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

253 results
Windsor, ON
2022 Jeep Grand Cherokee Limited 4WD Windsor Hyundai

2022 Jeep Grand Cherokee

Limited 4WD

49,329 kilometres

$39,995

Good Deal
Windsor, ON
13 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:
Diamond Black Crystal Pearl
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Global Black w/Global Black
Transmission:
Automatic
Mileage:
49,329
Stock number:
916WHU
VIN:
1C4RJHBG6N8601936

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2021 Jeep Grand Cherokee Altitude 4WD

2021 Jeep Grand Cherokee

Altitude 4WD

98,265 kilometres

$29,023

Good Deal
Windsor, ON
10 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Engine:
295 hp 3.6L V6
Exterior colour:
White
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
98,265
Stock number:
DR25799A
VIN:
1C4RJFAG4MC843688

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2020 Jeep Grand Cherokee Summit 4WD

2020 Jeep Grand Cherokee

Summit 4WD

84,012 kilometres

$35,508

Good Deal
London, ON
158 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:
Dark Red
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Brown
Transmission:
8-Speed Automatic
Mileage:
84,012
Stock number:
25509A
VIN:
1C4RJFJG7LC352580

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2022 Jeep Grand Cherokee Limited 4WD

2022 Jeep Grand Cherokee

Limited 4WD

78,032 kilometres

$31,799

Great Deal
Kitchener, ON
242 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:
78,032
Stock number:
25F4790C
VIN:
1C4RJHBG5N8550722

2023 Jeep Grand Cherokee Overland 4WD

2023 Jeep Grand Cherokee

Overland 4WD

17,554 kilometres

$51,799

Great Deal
Essex, ON
23 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:
17,554
Stock number:
251911
VIN:
1C4RJHDG4P8875460

2018 Jeep Grand Cherokee Limited 4WD

2018 Jeep Grand Cherokee

Limited 4WD

107,927 kilometres

$22,664

Great Deal
Aylmer, ON
175 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:
107,927
Stock number:
P1352
VIN:
1C4RJFBG1JC153021

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2021 Jeep Grand Cherokee

Overland 4WD

68,827 kilometres

$35,999

Great Deal
Wallaceburg, ON
61 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:
Silver
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
68,827
Stock number:
MC748876T
VIN:
1C4RJFCG5MC748876

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2021 Jeep Grand Cherokee

Altitude 4WD

66,518 kilometres

$31,988

Great Deal
Leamington, ON
45 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Engine:
295 hp 3.6L V6
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
66,518
Stock number:
14390
VIN:
1C4RJFAG0MC744270

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2019 Jeep Grand Cherokee

Limited 4WD

99,950 kilometres

$23,995

Great Deal
London, 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:
99,950
Stock number:
s172
VIN:
1C4RJFBG3KC681810

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2021 Jeep Grand Cherokee

Limited X 4WD

99,318 kilometres

$30,999

Great Deal
Kitchener, ON
243 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
Interior colour:
Black
Transmission:
Automatic
Mileage:
99,318
Stock number:
4751
VIN:
1C4RJFBGXMC820995

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2024 Jeep Grand Cherokee

Summit Reserve 4WD

17,120 kilometres

$62,995

Great Deal
Windsor, ON
10 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:
Silver
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
17,120
Stock number:
25219A
VIN:
1C4RJHEG4R8944181

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2024 Jeep Grand Cherokee

Summit Reserve 4WD

29,125 kilometres

$62,899

Great Deal
Certified Pre-Owned
Tillsonburg, ON
200 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:
29,125
Stock number:
F25-044
VIN:
1C4RJHEG0R8932707

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2020 Jeep Grand Cherokee

Summit 4WD

84,012 kilometres

$35,508

Good Deal
London, ON
158 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:
Dark Red
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Brown
Transmission:
8-Speed Automatic
Mileage:
84,012
Stock number:
25509A
VIN:
1C4RJFJG7LC352580

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2025 Jeep Grand Cherokee

Overland 4WD

9,890 kilometres

$67,333

Good Deal
Waterloo, ON
242 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:
9,890
Stock number:
45550
VIN:
1C4RJHDG3S8659964

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2019 Jeep Grand Cherokee

Summit 4WD

61,793 kilometres

$33,998

Good Deal
Simcoe, ON
232 km away
Year:
2019
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
360 hp 5.7L V8
Exterior colour:
Black
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
61,793
Stock number:
A02390
VIN:
1C4RJFJT1KC819603

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