Used Toyota Highlander for Sale nearWinslow, IL
306 vehicles found
See the total price upfront.
Only show listings that include dealer fees- 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:
- Moon Dust
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 61,955
- Stock #:
- H260294A
- VIN:
- 5TDHZRBH5MS079992
Sponsored by McGrath Volkswagen Hyundai of Dubuque
2021 Toyota Highlander
XLE AWD
61,955 mi
$34,175
- 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:
- Black
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 52,935
- Stock #:
- 3P26052
- VIN:
- 5TDFZRBH7MS157020
Sponsored Listing
2021 Toyota Highlander
Platinum AWD
52,935 mi
$38,848
- Year:
- 2007
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 215 hp 3.3L V6
- Exterior color:
- Red
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 5-Speed Automatic
- Mileage:
- 172,443
- Stock #:
- 187631
- VIN:
- JTEHP21A370187631
Sponsored Listing
2007 Toyota Highlander
Sport V6 AWD
172,443 mi
$7,225
- 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:
- White (Blizzard Pearl)
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 151,960
- Stock #:
- 26292B
- VIN:
- 5TDDKRFH6FS148480
2015 Toyota Highlander
Limited Platinum AWD
151,960 mi
$16,960
- Year:
- 2017
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Silver
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 111,963
- Stock #:
- 1380
- VIN:
- 5TDZARFH4HS024283
-$500
2017 Toyota Highlander
LE
111,963 mi
$17,839
$17,339
- 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:
- Salsa Red Pearl
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 97,457
- Stock #:
- J5385A
- VIN:
- 5TDJZRFH9KS609860
2019 Toyota Highlander
SE AWD
97,457 mi
$25,390
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 48,823
- Stock #:
- B540B
- VIN:
- 5TDKDRBH1PS033892
2023 Toyota Highlander
LE AWD
48,823 mi
$31,392
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Predawn Gray Mica
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 6-Speed Automatic
- Mileage:
- 113,565
- Stock #:
- H33456A
- VIN:
- 5TDZARFH9KS043192
-$484
2019 Toyota Highlander
LE FWD
113,565 mi
$17,764
$17,280
- 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:
- Red
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 8-Speed Automatic
- Mileage:
- 88,662
- Stock #:
- WYC-562432
- VIN:
- 5TDDZRBH5NS562432
2022 Toyota Highlander
Limited AWD
88,662 mi
$32,999
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Blueprint
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 24,090
- Stock #:
- M15957
- VIN:
- 5TDKDRBH9SS586329
-$1,999
2025 Toyota Highlander
XSE AWD
24,090 mi
$47,179
$45,180
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White (Blizzard Pearl)
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 86,687
- Stock #:
- M15947
- VIN:
- 5TDZARFH3JS040349
2018 Toyota Highlander
LE
86,687 mi
$21,959
- 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:
- Champagne
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 160,896
- Stock #:
- L4545
- VIN:
- 5TDDKRFH5GS228421
2016 Toyota Highlander
Limited AWD
160,896 mi
$17,078
- 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:
- 90,906
- Stock #:
- 27000A
- VIN:
- 5TDJZRFH5KS629393
2019 Toyota Highlander
XLE AWD
90,906 mi
$24,164
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:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Salsa Red Pearl
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 149,250
- Stock #:
- PH0177
- VIN:
- 5TDJZRFH0JS845862
2018 Toyota Highlander
SE AWD
149,250 mi
$17,247
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 30,308
- Stock #:
- C60678A
- VIN:
- 5TDKDRBH4PS520939
2023 Toyota Highlander
XSE AWD
30,308 mi
$39,891
- 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
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 92,951
- Stock #:
- 68432A
- VIN:
- 5TDJZRFH6KS575960
2019 Toyota Highlander
XLE AWD
92,951 mi
$24,158
- Year:
- 2016
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Silver
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 62,296
- Stock #:
- 70003549
- VIN:
- 5TDZARFHXGS018227
2016 Toyota Highlander
LE
62,296 mi
$23,397
- Year:
- 2025
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 34,767
- Stock #:
- 24P4847
- VIN:
- 5TDKDRBHXSS579194
2025 Toyota Highlander
XSE AWD
34,767 mi
$41,814
- 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:
- Silver Sky Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 131,962
- Stock #:
- 3250326C
- VIN:
- 5TDDKRFH3FS166290
2015 Toyota Highlander
Limited AWD
131,962 mi
$19,403
- 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:
- Automatic
- Mileage:
- 44,045
- Stock #:
- E260163A
- VIN:
- 5TDKDRBH3RS545026
2024 Toyota Highlander
Platinum AWD
44,045 mi
$43,594
- 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:
- 26,764
- Stock #:
- P132427
- VIN:
- 5TDKDRAH1SS554959
2025 Toyota Highlander
XLE FWD
26,764 mi
$37,228
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 176,786
- Stock #:
- T96006A
- VIN:
- 5TDJZRFH0JS548039
2018 Toyota Highlander
SE AWD
176,786 mi
$17,410
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 48,823
- Stock #:
- B540B
- VIN:
- 5TDKDRBH1PS033892
Sponsored Listing
2023 Toyota Highlander
LE AWD
48,823 mi
$31,392
FAQs
How much does the Toyota Highlander cost in Winslow, IL?
How many Toyota Highlander vehicles in Winslow, IL 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
- New Model Premium: The 2026 Toyota Highlander is priced at $52,518, representing a 13.5% increase over its MSRP, indicating strong demand for the latest model.
- Steep Depreciation for Older Models: The 2016 Highlander shows a significant depreciation of -38.5% from its original MSRP, reflecting the typical depreciation curve for vehicles over time.
- Best Value Year: The 2021 model is currently priced at $30,878, which is -12.4% below MSRP, making it an attractive option for budget-conscious buyers.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $46,270 | $52,518 | +13.5% |
| 2025 Toyota Highlander | $40,320 | $41,288 | +2.4% |
| 2024 Toyota Highlander | $39,270 | $39,387 | +0.3% |
| 2023 Toyota Highlander | $36,620 | $36,349 | -0.7% |
| 2022 Toyota Highlander | $35,855 | $33,872 | -5.5% |
| 2021 Toyota Highlander | $35,085 | $30,878 | -12.4% |
| 2020 Toyota Highlander | $34,600 | $28,579 | -17.5% |
| 2019 Toyota Highlander | $31,830 | $24,400 | -23.3% |
| 2018 Toyota Highlander | $31,230 | $22,487 | -28.0% |
| 2017 Toyota Highlander | $30,630 | $20,990 | -31.5% |
| 2016 Toyota Highlander | $30,490 | $18,777 | -38.5% |
Pricing by Popular US Cities
Market Area: Nationwide
Key Insights
- Highest Prices in New York: The New York, NY market has the highest average price at $26,708, likely due to higher demand and lower inventory.
- Lowest Prices in Chicago: Chicago, IL offers the lowest average price at $24,600, indicating a more competitive market with potentially higher inventory levels.
- Price Variation Across Cities: Significant price differences exist, with Los Angeles, CA averaging $25,841, suggesting regional preferences and demand dynamics.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| New York, NY | 648 | $26,708 |
| Los Angeles, CA | 523 | $25,841 |
| Chicago, IL | 350 | $24,600 |
| Dallas, TX | 369 | $26,691 |
| Philadelphia, PA | 272 | $28,176 |
| Houston, TX | 372 | $25,539 |
| Miami, FL | 201 | $29,898 |
| Washington, DC | 467 | $26,938 |
| Atlanta, GA | 306 | $27,223 |
| Boston, MA | 657 | $28,482 |
Pricing by Trim Packages
Key Insights
- XLE AWD Dominates Inventory: The XLE AWD trim leads with 3,171 listings, indicating strong consumer preference for this configuration.
- Premium Pricing for Limited Trim: The Limited AWD trim, priced at $50,725, reflects a significant markup due to its luxury features, appealing to buyers seeking higher-end options.
- Consistent Drivetrain Preference: All trims listed are AWD, suggesting a strong market demand for all-weather capability in the Highlander lineup.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 3,171 | $46,270 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 1,233 | $50,725 | AWD | 2.4L 265 hp I4 |
| XSE AWD | 702 | $48,340 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 566 | $53,925 | AWD | 2.4L 265 hp I4 |
These recommendations are based on CarGurus' proprietary market data from July 9, 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$33,175
- User rating4.4444
2020 Toyota Highlander
- Expert review8/10
- MSRP$34,600-$48,800
- Avg. price$28,104
- User rating4.6
2021 Toyota Highlander
- Expert review8/10
- MSRP$35,085-$49,190
- Avg. price$30,319
- User rating4.8636
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