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

495 results
Orillia, ON
2021 Jeep Grand Cherokee Altitude 4WD Bourgeois Midland Chrysler

2021 Jeep Grand Cherokee

Altitude 4WD

117,736 kilometres

$25,900

Fair Deal
Midland, ON
39 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
Gray
Interior colour:
Black
Transmission:
Automatic
Mileage:
117,736
Stock number:
00U3
VIN:
1C4RJFAG9MC876184

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2021 Jeep Grand Cherokee 80th Anniversary Edition 4WD

2021 Jeep Grand Cherokee

80th Anniversary Edition 4WD

143,181 kilometres

$26,995

Fair Deal
Mississauga, 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
Transmission:
8-Speed Automatic
Mileage:
143,181
Stock number:
250932A
VIN:
1C4RJFBGXMC820804

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2024 Jeep Grand Cherokee Altitude 4WD

2024 Jeep Grand Cherokee

Altitude 4WD

68,568 kilometres

$39,590

Fair Deal
Toronto, ON
101 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:
Automatic
Mileage:
68,568
Stock number:
44007A
VIN:
1C4RJHAG9RC156791

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2015 Jeep Grand Cherokee Laredo 4WD

2015 Jeep Grand Cherokee

Laredo 4WD

136,816 kilometres

$10,888

Great Deal
Newmarket, ON
59 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

2020 Jeep Grand Cherokee Altitude 4WD

2020 Jeep Grand Cherokee

Altitude 4WD

74,634 kilometres

$26,388

Great Deal
Burlington, ON
141 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:
T31145S
VIN:
1C4RJFAG6LC165217

2024 Jeep Grand Cherokee Limited 4WD

2024 Jeep Grand Cherokee

Limited 4WD

26,820 kilometres

$44,995

Great Deal
Mississauga, ON
119 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

181,814 kilometres

$19,899

Great Deal
Innisfil, ON
44 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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2020 Jeep Grand Cherokee

Overland 4WD

93,137 kilometres

$29,495

Great Deal
Barrie, ON
37 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:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
93,137
Stock number:
K0263
VIN:
1C4RJFCG1LC221836

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2024 Jeep Grand Cherokee

Limited 4WD

82,847 kilometres

$36,000

Great Deal
Stratford, ON
184 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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2023 Jeep Grand Cherokee

Limited 4WD

91,270 kilometres

$29,888

Great Deal
Welland, ON
179 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:
Black
Transmission:
Automatic
Mileage:
91,270
Stock number:
540062
VIN:
1C4RJHBG5PC540062

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2021 Jeep Grand Cherokee

Summit 4WD

140,750 kilometres

$26,998

Great Deal
Hamilton, ON
155 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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2023 Jeep Grand Cherokee

Limited 4WD

94,933 kilometres

$29,888

Great Deal
Welland, ON
179 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:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
94,933
Stock number:
613115
VIN:
1C4RJHBG4PC613115

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2011 Jeep Grand Cherokee

Laredo 4WD

214,000 kilometres

$7,991

Great Deal
London, ON
232 km away
Year:
2011
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
290 hp 3.6L V6
Exterior colour:
Blue
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
214,000
Stock number:
8046
VIN:
1J4RR4GG6BC553691

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2015 Jeep Grand Cherokee

135,000 kilometres

$12,608

Great Deal
London, ON
227 km away
Year:
2015
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Engine:
290 hp 3.6L V6
Exterior colour:
Red
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
135,000
Stock number:
N8780
VIN:
1C4RJFAG0FC198623

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2019 Jeep Grand Cherokee

Altitude 4WD

95,339 kilometres

$20,995

Great Deal
Scarborough, ON
90 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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2022 Jeep Grand Cherokee

Summit 4WD

58,343 kilometres

$46,777

Great Deal
Waterloo, ON
154 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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2021 Jeep Grand Cherokee

Limited 4WD

117,810 kilometres

$24,995

Great Deal
Burlington, ON
143 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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2019 Jeep Grand Cherokee

Overland 4WD

118,071 kilometres

$17,995

Great Deal
Scarborough, ON
90 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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2015 Jeep Grand Cherokee

Summit 4WD

206,323 kilometres

$10,998

Great Deal
Pickering, ON
91 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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2022 Jeep Grand Cherokee

Summit Reserve 4WD

85,325 kilometres

$39,695

Great Deal
Waterloo, ON
153 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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2018 Jeep Grand Cherokee

Limited 4WD

110,271 kilometres

$23,200

Good Deal
Caledon, ON
87 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:
White
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
110,271
Stock number:
A406
VIN:
1C4RJFBG1JC417628

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2023 Jeep Grand Cherokee

Summit Reserve 4WD

40,190 kilometres

$52,980

Good Deal
Certified Pre-Owned
Burlington, ON
144 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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2021 Jeep Grand Cherokee

Altitude 4WD

58,171 kilometres

$29,990

Good Deal
Waterloo, ON
153 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
BRIGHT WHITE
Interior colour:
Black
Transmission:
Automatic
Mileage:
58,171
Stock number:
DW1923A
VIN:
1C4RJFAG1MC542456

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2023 Jeep Grand Cherokee

Overland 4WD

86,700 kilometres

$39,999

Good Deal
Mississauga, ON
110 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:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
86,700
Stock number:
JG2313
VIN:
1C4RJHDG6PC619513

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