Used 2008 Toyota Highlander for Sale near Chicago, IL
36 results
- Year:
- 2009
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 174,107
- Stock #:
- DS4669A
- VIN:
- JTEES42A492149439


Sponsored by McGrath Honda
2009 Toyota Highlander
Limited 4WD
174,107 mi
$9,999
- Year:
- 2008
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- White
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- BIEGE
- Transmission:
- Automatic
- Mileage:
- 156,637
- Stock #:
- 10250
- VIN:
- JTEES41A282106606

Sponsored Listing
2008 Toyota Highlander
Base 4WD
156,637 mi
$8,373
- Year:
- 2007
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 155 hp 2.4L I4
- Exterior color:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 5-Speed Automatic
- Mileage:
- 193,611
- Stock #:
- WBA-141473
- VIN:
- JTEGP21A770141473

-$451
Sponsored Listing
2007 Toyota Highlander
Base
193,611 mi
$6,050
$5,599
- Year:
- 2008
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Gold
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Beige)
- Mileage:
- 101,461
- Stock #:
- 2656
- VIN:
- JTEES42A282074254
2008 Toyota Highlander
Limited 4WD
101,461 mi
$11,500
- Year:
- 2009
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 174,107
- Stock #:
- DS4669A
- VIN:
- JTEES42A492149439

2009 Toyota Highlander
Limited 4WD
174,107 mi
$9,999
- Year:
- 2008
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 163,715
- Stock #:
- 08989700
- VIN:
- JTEES42A982089897

2008 Toyota Highlander
Limited 4WD
163,715 mi
$8,516
- Year:
- 2008
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Black
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 143,299
- Stock #:
- 3683
- VIN:
- JTEES42A982021521

2008 Toyota Highlander
Limited 4WD
143,299 mi
$10,150
- Year:
- 2009
- 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
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 183,884
- Stock #:
- 60536A
- VIN:
- JTEES42A292121879

2009 Toyota Highlander
Limited 4WD
183,884 mi
$8,595
- 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:
- Gray
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 134,511
- Stock #:
- 24987
- VIN:
- JTEDS41A882024987

2008 Toyota Highlander
Base
134,511 mi
$9,873
- Year:
- 2008
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Silver
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 173,122
- Stock #:
- 17244
- VIN:
- JTEES43A982011716

2008 Toyota Highlander
Sport 4WD
173,122 mi
$6,411
- Year:
- 2008
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- White
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- BIEGE
- Transmission:
- Automatic
- Mileage:
- 156,637
- Stock #:
- 10250
- VIN:
- JTEES41A282106606

2008 Toyota Highlander
Base 4WD
156,637 mi
$8,373
- Year:
- 2007
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 215 hp 3.3L V6
- Exterior color:
- Bluestone Metallic
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 174,260
- Stock #:
- G998
- VIN:
- JTEHP21A470212486

2007 Toyota Highlander
Base V6 AWD
174,260 mi
$7,362
- Year:
- 2008
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Brown (TAN)
- Transmission:
- 5-Speed Automatic
- Mileage:
- 169,760
- Stock #:
- 37230A
- VIN:
- JTEES43A982093785
2008 Toyota Highlander
Sport 4WD
169,760 mi
$7,999
About 2008 Toyota Highlander
- 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
- Transmission:
- Automatic
- Mileage:
- 85,719
- Stock #:
- 17596
- VIN:
- JTEDS43A782067472
Preparing for a close up...
Photos coming soon
2008 Toyota Highlander
Sport
85,719 mi
$12,495
- Year:
- 2008
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Red
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 173,953
- Stock #:
- TLW3402A
- VIN:
- JTEES41A782027982

2008 Toyota Highlander
Base 4WD
173,953 mi
$7,963
- Year:
- 2009
- 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:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Tan)
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 188,324
- Stock #:
- 812
- VIN:
- JTEES41A392129815

2009 Toyota Highlander
Base 4WD
188,324 mi
$7,490
- Year:
- 2008
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Green
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Sand Beige)
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 188,018
- Stock #:
- M1309A
- VIN:
- JTEES41A782099250

2008 Toyota Highlander
Base 4WD
188,018 mi
$8,170
- 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:
- Gold
- Fuel type:
- Gasoline
- Interior color:
- Brown (Beige)
- Transmission:
- 5-Speed Automatic
- Mileage:
- 77,475
- VIN:
- JTEDS41A882046682

2008 Toyota Highlander
Base
77,475 mi
$12,838
- Year:
- 2009
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Silver
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Beige)
- Transmission:
- Automatic
- Mileage:
- 123,779
- Stock #:
- 140038
- VIN:
- JTEES42A792140038

2009 Toyota Highlander
Limited 4WD
123,779 mi
$11,495
- Year:
- 2009
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Silver
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 230,101
- Stock #:
- 3612
- VIN:
- JTEDS43AX92072182
Preparing for a close up...
Photos coming soon
2009 Toyota Highlander
Sport
230,101 mi
$7,713
- Year:
- 2008
- 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
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 177,015
- Stock #:
- SP1141
- VIN:
- JTEES42A282105423

2008 Toyota Highlander
Limited 4WD
177,015 mi
$9,018
- Year:
- 2008
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Green
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (BEIGE)
- Transmission:
- Automatic
- Mileage:
- 178,830
- Stock #:
- 12579
- VIN:
- JTEES41A882033404

2008 Toyota Highlander
Base 4WD
178,830 mi
$6,400
- Year:
- 2008
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Brown (Beige)
- Transmission:
- 5-Speed Automatic
- Mileage:
- 228,948
- Stock #:
- WBA-102540
- VIN:
- JTEES41A082102540

-$451
Sponsored Listing
2008 Toyota Highlander
Base 4WD
228,948 mi
$5,050
$4,599
2008 Toyota Highlander test drive
overall

After a successful 7-year run, the original-recipe Toyota Highlander gets replaced for 2008 by an all-new version that sets the bar ever higher for midsize crossover SUVs.
Arguably, the Toyota Highlander established the blueprint for all family-sized, 3-row crossover SUVs to follow. Its combination of reliability, quality, performance, and safety ensured that competitors came to the game ready for battle. And now, the redesigned 2008 Toyota Highlander moves the goalposts. It comes in base, Sport, and Limited trim levels, all powered by a V6 engine driving the front or all four wheels.
Relevant articles

The Best Three-Row SUVs of 2026
There’s no escaping it: SUVs are everywhere. Minivans offer the space for the most passengers and gear, but big, three-row SUVs deliver on both while offering some level of performance, on and off the paved roads.

The Best Used SUVs Under $10,000 in 2026
Can you get a great SUV for less than $10,000? Heck, yes! Our guide runs through the top 10, with options including family favorites and some upscale options.

Toyota Highlander Buying Guide: Cost, Reliability, and the Best Years to Buy
Discover the ultimate buying guide for purchasing a used Toyota Highlander, covering every generation since 2001. Whether you're a first-time buyer or a Toyota loyalist, this comprehensive overview will help you research your next pre-owned Toyota Highlander.
4.7 Overall rating
Filter by rating
James S
Reviewed a 2008 Toyota Highlander on Jul 16, 2024
We own 2 of these. One is the limited and the other is the all wheel drive. Over 150,000 on each and really just general maintenance issues so far with each. The clear coat is peeling and fading on the rear valance of each and the shocks and struts need to be replaced at this age. We have taken our limited everywhere including Texas, Colorado, North Carolina, Maryland, West Virginia, and more. Very good for families or dog owners and flexible with the third row seating. No major issues with either one so far!
Birch T
Reviewed a 2008 Toyota Highlander on Jul 1, 2024
Fantastic car with an affordable price. Very happy with it!
Jay B
Reviewed a 2008 Toyota Sport 4WD on Apr 14, 2014
All around if you have a larger family you can't go wrong with the 2008 highlander. Easy to drive. Safe with the side curtain air bags. Plenty of power. Good MPG. Lots of interior seating space. Stow and go walk through seating keeps the kids off the 2nd row of seats and if you need more seating just pull out the other seat. Use Synthetic oil and you will have it for years. I have a hitch attachment that I can put on for long trips that add storage if needed. All around Excellent SUV.
Anonymous
Reviewed a 2008 Toyota Limited 4WD on Nov 16, 2011
It is my dream car. Fun to drive, passengers love it too because its comfortable and has individual heated seats and back row controls for heat and ac. The styling is fantastic, it is a great looking car inside and out. I live in Illinois and it handles all the horrible weather we get. Wondergul handling, killer sound system, I love, love, love my Highlander!
2008 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| Base 4WD | $28,750 |
| SR5 | -- |
| Sport | $29,950 |
| Base | $27,300 |
| Limited | $32,700 |
| Sport 4WD | $31,400 |
| Limited 4WD | $34,150 |
2008 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2008 Toyota Highlander prices has changed over time.
See more price trends