Used Toyota Highlander for Sale nearChesterfield, MA
841 vehicles found
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Red
- Transmission:
- 8-Speed Automatic
- Mileage:
- 25,613
- Stock #:
- 130437A
- VIN:
- 5TDKDRAH0PS508370
Sponsored by Gale Toyota
2023 Toyota Highlander
XSE FWD
25,613 mi
$40,599
- Year:
- 2024
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 12,207
- Stock #:
- T53100A
- VIN:
- 5TDKDRBH9RS547475
Sponsored Listing
2024 Toyota Highlander
LE AWD
12,207 mi
$39,604
- Year:
- 2017
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Shoreline Blue Pearl
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 73,648
- Stock #:
- C50939A
- VIN:
- 5TDBZRFH1HS408547
Sponsored Listing
2017 Toyota Highlander
LE Plus AWD
73,648 mi
$22,061
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Gray
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 63,590
- Stock #:
- 516784
- VIN:
- 5TDKDRBH3PS516784
2023 Toyota Highlander
L AWD
63,590 mi
$31,617
- Year:
- 2017
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Shoreline Blue Pearl
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 73,648
- Stock #:
- C50939A
- VIN:
- 5TDBZRFH1HS408547
2017 Toyota Highlander
LE Plus AWD
73,648 mi
$22,061
- Year:
- 2016
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Silver Sky Metallic
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 6-Speed Automatic
- Mileage:
- 130,136
- VIN:
- 5TDDKRFH6GS335963
2016 Toyota Highlander
Limited AWD
130,136 mi
$19,170
- Year:
- 2017
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Red (Maroon)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 94,370
- Stock #:
- 360406B
- VIN:
- 5TDDZRFH4HS366559
2017 Toyota Highlander
Limited AWD
94,370 mi
$24,594
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 69,733
- Stock #:
- H260416B
- VIN:
- 5TDJZRFH2KS605777
2019 Toyota Highlander
XLE AWD
69,733 mi
$28,493
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Pearl
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 55,567
- Stock #:
- TS724509A
- VIN:
- 5TDLZRBH5NS183071
2022 Toyota Highlander
XSE AWD
55,567 mi
$37,549
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Amber
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 61,055
- Stock #:
- 80280A
- VIN:
- 5TDGZRBH7MS136219
2021 Toyota Highlander
XLE AWD
61,055 mi
$30,283
- Year:
- 2020
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 113,517
- Stock #:
- 513675
- VIN:
- 5TDGZRBH3LS513675
2020 Toyota Highlander
XLE AWD
113,517 mi
$25,136
- Year:
- 2016
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 100,550
- Stock #:
- N26395A
- VIN:
- 5TDJKRFH5GS265925
2016 Toyota Highlander
XLE AWD
100,550 mi
$19,637
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Celestial Silver Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 22,780
- Stock #:
- KN6577A
- VIN:
- 5TDGZRBH5NS594973
2022 Toyota Highlander
XLE AWD
22,780 mi
$37,072
Recommended model year:
2024 Toyota Highlander
Shop 2024 Toyota Highlander »With 4,139 currently listed for sale and an average price of $39,141.00, 36.5% of 2024 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2024 Toyota Highlander 5 / 5 stars.
88.5% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander features innovative design and family-friendly comfort, with advanced technologies and spacious three-row seating.
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 55,506
- Stock #:
- 11675TB
- VIN:
- 5TDGZRBHXNS163268
2022 Toyota Highlander
XLE AWD
55,506 mi
$35,799
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 53,636
- Stock #:
- 11639TB
- VIN:
- 5TDKDRBHXPS028075
2023 Toyota Highlander
XSE AWD
53,636 mi
$38,099
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 93,337
- Stock #:
- FAD10046
- VIN:
- 5TDGZRAH1MS529442
-$2,500
2021 Toyota Highlander
XLE FWD
93,337 mi
$28,266
$25,766
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 62,854
- Stock #:
- 26DP030
- VIN:
- 5TDBZRBH1NS574083
2022 Toyota Highlander
LE AWD
62,854 mi
$30,099
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Ooh La La Rouge Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 130,090
- Stock #:
- H260431B
- VIN:
- 5TDJZRFH3JS903835
2018 Toyota Highlander
XLE AWD
130,090 mi
$20,394
- Year:
- 2012
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Magnetic Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 100,504
- Stock #:
- 143980T
- VIN:
- 5TDDK3EH9CS143980
2012 Toyota Highlander
Limited AWD
100,504 mi
$15,197
- Year:
- 2016
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Silver Sky Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 77,759
- Stock #:
- S2005A
- VIN:
- 5TDBKRFH1GS287277
-$600
2016 Toyota Highlander
LE Plus AWD
77,759 mi
$22,104
$21,504
- Year:
- 2011
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 187 hp 2.7L I4
- Exterior color:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 5-Speed Automatic
- Mileage:
- 103,465
- Stock #:
- 393
- VIN:
- 5TDBK3EH5BS062299
2011 Toyota Highlander
Base
103,465 mi
$13,698
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 47,605
- Stock #:
- M26204A
- VIN:
- 5TDDZRBH6NS214140
2022 Toyota Highlander
Limited AWD
47,605 mi
$37,069
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Pearl
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Harvest Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 33,552
- Stock #:
- 26CP061
- VIN:
- 5TDKDRBH4PS501291
Sponsored Listing
2023 Toyota Highlander
XLE AWD
33,552 mi
$39,594
FAQs
How much does the Toyota Highlander cost in Chesterfield, MA?
How many Toyota Highlander vehicles in Chesterfield, MA have no reported accidents or damage?
What fuel types are available?
4.7 Overall rating
Customers say
Overall, the Toyota Highlander has built a strong reputation across its model years for reliability, comfort, and family-friendly features. Drivers appreciate its spacious interiors and smooth rides, often highlighting its impressive safety features as a key asset. Many also enjoy the performance and power of the engines. However, some common criticisms include a lack of advanced infotainment options in older models, tight third-row seating, and varying cargo space depending on configuration. Overall, the Highlander is seen as a dependable choice for families and an excellent value in the SUV market.
AI generated from the text of customer reviews.
Filter by year
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What people say
Anonymous
Reviewed a 2024 Toyota XLE AWD on Dec 10, 2025
The 2024 Toyota Highlander XLE offers insane cabin room, comfort and luxury feel. The chassis makes an absolute smooth, dream and comfortable ride. Cabin rear chairs makes four adults feel like your in a Sequoia with room. Absolute beautiful and enjoyable ride and purchase
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.
Luong S
Reviewed a 2012 Toyota Base on Apr 26, 2026
This car's features are very good and have great value the only missing is it has only one key.
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.
Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| Platinum AWD | $53,925 |
| XLE AWD | $46,270 |
| XSE AWD | $48,340 |
| Limited AWD | $50,725 |
Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of Toyota Highlander prices has changed over time.
See more price trendsToyota Highlander Pricing Analysis
Pricing Analysis by Model Year
Key Insights
- Significant Depreciation for Older Models: The 2016 Toyota Highlander shows the steepest decline, with a current average price of $18,897, reflecting a -38.5% depreciation from its original MSRP.
- Recent Models Retain Value: The 2026 model is currently priced at $51,737, which is +11.0% above its MSRP, indicating strong demand for the latest model.
- Best Value Year: The 2022 Highlander is priced at $33,940, representing a -5.1% depreciation, making it a potentially attractive option for buyers seeking a balance between price and features.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $46,270 | $51,737 | +11.0% |
| 2025 Toyota Highlander | $40,320 | $41,573 | +3.1% |
| 2024 Toyota Highlander | $39,270 | $39,197 | -0.2% |
| 2023 Toyota Highlander | $36,620 | $36,418 | -0.6% |
| 2022 Toyota Highlander | $35,855 | $33,940 | -5.1% |
| 2021 Toyota Highlander | $35,085 | $30,923 | -12.0% |
| 2020 Toyota Highlander | $34,600 | $28,787 | -16.8% |
| 2019 Toyota Highlander | $31,830 | $24,537 | -22.9% |
| 2018 Toyota Highlander | $31,230 | $22,596 | -27.8% |
| 2017 Toyota Highlander | $30,630 | $20,935 | -31.6% |
| 2016 Toyota Highlander | $30,490 | $18,897 | -38.5% |
Pricing by Popular US Cities
Market Area: Nationwide
Key Insights
- Highest Prices in New York: The average price in New York, NY is $26,703, indicating a premium market likely driven by demand and limited supply.
- Lowest Prices in Chicago: Chicago, IL offers the lowest average price at $24,808, suggesting a more competitive market with higher inventory levels.
- Price Variation Across Cities: Cities like Dallas, TX and Philadelphia, PA show average prices of $26,745 and $29,400, respectively, indicating regional differences in demand and pricing strategies.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| New York, NY | 653 | $26,703 |
| Los Angeles, CA | 521 | $25,837 |
| Chicago, IL | 341 | $24,808 |
| Dallas, TX | 384 | $26,745 |
| Philadelphia, PA | 295 | $29,400 |
| Houston, TX | 385 | $25,025 |
| Miami, FL | 223 | $29,432 |
| Washington, DC | 486 | $27,474 |
| Atlanta, GA | 336 | $26,870 |
| Boston, MA | 635 | $28,044 |
Pricing by Trim Packages
Key Insights
- XLE AWD is the Most Common Trim: With 3,182 listings, the XLE AWD trim is the most prevalent, indicating strong consumer preference for this configuration.
- Premium Pricing for Limited AWD: The Limited AWD trim, priced at $50,725, commands a significant premium, reflecting its extensive feature set and luxury appeal.
- Feature-Rich Trims: All trims offer a robust set of features, with the Platinum AWD trim providing the highest level of luxury and technology, justifying its higher MSRP.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 3,182 | $46,270 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 1,221 | $50,725 | AWD | 2.4L 265 hp I4 |
| XSE AWD | 716 | $48,340 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 573 | $53,925 | AWD | 2.4L 265 hp I4 |
These recommendations are based on CarGurus' proprietary market data from July 2, 2026, CarGurus experts' opinions, and generative AI.
CarGurus recommends the 2024 Toyota Highlander
Summary
With 4,139 currently listed for sale and an average price of $39,141.00, 36.5% of 2024 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2024 Toyota Highlander 5 / 5 stars.
88.5% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander features innovative design and family-friendly comfort, with advanced technologies and spacious three-row seating.
Why it stands out
The 2024 Toyota Highlander stands out in the crowded midsize SUV market with its strong reputation for reliability, spacious interiors, and family-friendly features. The vehicle features an innovative unibody design that enhances fuel efficiency and driving dynamics, making it a favorite among families. It also includes a user-friendly infotainment system and a suite of advanced safety technologies. This model offers a comfortable ride, excellent handling, and an impressive amount of cargo space. The Highlander’s combination of upscale features and overall affordability solidifies its appeal to potential buyers looking for a versatile and dependable family vehicle.
Other model years to consider
- Average price: $36,279.00
- Good/great deal percentage: 35.1%
- User rating: 4.75 / 5
- Total listings: 4,691
- Average price: $16,094.00
- Good/great deal percentage: 34.3%
- User rating: 4.78 / 5
- Total listings: 1,198
- Average price: $33,550.00
- Good/great deal percentage: 34.9%
- User rating: 4.44 / 5
- Total listings: 4,964
These recommendations are based on CarGurus' proprietary market data from June 29, 2026, CarGurus experts' opinions, and generative AI.
Recent expert test drives
2022 Toyota Highlander
- Expert review8/10
- MSRP$35,855-$49,960
- Avg. price$33,236
- User rating4.4444
2020 Toyota Highlander
- Expert review8/10
- MSRP$34,600-$48,800
- Avg. price$28,205
- User rating4.6
2021 Toyota Highlander
- Expert review8/10
- MSRP$35,085-$49,190
- Avg. price$30,374
- User rating4.8636
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