Used 2020 Toyota Highlander for Sale near Boston, MA
275 results
CarGurus Analysis:
2020 Toyota Highlander
With 277 currently listed for sale near Boston, MA and an average price of $29,224.00, 34.3% of 2020 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Toyota Highlander 4.6 / 5 stars.
91.0% of 2020 Highlander models on CarGurus are accident free.
The 2020 Toyota Highlander offers a smooth ride and ample space, making it a favorite among families, coupled with advanced safety features and high comfort levels.
CarGurus Analysis: 2020 Toyota Highlander
overall
Summary
With 277 currently listed for sale near Boston, MA and an average price of $29,224.00, 34.3% of 2020 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Toyota Highlander 4.6 / 5 stars.
91.0% of 2020 Highlander models on CarGurus are accident free.
The 2020 Toyota Highlander offers a smooth ride and ample space, making it a favorite among families, coupled with advanced safety features and high comfort levels.
Why it stands out
The 2020 Toyota Highlander excels in providing a comfortable and spacious three-row SUV experience, making it especially appealing for families. Redesigned for 2020, it boasts a noise-reducing cabin, a soft ride, and a high-quality interior that rivals luxury vehicles, such as certain Lexus models. Its impressive V6 engine delivers smooth acceleration, contributing to a relaxed driving experience. Although it may disappoint those seeking sharp handling, the Highlander prioritizes comfort and ease of driving, which is what most buyers desire in this segment.
The model also includes a suite of standard safety features through Toyota Safety Sense 2.0, ensuring peace of mind for drivers and passengers alike. Despite its few drawbacks, like uninspired styling and softer steering response, the Highlander's blend of practicality, safety, and comfort makes it a strong contender in the midsize SUV market.
Other model years to consider
- Average price: $40,896.00
- Good/great deal percentage: 56.5%
- User rating: 5 / 5
- Total listings: 214
- Average price: $25,502.00
- Good/great deal percentage: 35.1%
- User rating: 4.76 / 5
- Total listings: 259
- Average price: $32,571.00
- Good/great deal percentage: 45.5%
- User rating: 4.86 / 5
- Total listings: 246
This analysis is based on CarGurus' proprietary market data from May 26, 2026, CarGurus experts' opinions, and generative AI.
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4.6 Overall rating
Filter by rating
Sarah T
Reviewed a 2020 Toyota Highlander on Dec 7, 2025
It’s well-equipped, comfortable, and family-friendly SUV with strong safety tech, a smooth ride, and premium touches (thanks to the platinum trim) like a panoramic moonroof, leather seating, and 12” touchscreen. Its V6 offers solid power and decent fuel efficiency for a 3-row SUV, and overall it feels modern, quiet, and refined. It’s a great value if you want a reliable, upscale daily driver! The main thing it’s missing is more usable third-row and cargo space. The 3rd row is tight for adults and cargo behind it is limited. Otherwise, it’s a strong all-around pick and fits exactly what I was looking for. I would compare this to the Kia Telluride, Hyundai Palisade, Honda Pilot, and the Ford Explorer.
Anonymous
Reviewed a 2020 Toyota Highlander on Nov 8, 2020
Most comfortable riding vehicle that we have ever purchased. Great features and a great looking vehicle as well.
Kris B
Reviewed a 2020 Toyota Highlander on May 22, 2023
Absolutely love this car. Great comfortable family vehicle with plenty of space, and features
Lee W
Reviewed a 2020 Toyota Highlander on Feb 28, 2020
The ride was smooth, the Highlander is quick and very quiet. I loved many of the features it had, like the posted speed limit on the instrument cluster. What really disappointed me was the passenger seat comfort. The seat bottom only adjusts fron-to-rear, not up or down so I wasn’t as comfortable in it as I was the Hyundai Palisade or the Kia Telluride. It’s still a really good vehicle.
2020 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| L AWD | $36,200 |
| LE FWD | $36,800 |
| LE AWD | $38,400 |
| Limited FWD | $43,650 |
| Limited AWD | $45,600 |
| Platinum AWD | $48,800 |
| XLE FWD | $39,600 |
| XLE AWD | $41,200 |
2020 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2020 Toyota Highlander prices has changed over time.
See more price trends2020 Toyota Highlander Pricing Analysis: Boston, MA Market Report
Pricing by Nearby Locations
Market Area: Boston, MA
Key Insights
- Highest Prices in Manchester, NH: The average price is $29,794, indicating stronger demand or limited supply.
- Lowest Prices in Groton, MA: Listings average $28,634, suggesting a potentially more competitive market.
- Price Stability Across Regions: The average prices across cities demonstrate minimal variation, with the highest and lowest differing by only $1,160.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Manchester, NH | 238 | $29,794 |
| Plymouth, MA | 235 | $28,692 |
| Worcester, MA | 287 | $28,257 |
| Providence, RI | 247 | $27,805 |
| Hartford, CT | 209 | $28,250 |
| Chicopee, MA | 227 | $26,365 |
| New Bedford, MA | 213 | $28,072 |
| Groton, MA | 278 | $28,634 |
Pricing by Trim Packages
Key Insights
- XLE AWD Dominates Inventory: The XLE AWD trim leads with 272 listings, capturing a strong segment of the market.
- Premium Trim = Limited AWD: The Limited AWD, priced at $45,600, features luxury enhancements and indicates significant consumer interest in higher trims.
- FWD vs. AWD Dynamics: The majority of inventory features AWD trims, suggesting a preference for all-weather capability in this region.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 272 | $41,200 | AWD | 3.5L 295 hp V6 |
| Limited AWD | 103 | $45,600 | AWD | 3.5L 295 hp V6 |
| LE AWD | 104 | $38,400 | AWD | 3.5L 295 hp V6 |
| XLE FWD | 42 | $39,600 | FWD | 3.5L 295 hp V6 |
| LE FWD | 42 | $36,800 | FWD | 3.5L 295 hp V6 |
| Platinum AWD | 58 | $48,800 | AWD | 3.5L 295 hp V6 |
| Limited FWD | 21 | $43,650 | FWD | 3.5L 295 hp V6 |
| L FWD | 16 | $34,600 | FWD | 3.5L 295 hp V6 |
Pricing Analysis by Model Year
Key Insights
- 2026 Model at Premium Pricing: The latest 2026 Highlander is priced at $49,875, approximately 8.0% above MSRP, indicating continued demand for new models.
- Significant Depreciation for Older Models: The 2019 Highlander shows a steep decline, averaging $25,463, translating to -20.6% compared to MSRP.
- Value in 2022-2023 Models: The 2023 Highlander retains a strong position, priced at only -2.3% below MSRP, indicating better value compared to older generations.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $45,870 | $49,875 | +8.0% |
| 2025 Toyota Highlander | $40,320 | $43,766 | +8.1% |
| 2024 Toyota Highlander | $39,270 | $40,890 | +4.1% |
| 2023 Toyota Highlander | $36,620 | $37,778 | -2.3% |
| 2022 Toyota Highlander | $35,855 | $34,053 | -5.0% |
| 2021 Toyota Highlander | $35,085 | $31,971 | -8.9% |
| 2019 Toyota Highlander | $31,830 | $25,463 | -20.6% |
| 2018 Toyota Highlander | $31,230 | $22,638 | -27.6% |
| 2017 Toyota Highlander | $30,630 | $19,889 | -35.1% |
| 2016 Toyota Highlander | $30,490 | $17,900 | -41.2% |
| 2015 Toyota Highlander | $29,765 | $16,947 | -43.0% |
These recommendations are based on CarGurus' proprietary market data from May 28, 2026, CarGurus experts' opinions, and generative AI.
