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Used 2008 Jeep Grand Cherokee Overland for Sale near Headingley, MB

135 results
Headingley, MB
2021 Jeep Grand Cherokee Altitude 4WD Auto Gallery of Winnipeg Inc.

2021 Jeep Grand Cherokee

Altitude 4WD

50,093 kilometres

$34,988

Fair Deal
Winnipeg, MB
7 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
50,093
Stock number:
27700
VIN:
1C4RJFAG4MC635536

Sponsored

2022 Jeep Grand Cherokee Limited 4WD

2022 Jeep Grand Cherokee

Limited 4WD

52,636 kilometres

$38,500

Good Deal
Selkirk, MB
49 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:
Red
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
52,636
Stock number:
1575
VIN:
1C4RJFBGXNC150446

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2018 Jeep Grand Cherokee Limited 4WD

2018 Jeep Grand Cherokee

Limited 4WD

200,246 kilometres

$17,873

Good Deal
Portage la Prairie, MB
66 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:
Diamond Black Crystal Pearl
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black/Black
Transmission:
8-Speed Automatic
Mileage:
200,246
Stock number:
PU1634A
VIN:
1C4RJFBGXJC185479

Sponsored

2021 Jeep Grand Cherokee Limited 4WD

2021 Jeep Grand Cherokee

Limited 4WD

90,718 kilometres

$30,390

Great Deal
Winnipeg, MB
27 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:
Velvet Red Pearl
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
90,718
Stock number:
F6F9CV
VIN:
1C4RJFBG5MC759457

2021 Jeep Grand Cherokee

2021 Jeep Grand Cherokee

89,986 kilometres

$29,499

Great Deal
Morden, MB
90 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Engine:
295 hp 3.6L V6
Exterior colour:
Bright White
Fuel type:
Gasoline
Interior colour:
Black
Mileage:
89,986
Stock number:
MU566
VIN:
1C4RJFAGXMC547803

2022 Jeep Grand Cherokee Limited 4WD

2022 Jeep Grand Cherokee

Limited 4WD

52,636 kilometres

$38,500

Good Deal
Selkirk, MB
49 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:
Red
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
52,636
Stock number:
1575
VIN:
1C4RJFBGXNC150446

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2020 Jeep Grand Cherokee

Altitude 4WD

68,909 kilometres

$29,999

Good Deal
Winnipeg, MB
20 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:
Velvet Red Pearl
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
68,909
Stock number:
T250876B
VIN:
1C4RJFAG4LC188866

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2023 Jeep Grand Cherokee

Limited 4WD

65,554 kilometres

$38,464

Good Deal
Winnipeg, MB
26 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
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
65,554
Stock number:
WT0155
VIN:
1C4RJHBG9PC632226

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2023 Jeep Grand Cherokee

Altitude 4WD

84,256 kilometres

$35,923

Good Deal
Winnipeg, MB
26 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
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
84,256
Stock number:
WT0162
VIN:
1C4RJHAG6P8799051

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2018 Jeep Grand Cherokee

Sterling Edition 4WD

146,948 kilometres

$22,694

Good Deal
Winnipeg, MB
23 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:
Red
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
146,948
Stock number:
25129A
VIN:
1C4RJFBG0JC163474

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2016 Jeep Grand Cherokee

Limited 4WD

191,647 kilometres

$16,000

Good Deal
Winnipeg, MB
18 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:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
191,647
Stock number:
ASIS-256943
VIN:
1C4RJFBG0GC398479

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2021 Jeep Grand Cherokee

Limited 4WD

55,567 kilometres

$35,574

Good Deal
Steinbach, MB
64 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:
Velvet Red Pearl
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
55,567
Stock number:
F6C2VA
VIN:
1C4RJFBG0MC636374

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2023 Jeep Grand Cherokee

Limited 4WD

82,609 kilometres

$36,000

Good Deal
Winnipeg, MB
18 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:
Bright White
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black (Global Blk w/Global Blk)
Transmission:
8-Speed Automatic
Mileage:
82,609
Stock number:
A138341
VIN:
1C4RJHBGXPC556791

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2018 Jeep Grand Cherokee

Limited 4WD

200,246 kilometres

$17,873

Good Deal
Portage la Prairie, MB
66 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:
Diamond Black Crystal Pearl
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black/Black
Transmission:
8-Speed Automatic
Mileage:
200,246
Stock number:
PU1634A
VIN:
1C4RJFBGXJC185479

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2023 Jeep Grand Cherokee

Limited 4WD

78,114 kilometres

$36,706

Good Deal
Winnipeg, MB
17 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:
78,114
Stock number:
25W4L36A
VIN:
1C4RJHBG9PC524818

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2024 Jeep Grand Cherokee

Limited 4WD

37,880 kilometres

$46,899

Good Deal
Winnipeg, MB
26 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
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
37,880
Stock number:
WW0029
VIN:
1C4RJHBG2RC706220

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2016 Jeep Grand Cherokee

Limited 4WD

184,991 kilometres

$15,795

Good Deal
Winnipeg, MB
17 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
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
184,991
Stock number:
25T442A
VIN:
1C4RJFBGXGC452385

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  1. Home
  2. / Used Cars
  3. / Jeep Grand Cherokee
  4. / Overland
  5. / Manitoba
  6. / Headingley
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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