Used 2021 Toyota Highlander for Sale near Boston, MA
254 results
![[1G3] Magnetic Gray Metallic 2022 Toyota Highlander XLE FWD SUV / Crossover Front-Wheel Drive Automatic](https://static.cargurus.com/images/forsale/2026/04/24/00/34/2022_toyota_highlander-pic-1285140681254082234-1024x768.jpeg?io=true&width=640&height=480&fit=bounds&format=jpg&auto=webp)
CarGurus Analysis:
2021 Toyota Highlander
With 246 currently listed for sale near Boston, MA and an average price of $32,571.00, 45.5% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.86 / 5 stars.
100.0% of 2021 Highlander models on CarGurus are accident free.
The 2021 Toyota Highlander stands out with its impressive comfort, spacious interior, and a strong reputation for reliability.
CarGurus Analysis: 2021 Toyota Highlander
overall
Summary
With 246 currently listed for sale near Boston, MA and an average price of $32,571.00, 45.5% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.86 / 5 stars.
100.0% of 2021 Highlander models on CarGurus are accident free.
The 2021 Toyota Highlander stands out with its impressive comfort, spacious interior, and a strong reputation for reliability.
Why it stands out
The 2021 Toyota Highlander emphasizes comfort and reliability, making it a favorite among families seeking a spacious three-row SUV. A hallmark of this model is its impressive safety ratings, bolstered by advanced driver assistance technologies included as standard. The Highlander also adds the new XSE trim for 2021, offering sportier styling and enhanced performance features without sacrificing comfort. Despite its strengths, buyers should note its underwhelming base engine performance and somewhat outdated technology interface compared to competitors. Overall, the 2021 Highlander successfully balances luxury, practicality, and safety, making it an attractive option in a crowded segment.
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: $37,975.00
- Good/great deal percentage: 65.5%
- User rating: 4.75 / 5
- Total listings: 229
This analysis is based on CarGurus' proprietary market data from May 26, 2026, CarGurus experts' opinions, and generative AI.
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4.9 Overall rating
Filter by rating
Julie W
Reviewed a 2021 Toyota Highlander on Jul 20, 2024
I loved my Highlander. I give my 2021 Toyota Highlander a 100 out of 10 on its safety. My car was a limited and it had most bells and whistles which I loved but what I loved most was that we all walked away from a collision where we were traveling 40 miles an hour and thanks to the safety design , we’re here.
Tony T
Reviewed a 2021 Toyota Highlander on Jul 5, 2022
Love this 2021 Highlander SXE model, got all the bells and whistles. No complaints. Can’t go wrong with Toyota. Out of the 20 SUV with 5000 lbs towing, this one is top IMO.
Melissa C
Reviewed a 2021 Toyota Highlander on May 6, 2024
Toyota knocked it out of the park again with this 2021 Highlander Platinum. Luxurious quiet ride Lexus feel like. Very happy with this purchase.
Frederick and Mariah P
Reviewed a 2021 Toyota Platinum AWD on Mar 5, 2023
Absolutely love the upgraded features of this car. The panoramic sunroof is stunning, the infotainment screen is huge and easy to operate, the seats are insanely comfortable, and the ride is so smooth and surprisingly quiet on the inside. We haven’t had the car for long but we are absolutely loving it so far. We are so glad that we decided to go with the platinum trim!
2021 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| LE FWD | $37,285 |
| LE AWD | $38,885 |
| XSE FWD | $41,680 |
| Limited AWD | $45,990 |
| XSE AWD | $43,630 |
| Platinum AWD | $49,190 |
| XLE FWD | $40,085 |
| XLE AWD | $41,685 |
2021 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2021 Toyota Highlander prices has changed over time.
See more price trends2021 Toyota Highlander Pricing Analysis: Boston, MA Market Report
Pricing by Nearby Locations
Market Area: Boston, MA
Key Insights
- Lowest Prices in Hartford: The Hartford, CT region has the lowest average price at $28,597, likely due to higher competition or stock levels.
- Comparatively High Prices in Plymouth: In contrast, Plymouth, MA has the highest average price at $32,521, suggesting lower inventory or higher demand for Highlanders in that area.
- Inventory Variation: Markets with higher listings, such as Worcester (266 listings), tend to maintain moderate pricing around $31,820, indicating stable supply and balanced demand.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Plymouth, MA | 215 | $32,521 |
| New Bedford, MA | 194 | $32,164 |
| Worcester, MA | 266 | $31,820 |
| Groton, MA | 249 | $31,578 |
| Providence, RI | 229 | $32,085 |
| Portsmouth, NH | 185 | $31,536 |
| Manchester, NH | 212 | $31,486 |
| Chicopee, MA | 199 | $31,773 |
| Brattleboro, VT | 183 | $30,461 |
| Hartford, CT | 183 | $28,597 |
Pricing by Trim Packages
Key Insights
- Most Common Trim = XLE AWD: The XLE AWD trim leads the inventory with 272 listings, indicating strong buyer preference for its combination of features and performance.
- Premium Features in Limited AWD: The Limited AWD trim, with an MSRP of $45,990, reflects the premium market segment, offering extensive luxury features.
- Entry-Level LE FWD Offers Value: The LE FWD trim is priced at $37,285 and remains accessible due to its competitive MSRP and desirable features, although it has lower availability at 42 listings.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 272 | $41,685 | AWD | 3.5L 295 hp V6 |
| Limited AWD | 103 | $45,990 | AWD | 3.5L 295 hp V6 |
| XSE AWD | 75 | $43,630 | AWD | 3.5L 295 hp V6 |
| LE AWD | 104 | $38,885 | AWD | 3.5L 295 hp V6 |
| XLE FWD | 42 | $40,085 | FWD | 3.5L 295 hp V6 |
| LE FWD | 42 | $37,285 | FWD | 3.5L 295 hp V6 |
| Limited FWD | 21 | $44,040 | FWD | 3.5L 295 hp V6 |
Pricing Analysis by Model Year
Key Insights
- Strong Demand for New Models: The 2026 model is priced at $49,875, significantly above its MSRP of $45,870, indicating robust market demand and limited availability.
- Depreciation Trends Over Time: The 2019 model shows significant depreciation of -20.0% versus its MSRP, reflecting typical market trends as new models are released.
- Best Value Years: The 2022 model remains close to its MSRP at $34,053, indicating less depreciation relative to the newer models, making it a notable value option.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $45,870 | $49,875 | +6.5% |
| 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 | +3.2% |
| 2022 Toyota Highlander | $35,855 | $34,053 | -5.0% |
| 2020 Toyota Highlander | $34,600 | $28,590 | -17.4% |
| 2019 Toyota Highlander | $31,830 | $25,463 | -20.0% |
| 2018 Toyota Highlander | $31,230 | $22,638 | -27.7% |
| 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 | -43.1% |
These recommendations are based on CarGurus' proprietary market data from May 28, 2026, CarGurus experts' opinions, and generative AI.
