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

357 results
Orangeville, ON
2022 Jeep Grand Cherokee Limited 4WD Whitby Oshawa Honda

2022 Jeep Grand Cherokee

Limited 4WD

30,114 kilometres

$38,500

Good Deal
Whitby, ON
96 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:
White
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
30,114
Stock number:
B3257
VIN:
1C4RJFBG9NC109600

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2024 Jeep Grand Cherokee Laredo 4WD

2024 Jeep Grand Cherokee

Laredo 4WD

12,800 kilometres

$43,995

Good Deal
Mississauga, ON
59 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:
8-Speed Automatic
Mileage:
12,800
Stock number:
240807 DMO(Service Loaner)
VIN:
1C4RJHAG2RC156616

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2025 Jeep Grand Cherokee Limited 4WD

2025 Jeep Grand Cherokee

Limited 4WD

4,689 kilometres

$63,454

Fair Deal
Orillia, ON
92 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 CRYSTAL PEARL
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
CAPRI LEATHERETTE SEATS W/PERF INSRT - GLOBAL BLAC
Transmission:
Automatic
Mileage:
4,689
Stock number:
15735
VIN:
1C4RJHBG3S8806335

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2025 Jeep Grand Cherokee Altitude 4WD

2025 Jeep Grand Cherokee

Altitude 4WD

12,862 kilometres

$48,999

Great Deal
Brampton, ON
38 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 Crystal Pearl
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Global Black with Global Black
Transmission:
Automatic
Mileage:
12,862
Stock number:
25-88355JB
VIN:
1C4RJHAG5SC288355

2015 Jeep Grand Cherokee Laredo 4WD

2015 Jeep Grand Cherokee

Laredo 4WD

136,816 kilometres

$10,888

Great Deal
Newmarket, ON
57 km away
Year:
2015
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
290 hp 3.6L V6
Exterior colour:
Red
Combined gas mileage:
12 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
136,816
Stock number:
P763
VIN:
1C4RJFAG7FC759240

2024 Jeep Grand Cherokee Altitude 4WD

2024 Jeep Grand Cherokee

Altitude 4WD

32,125 kilometres

$39,586

Great Deal
Orillia, ON
92 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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2018 Jeep Grand Cherokee

Limited 4WD

103,028 kilometres

$20,600

Great Deal
Guelph, ON
46 km away
Year:
2018
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:
103,028
Stock number:
25-356A
VIN:
1C4RJFBG5JC510376

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2021 Jeep Grand Cherokee

Overland 4WD

143,925 kilometres

$24,999

Great Deal
Maple, ON
47 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:
Billet Silver Metallic (PSC)
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
143,925
Stock number:
P-3373A
VIN:
1C4RJFCG1MC867928

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2024 Jeep Grand Cherokee

Limited 4WD

26,820 kilometres

$44,995

Great Deal
Mississauga, ON
59 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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2019 Jeep Grand Cherokee

Limited 4WD

112,700 kilometres

$21,999

Great Deal
North York, ON
52 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:
White
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
112,700
Stock number:
10072503
VIN:
1C4RJFBG2KC664982

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2015 Jeep Grand Cherokee

Limited 4WD

240,908 kilometres

$8,500

Great Deal
Etobicoke, ON
56 km away
Year:
2015
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
290 hp 3.6L V6
Combined gas mileage:
12 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
240,908
Stock number:
pdc044
VIN:
1C4RJFBG3FC892527

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2024 Jeep Grand Cherokee

Limited 4WD

82,847 kilometres

$35,500

Great Deal
Stratford, ON
90 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:
82,847
Stock number:
SU3792
VIN:
1C4RJHBG3R8512654

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2019 Jeep Grand Cherokee

Altitude 4WD

95,339 kilometres

$20,995

Great Deal
Scarborough, ON
67 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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2015 Jeep Grand Cherokee

Summit 4WD

206,323 kilometres

$10,998

Great Deal
Pickering, ON
81 km away
Year:
2015
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Transmission:
8-Speed Automatic
Mileage:
206,323
Stock number:
PC22495A
VIN:
1C4RJFJM6FC731788

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2025 Jeep Grand Cherokee

Altitude 4WD

9,006 kilometres

$49,995

Great Deal
Mississauga, ON
59 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:
White
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
9,006
Stock number:
250914A
VIN:
1C4RJHAG2SC315656

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2025 Jeep Grand Cherokee

Overland 4WD

3,680 kilometres

$64,974

Great Deal
Brampton, ON
35 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:
Red
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
3,680
Stock number:
N27SA494
VIN:
1C4RJHDG6S8727349

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2021 Jeep Grand Cherokee

181,814 kilometres

$18,999

Great Deal
Innisfil, ON
56 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Engine:
295 hp 3.6L V6
Exterior colour:
Black
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
181,814
Stock number:
106
VIN:
1C4RJFAG0MC545588

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2021 Jeep Grand Cherokee

Limited 4WD

117,810 kilometres

$24,995

Great Deal
Burlington, ON
67 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:
117,810
Stock number:
F3913
VIN:
1C4RJFBG5MC531586

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2022 Jeep Grand Cherokee

Summit 4WD

58,343 kilometres

$44,444

Great Deal
Waterloo, ON
60 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
Interior colour:
Black
Transmission:
Automatic
Mileage:
58,343
Stock number:
L38395
VIN:
1C4RJHEG1N8582403

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2019 Jeep Grand Cherokee

Overland 4WD

118,071 kilometres

$17,995

Great Deal
Scarborough, ON
67 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:
Red (Burgundy)
Fuel type:
Gasoline
Interior colour:
Black
Mileage:
118,071
Stock number:
96774
VIN:
1C4RJFCGXKC796774

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2022 Jeep Grand Cherokee

Limited 4WD

71,631 kilometres

$34,490

Good Deal
Waterloo, ON
59 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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2021 Jeep Grand Cherokee

Overland 4WD

58,129 kilometres

$35,420

Good Deal
Richmond Hill, ON
53 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:
White
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
58,129
Stock number:
TY48740A
VIN:
1C4RJFCG1MC839398

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2023 Jeep Grand Cherokee

Summit Reserve 4WD

40,190 kilometres

$52,980

Good Deal
Certified Pre-Owned
Burlington, ON
68 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:
Blue
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Brown
Transmission:
8-Speed Automatic
Mileage:
40,190
Stock number:
U21541
VIN:
1C4RJHEG1P8730956

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2024 Jeep Grand Cherokee

Limited 4WD

75,200 kilometres

$39,900

Fair Deal
Brampton, ON
38 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:
Gray
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
75,200
Stock number:
26441
VIN:
1C4RJHBG2RC205215

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  1. Home
  2. / Used Cars
  3. / Jeep Grand Cherokee
  4. / Overland
  5. / Ontario
  6. / Orangeville
Reviews

4 Overall rating

(1 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.

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