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

511 results
Port Elgin, ON
2019 Jeep Grand Cherokee Laredo 4WD Top Notch Auto Sales Inc.

2019 Jeep Grand Cherokee

Laredo 4WD

198,756 kilometres

$15,950

Good Deal
Toronto, ON
154 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:
198,756
Stock number:
822194
VIN:
1C4RJFAGXKC822194

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2025 Jeep Grand Cherokee Limited 4WD

2025 Jeep Grand Cherokee

Limited 4WD

877 kilometres

$56,988

Good Deal
Oshawa, ON
195 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:
Silver
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
877
Stock number:
S0217
VIN:
1C4RJHBG6S8751329

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2018 Jeep Grand Cherokee Limited 4WD

2018 Jeep Grand Cherokee

Limited 4WD

113,500 kilometres

$24,995

Fair Deal
Caledon, ON
138 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:
113,500
Stock number:
23907
VIN:
1C4RJFBG1JC417628

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2021 Jeep Grand Cherokee Altitude 4WD

2021 Jeep Grand Cherokee

Altitude 4WD

85,600 kilometres

$25,900

Great Deal
Concord, ON
156 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
White
Transmission:
Automatic
Mileage:
85,600
Stock number:
M04-726099
VIN:
1C4RJFAG3MC726099

2015 Jeep Grand Cherokee Laredo 4WD

2015 Jeep Grand Cherokee

Laredo 4WD

136,816 kilometres

$10,888

Great Deal
Newmarket, ON
145 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 Limited 4WD

2024 Jeep Grand Cherokee

Limited 4WD

62,679 kilometres

$38,288

Great Deal
Certified Pre-Owned
Guelph, ON
133 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

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2022 Jeep Grand Cherokee

Summit Reserve 4WD

59,059 kilometres

$47,980

Great Deal
Certified Pre-Owned
Burlington, ON
174 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
178 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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2016 Jeep Grand Cherokee

Limited 4WD

105,045 kilometres

$16,999

Great Deal
Sarnia, ON
203 km away
Year:
2016
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:
8-Speed Automatic
Mileage:
105,045
Stock number:
GC402334P
VIN:
1C4RJFBG7GC402334

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2025 Jeep Grand Cherokee

Altitude 4WD

15,986 kilometres

$48,999

Great Deal
Brampton, ON
147 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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2015 Jeep Grand Cherokee

135,000 kilometres

$12,608

Great Deal
London, ON
175 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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2023 Jeep Grand Cherokee

Limited 4WD

81,301 kilometres

$33,995

Great Deal
Mississauga, ON
168 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:
8-Speed Automatic
Mileage:
81,301
Stock number:
P8403
VIN:
1C4RJHBG2PC538365

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2017 Jeep Grand Cherokee

Overland 4WD

149,684 kilometres

$19,995

Great Deal
Barrie, ON
114 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:
Gray
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
149,684
Stock number:
39430B
VIN:
1C4RJFCGXHC848851

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2023 Jeep Grand Cherokee

Summit Reserve 4WD

58,785 kilometres

$47,480

Great Deal
Oakville, ON
166 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:
Gray
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
58,785
Stock number:
JS30B
VIN:
1C4RJHEG8P8844727

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2023 Jeep Grand Cherokee

Limited 4WD

74,628 kilometres

$33,792

Great Deal
Scarborough, ON
173 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:
Automatic
Mileage:
74,628
Stock number:
P3374
VIN:
1C4RJHBG8PC551430

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2025 Jeep Grand Cherokee

Altitude 4WD

6,861 kilometres

$51,988

Great Deal
Oshawa, ON
195 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:
Automatic
Mileage:
6,861
Stock number:
S0164
VIN:
1C4RJHAG5SC325307

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2022 Jeep Grand Cherokee

Summit 4WD

58,343 kilometres

$44,888

Great Deal
Waterloo, ON
134 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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2023 Jeep Grand Cherokee

Summit 4WD

73,835 kilometres

$44,995

Great Deal
Certified Pre-Owned
Niagara Falls, ON
231 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:
Gray
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
73,835
Stock number:
4669
VIN:
1C4RJHEG3P8892958

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2018 Jeep Grand Cherokee

Altitude 4WD

163,479 kilometres

$17,995

Great Deal
Hamilton, ON
188 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
Interior colour:
Black
Transmission:
Automatic
Mileage:
163,479
VIN:
1C4RJFAG5JC161737

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2020 Jeep Grand Cherokee

Limited 4WD

124,868 kilometres

$22,195

Great Deal
Cambridge, ON
145 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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2019 Jeep Grand Cherokee

Altitude 4WD

95,339 kilometres

$20,995

Great Deal
Scarborough, ON
170 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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2014 Jeep Grand Cherokee

Overland 4WD

181,434 kilometres

$10,900

Great Deal
Milton, ON
152 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:
181,434
Stock number:
232
VIN:
1C4RJFCG7EC512683

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2015 Jeep Grand Cherokee

Limited 4WD

134,259 kilometres

$12,888

Great Deal
North York, ON
166 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:
White
Combined gas mileage:
12 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
134,259
Stock number:
200887
VIN:
1C4RJFBG2FC876260

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2015 Jeep Grand Cherokee

Summit 4WD

240,650 kilometres

$10,588

Good Deal
North York, ON
155 km away
Year:
2015
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
360 hp 5.7L V8
Exterior colour:
Gray
Combined gas mileage:
15 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
240,650
Stock number:
AE 122
VIN:
1C4RJFJT1FC928083

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