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

307 results
Ajax, ON
2024 Jeep Grand Cherokee Limited 4WD AutoPlanet Direct - Durham

2024 Jeep Grand Cherokee

Limited 4WD

79,333 kilometres

$38,795

Fair Deal
Clarington, ON
28 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:
8-Speed Automatic
Mileage:
79,333
Stock number:
R06A6323
VIN:
1C4RJHBG2R8512631

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2022 Jeep Grand Cherokee Summit 4WD

2022 Jeep Grand Cherokee

Summit 4WD

88,000 kilometres

$47,999

Fair Deal
Barrie, ON
77 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:
Black
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Brown
Transmission:
Automatic
Mileage:
88,000
Stock number:
6062-19B
VIN:
1C4RJHET5N8522167

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2024 Jeep Grand Cherokee Limited 4WD

2024 Jeep Grand Cherokee

Limited 4WD

55,361 kilometres

$44,995

Fair Deal
Barrie, ON
77 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:
Blue
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
55,361
Stock number:
P13880A
VIN:
1C4RJHBG7R8932322

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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
55 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

2022 Jeep Grand Cherokee Summit Reserve 4WD

2022 Jeep Grand Cherokee

Summit Reserve 4WD

59,059 kilometres

$47,980

Great Deal
Certified Pre-Owned
Burlington, ON
83 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

2020 Jeep Grand Cherokee Limited 4WD

2020 Jeep Grand Cherokee

Limited 4WD

213,000 kilometres

$13,888

Great Deal
Toronto, ON
49 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:
213,000
Stock number:
P0002
VIN:
1C4RJFBG4LC340580

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2021 Jeep Grand Cherokee

80th Anniversary Edition 4WD

41,082 kilometres

$35,380

Great Deal
Barrie, ON
77 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:
41,082
Stock number:
R233102A
VIN:
1C4RJFBG3MC614157

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2020 Jeep Grand Cherokee

163,962 kilometres

$17,989

Great Deal
Woodbridge, ON
43 km away
Year:
2020
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Engine:
295 hp 3.6L V6
Exterior colour:
Gray
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
163,962
Stock number:
1857
VIN:
1C4RJFAG0LC125487

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2021 Jeep Grand Cherokee

Altitude 4WD

99,015 kilometres

$26,000

Great Deal
Oakville, ON
71 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
Gray
Interior colour:
Black
Transmission:
Automatic
Mileage:
99,015
Stock number:
EVT25046PA
VIN:
1C4RJFAG5MC542668

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2018 Jeep Grand Cherokee

Limited 4WD

169,000 kilometres

$15,999

Great Deal
Mississauga, ON
64 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
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
169,000
Stock number:
25058.
VIN:
1C4RJFBG2JC108802

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2025 Jeep Grand Cherokee

Altitude 4WD

1,342 kilometres

$48,499

Great Deal
Toronto, ON
46 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:
1,342
Stock number:
43621A
VIN:
1C4RJHAG7SC325339

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2011 Jeep Grand Cherokee

Laredo 4WD

228,000 kilometres

$5,995

Great Deal
Concord, ON
41 km away
Year:
2011
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:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
228,000
Stock number:
549713
VIN:
1J4RR4GG3BC549713

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2018 Jeep Grand Cherokee

Summit 4WD

162,000 kilometres

$17,995

Great Deal
Toronto, ON
39 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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2019 Jeep Grand Cherokee

Altitude 4WD

95,339 kilometres

$21,995

Great Deal
Scarborough, ON
22 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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2021 Jeep Grand Cherokee

80th Anniversary Edition 4WD

183,323 kilometres

$19,995

Great Deal
North York, ON
37 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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2019 Jeep Grand Cherokee

Overland 4WD

118,071 kilometres

$17,995

Great Deal
Scarborough, ON
22 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:
Red (Burgundy)
Fuel type:
Gasoline
Interior colour:
Black
Mileage:
118,071
Stock number:
96774
VIN:
1C4RJFCGXKC796774

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2024 Jeep Grand Cherokee

Summit Reserve 4WD

32,159 kilometres

$59,980

Great Deal
Certified Pre-Owned
Burlington, ON
83 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:
32,159
Stock number:
U21519
VIN:
1C4RJHEG5RC189667

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2020 Jeep Grand Cherokee

Altitude 4WD

74,634 kilometres

$26,888

Great Deal
Burlington, ON
81 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:
Gray
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
74,634
Stock number:
T31145
VIN:
1C4RJFAG6LC165217

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2017 Jeep Grand Cherokee

Limited 4WD

167,566 kilometres

$13,995

Great Deal
North York , ON
39 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:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
167,566
Stock number:
789656
VIN:
1C4RJFBGXHC789656

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2020 Jeep Grand Cherokee

Overland 4WD

93,137 kilometres

$29,495

Great Deal
Barrie, ON
77 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

Summit 4WD

140,750 kilometres

$26,998

Great Deal
Hamilton, ON
90 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:
140,750
Stock number:
B3EC40
VIN:
1C4RJFJG3MC866489

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2025 Jeep Grand Cherokee

Overland 4WD

3,680 kilometres

$64,974

Great Deal
Brampton, ON
64 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:
Red
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
3,680
Stock number:
N27SA494
VIN:
1C4RJHDG6S8727349

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2023 Jeep Grand Cherokee

Limited 4WD

101,350 kilometres

$28,980

Great Deal
Barrie, ON
77 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:
Automatic
Mileage:
101,350
Stock number:
K0322
VIN:
1C4RJHBG1PC539541

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2023 Jeep Grand Cherokee

Limited 4WD

74,628 kilometres

$34,992

Good Deal
Scarborough, ON
24 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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  1. Home
  2. / Used Cars
  3. / Jeep Grand Cherokee
  4. / Overland
  5. / Ontario
  6. / Ajax
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

  • 2011 Jeep Grand Cherokee Overland in Ajax ON

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