 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, road-sign assist, adaptive cruise control, lane-departure warning, lane-keeping assist, lane-tracing assist, and automatic high beams. Those features are standard across the lineup.
• Infotainment: Lower trims use an 8-inch touchscreen, while Limited offers a 12.3-inch unit and Platinum gets it standard. Android Auto and Apple CarPlay are standard across the lineup, and the larger screen is bright and crisp, though some functions still feel constrained by the interface layout.
• Fuel efficiency: The V6 is rated at 21 mpg city, 29 highway, 24 combined with front-wheel drive, and 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 trim.

Here's the short version:

• LE: This is the entry point if you want the Highlander’s core strengths at the lowest price, including the standard safety suite and the V6 powertrain. It makes sense if you care more about value and family utility than upscale extras.
• XLE: This trim adds more equipment and is the better everyday pick if you want a more complete family SUV without jumping into luxury pricing. It’s a strong middle-ground choice for shoppers who want comfort and convenience features to feel more rounded.
• XSE: This is the best fit if you want the Highlander to look a little sportier and feel slightly firmer on the road. It adds suspension tuning and an appearance package, but it’s still more style-and-attitude than true performance.
• Limited: This is the best-value trim for shoppers who want the Highlander to feel genuinely upscale. It brings the more premium interior presentation and unlocks the larger touchscreen option, making it the sweet spot for many buyers.
• Platinum: Choose this if you want the most fully equipped Highlander and want the 12.3-inch touchscreen standard. It’s the top-tier choice for buyers who want the most features and the most polished cabin experience.
• Limited trim: This trim sits just below Platinum and is the one the expert review highlights for its upscale look and feel, especially inside. If you’re shopping used and want a near-luxury experience without going all the way to the top, this is the trim to target.

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

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

This is a moderate market for selective buyers, so you can shop with some leverage if you’re patient.

• Deal availability: 35.4% of listings are priced as good or great deals.
• Inventory: There are 3,228 listings available.
• Price trend: Prices have softened 5.76% compared with last year.
• Clean inventory: 76.1% of listings are accident-free.

If you find a listing below $29,155, 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 $29,852 sits slightly below last year's $31,675.

That softer pricing can help you as a buyer now, but it also suggests resale values have eased compared with the prior year. If you plan to sell later, you should expect the market to reward clean condition, strong maintenance records, and desirable equipment rather than simply the badge alone.

Because the Highlander still has broad family appeal, well-kept examples should remain easier to move than less practical rivals. Stronger trims and accident-free history can help support a better future sale price.

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 standard safety package even before you move up the trim ladder.

The main safety caveat is that the Highlander’s standout protection comes from its strong standard equipment rather than from trim-specific upgrades, so you don’t need to chase a higher trim to get the core safety tech.

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:

• 35.4% of listings are priced as good or great deals.
• Accident-free inventory is solid at 76.1% — always verify the vehicle history report.
• Price trend: Prices have softened 5.76% compared with last year.
• Owners rate it 4.86/5 — a strong satisfaction signal.
• It adds Toyota Safety Sense 2.5+ standard, including intersection support.

Consider the 2020 if:

• At $27,605, the 2020 costs less than the current year's $29,852 average.
• It was redesigned for 2020 and emphasizes comfort, quiet, and a cosseting interior.

Consider the 2022 if:

• At $32,384, the 2022 costs more than the current year's $29,852 average.
• It adds versatility and easy-to-use technology while keeping standard safety features.

The bottom line: If you want the best balance of price, safety, and family-friendly comfort, the 2021 is the sensible target. If your budget is tighter, the 2020 can save you money while keeping the same comfort-first character. If you’re willing to spend more for a newer-feeling alternative, the 2022 is worth a look, but the 2021 remains the value-minded sweet spot.

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