Used 2020 Toyota Highlander for Sale nearBoston, MA

How much does the 2020 Toyota Highlander cost?

Prices have softened 4.21% compared to this time last year, making it a favorable time to shop this model year.

There are 3,204 listings available, which gives you a solid amount of inventory to compare.

Is the 2020 Toyota Highlander a good car?

Yes — the 2020 Toyota Highlander earns a 4.6/5 user rating and a 7.67/10 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. The main trade-offs are its uninspired styling and poor handling, which make it better suited to calm family use than spirited driving. That fits the Highlander’s role as a comfort-first three-row SUV with a quiet cabin and a premium feel, especially in upper trims. With 34.0% of listings marked as good or great deals, the market still offers some room to shop selectively.

Is the 2020 Toyota Highlander reliable?

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

User feedback points to a dependable, trouble-free ownership experience, with owners often describing it as a vehicle they can count on for family duty. The expert evaluation also emphasizes its calm, muted driving character and Lexus-like refinement, which supports the sense that it is built for steady everyday use. Toyota includes two years of maintenance and roadside assistance, which adds a helpful ownership perk. For used buyers, the main long-term risk is less about outright durability and more about finding one that has been maintained well and not worn down by heavy family use.

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 start with a vehicle history report and then prioritize a thorough pre-purchase inspection, especially if you are considering a higher-mileage family hauler. Focus on signs of prior bodywork, uneven wear, and interior condition, since comfort and cabin quality are central to this model’s appeal. If possible, test the ride, steering feel, and braking response on a mixed route so you can judge whether the vehicle still feels composed.

Key things to evaluate:

• Trim level: Every trim except the base L has projector-beam LED headlights and fog lights, while the higher trims add prettier LED running lamps; Limited and Platinum also get 20-inch wheels and a more upscale cabin presentation.
• Powertrain: The Highlander uses a 3.5-liter V6 with 295 horsepower and 263 pound-feet of torque, paired with an eight-speed automatic and offered with FWD or AWD. It delivers smooth, quiet acceleration and very good fuel economy for a large SUV.
• Safety package: Toyota Safety Sense 2.0 is standard and includes 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. The main touchscreen is 8 inches, and a 12.3-inch screen is available on higher trims; the system also includes standard SiriusXM, HD radio, WiFi, and four USB-A ports.
• Fuel efficiency: The FWD model is rated at 21 mpg city, 29 mpg highway, and 24 mpg combined, while AWD returns 20 mpg city, 27 mpg highway, and 23 mpg combined.

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 still gives you the Highlander’s core comfort and safety appeal. It makes sense if you want the lowest starting price and can live without the nicer lighting and upscale touches found higher up.
• LE: This is the best-value trim. It sits in the low $40,000 range and is the sweet spot if you want a strong mix of equipment, comfort, and value without stretching into luxury-priced territory.
• XLE: This trim adds more convenience and family-friendly appeal while staying below the premium upper trims. It is the right choice if you want a more polished daily driver without going all the way to Limited pricing.
• Limited: This is where the Highlander starts to feel especially close to a Lexus in quality and presentation. It brings a richer cabin and more upscale features, making it a strong pick if comfort matters most.
• Platinum: This is the top trim and the most luxurious version of the gas Highlander. It is the one to choose if you want the most premium interior and the most fully equipped experience.

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 is a moderate market for selective buyers, so it makes sense to shop carefully and compare listings.

• Deal availability: 34.0% of listings are priced as good or great deals.
• Inventory: There are 3,204 listings available.
• Price trend: Prices have softened 4.21% 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 $27,701 sits slightly below last year's $28,918.

That price movement suggests the Highlander has softened enough to create a better entry point for used buyers, but it also means future sellers may need to price competitively to stand out. The model’s broad family appeal, strong comfort reputation, and standard safety equipment should help support demand over time. Because shoppers tend to value well-kept three-row SUVs with strong satisfaction scores, clean-condition examples should remain easier to move than neglected ones.

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 rating 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 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 confirm whether a used example has the extra driver-assistance features you want.

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:

• 34.0% 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 4.21% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• It was redesigned for 2020, with a quieter ride and more premium cabin feel.

Consider the 2021 if:

• At $29,909, the 2021 costs more than the current year's $27,701 average.
• It adds more standard safety-feature technology.

The bottom line: If you want the better value, the 2020 is the smarter buy because it combines a lower average price with strong comfort, safety, and owner satisfaction. If you are willing to pay more for added standard safety technology, the 2021 is the cleaner upgrade path.

These recommendations are based on CarGurus' proprietary market data from September 15, 2026, CarGurus experts' opinions, and generative AI.