Used 2021 Toyota Highlander for Sale near East Hampton, NY

How much does the 2021 Toyota Highlander cost?

Prices have softened 6.31% compared to this time last year, making it a favorable time to shop this model year.

There are 3,138 listings available, which suggests healthy inventory for shoppers comparing prices and trims.

If you find a listing below $29,157.26, that's toward the low end of the year-round range and worth acting on quickly.

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, smooth ride, high-quality interior, spaciousness, and safety features. It fits especially well if you want a practical three-row family SUV that prioritizes everyday usability over flash.

The trade-offs are clear too: the styling is uninspired, the base engine is underwhelming, and the technology feels outdated. That makes it a stronger match if you value comfort and reassurance more than excitement or the latest infotainment polish.

With the Highlander positioned as a familiar three-row family SUV, it makes the most sense for shoppers who want a calm, capable hauler rather than a sporty statement piece.

A 30.3% good-or-great-deal rate suggests there are still worthwhile listings to find if you shop carefully.

Is the 2021 Toyota Highlander reliable?

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

Drivers describe it as reliable and appreciate its comfort, smooth ride, high-quality interior, and safety features. The expert review also points to a reputation for reliability and smooth, predictable operation, which supports the Highlander’s appeal if you want something easy to live with over time.

Toyota’s first scheduled maintenance visit is on the house, which helps early ownership costs feel a little more manageable.

For used buyers, the main long-term risk is less about the core reputation 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 76.7% — always verify the vehicle history report.

You should still check the history report carefully, because accident-free status is only a starting point. Prioritize a pre-purchase inspection, especially if you’re considering a higher-mileage example or a trim with more equipment. Focus on overall condition, interior wear, and whether the features you care about work as expected.

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 a bit of suspension tuning, while Limited brings a more upscale look and a richer interior. Base trims are more straightforward, so you should compare them carefully if you want the nicer cabin materials and appearance upgrades.
• 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, with front-wheel drive or all-wheel drive available. The setup is smooth and predictable, but it is not built for quick launches or sporty driving.
• 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 available across the lineup.
• Infotainment: Lower trims use an 8-inch touchscreen, while Limited offers a 12.3-inch screen as an option and Platinum makes it standard. Android Auto and Apple CarPlay are standard, but navigation and the larger screen are worth evaluating closely if you care about tech polish.
• Fuel efficiency: The V6 returns 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 paying for extras you may not need.
• XLE: This is the best-value trim for many shoppers because it adds meaningful equipment without jumping all the way to the pricier upper trims.
• XSE: Choose this if you want the sportier-looking version with the more aggressive front end, 20-inch wheels, and suspension tuning.
• Limited: This is the sweet spot if you want the upscale cabin feel, the stronger visual presence, and the more premium interior experience.
• Platinum: Pick this if you want the most fully equipped Highlander, including the standard 12.3-inch touchscreen.
• Limited AWD: Choose this if you want the Limited’s upscale character with all-wheel drive already included.

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

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

This looks like a moderate, selective buyer’s market, so you can shop with some leverage if you compare listings carefully.

• Deal availability: 30.3% of listings are priced as good or great deals.
• Inventory: There are 3,138 listings available.
• Price trend: Prices have softened 6.31% compared with last year.
• Clean inventory: 76.7% of listings are accident-free.

If you find a listing below $29,157.26, 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 $29,969 sits slightly below last year's $31,988.

That price movement suggests the market has cooled a bit, which can help you buy more confidently now. For a future seller, the softer trend means you should be realistic about appreciation and focus instead on buying a clean, well-kept example that will stay attractive later. Strong condition, desirable equipment, and a solid history matter more when the market is already leaning downward.

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+ 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 gives you a broad standard safety package across the lineup.

The main takeaway is that safety is one of the Highlander’s strongest selling points, and Toyota clearly made it a priority for this model year.

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:

• 30.3% of listings are priced as good or great deals.
• Accident-free inventory is solid at 76.7% — always verify the vehicle history report.
• Price trend: Prices have softened 6.31% compared with last year.
• Owners rate it 4.86/5 — a strong satisfaction signal.
• Toyota adds additional safety-feature technology as standard equipment.

Consider the 2020 if:

• At $27,779, the 2020 costs less than the current year's $29,969 average.
• It was redesigned for 2020 and emphasizes calm comfort and upscale feel.

Consider the 2022 if:

• At $32,848, the 2022 costs more than the current year's $29,969 average.
• It adds a polished, family-friendly package with strong basics and standard safety features.

The bottom line: If you want the best balance of price, safety, and broad appeal, the 2021 is the smart default. If your budget is tighter, the 2020 can save you money while keeping the Highlander’s core comfort and character. If you’re willing to spend more for a newer-year alternative, the 2022 is worth a look, but the 2021 already covers the essentials well.

These recommendations are based on CarGurus' proprietary market data from August 28, 2026, CarGurus experts' opinions, and generative AI.