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

275 results
Merlin, ON
2018 Jeep Grand Cherokee Limited 4WD Auto Moto

2018 Jeep Grand Cherokee

Limited 4WD

154,750 kilometres

$17,995

Good Deal
Burlington, ON
223 km away
Year:
2018
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Gray
Interior colour:
Black
Transmission:
Automatic
Mileage:
154,750
Stock number:
A3940
VIN:
1C4RJFBG2JC140570

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2014 Jeep Grand Cherokee Limited 4WD

2014 Jeep Grand Cherokee

Limited 4WD

291,192 kilometres

$7,999

Fair Deal
Hamilton, ON
219 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
Transmission:
Automatic
Mileage:
291,192
Stock number:
10960
VIN:
1C4RJFBGXEC559109

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2022 Jeep Grand Cherokee Overland 4WD

2022 Jeep Grand Cherokee

Overland 4WD

45,714 kilometres

$44,998

Fair Deal
Certified Pre-Owned
New Hamburg, ON
163 km away
Year:
2022
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Interior colour:
Black
Transmission:
Automatic
Mileage:
45,714
Stock number:
25033A
VIN:
1C4RJHDG7N8576168

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2024 Jeep Grand Cherokee Limited 4WD

2024 Jeep Grand Cherokee

Limited 4WD

62,679 kilometres

$37,988

Great Deal
Certified Pre-Owned
Guelph, ON
199 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
Interior colour:
Black
Transmission:
Automatic
Mileage:
62,679
Stock number:
25-404A
VIN:
1C4RJHBG5R8512641

2024 Jeep Grand Cherokee Limited 4WD

2024 Jeep Grand Cherokee

Limited 4WD

18,741 kilometres

$44,197

Great Deal
Chatham-Kent, ON
2 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
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
18,741
Stock number:
LK00819T
VIN:
1C4RJHBGXRC195856

2025 Jeep Grand Cherokee Altitude 4WD

2025 Jeep Grand Cherokee

Altitude 4WD

15,986 kilometres

$48,999

Great Deal
Brampton, ON
247 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:
8-Speed Automatic
Mileage:
15,986
Stock number:
25-88355JB
VIN:
1C4RJHAG5SC288355

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2022 Jeep Grand Cherokee

Summit Reserve 4WD

59,059 kilometres

$47,980

Great Deal
Certified Pre-Owned
Burlington, ON
222 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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2025 Jeep Grand Cherokee

Overland 4WD

7,750 kilometres

$63,777

Great Deal
London, ON
97 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:
7,750
Stock number:
25574D
VIN:
1C4RJHDG0S8802451

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2020 Jeep Grand Cherokee

Altitude 4WD

203,406 kilometres

$15,990

Great Deal
Brampton, ON
247 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:
203,406
Stock number:
TC455
VIN:
1C4RJFAG3LC437321

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2020 Jeep Grand Cherokee

Limited 4WD

124,868 kilometres

$22,195

Great Deal
Cambridge, ON
189 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:
Blue
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
124,868
Stock number:
A9289A
VIN:
1C4RJFBG0LC282015

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2015 Jeep Grand Cherokee

135,000 kilometres

$12,608

Great Deal
London, ON
108 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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2024 Jeep Grand Cherokee

Limited 4WD

64,798 kilometres

$40,990

Great Deal
Brampton, ON
249 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:
64,798
Stock number:
148421
VIN:
1C4RJHBG4RC148421

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2019 Jeep Grand Cherokee

Trailhawk 4WD

145,958 kilometres

$22,999

Great Deal
Wallaceburg, ON
25 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:
8-Speed Automatic
Mileage:
145,958
Stock number:
KC665010T
VIN:
1C4RJFLG3KC665010

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2025 Jeep Grand Cherokee

Summit 4WD

6,608 kilometres

$68,956

Great Deal
London, ON
108 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:
6,608
Stock number:
15-25424A
VIN:
1C4RJHEG0S8795242

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2018 Jeep Grand Cherokee

Limited 4WD

150,992 kilometres

$17,998

Great Deal
London, ON
94 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:
Gray (Dark Grey)
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
150,992
Stock number:
(2-58) 155430
VIN:
1C4RJFBG6JC155431

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2013 Jeep Grand Cherokee

Laredo 4WD

235,737 kilometres

$4,900

Great Deal
Mississauga, ON
248 km away
Year:
2013
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
290 hp 3.6L V6
Fuel type:
Gasoline
Transmission:
6-Speed Automatic
Mileage:
235,737
Stock number:
P8594A (AS IS)
VIN:
1C4RJFAG7DC608976

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2025 Jeep Grand Cherokee

Summit 4WD

4,346 kilometres

$68,909

Great Deal
Milton, ON
225 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:
4,346
Stock number:
P7083
VIN:
1C4RJHEG0S8693309

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2021 Jeep Grand Cherokee

Summit 4WD

114,845 kilometres

$31,498

Great Deal
Windsor, ON
76 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Interior colour:
Black
Transmission:
Automatic
Mileage:
114,845
Stock number:
RCCA02806A
VIN:
1C4RJFJG0MC866207

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2022 Jeep Grand Cherokee

Summit 4WD

58,343 kilometres

$43,999

Great Deal
Waterloo, ON
182 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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2020 Jeep Grand Cherokee

Altitude 4WD

103,780 kilometres

$25,988

Great Deal
Paris, ON
174 km away
Year:
2020
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Transmission:
8-Speed Automatic
Mileage:
103,780
Stock number:
SB-0023
VIN:
1C4RJFAG9LC414688

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2025 Jeep Grand Cherokee

Altitude 4WD

9,006 kilometres

$48,995

Great Deal
Mississauga, ON
248 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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2022 Jeep Grand Cherokee

63,885 kilometres

$35,895

Great Deal
Oakville, ON
235 km away
Year:
2022
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
Gray
Transmission:
Automatic
Mileage:
63,885
Stock number:
A0714
VIN:
1C4RJFAG4NC186201

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2018 Jeep Grand Cherokee

Limited 4WD

103,028 kilometres

$18,998

Great Deal
Guelph, ON
199 km away
Year:
2018
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Transmission:
Automatic
Mileage:
103,028
Stock number:
25-356A
VIN:
1C4RJFBG5JC510376

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2021 Jeep Grand Cherokee

Altitude 4WD

96,063 kilometres

$26,703

Good Deal
Windsor, ON
66 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
White
Transmission:
Automatic
Mileage:
96,063
Stock number:
P0265
VIN:
1C4RJFAG9MC800674

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