Used Toyota Highlander for Sale Under $40,000 NearWindermere, FL
187 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Automatic
- Mileage:
- 41,006
- Stock #:
- PS046795
- VIN:
- 5TDKDRAH0PS046795
Sponsored by AutoNation Toyota Winter Park
2023 Toyota Highlander
L FWD
41,006 mi
Winter Park, FL
18 mi away
Good Deal
$29,860
- 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
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 6,305
- Stock #:
- F21190B
- VIN:
- 5TDKDRAH1SS554038
Price drop
-$3,358
Sponsored Listing
2025 Toyota Highlander
XLE FWD
6,305 mi
Orlando, FL
9 mi away
Great Deal
$41,353
$39,353
- 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:
- Gray
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 94,276
- Stock #:
- 546782
- VIN:
- 5TDGZRAH9NS546782
Sponsored Listing
2022 Toyota Highlander
XLE FWD
94,276 mi
Orlando, FL
11 mi away
Good Deal
$26,889
- 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:
- Moon Dust
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 26,887
- Stock #:
- 26K853A
- VIN:
- 5TDKDRAH7RS528893
2024 Toyota Highlander
XLE FWD
26,887 mi
Lakeland, FL
39 mi away
Fair Deal
$39,234
- 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:
- White (Blizzard Pearl)
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 108,500
- Stock #:
- S045758T
- VIN:
- 5TDZARFHXKS045758
2019 Toyota Highlander
LE FWD
108,500 mi
Deland, FL
38 mi away
Good Deal
$19,600
- 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:
- Moon Dust
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 45,783
- Stock #:
- 5541520A
- VIN:
- 5TDYZRAHXLS016032
2020 Toyota Highlander
Limited FWD
45,783 mi
Leesburg, FL
31 mi away
Great Deal
$31,636
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Red
- Transmission:
- 8-Speed Automatic
- Mileage:
- 42,115
- Stock #:
- 050211T
- VIN:
- 5TDLZRAHXMS050211
2021 Toyota Highlander
XSE FWD
42,115 mi
Titusville, FL
46 mi away
Fair Deal
$33,988
- 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:
- Almond
- Transmission:
- 8-Speed Automatic
- Mileage:
- 95,830
- Stock #:
- G449204A
- VIN:
- 5TDJZRFH6JS900489
2018 Toyota Highlander
XLE AWD
95,830 mi
Leesburg, FL
31 mi away
Fair Deal
$23,636
- Year:
- 2021
- 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
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 60,331
- Stock #:
- 7016603A
- VIN:
- 5TDGZRAH9MS043865
2021 Toyota Highlander
XLE FWD
60,331 mi
Clermont, FL
8 mi away
Great Deal
$29,215
- 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 (Blizzard Pearl)
- Fuel type:
- Gasoline
- Interior color:
- Almond
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 91,975
- Stock #:
- TU508585A
- VIN:
- 5TDKKRFHXGS162407
2016 Toyota Highlander
XLE
91,975 mi
Sanford, FL
25 mi away
Fair Deal
$20,940
- 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:
- Brown (Beige)
- Transmission:
- 6-Speed Automatic
- Mileage:
- 115,070
- Stock #:
- 10259
- VIN:
- 5TDYKRFH2GS127855
2016 Toyota Highlander
Limited
115,070 mi
Altamonte Springs, FL
15 mi away
Good Deal
$18,199
- 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:
- 46,277
- Stock #:
- L302357A
- VIN:
- 5TDKDRBH7RS563514
Price drop
-$3,522
2024 Toyota Highlander
XLE AWD
46,277 mi
Wesley Chapel, FL
50 mi away
Good Deal
$38,080
$36,643
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Silver
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 89,168
- Stock #:
- PK22427A
- VIN:
- 5TDGZRAH0MS081341
Price drop
-$4,100
2021 Toyota Highlander
XLE FWD
89,168 mi
Longwood, FL
20 mi away
Good Deal
$30,999
$26,899
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 8-Speed Automatic
- Mileage:
- 51,308
- VIN:
- 5TDHZRBH7LS503767
2020 Toyota Highlander
XLE FWD
51,308 mi
Orlando, FL
18 mi away
Good Deal
$28,495
- Year:
- 2012
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 187 hp 2.7L I4
- Exterior color:
- White
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Tan)
- Transmission:
- Automatic
- Mileage:
- 151,938
- Stock #:
- CS080618
- VIN:
- 5TDZK3EH8CS080618
2012 Toyota Highlander
Base
151,938 mi
Orlando, FL
19 mi away
Great Deal
$9,287
- Year:
- 2016
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 92,907
- Stock #:
- GS280419
- VIN:
- 5TDJKRFHXGS280419
2016 Toyota Highlander
XLE AWD
92,907 mi
Orlando, FL
16 mi away
Fair Deal
$22,243
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 61,205
- Stock #:
- MS059075
- VIN:
- 5TDZZRAH4MS059075
New arrival
2021 Toyota Highlander
LE FWD
61,205 mi
Lakeland, FL
38 mi away
Good Deal
$26,296
- 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:
- Silver
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 71,423
- Stock #:
- 70125029
- VIN:
- 5TDFZRBHXLS001973
2020 Toyota Highlander
Platinum AWD
71,423 mi
Store transfer to Orlando, FL
Price includes $1,199 shipping
Fair Deal
$34,197
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Celestial Silver Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Harvest Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 61,045
- Stock #:
- N415166B
- VIN:
- 5TDFZRAH0MS089323
New arrival
2021 Toyota Highlander
Platinum FWD
61,045 mi
Orlando, FL
8 mi away
Fair Deal
$36,749
- 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:
- Brown (Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 67,543
- Stock #:
- 125
- VIN:
- 5TDKDRAH3PS007604
2023 Toyota Highlander
XLE FWD
67,543 mi
Orlando, FL
10 mi away
Good Deal
$29,590
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 34,083
- Stock #:
- PS515469
- VIN:
- 5TDKDRAHXPS515469
2023 Toyota Highlander
XLE FWD
34,083 mi
Longwood, FL
21 mi away
Fair Deal
$35,212
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 28,329
- Stock #:
- 7016553A
- VIN:
- 5TDKDRAH5PS033119
2023 Toyota Highlander
XLE FWD
28,329 mi
Clermont, FL
8 mi away
Good Deal
$35,050
- 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:
- Ooh La La Rouge Mica
- Fuel type:
- Gasoline
- Interior color:
- Almond
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 79,223
- Stock #:
- P6278A
- VIN:
- 5TDJKRFH3GS266541
Price drop
-$1,348
2016 Toyota Highlander
XLE AWD
79,223 mi
Longwood, FL
22 mi away
Good Deal
$22,752
$21,404
- Year:
- 2008
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Black
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Beige)
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 196,688
- Stock #:
- 0347
- VIN:
- JTEDS43AX82022882
Sponsored Listing
2008 Toyota Highlander
Sport
196,688 mi
Orlando, FL
10 mi away
Fair Deal
$6,299
Used White Toyota Highlander for Sale in WindermereUsed Blue Toyota Highlander for Sale in WindermereUsed Red Toyota Highlander for Sale in WindermereUsed Black Toyota Highlander for Sale in WindermereUsed Silver Toyota Highlander for Sale in WindermereUsed Gray Toyota Highlander for Sale in Windermere
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