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

389 results
Maple, ON
2025 Jeep Grand Cherokee Summit 4WD Ontario Chrysler Jeep Dodge Ram

2025 Jeep Grand Cherokee

Summit 4WD

2,534 kilometres

$77,888

Fair Deal
Mississauga, ON
27 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
Interior colour:
Black
Transmission:
Automatic
Mileage:
2,534
Stock number:
DEMO-700832
VIN:
1C4RJHEG2S8724334

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2015 Jeep Grand Cherokee Laredo 4WD

2015 Jeep Grand Cherokee

Laredo 4WD

211,467 kilometres

$10,450

Fair Deal
Etobicoke, ON
14 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:
Black
Combined gas mileage:
12 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
211,467
VIN:
1C4RJFAG1FC881303

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2022 Jeep Grand Cherokee

2022 Jeep Grand Cherokee

55,000 kilometres

$32,490

Good Deal
29 km away
Year:
2022
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Engine:
293 hp 3.6L V6
Exterior colour:
Red
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
55,000
Stock number:
101801
VIN:
1C4RJFAG6NC150784

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2024 Jeep Grand Cherokee Limited 4WD

2024 Jeep Grand Cherokee

Limited 4WD

62,679 kilometres

$38,288

Great Deal
Certified Pre-Owned
Guelph, ON
72 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

2025 Jeep Grand Cherokee Altitude 4WD

2025 Jeep Grand Cherokee

Altitude 4WD

15,986 kilometres

$48,999

Great Deal
Brampton, ON
25 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

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
63 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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2022 Jeep Grand Cherokee

47,413 kilometres

$31,999

Great Deal
Toronto, ON
19 km away
Year:
2022
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Engine:
293 hp 3.6L V6
Exterior colour:
Black
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
47,413
Stock number:
44205A
VIN:
1C4RJFAG9NC176327

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2015 Jeep Grand Cherokee

Summit 4WD

206,323 kilometres

$10,998

Great Deal
Pickering, ON
37 km away
Year:
2015
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Transmission:
8-Speed Automatic
Mileage:
206,323
Stock number:
PC22495A
VIN:
1C4RJFJM6FC731788

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2022 Jeep Grand Cherokee

Summit 4WD

58,343 kilometres

$44,888

Great Deal
Waterloo, ON
89 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
93 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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2020 Jeep Grand Cherokee

Limited 4WD

124,868 kilometres

$22,195

Great Deal
Cambridge, ON
82 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

Limited 4WD

240,908 kilometres

$7,990

Great Deal
Etobicoke, ON
27 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
Combined gas mileage:
12 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
240,908
Stock number:
pdc044
VIN:
1C4RJFBG3FC892527

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2016 Jeep Grand Cherokee

Limited 4WD

234,929 kilometres

$9,499

Great Deal
Newmarket, ON
21 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
Interior colour:
Black
Transmission:
Automatic
Mileage:
234,929
Stock number:
56847A
VIN:
1C4RJFBG7GC326257

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2017 Jeep Grand Cherokee

Overland 4WD

176,489 kilometres

$17,999

Great Deal
Brampton, ON
25 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:
Diamond Black Crystal P.C.
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Nappa Leather-Faced w/ Ventilation - Black
Transmission:
Automatic
Mileage:
176,489
Stock number:
26014T1
VIN:
1C4RJFCG3HC807882

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2021 Jeep Grand Cherokee

Limited 4WD

64,146 kilometres

$29,868

Great Deal
Newmarket, ON
22 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:
8-Speed Automatic
Mileage:
64,146
Stock number:
N17293
VIN:
1C4RJFBG7MC531069

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2021 Jeep Grand Cherokee

181,814 kilometres

$18,799

Great Deal
Innisfil, ON
38 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Engine:
295 hp 3.6L V6
Exterior colour:
Black
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
181,814
Stock number:
106
VIN:
1C4RJFAG0MC545588

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2017 Jeep Grand Cherokee

Overland 4WD

149,684 kilometres

$19,995

Great Deal
Barrie, ON
57 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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2019 Jeep Grand Cherokee

Altitude 4WD

95,339 kilometres

$20,995

Great Deal
Scarborough, ON
23 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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2019 Jeep Grand Cherokee

Limited 4WD

112,700 kilometres

$21,999

Great Deal
North York, ON
12 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:
112,700
Stock number:
10072503
VIN:
1C4RJFBG2KC664982

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2025 Jeep Grand Cherokee

Altitude 4WD

9,006 kilometres

$48,995

Great Deal
Mississauga, ON
37 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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2017 Jeep Grand Cherokee

Limited 4WD

197,828 kilometres

$10,888

Great Deal
Newmarket, ON
21 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:
197,828
Stock number:
28440T
VIN:
1C4RJFBG3HC606940

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2021 Jeep Grand Cherokee

Overland 4WD

150,767 kilometres

$22,499

Great Deal
Maple, ON
5 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
Transmission:
Automatic
Mileage:
150,767
Stock number:
P-3373A
VIN:
1C4RJFCG1MC867928

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2019 Jeep Grand Cherokee

Overland 4WD

118,071 kilometres

$17,995

Great Deal
Scarborough, ON
23 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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2023 Jeep Grand Cherokee

Altitude 4WD

65,586 kilometres

$37,995

Fair Deal
Oakville, ON
49 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:
65,586
Stock number:
A0775
VIN:
1C4RJHAG3PC644647

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