Used Toyota Highlander for Sale nearWinnetka, IL
341 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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
Sponsored by My Cars
2017 Toyota Highlander
LE
111,963 mi
$17,339
- 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:
- 72,191
- Stock #:
- L1219A
- VIN:
- 5TDFZRBH4NS180529
Sponsored Listing
2022 Toyota Highlander
Platinum AWD
72,191 mi
$36,328
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 55,834
- Stock #:
- DT1354A
- VIN:
- 5TDKDRBH5RS575239
-$1,400
Sponsored Listing
2024 Toyota Highlander
XLE AWD
55,834 mi
$38,373
$36,973
- 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:
- 50,689
- Stock #:
- P7340
- VIN:
- 5TDDZRBH6NS576243
2022 Toyota Highlander
Limited AWD
50,689 mi
$35,969
- 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:
- Predawn Gray Mica
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 6-Speed Automatic
- Mileage:
- 85,967
- Stock #:
- B26193A
- VIN:
- 5TDZARFH5HS030710
2017 Toyota Highlander
LE
85,967 mi
$19,061
- 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:
- Magnetic Gray Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 35,457
- Stock #:
- C250187A
- VIN:
- 5TDKDRAH0PS513035
2023 Toyota Highlander
L FWD
35,457 mi
$32,988
- 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:
- 72,191
- Stock #:
- L1219A
- VIN:
- 5TDFZRBH4NS180529
2022 Toyota Highlander
Platinum AWD
72,191 mi
$36,328
- 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
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 115,211
- Stock #:
- 93294A
- VIN:
- 5TDJZRFH3JS548357
2018 Toyota Highlander
XLE AWD
115,211 mi
$21,907
- 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:
- Predawn Gray Mica
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 102,349
- Stock #:
- 25T1593A
- VIN:
- 5TDBZRFH1KS960413
2019 Toyota Highlander
LE AWD
102,349 mi
$20,145
- Year:
- 2024
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- Automatic
- Mileage:
- 61,338
- Stock #:
- LU1997
- VIN:
- 5TDKDRAH4RS533338
2024 Toyota Highlander
LE FWD
61,338 mi
$28,221
- 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:
- Attitude Black Metallic
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 105,840
- Stock #:
- 20134
- VIN:
- 5TDDKRFH7FS152750
2015 Toyota Highlander
Limited AWD
105,840 mi
$18,873
- 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
2017 Toyota Highlander
LE
111,963 mi
$17,339
- Year:
- 2014
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Predawn Gray Mica
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 177,842
- Stock #:
- 20133
- VIN:
- 5TDDKRFH6ES044070
2014 Toyota Highlander
Limited AWD
177,842 mi
$14,873
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:
- 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:
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 52,785
- Stock #:
- H0045A
- VIN:
- 5TDGZRBH8MS156091
-$1,000
2021 Toyota Highlander
XLE AWD
52,785 mi
$30,373
$29,373
- 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
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 149,343
- Stock #:
- 60351S
- VIN:
- 5TDJZRFHXHS512868
2017 Toyota Highlander
XLE AWD
149,343 mi
$16,993
- 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:
- 2025
- 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:
- 18,171
- Stock #:
- 93F03513
- VIN:
- 5TDKDRBH6SS586062
2025 Toyota Highlander
XLE AWD
18,171 mi
$40,258
- 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:
- Magnetic Gray Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 88,024
- Stock #:
- MS260221C
- VIN:
- 5TDGZRBH7MS098720
2021 Toyota Highlander
XLE AWD
88,024 mi
$28,603
- 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 Blue Pearl
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 93,573
- Stock #:
- E2032B
- VIN:
- 5TDJZRFH7JS872783
-$745
2018 Toyota Highlander
XLE AWD
93,573 mi
$23,373
$22,628
- 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 (Blizzard Pearl)
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 120,922
- Stock #:
- 50352A
- VIN:
- 5TDJKRFHXGS279836
-$500
Sponsored Listing
2016 Toyota Highlander
XLE AWD
120,922 mi
$19,346
$18,846
FAQs
How much does the Toyota Highlander cost in Winnetka, IL?
How many Toyota Highlander vehicles in Winnetka, 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$33,147
- User rating4.4444
2020 Toyota Highlander
- Expert review8/10
- MSRP$34,600-$48,800
- Avg. price$28,042
- User rating4.6
2021 Toyota Highlander
- Expert review8/10
- MSRP$35,085-$49,190
- Avg. price$30,250
- User rating4.8636
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