Used Toyota Highlander for Sale Under $40,000 NearFreeport, IL
338 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Shoreline Blue Pearl
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 144,485
- Stock #:
- 29892A
- VIN:
- 5TDJZRFH1KS921056
Sponsored by Lexus of Brookfield
2019 Toyota Highlander
144,485 mi
Brookfield, WI
89 mi away
Fair Deal
$20,767
- 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:
- Black
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 53,021
- Stock #:
- D68534B
- VIN:
- 5TDDZRFH0KS995050
Sponsored Listing
2019 Toyota Highlander
Limited AWD
53,021 mi
Streamwood, IL
75 mi away
Good Deal
$30,358
- 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:
- Silver
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 60,693
- Stock #:
- P21976
- VIN:
- 5TDKDRBHXPS022292
Sponsored Listing
2023 Toyota Highlander
Platinum AWD
60,693 mi
Streamwood, IL
75 mi away
Fair Deal
$39,858
- 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:
- 151,965
- Stock #:
- 26292B
- VIN:
- 5TDDKRFH6FS148480
2015 Toyota Highlander
Limited Platinum AWD
151,965 mi
Clinton, IA
47 mi away
Good Deal
$15,860
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 67,106
- Stock #:
- GM6740A
- VIN:
- 5TDGZRAH5NS135802
2022 Toyota Highlander
XLE FWD
67,106 mi
Niles, IL
94 mi away
Good Deal
$30,685
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 104,999
- Stock #:
- TE153743A
- VIN:
- 5TDGZRBH0MS135963
2021 Toyota Highlander
XLE AWD
104,999 mi
Bristol, WI
87 mi away
Good Deal
$26,171
- 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
69 mi away
Fair Deal
$35,903
- Year:
- 2012
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Red (Sizzling Crimson Mica)
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 159,054
- Stock #:
- 51614
- VIN:
- 5TDBK3EH8CS148692
New arrival
2012 Toyota Highlander
SE AWD
159,054 mi
Middleton, WI
55 mi away
Good Deal
$12,389
- 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
New arrival
2023 Toyota Highlander
Limited AWD
54,557 mi
Sauk City, WI
66 mi away
Fair Deal
$38,309
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 85,614
- Stock #:
- P32242
- VIN:
- 5TDJZRFH7HS519910
2017 Toyota Highlander
XLE AWD
85,614 mi
Davenport, IA
71 mi away
Good Deal
$22,908
- 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
Elgin, IL
74 mi away
Great Deal
$16,403
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Pearl
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 46,311
- Stock #:
- Z5548
- VIN:
- 5TDGZRAH9NS556535
2022 Toyota Highlander
XLE FWD
46,311 mi
Riverside, IL
99 mi away
Good Deal
$33,494
- 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:
- Cockpit Red
- Transmission:
- Automatic
- Mileage:
- 46,177
- Stock #:
- B49503A
- VIN:
- 5TDJZRBH5NS177505
2022 Toyota Highlander
XSE AWD
46,177 mi
Naperville, IL
83 mi away
Good Deal
$36,690
- 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:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 188,861
- Stock #:
- T0010A
- VIN:
- 5TDJKRFH6GS308720
New arrival
2016 Toyota Highlander
XLE AWD
188,861 mi
Lincolnwood, IL
99 mi away
Fair Deal
$14,168
- 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:
- 48,649
- Stock #:
- 049153
- VIN:
- 5TDBZRBH5LS049153
New arrival
2020 Toyota Highlander
LE AWD
48,649 mi
Rockford, IL
32 mi away
Fair Deal
$29,363
- 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:
- 134,554
- Stock #:
- A25989B
- VIN:
- 5TDDZRFH6JS877387
2018 Toyota Highlander
Limited Platinum AWD
134,554 mi
Hoffman Estates, IL
80 mi away
Fair Deal
$22,358
- Year:
- 2012
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Classic Silver Metallic
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 106,070
- Stock #:
- 270042-1
- VIN:
- 5TDBK3EHXCS138598
New arrival
2012 Toyota Highlander
SE AWD
106,070 mi
Milwaukee, WI
93 mi away
Fair Deal
$15,318
- 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:
- Black
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 65,579
- Stock #:
- P3694A
- VIN:
- 5TDJZRFH6KS980331
2019 Toyota Highlander
SE AWD
65,579 mi
Roselle, IL
84 mi away
Good Deal
$27,411
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 47,796
- Stock #:
- X0261061A
- VIN:
- 5TDKDRBHXPS527443
2023 Toyota Highlander
Limited AWD
47,796 mi
Schaumburg, IL
82 mi away
Good Deal
$38,301
- 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:
- Blue
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 36,979
- Stock #:
- 62323
- VIN:
- 5TDKDRAH1SS552015
Price drop
-$1,378
2025 Toyota Highlander
LE FWD
36,979 mi
Des Plaines, IL
92 mi away
Good Deal
$34,699
$33,699
- 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:
- White
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 108,210
- Stock #:
- 28207193
- VIN:
- 5TDYKRFH9GS149223
2016 Toyota Highlander
Limited
108,210 mi
Store transfer to Madison, WI
Price includes $1,099 shipping
Fair Deal
$22,097
- 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:
- Black
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 26,011
- Stock #:
- 62028
- VIN:
- 5TDKDRAH1SS553889
Price drop
-$1,529
2025 Toyota Highlander
LE FWD
26,011 mi
Des Plaines, IL
92 mi away
Good Deal
$35,749
$34,598
- 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:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 46,619
- Stock #:
- BC2311
- VIN:
- 5TDBZRBH7NS594421
2022 Toyota Highlander
LE AWD
46,619 mi
North Riverside, IL
99 mi away
Fair Deal
$31,524
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 129,294
- Stock #:
- P10773
- VIN:
- 5TDKDRBH9PS040508
Sponsored Listing
2023 Toyota Highlander
XLE AWD
129,294 mi
Naperville, IL
83 mi away
Fair Deal
$28,688
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