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

493 results
Collingwood, ON
2025 Jeep Grand Cherokee Overland 4WD Stockie Chrysler Dodge Jeep Ram

2025 Jeep Grand Cherokee

Overland 4WD

16,466 kilometres

$62,888

Great Deal
Waterloo, ON
117 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 Pearlcoat
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
16,466
Stock number:
45550
VIN:
1C4RJHDG3S8659964

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2021 Jeep Grand Cherokee Altitude 4WD

2021 Jeep Grand Cherokee

Altitude 4WD

185,189 kilometres

$19,995

Good Deal
London, ON
193 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
Black
Interior colour:
Black
Transmission:
Automatic
Mileage:
185,189
Stock number:
54279
VIN:
1C4RJFAG9MC685106

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2021 Jeep Grand Cherokee Laredo 4WD

2021 Jeep Grand Cherokee

Laredo 4WD

80,602 kilometres

$26,800

Good Deal
St Catharines, ON
166 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
Gray
Transmission:
8-Speed Automatic
Mileage:
80,602
Stock number:
R112
VIN:
1C4RJFAG2MC756579

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2017 Jeep Grand Cherokee Laredo 4WD

2017 Jeep Grand Cherokee

Laredo 4WD

119,996 kilometres

$16,100

Great Deal
Caledon, ON
82 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

2025 Jeep Grand Cherokee Overland 4WD

2025 Jeep Grand Cherokee

Overland 4WD

5,900 kilometres

$66,977

Great Deal
London, ON
189 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
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
5,900
Stock number:
25563D
VIN:
1C4RJHDG8S8788024

2020 Jeep Grand Cherokee Limited 4WD

2020 Jeep Grand Cherokee

Limited 4WD

210,000 kilometres

$14,888

Great Deal
Toronto, ON
115 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:
210,000
Stock number:
P0002
VIN:
1C4RJFBG4LC340580

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2023 Jeep Grand Cherokee

Overland 4WD

24,285 kilometres

$46,995

Great Deal
Cayuga, ON
175 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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2025 Jeep Grand Cherokee

Overland 4WD

4,950 kilometres

$65,977

Great Deal
London, ON
189 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
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
4,950
Stock number:
25574D
VIN:
1C4RJHDG0S8802451

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2022 Jeep Grand Cherokee

Summit Reserve 4WD

59,059 kilometres

$47,980

Great Deal
Certified Pre-Owned
Burlington, ON
132 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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2018 Jeep Grand Cherokee

Summit 4WD

162,000 kilometres

$17,995

Great Deal
Toronto, ON
101 km away
Year:
2018
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
241 hp 3L V6 Diesel
Exterior colour:
Black
Combined gas mileage:
10 L/100km
Fuel type:
Diesel
Transmission:
Automatic
Mileage:
162,000
Stock number:
19058
VIN:
1C4RJFJM9JC436063

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2020 Jeep Grand Cherokee

Laredo 4WD

123,691 kilometres

$19,790

Great Deal
113 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:
Silver
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
123,691
Stock number:
80797
VIN:
1C4RJFAG7LC125454

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2025 Jeep Grand Cherokee

Summit Reserve 4WD

11,809 kilometres

$71,995

Great Deal
Woodbridge, ON
96 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
Interior colour:
Brown (Tan)
Transmission:
Automatic
Mileage:
11,809
Stock number:
T724345
VIN:
1C4RJHEG7S8724345

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2021 Jeep Grand Cherokee

Summit 4WD

62,588 kilometres

$34,995

Great Deal
Mississauga, ON
117 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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2025 Jeep Grand Cherokee

Summit Reserve 4WD

1,520 kilometres

$73,998

Great Deal
Trenton, ON
211 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:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
1,520
Stock number:
15016P
VIN:
1C4RJHEG7S8691783

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2024 Jeep Grand Cherokee

Laredo 4WD

1,000 kilometres

$45,998

Great Deal
Certified Pre-Owned
Petrolia, ON
241 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:
1,000
Stock number:
5276
VIN:
1C4RJHAG3R8513501

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2024 Jeep Grand Cherokee

Limited 4WD

82,847 kilometres

$37,000

Great Deal
Stratford, 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:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
82,847
Stock number:
SU3792
VIN:
1C4RJHBG3R8512654

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2025 Jeep Grand Cherokee

Summit 4WD

501 kilometres

$75,950

Great Deal
Hamilton, ON
146 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:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Brown (Tan)
Transmission:
8-Speed Automatic
Mileage:
501
Stock number:
257761
VIN:
1C4RJHEG8S8750453

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2023 Jeep Grand Cherokee

Summit 4WD

15,143 kilometres

$55,932

Great Deal
London, ON
182 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
Transmission:
8-Speed Automatic
Mileage:
15,143
Stock number:
15-U1253
VIN:
1C4RJHEG1PC578836

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2021 Jeep Grand Cherokee

Limited 4WD

81,302 kilometres

$29,995

Great Deal
London, ON
186 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:
81,302
Stock number:
FM1885
VIN:
1C4RJFBG7MC638669

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2020 Jeep Grand Cherokee

Overland 4WD

93,137 kilometres

$30,682

Great Deal
Barrie, ON
46 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
Transmission:
Automatic
Mileage:
93,137
Stock number:
K0263
VIN:
1C4RJFCG1LC221836

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2021 Jeep Grand Cherokee

80th Anniversary Edition 4WD

183,323 kilometres

$19,995

Great Deal
North York, ON
101 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:
183,323
Stock number:
STK-510979
VIN:
1C4RJFBG7MC510979

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2025 Jeep Grand Cherokee

Overland 4WD

16,466 kilometres

$62,888

Great Deal
Waterloo, ON
117 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 Pearlcoat
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
16,466
Stock number:
45550
VIN:
1C4RJHDG3S8659964

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2025 Jeep Grand Cherokee

Altitude 4WD

1,000 kilometres

$52,999

Great Deal
Tillsonburg, ON
186 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:
Automatic
Mileage:
1,000
Stock number:
25-149-demo
VIN:
1C4RJHAG5SC350630

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2025 Jeep Grand Cherokee

Limited 4WD

5,762 kilometres

$59,988

Fair Deal
Oshawa, ON
128 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:
Gray
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
5,762
Stock number:
S0100
VIN:
1C4RJHBGXSC316116

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  4. / Overland
  5. / Ontario
  6. / Collingwood
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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