Used 2020 Toyota Highlander for Sale near Massachusetts

How much does the 2020 Toyota Highlander cost?

Prices have softened 4.33% compared to this time last year, making it a favorable time to shop this model year.

There are 3,241 listings available, which gives you a solid amount of inventory to compare.

Is the 2020 Toyota Highlander a good car?

Yes — it earns a 4.6/5 from owners and a 7.67/10 expert rating. The model scores 9/10 across Form and function and Safety.

Owners consistently praise the smooth ride, advanced features, and spacious interior, and the safety equipment is another recurring strength. The Highlander is also described as a favorite for families, which fits its comfort-first, three-row mission.

The trade-offs are clear: the expert review calls out poor handling and uninspired styling. In practical terms, that means you should buy it for calm commuting, family hauling, and easy long-distance comfort rather than engaging driving.

The Highlander’s appeal is strongest if you want a comfortable, well-equipped midsize three-row SUV that puts ease of use ahead of excitement. With 33.0% of listings marked as good or great deals, there’s still 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 dependable, trouble-free ownership experience, with repeated praise for the Highlander’s smoothness and family-friendly usability. The expert review also emphasizes its calm, muted driving character and notes that Toyota includes two years of maintenance and roadside assistance.

That combination suggests you’re looking at a used SUV that should be easy to live with over time, though you should still pay close attention to maintenance history and overall condition before buying.

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

At 70.8% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should run a vehicle history report before you get too far into the process, then prioritize a thorough inspection of bodywork, alignment, and interior condition. Because this model is valued for comfort and refinement, you’ll want to focus on signs of wear that could undermine that experience, especially in the cabin and suspension feel.

Key things to evaluate:

• Trim level: Every trim except the base L has projector-beam LED headlights and fog lights, while Limited and Platinum add prettier LED running lamps and 20-inch wheels. The cabin quality is a major strength, and the upper trims add richer materials and a more upscale feel.
• Powertrain: The Highlander uses a 3.5-liter V6 with front-wheel drive or all-wheel drive. It delivers brisk acceleration, smooth operation, and strong highway composure, though the steering and suspension are tuned more for comfort than sharp response.
• Safety package: Toyota Safety Sense 2.0 is standard and 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.
• Infotainment: Apple CarPlay, Android Auto, and Amazon Alexa integration come standard. The system uses an 8-inch touchscreen, while a 12.3-inch screen is optional on Limited and standard on Platinum; the larger display still doesn’t fully expand usable map or vehicle-control space.
• Fuel efficiency: The Highlander FWD is EPA rated at 21 mpg city, 29 mpg highway, and 24 mpg combined. AWD models are rated at 20/27/23.

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 misses some of the nicer lighting and upscale touches found higher up the range. It makes sense if you want the lowest starting price and are mainly focused on getting the Highlander’s comfort and safety basics.
• LE: This is the best-value trim. It sits in the low $40,000 range and gives you a strong balance of equipment and price without pushing too far into luxury territory.
• XLE: This trim adds more comfort and convenience content and is a good step up if you want a better-equipped family SUV without going all the way to the premium trims.
• Limited: This is where the Highlander starts to feel especially upscale, with richer cabin materials and more of the premium character that makes the SUV feel Lexus-like.
• Platinum: This is the top trim and brings the most upscale presentation, including the 12.3-inch touchscreen as standard and the most premium interior treatment.

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 with some leverage if you’re patient.

• Deal availability: 33.0% of listings are priced as good or great deals.
• Inventory: There are 3,241 listings available.
• Price trend: Prices have softened 4.33% compared with last year.
• Clean inventory: 70.8% of listings are accident-free.

If you find a listing below $26,980, 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 $27,731 sits slightly below last year's $28,988.

That price movement suggests the market has cooled enough to give you a better entry point now than a year ago. If you buy well and keep the vehicle in strong condition, you may be able to limit depreciation pressure compared with paying a higher price at the peak.

For a future seller, the key is that the Highlander still has broad family appeal and a strong reputation for comfort and safety. Those traits help support demand, especially when the vehicle is clean, well maintained, and equipped with desirable features.

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 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. A driver's knee airbag and a special cushion airbag for the front passenger are also standard.

Blind-spot monitoring, parking sensors, and rear emergency braking are optional, so you should check whether a used example has those extras if safety tech matters to you.

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:

• 33.0% of listings are priced as good or great deals.
• At 70.8% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 4.33% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• The 2020 redesign brings a quieter ride, a softer suspension, and a more premium-feeling cabin.

Consider the 2021 if:

• At $29,947, the 2021 costs more than the current year's $27,731 average.
• It adds even more standard safety-feature technology.

The bottom line: If you want the better value today, the 2020 is the smarter buy because it combines a lower average price with strong owner satisfaction and a comfort-first driving experience. If you’re willing to spend more for added standard safety technology, the 2021 is the better secondary path.

These recommendations are based on CarGurus' proprietary market data from September 11, 2026, CarGurus experts' opinions, and generative AI.