Used Toyota Highlander for Sale nearWinchester, MA
641 vehicles found
- 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:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 69,152
- Stock #:
- TL36761A
- VIN:
- 5TDGZRBH1NS241372
Sponsored by Koch Rt. 2 Toyota
2022 Toyota Highlander
XLE AWD
69,152 mi
$34,493
- 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:
- 86,271
- Stock #:
- S267847M
- VIN:
- 5TDJZRFH7JS912022
Sponsored Listing
2018 Toyota Highlander
XLE AWD
86,271 mi
$23,488
- 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:
- Wind Chill Pearl Off- White
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 47,000
- Stock #:
- N27619C
- VIN:
- 5TDKDRBH6PS512633
Sponsored Listing
2023 Toyota Highlander
XSE AWD
47,000 mi
$39,295
- 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:
- White (Blizzard Pearl)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 88,761
- Stock #:
- DP7133AB
- VIN:
- 5TDJZRFH0JS889926
2018 Toyota Highlander
XLE AWD
88,761 mi
$23,987
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 123,068
- Stock #:
- 56456A
- VIN:
- 5TDKDRBH3PS030413
2023 Toyota Highlander
XLE AWD
123,068 mi
$24,539
- 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:
- Red
- Transmission:
- 8-Speed Automatic
- Mileage:
- 50,077
- Stock #:
- 26485A
- VIN:
- 5TDJZRBH7NS193771
2022 Toyota Highlander
XSE AWD
50,077 mi
$36,149
- 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:
- Magnetic Gray Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 57,784
- Stock #:
- P3675A
- VIN:
- 5TDKDRBH9PS006522
2023 Toyota Highlander
XSE AWD
57,784 mi
$38,425
- Year:
- 2015
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Blue
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 135,113
- Stock #:
- 15C139B
- VIN:
- 5TDJKRFH6FS102120
2015 Toyota Highlander
XLE
135,113 mi
$15,486
- 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:
- Moon Dust
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 57,317
- Stock #:
- SB15780A
- VIN:
- 5TDHZRBHXNS227961
2022 Toyota Highlander
XLE AWD
57,317 mi
$34,549
- 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:
- White (Blizzard Pearl)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 78,010
- Stock #:
- AN5876AA
- VIN:
- 5TDJZRFH3KS617601
2019 Toyota Highlander
XLE AWD
78,010 mi
$25,990
- 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:
- White (Blizzard Pearl)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 130,703
- Stock #:
- HM22287T
- VIN:
- 5TDBZRFH1JS813412
-$628
2018 Toyota Highlander
LE AWD
130,703 mi
$16,668
$16,040
- 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:
- Shoreline Mist
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 82,671
- Stock #:
- 67423A
- VIN:
- 5TDBZRFH6JS905406
2018 Toyota Highlander
LE AWD
82,671 mi
$21,657
- 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:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 78,722
- Stock #:
- V260385A
- VIN:
- 5TDFZRBH7NS191203
2022 Toyota Highlander
Platinum AWD
78,722 mi
$35,987
Recommended model year:
2024 Toyota Highlander
Shop 2024 Toyota Highlander »With 3,978 currently listed for sale and an average price of $39,108.00, 34.9% 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.
88.8% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander features a spacious interior, advanced safety technology, and a smooth ride, making it an excellent choice for families.
- Year:
- 2015
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- White
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Transmission:
- 6-Speed Automatic
- Mileage:
- 157,311
- Stock #:
- 9027
- VIN:
- 5TDJKRFH0FS218395
2015 Toyota Highlander
XLE
157,311 mi
$14,495
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 73,080
- Stock #:
- T15310C
- VIN:
- 5TDJZRFH8KS591917
2019 Toyota Highlander
XLE AWD
73,080 mi
$27,794
- 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:
- White (Blizzard Pearl)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 99,971
- Stock #:
- HL5512A
- VIN:
- 5TDJZRFH8HS513212
2017 Toyota Highlander
XLE AWD
99,971 mi
$21,906
- 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
- Fuel type:
- Gasoline
- Interior color:
- Unk
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 104,206
- Stock #:
- HL13270A
- VIN:
- 5TDJKRFH3GS501360
2016 Toyota Highlander
XLE AWD
104,206 mi
$20,841
- Year:
- 2015
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Transmission:
- 6-Speed Automatic
- Mileage:
- 118,953
- Stock #:
- 136654
- VIN:
- 5TDBKRFH9FS136654
2015 Toyota Highlander
LE AWD
118,953 mi
$15,494
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Silver
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 18,812
- Stock #:
- 56581
- VIN:
- 5TDKDRAH7SS554674
2025 Toyota Highlander
LE FWD
18,812 mi
$35,798
- 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:
- Ooh La La Rouge Mica
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 130,357
- Stock #:
- TP3772B
- VIN:
- 5TDDKRFH3GS233276
2016 Toyota Highlander
Limited AWD
130,357 mi
$17,468
- 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:
- White
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Transmission:
- 6-Speed Automatic
- Mileage:
- 134,398
- Stock #:
- NEW257551
- VIN:
- 5TDDKRFH9GS257551
2016 Toyota Highlander
Limited Platinum AWD
134,398 mi
$18,478
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 82,291
- Stock #:
- TU1088
- VIN:
- 5TDFZRBH0MS115417
2021 Toyota Highlander
Platinum AWD
82,291 mi
$34,174
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Glazed Caramel
- Transmission:
- 8-Speed Automatic
- Mileage:
- 21,887
- Stock #:
- P9912
- VIN:
- 5TDKDRBH3RS535032
Sponsored Listing
2024 Toyota Highlander
Platinum AWD
21,887 mi
$49,654
FAQs
How much does the Toyota Highlander cost in Winchester, MA?
How many Toyota Highlander vehicles in Winchester, 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
Filter by rating
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 3,978 currently listed for sale and an average price of $39,108.00, 34.9% 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.
88.8% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander features a spacious interior, advanced safety technology, and a smooth ride, making it an excellent choice for families.
Why it stands out
The 2024 Toyota Highlander continues to build on its reputation as a reliable and family-friendly SUV. With its spacious interior and comfortable seating for up to eight passengers, it caters to families who need room for both kids and cargo. The Highlander is equipped with a suite of advanced safety features, including Toyota Safety Sense, which enhances its appeal to safety-conscious buyers. Additionally, the Highlander's smooth ride and refined handling make it a pleasure to drive, while its strong reliability ratings ensure peace of mind for long-term ownership.
Other model years to consider
- Average price: $36,251.00
- Good/great deal percentage: 35.1%
- User rating: 4.75 / 5
- Total listings: 4,632
- Average price: $16,128.00
- Good/great deal percentage: 34.6%
- User rating: 4.78 / 5
- Total listings: 1,225
- Average price: $33,589.00
- Good/great deal percentage: 35.1%
- User rating: 4.44 / 5
- Total listings: 4,931
These recommendations are based on CarGurus' proprietary market data from July 6, 2026, CarGurus experts' opinions, and generative AI.
Recent expert test drives
2022 Toyota Highlander
- Expert review8/10
- MSRP$35,855-$49,960
- Avg. price$33,163
- User rating4.4444
2020 Toyota Highlander
- Expert review8/10
- MSRP$34,600-$48,800
- Avg. price$28,233
- User rating4.6
2021 Toyota Highlander
- Expert review8/10
- MSRP$35,085-$49,190
- Avg. price$30,363
- User rating4.8636
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