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Used 2008 Jeep Grand Cherokee Overland for Sale near Hiawatha, ON

427 results
Peterborough, ON
2025 Jeep Grand Cherokee Limited 4WD Southbank Dodge Chrysler LTD

2025 Jeep Grand Cherokee

Limited 4WD

19,447 kilometres

$59,499

Fair Deal
Ottawa, ON
242 km away
Year:
2025
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
293 hp 3.6L V6
Exterior colour:
DIAMOND_BLACK_CRYS
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
19,447
Stock number:
D00121
VIN:
1C4RJHBG9SC265658

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2024 Jeep Grand Cherokee Altitude 4WD

2024 Jeep Grand Cherokee

Altitude 4WD

32,125 kilometres

$44,000

Fair Deal
Orillia, ON
93 km away
Year:
2024
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
293 hp 3.6L V6
Exterior colour:
Black (Charcoal)
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black (Global Blk w/Global Blk)
Transmission:
Automatic
Mileage:
32,125
Stock number:
15466A
VIN:
1C4RJHAG1RC249269

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2024 Jeep Grand Cherokee Laredo 4WD

2024 Jeep Grand Cherokee

Laredo 4WD

11,618 kilometres

$44,295

Good Deal
Ajax, ON
73 km away
Year:
2024
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
293 hp 3.6L V6
Exterior colour:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
11,618
Stock number:
P5574
VIN:
1C4RJHAG1RC701477

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2022 Jeep Grand Cherokee Laredo 4WD

2022 Jeep Grand Cherokee

Laredo 4WD

60,029 kilometres

$30,490

Great Deal
North York, ON
101 km away
Year:
2022
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
293 hp 3.6L V6
Exterior colour:
Gray
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
60,029
Stock number:
8P6848A
VIN:
1C4RJHAG9N8574135

2017 Jeep Grand Cherokee Laredo 4WD

2017 Jeep Grand Cherokee

Laredo 4WD

119,996 kilometres

$16,100

Great Deal
Caledon, ON
120 km away
Year:
2017
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
295 hp 3.6L V6
Exterior colour:
Red
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
119,996
Stock number:
2121
VIN:
1C4RJFAG3HC885632

2020 Jeep Grand Cherokee Altitude 4WD

2020 Jeep Grand Cherokee

Altitude 4WD

74,634 kilometres

$26,888

Great Deal
Burlington, ON
155 km away
Year:
2020
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
295 hp 3.6L V6
Exterior colour:
Gray
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
74,634
Stock number:
T31145
VIN:
1C4RJFAG6LC165217

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2014 Jeep Grand Cherokee

Limited 4WD

161,157 kilometres

$12,495

Great Deal
Kemptville, ON
227 km away
Year:
2014
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
290 hp 3.6L V6
Exterior colour:
Silver
Combined gas mileage:
12 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
161,157
VIN:
1C4RJFBG4EC307176

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2023 Jeep Grand Cherokee

Overland 4WD

24,285 kilometres

$46,495

Great Deal
Cayuga, ON
196 km away
Year:
2023
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
293 hp 3.6L V6
Exterior colour:
White
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Gray
Transmission:
Automatic
Mileage:
24,285
Stock number:
450981
VIN:
1C4RJHDG0PC542346

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2022 Jeep Grand Cherokee

Summit Reserve 4WD

59,059 kilometres

$47,980

Great Deal
Certified Pre-Owned
Burlington, ON
158 km away
Year:
2022
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
357 hp 5.7L V8
Exterior colour:
Silver
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
59,059
Stock number:
U21521
VIN:
1C4RJHET3N8508929

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2020 Jeep Grand Cherokee

Limited 4WD

213,000 kilometres

$13,888

Great Deal
Toronto, ON
123 km away
Year:
2020
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
295 hp 3.6L V6
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
213,000
Stock number:
P0002
VIN:
1C4RJFBG4LC340580

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2022 Jeep Grand Cherokee

Summit Reserve 4WD

85,325 kilometres

$39,995

Great Deal
Waterloo, ON
197 km away
Year:
2022
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
293 hp 3.6L V6
Exterior colour:
Silver
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
85,325
Stock number:
PC2647A
VIN:
1C4RJHEG0N8576169

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2021 Jeep Grand Cherokee

Altitude 4WD

99,015 kilometres

$26,000

Great Deal
Oakville, ON
145 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
Gray
Interior colour:
Black
Transmission:
Automatic
Mileage:
99,015
Stock number:
EVT25046PA
VIN:
1C4RJFAG5MC542668

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2019 Jeep Grand Cherokee

Altitude 4WD

95,339 kilometres

$21,995

Great Deal
Scarborough, ON
94 km away
Year:
2019
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
295 hp 3.6L V6
Exterior colour:
Gray
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
95,339
Stock number:
96357
VIN:
1C4RJFAG5KC696357

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2021 Jeep Grand Cherokee

Limited X 4WD

177,000 kilometres

$24,900

Great Deal
Toronto, ON
119 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
295 hp 3.6L V6
Exterior colour:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
177,000
Stock number:
Stk15
VIN:
1C4RJFBGXMC744663

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2021 Jeep Grand Cherokee

80th Anniversary Edition 4WD

41,082 kilometres

$34,980

Great Deal
Barrie, ON
108 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
295 hp 3.6L V6
Exterior colour:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
41,082
Stock number:
R233102A
VIN:
1C4RJFBG3MC614157

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2023 Jeep Grand Cherokee

Limited 4WD

82,751 kilometres

$32,998

Great Deal
Cambridge, ON
188 km away
Year:
2023
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
293 hp 3.6L V6
Exterior colour:
White
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
82,751
Stock number:
260243A
VIN:
1C4RJHBG0PC503985

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2021 Jeep Grand Cherokee

80th Anniversary Edition 4WD

30,100 kilometres

$34,994

Great Deal
Gatineau, QC
243 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
295 hp 3.6L V6
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
30,100
Stock number:
26170A
VIN:
1C4RJFBG5MC821049

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2024 Jeep Grand Cherokee

Limited 4WD

26,820 kilometres

$44,995

Great Deal
Mississauga, ON
130 km away
Year:
2024
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
293 hp 3.6L V6
Exterior colour:
Red
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
26,820
Stock number:
P8599
VIN:
1C4RJHBG4RC680123

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2021 Jeep Grand Cherokee

Summit 4WD

62,588 kilometres

$33,995

Great Deal
Mississauga, ON
130 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
295 hp 3.6L V6
Exterior colour:
Blue
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
62,588
Stock number:
250744A
VIN:
1C4RJFJG1MC551755

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2022 Jeep Grand Cherokee

Overland 4WD

87,239 kilometres

$34,290

Great Deal
121 km away
Year:
2022
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
293 hp 3.6L V6
Exterior colour:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
87,239
Stock number:
78752
VIN:
1C4RJHDG9N8599239

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2020 Jeep Grand Cherokee

164,962 kilometres

$17,599

Great Deal
Woodbridge, ON
113 km away
Year:
2020
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Engine:
295 hp 3.6L V6
Exterior colour:
Gray
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
164,962
Stock number:
1857
VIN:
1C4RJFAG0LC125487

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2024 Jeep Grand Cherokee

Limited 4WD

41,070 kilometres

$42,536

Great Deal
Huntsville, ON
137 km away
Year:
2024
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
293 hp 3.6L V6
Exterior colour:
White
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
41,070
Stock number:
T70RA001
VIN:
1C4RJHBG7RC136344

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2021 Jeep Grand Cherokee

Summit 4WD

140,750 kilometres

$26,998

Great Deal
Hamilton, ON
164 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
295 hp 3.6L V6
Exterior colour:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
140,750
Stock number:
B3EC40
VIN:
1C4RJFJG3MC866489

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2022 Jeep Grand Cherokee

Limited 4WD

71,631 kilometres

$34,500

Good Deal
Waterloo, ON
198 km away
Year:
2022
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
293 hp 3.6L V6
Exterior colour:
BRIGHT WHITE
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
71,631
Stock number:
AW1180
VIN:
1C4RJFBG5NC170412

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  4. / Overland
  5. / Ontario
  6. / Hiawatha
Reviews

4.5 Overall rating

(2 reviews)
Anonymous
4.0
Reviewed a 2008 Jeep Overland on Aug. 28, 2008

I love the new interior, it's almost perfect. However, the center console is cheap-feeling, and the plastic chrome accents are not solid and look really fake. The HEMI has more power over the 4.7L, however it's MDS feature is worthless, adding an advertised 15% better gas mileage, but in reality it's much worse than that. The car weights over 6,000 lbs so gas mileage is pretty crappy, but that's no surprise for a 5.7L V8. I get about 12 MPG average in city and highway driving. The seats are not 8-way power like my old 1999 Grand Cherokee Limited, with manual lumbar adjustment, the passenger seat only 4-way power (can't move up/down), driver is 6-way power -- but the front of the seat doesn't go up as high as I would like it to. The wood and leather steering wheel is a very nice touch, but where the wood meats the leather, big gaps are visible which make it look cheap. I hate how the door locks are in the exact same spot as where I like to put my arm while driving, and the window sill is too high. The 1999 GC Limited didn't have these issues. Sirius satellite, while free for the first year, sounds TERRIBLE, even when compared to standard FM. This is a known issue (google it), with XM offering slightly better quality. The Sirius real-time traffic is neat, but not very practical, as it only shows major roadways and sometimes nothing at all. Once my subscription runs out I will not be renewing. The navigation/radio system sometimes gets "stuck" and won't let you press a button unless you "refresh" it by going to another screen and then back again. I'm sure there will be a software update to address this problem. The last negative thing I can think of is that the seat doesn't offer adequate side support, and I feel that I need to hold on to the center console when making sharp turns. You can't hold onto the shifter like with the < 2005 models because you will shift the gear down/up -- pretty annoying, but not a big deal. OK, now for the things I like. There are waaaaay too many to list, but I will try to touch on the best ones. The 30GB HDD is absolutely great! It has about 16 GB of space for your own music/pictures, which is more than plenty. I recommend buying a 16 GB flash drive (~ $50 on Amazon), and use it to hold your music collection including playlists. The navigation is solid, and very useful. The LED-illuminated instrument panel looks very good and is very functional. Love the HID headlights with the SmartBeam and auto-leveling features. The exterior styling is superb, looks great at any angle. Gas mileage aside, I absolutely love this car.

David W
5.0
Reviewed a 2008 Jeep Overland on Jan. 12, 2008

its the best

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