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

328 results
Lincoln, ON
2017 Jeep Grand Cherokee Summit 4WD Mike Yarek Dodge Chrysler Jeep Ram

2017 Jeep Grand Cherokee

Summit 4WD

78,950 kilometres

$26,988

Fair Deal
Paris, ON
72 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:
White
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
78,950
Stock number:
UP-2594A
VIN:
1C4RJFJG6HC938842

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2021 Jeep Grand Cherokee Laredo 4WD

2021 Jeep Grand Cherokee

Laredo 4WD

109,192 kilometres

$24,788

Good Deal
Woodbridge, ON
69 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
Gray
Interior colour:
Black
Transmission:
Automatic
Mileage:
109,192
Stock number:
T718736
VIN:
1C4RJFAG0MC718736

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2024 Jeep Grand Cherokee Summit Reserve 4WD

2024 Jeep Grand Cherokee

Summit Reserve 4WD

40,758 kilometres

$60,980

Great Deal
Certified Pre-Owned
Burlington, ON
33 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:
Gray
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
40,758
Stock number:
U21624
VIN:
1C4RJHEG6R8599039

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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
72 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

2022 Jeep Grand Cherokee Laredo 4WD

2022 Jeep Grand Cherokee

Laredo 4WD

60,029 kilometres

$31,185

Great Deal
North York, ON
64 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:
Gray
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
60,029
Stock number:
8P6848A
VIN:
1C4RJHAG9N8574135

2024 Jeep Grand Cherokee Summit Reserve 4WD

2024 Jeep Grand Cherokee

Summit Reserve 4WD

40,758 kilometres

$60,980

Great Deal
Certified Pre-Owned
Burlington, ON
33 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:
Gray
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
40,758
Stock number:
U21624
VIN:
1C4RJHEG6R8599039

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2024 Jeep Grand Cherokee

Summit Reserve 4WD

32,594 kilometres

$55,488

Great Deal
Guelph, ON
79 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:
Brown (Beige)
Transmission:
Automatic
Mileage:
32,594
Stock number:
25-240X
VIN:
1C4RJHEG1R8512292

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2018 Jeep Grand Cherokee

Limited 4WD

103,028 kilometres

$20,600

Great Deal
Guelph, ON
79 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
Transmission:
Automatic
Mileage:
103,028
Stock number:
25-356A
VIN:
1C4RJFBG5JC510376

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2023 Jeep Grand Cherokee

Limited 4WD

91,270 kilometres

$29,888

Great Deal
Welland, ON
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
Exterior colour:
White
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
91,270
Stock number:
540062
VIN:
1C4RJHBG5PC540062

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2021 Jeep Grand Cherokee

Laredo 4WD

101,222 kilometres

$23,888

Great Deal
Mississauga, ON
48 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Transmission:
Automatic
Mileage:
101,222
Stock number:
M0143
VIN:
1C4RJFAGXMC756569

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2015 Jeep Grand Cherokee

Summit 4WD

206,323 kilometres

$10,998

Great Deal
Pickering, ON
79 km away
Year:
2015
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
241 hp 3L V6 Diesel
Exterior colour:
White
Combined gas mileage:
10 L/100km
Fuel type:
Diesel
Transmission:
8-Speed Automatic
Mileage:
206,323
Stock number:
PC22495A
VIN:
1C4RJFJM6FC731788

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2025 Jeep Grand Cherokee

Altitude 4WD

6,845 kilometres

$51,988

Great Deal
Oshawa, ON
92 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:
6,845
Stock number:
S0164
VIN:
1C4RJHAG5SC325307

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2021 Jeep Grand Cherokee

Summit 4WD

140,750 kilometres

$26,998

Great Deal
Hamilton, ON
24 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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2020 Jeep Grand Cherokee

High Altitude 4WD

85,846 kilometres

$30,300

Great Deal
Unionville, ON
78 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
Interior colour:
Black
Transmission:
Automatic
Mileage:
85,846
Stock number:
RN48129A
VIN:
1C4RJFCGXLC406550

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2025 Jeep Grand Cherokee

Altitude 4WD

9,006 kilometres

$50,995

Great Deal
Mississauga, ON
43 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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2021 Jeep Grand Cherokee

Summit 4WD

100,331 kilometres

$31,290

Great Deal
50 km away
Year:
2021
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:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Brown (Beige)
Transmission:
Automatic
Mileage:
100,331
Stock number:
82228
VIN:
1C4RJFJT4MC686063

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2023 Jeep Grand Cherokee

Limited 4WD

94,933 kilometres

$29,888

Great Deal
Welland, ON
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
Exterior colour:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
94,933
Stock number:
613115
VIN:
1C4RJHBG4PC613115

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2021 Jeep Grand Cherokee

Altitude 4WD

62,938 kilometres

$28,995

Great Deal
Waterloo, ON
89 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
Diamond Black Crystal Pearl
Interior colour:
Black
Transmission:
Automatic
Mileage:
62,938
Stock number:
269616A
VIN:
1C4RJFAG6MC531517

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2019 Jeep Grand Cherokee

Altitude 4WD

95,339 kilometres

$20,995

Great Deal
Scarborough, ON
72 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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2025 Jeep Grand Cherokee

Overland 4WD

3,680 kilometres

$64,974

Great Deal
Brampton, ON
65 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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2021 Jeep Grand Cherokee

Limited 4WD

117,810 kilometres

$24,995

Great Deal
Burlington, ON
33 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
Interior colour:
Black
Transmission:
Automatic
Mileage:
117,810
Stock number:
F3913
VIN:
1C4RJFBG5MC531586

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2019 Jeep Grand Cherokee

Overland 4WD

118,071 kilometres

$17,995

Great Deal
Scarborough, ON
72 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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2022 Jeep Grand Cherokee

Summit 4WD

58,343 kilometres

$44,999

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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2020 Jeep Grand Cherokee

Limited 4WD

124,868 kilometres

$22,595

Good Deal
Cambridge, ON
74 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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  1. Home
  2. / Used Cars
  3. / Jeep Grand Cherokee
  4. / Overland
  5. / Ontario
  6. / Smithville
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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