Used 2020 Toyota Highlander for Sale near Massachusetts

How much does the 2020 Toyota Highlander cost?

Prices have softened 3.82% compared to this time last year, making it a favorable time to shop this model year.

There are 3,441 listings available, which suggests solid inventory for used shoppers.

Is the 2020 Toyota Highlander a good car?

Yes — the 2020 Toyota Highlander earns a 4.6/5 user rating and a 7.7/10 expert rating. The model scores 9/10 across Form and function and Safety.

Owners consistently praise its smooth ride, advanced features, and spacious interior, and many also highlight its safety features and handling. The trade-offs are front-seat comfort and interior material quality, which some reviewers say can feel shallow or cheap. In use, that makes the Highlander especially appealing if you want a family-friendly three-row SUV that prioritizes comfort and everyday livability over excitement. It also closes with 37.4% of listings marked as good or great deals, which gives you some room to shop selectively.

Is the 2020 Toyota Highlander reliable?

Owners rate it 4.6/5, a strong signal of long-term satisfaction.

The owner feedback points to a vehicle people feel they can count on, with repeated praise for its smooth ride, advanced features, and family-friendly usefulness. The expert review also describes the Highlander as smooth and practically silent at idle, with a powertrain that delivers brisk acceleration without much effort. Toyota includes two years of maintenance and roadside assistance, which helps reduce early ownership friction. For used buyers, the main long-term risk is that comfort-focused engineering can still leave you with a vehicle that needs careful inspection for wear, especially if previous owners used it heavily.

What should I look for when buying a used 2020 Toyota Highlander?

At 69.5% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should start with a vehicle history report and then prioritize a pre-purchase inspection, especially if the listing price looks unusually attractive. Focus on signs of prior bodywork, uneven panel gaps, tire wear, and any evidence that the suspension or steering has been stressed. Because this model is valued for comfort and family use, it also makes sense to pay close attention to cabin condition, seat wear, and interior materials.

Key things to evaluate:

• Trim level: The base L trim misses projector-beam LED headlights and fog lights, while higher trims add more upscale lighting and, on the Limited and Platinum, 20-inch wheels and prettier LED running lamps.
• Powertrain: You get a 3.5-liter V6 with front-wheel drive or all-wheel drive, and the engine is described as smooth, practically silent, and brisk without much effort.
• Safety package: Toyota Safety Sense 2.0 is standard, with automatic emergency braking with pedestrian and cyclist detection, lane-keeping assist, adaptive cruise control, and automatic high beams. Blind-spot monitoring, parking sensors, and rear emergency braking are optional.
• Infotainment: Apple CarPlay, Android Auto, and Amazon Alexa integration come standard, along with an 8-inch touchscreen; the optional 12.3-inch screen is not fully dedicated to maps or vehicle settings.
• Fuel efficiency: The Highlander FWD is rated at 21 mpg city and 29 mpg highway, while AWD is rated at 20 mpg city and 27 mpg highway.

Which 2020 Toyota Highlander trim should I buy?

The 2020 Toyota Highlander is offered in 5 trim levels: L, LE, XLE, Limited, Platinum.

Here's the short version:

• L: This is the entry point, but it leaves out some of the nicer exterior lighting and is best only if you want the lowest starting price.
• LE: This is the best-value trim in the low $40,000 range, giving you the strongest balance of equipment and price.
• XLE: This is the trim to target if you want a more upscale daily driver without jumping all the way to the top end.
• Limited: This trim adds a more premium feel, including the richer cabin presentation and the larger available touchscreen.
• Platinum: This is the most luxurious choice, with the most upscale presentation and the standard 12.3-inch touchscreen.

Toyota Safety Sense 2.0 is standard across the lineup, while blind-spot monitoring, parking sensors, and rear emergency braking remain optional.

Is now a good time to buy a used 2020 Toyota Highlander?

This looks like a moderate, selective buyer’s market, so you can shop patiently but still move quickly on strong listings.

• Deal availability: 37.4% of listings are priced as good or great deals.
• Inventory: There are 3,441 listings available.
• Price trend: Prices have softened 3.82% compared with last year.
• Clean inventory: 69.5% of listings are accident-free.

If you find a listing below $26,944, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2020 Toyota Highlander's resale value?

The current average of $27,242 sits slightly below last year's $28,324.

That decline suggests the market has eased 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 whether the vehicle has a clean history. Well-kept examples should remain easier to move because the Highlander still has strong family appeal and broad market recognition.

Vehicles with strong owner satisfaction ratings, like this model year's 4.6/5, tend to retain buyer demand, which supports resale value over time.

Is the 2020 Toyota Highlander safe?

The 2020 Toyota Highlander earns a Top Safety Pick from IIHS.

It earns a 9/10 safety score from our experts.

Toyota Safety Sense 2.0 is standard, and it includes automatic emergency braking with pedestrian detection and cyclist detection, lane-keeping assist, adaptive cruise control, and automatic high beams. Blind-spot monitoring, parking sensors, and rear emergency braking are optional. A driver's knee airbag and a special cushion airbag for the front passenger are standard. One caveat is that the IIHS recognition depends on the optional headlights and emergency braking performance in tests against cars and pedestrians.

Should I buy a 2020 Toyota Highlander or consider a different year?

If you're weighing the 2020 against nearby model years, here's how to think about it:

Choose the 2020 if:

• 37.4% of listings are priced as good or great deals.
• At 69.5% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 3.82% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• The 2020 redesign emphasizes a quieter ride, softer comfort, and a more premium cabin feel.

Consider the 2021 if:

• At $29,317, the 2021 costs more than the current year's $27,242 average.
• It adds more standard safety-feature technology.

The bottom line: If you want the better value, the 2020 is the smarter starting point because it combines a lower average price with strong owner satisfaction and a comfort-first driving experience. If you’re willing to pay more for added standard safety tech, the 2021 is the better alternative.

How does the 2020 Toyota Highlander compare to the 2020 Honda Pilot?

Expert Pros & Cons (per CarGurus review team)

2020 Toyota Highlander:

• Pros: Standard advanced safety features, Spacious.
• Cons: Poor handling, Uninspired styling.

2020 Honda Pilot:

• Pros: Powerful engine, Standard advanced safety features.
• Cons: Unintuitive technology, Interior materials feel cheap.

Our experts score the 2020 Toyota Highlander 7.7/10 and the 2020 Honda Pilot 8/10. The Highlander leans harder into comfort and a premium-feeling cabin, while the Pilot counters with a stronger engine and a slightly higher expert score. If you care most about a quiet, spacious family SUV, the Highlander makes a strong case; if you want more power and can live with less polished tech and materials, the Pilot may fit better.

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

These recommendations are based on CarGurus' proprietary market data from November 3, 2026, CarGurus experts' opinions, and generative AI.