Used Gray Toyota Highlander for Sale inPleasant Prairie, WI
178 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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
Sponsored by Toyota of Brookfield
2025 Toyota Highlander
LE AWD
33,935 mi
Brookfield, WI
41 mi away
Good Deal
$37,656
- 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:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 11,141
- Stock #:
- P23399T
- VIN:
- 5TDKDRBH7SS586619
Sponsored Listing
2025 Toyota Highlander
XLE AWD
11,141 mi
Milwaukee, WI
29 mi away
Fair Deal
$46,496
- 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:
- Gray
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 42,518
- Stock #:
- P3009
- VIN:
- 5TDGZRBH8MS528223
New arrival
Sponsored Listing
2021 Toyota Highlander
XLE AWD
42,518 mi
Fox Lake, IL
18 mi away
Good Deal
$31,850
- 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:
- 48,664
- Stock #:
- T17128A
- VIN:
- 5TDKDRAH2PS525056
New arrival
2023 Toyota Highlander
XLE FWD
48,664 mi
Brookfield, WI
41 mi away
Great Deal
$32,707
- 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:
- Gray
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 60,845
- Stock #:
- 28843553
- VIN:
- 5TDDZRBHXMS525181
Price drop
-$1,000
2021 Toyota Highlander
Limited AWD
60,845 mi
Store transfer to Kenosha, WI
Price includes $799 shipping
Good Deal
$34,797
$33,797
- 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
Price drop
-$800
2016 Toyota Highlander
XLE AWD
106,638 mi
Muskego, WI
29 mi away
Good Deal
$19,999
$19,199
- 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
2025 Toyota Highlander
LE AWD
33,935 mi
Brookfield, WI
41 mi away
Good Deal
$37,656
- 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:
- Gray
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 70,915
- Stock #:
- B49926A
- VIN:
- 5TDJZRBH6MS058294
Price drop
-$1,000
2021 Toyota Highlander
XSE AWD
70,915 mi
Chicago, IL
45 mi away
Great Deal
$30,901
$29,901
- 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:
- Almond
- Transmission:
- 6-Speed Automatic
- Mileage:
- 112,927
- Stock #:
- P5705
- VIN:
- 5TDJKRFH6ES064984
2014 Toyota Highlander
XLE AWD
112,927 mi
Barrington, IL
30 mi away
Fair Deal
$18,408
- 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
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 121,909
- Stock #:
- SC260438A
- VIN:
- 5TDDKRFH7FS186204
2015 Toyota Highlander
Limited Platinum AWD
121,909 mi
St. Charles, IL
48 mi away
Good Deal
$18,513
- Year:
- 2013
- 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:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 5-Speed Automatic
- Mileage:
- 138,742
- Stock #:
- CYC-276912
- VIN:
- 5TDBK3EH9DS276912
New arrival
2013 Toyota Highlander
Plus AWD
138,742 mi
Home delivery from Crestwood, IL
Free home delivery
Fair Deal
$12,376
- 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:
- Predawn Gray Mica
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Almond
- Transmission:
- 6-Speed Automatic
- Mileage:
- 51,884
- Stock #:
- KY147039
- VIN:
- 5TDDKRFHXFS147039
2015 Toyota Highlander
Limited Platinum AWD
51,884 mi
Skokie, IL
36 mi away
Good Deal
$23,408
- 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:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 61,830
- Stock #:
- 605087H
- VIN:
- 5TDJZRFHXKS605087
Price drop
-$1,237
2019 Toyota Highlander
XLE AWD
61,830 mi
Chicago, IL
45 mi away
Good Deal
$28,812
$27,575
- Year:
- 2011
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 98,704
- Stock #:
- P3694B
- VIN:
- 5TDYK3EH6BS048776
New arrival
2011 Toyota Highlander
Limited
98,704 mi
Roselle, IL
39 mi away
Fair Deal
$15,400
- 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:
- 103,454
- Stock #:
- DK6540A
- VIN:
- 5TDJZRFH5HS461053
2017 Toyota Highlander
XLE AWD
103,454 mi
Fox Lake, IL
18 mi away
Fair Deal
$21,618
- 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:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 88,691
- Stock #:
- XBP8676
- VIN:
- 5TDJZRFH2KS574742
2019 Toyota Highlander
XLE AWD
88,691 mi
Libertyville, IL
20 mi away
Fair Deal
$25,550
- Year:
- 2020
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 102,768
- Stock #:
- 15140
- VIN:
- 5TDHZRAH8LS506453
2020 Toyota Highlander
XLE FWD
102,768 mi
Home delivery from National City, CA
Price includes $2,072 shipping
Fair Deal
$25,067
- 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:
- Gray
- Transmission:
- Automatic
- Mileage:
- 122,061
- Stock #:
- 343426
- VIN:
- 5TDDKRFH9GS343426
2016 Toyota Highlander
Limited AWD
122,061 mi
Home delivery from Fort Dodge, IA
Price includes $482 shipping
Fair Deal
$20,222
- 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:
- Gray
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 68,325
- Stock #:
- 29026681
- VIN:
- 5TDFZRBH7LS051682
2020 Toyota Highlander
Platinum AWD
68,325 mi
Store transfer to Kenosha, WI
Price includes $499 shipping
Fair Deal
$35,497
- 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:
- 28,395
- Stock #:
- GH4311A
- VIN:
- 5TDGZRBH5NS590132
2022 Toyota Highlander
XLE AWD
28,395 mi
Gurnee, IL
11 mi away
Fair Deal
$37,699
- 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:
- Gray
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 42,518
- Stock #:
- P3009
- VIN:
- 5TDGZRBH8MS528223
New arrival
2021 Toyota Highlander
XLE AWD
42,518 mi
Fox Lake, IL
18 mi away
Good Deal
$31,850
- 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:
- 23,576
- Stock #:
- OP34515
- VIN:
- 5TDKDRBH5SS587428
2025 Toyota Highlander
XSE AWD
23,576 mi
Home delivery from Fenton, MI
Price includes $316 shipping
Great Deal
$40,130
- 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:
- Gray
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 33,742
- Stock #:
- L22877
- VIN:
- 5TDKDRAH8PS006366
2023 Toyota Highlander
XLE FWD
33,742 mi
Home delivery from Lehi, UT
Price includes $1,869 shipping
Fair Deal
$36,762
- 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:
- Almond
- Transmission:
- 6-Speed Automatic
- Mileage:
- 112,927
- Stock #:
- P5705
- VIN:
- 5TDJKRFH6ES064984
Sponsored Listing
2014 Toyota Highlander
XLE AWD
112,927 mi
Barrington, IL
30 mi away
Fair Deal
$18,408
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