Used Toyota Highlander for Sale Under $40,000 NearWinnebago, IL
440 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2013
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- White
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 91,184
- Stock #:
- P22063A
- VIN:
- 5TDBK3EHXDS192145
New arrival
Sponsored by Elgin Toyota
2013 Toyota Highlander
91,184 mi
Streamwood, IL
56 mi away
Great Deal
$16,358
- 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:
- Attitude Black Metallic
- Fuel type:
- Gasoline
- Interior color:
- Almond
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 196,682
- Stock #:
- 53340
- VIN:
- 5TDJKRFH9ES035169
Price drop
-$856
Sponsored Listing
2014 Toyota Highlander
XLE AWD
196,682 mi
Madison, WI
60 mi away
Good Deal
$12,253
$11,397
- 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:
- White (Blizzard Pearl)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 76,755
- Stock #:
- 7461
- VIN:
- 5TDDZRBH2MS113661
Sponsored Listing
2021 Toyota Highlander
Limited AWD
76,755 mi
Racine, WI
76 mi away
Fair Deal
$34,197
- 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:
- Ooh La La Rouge Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 103,028
- Stock #:
- P6279
- VIN:
- 5TDJZRFH4KS707792
Price drop
-$1,175
2019 Toyota Highlander
XLE AWD
103,028 mi
Elmhurst, IL
71 mi away
Good Deal
$23,838
$22,663
- 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:
- Gray
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 20,360
- Stock #:
- 70158349
- VIN:
- 5TDJZRFH2HS446459
2017 Toyota Highlander
XLE AWD
20,360 mi
Store transfer to Madison, WI
Price includes $699 shipping
Fair Deal
$32,697
- 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:
- 66,508
- Stock #:
- V5993A
- VIN:
- 5TDGZRBH7MS076085
New arrival
2021 Toyota Highlander
XLE AWD
66,508 mi
Oak Park, IL
79 mi away
Good Deal
$29,495
- 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:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 54,557
- Stock #:
- SP3979A
- VIN:
- 5TDKDRBH6PS028171
2023 Toyota Highlander
Limited AWD
54,557 mi
Sauk City, WI
74 mi away
Good Deal
$37,451
- 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:
- 67,662
- Stock #:
- Q31312
- VIN:
- 5TDHZRBH1NS228397
2022 Toyota Highlander
XLE AWD
67,662 mi
Dubuque, IA
76 mi away
Good Deal
$32,621
- 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:
- Gray
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 106,638
- Stock #:
- MT502694
- VIN:
- 5TDJKRFH4GS502694
2016 Toyota Highlander
XLE AWD
106,638 mi
Muskego, WI
73 mi away
Good Deal
$19,199
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 25,685
- Stock #:
- 153961A
- VIN:
- 5TDKDRAH9PS030420
2023 Toyota Highlander
L FWD
25,685 mi
Greenfield, WI
81 mi away
Great Deal
$30,109
- 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:
- 67,041
- Stock #:
- S24952A
- VIN:
- 5TDGZRBH6MS143629
2021 Toyota Highlander
XLE AWD
67,041 mi
St. Charles, IL
57 mi away
Good Deal
$29,208
- 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 1g3
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black Eb20
- Transmission:
- 8-Speed Automatic
- Mileage:
- 44,460
- Stock #:
- PS592451
- VIN:
- 5TDGZRBH9NS592451
2022 Toyota Highlander
XLE AWD
44,460 mi
Dekalb, IL
36 mi away
Good Deal
$34,476
- 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:
- Almond
- Transmission:
- 8-Speed Automatic
- Mileage:
- 95,092
- Stock #:
- TA6537A
- VIN:
- 5TDDZRFH3KS738576
New arrival
2019 Toyota Highlander
Limited Platinum AWD
95,092 mi
Ottawa, IL
65 mi away
Fair Deal
$28,410
- 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:
- Blue
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic
- Mileage:
- 110,612
- Stock #:
- 232289
- VIN:
- 5TDJKRFH3GS232289
2016 Toyota Highlander
XLE AWD
110,612 mi
Richfield, WI
88 mi away
Good Deal
$18,394
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 80,238
- Stock #:
- 2337A
- VIN:
- 5TDDZRFH5JS494847
2018 Toyota Highlander
Limited AWD
80,238 mi
Chicago, IL
81 mi away
Fair Deal
$26,278
- 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:
- Jade Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Almond
- Transmission:
- 8-Speed Automatic
- Mileage:
- 96,122
- Stock #:
- 26216-1
- VIN:
- 5TDJZRFHXJS870722
2018 Toyota Highlander
XLE AWD
96,122 mi
North Aurora, IL
55 mi away
Good Deal
$22,328
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 96,355
- Stock #:
- P4332A
- VIN:
- 5TDGZRBH2LS505146
2020 Toyota Highlander
XLE AWD
96,355 mi
Gurnee, IL
66 mi away
Good Deal
$25,789
- 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:
- Magnetic Gray Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 41,267
- Stock #:
- S260611A
- VIN:
- 5TDDZRBH4LS007095
2020 Toyota Highlander
Limited AWD
41,267 mi
Elgin, IL
49 mi away
Fair Deal
$34,902
- 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:
- 63,704
- Stock #:
- H21797A
- VIN:
- 5TDGZRBH5NS253072
2022 Toyota Highlander
XLE AWD
63,704 mi
Moline, IL
82 mi away
Great Deal
$30,968
- 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:
- 70,129
- Stock #:
- 50859A
- VIN:
- 5TDHZRBH3MS528795
2021 Toyota Highlander
XLE AWD
70,129 mi
Tinley Park, IL
87 mi away
Good Deal
$29,346
- 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:
- CELESTIAL SILVER
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 32,630
- Stock #:
- F44528A
- VIN:
- 5TDBZRFH3JS488987
New arrival
2018 Toyota Highlander
LE Plus AWD
32,630 mi
Glenview, IL
76 mi away
Good Deal
$27,123
- 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:
- 33,935
- Stock #:
- PSW1202
- VIN:
- 5TDKDRBHXSS583469
Price drop
-$1,007
2025 Toyota Highlander
LE AWD
33,935 mi
Brookfield, WI
80 mi away
Good Deal
$37,209
$36,202
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 83,739
- Stock #:
- K20256A
- VIN:
- 5TDKDRAH4PS048386
2023 Toyota Highlander
L FWD
83,739 mi
Palatine, IL
64 mi away
Good Deal
$26,965
- 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 1g3
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black Eb20
- Transmission:
- 8-Speed Automatic
- Mileage:
- 44,460
- Stock #:
- PS592451
- VIN:
- 5TDGZRBH9NS592451
Sponsored Listing
2022 Toyota Highlander
XLE AWD
44,460 mi
Dekalb, IL
36 mi away
Good Deal
$34,476
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