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Used 2008 Jeep Grand Cherokee Overland for Sale near Jacksons Point, ON

300 results
Sutton West, ON
2025 Jeep Grand Cherokee Altitude 4WD NewRoads Chrysler Dodge Jeep Ram

2025 Jeep Grand Cherokee

Altitude 4WD

25,432 kilometres

$46,888

Fair Deal
Certified Pre-Owned
Newmarket, ON
29 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
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
25,432
Stock number:
28387P
VIN:
1C4RJHAG7SC318097

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2021 Jeep Grand Cherokee Overland 4WD

2021 Jeep Grand Cherokee

Overland 4WD

58,129 kilometres

$36,497

Good Deal
Richmond Hill, ON
44 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
Transmission:
Automatic
Mileage:
58,129
Stock number:
TY48740A
VIN:
1C4RJFCG1MC839398

Sponsored

2021 Jeep Grand Cherokee Altitude 4WD

2021 Jeep Grand Cherokee

Altitude 4WD

37,223 kilometres

$32,888

Fair Deal
Certified Pre-Owned
Newmarket, ON
29 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Transmission:
Automatic
Mileage:
37,223
Stock number:
28421T
VIN:
1C4RJFAG9MC800514

Sponsored

2021 Jeep Grand Cherokee Altitude 4WD

2021 Jeep Grand Cherokee

Altitude 4WD

85,600 kilometres

$25,900

Great Deal
Concord, ON
55 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
62 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

2015 Jeep Grand Cherokee Laredo 4WD

2015 Jeep Grand Cherokee

Laredo 4WD

136,816 kilometres

$10,888

Great Deal
Newmarket, ON
25 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:
Red
Combined gas mileage:
12 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
136,816
Stock number:
P763
VIN:
1C4RJFAG7FC759240

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2015 Jeep Grand Cherokee

Summit 4WD

206,323 kilometres

$10,998

Great Deal
Pickering, ON
53 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
56 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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2020 Jeep Grand Cherokee

High Altitude 4WD

85,846 kilometres

$30,300

Great Deal
Unionville, ON
48 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
85 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
76 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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2019 Jeep Grand Cherokee

Altitude 4WD

95,339 kilometres

$20,995

Great Deal
Scarborough, ON
54 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
76 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

181,814 kilometres

$18,999

Great Deal
Innisfil, ON
21 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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2023 Jeep Grand Cherokee

Limited 4WD

101,430 kilometres

$28,100

Great Deal
Barrie, ON
31 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:
101,430
Stock number:
K0322
VIN:
1C4RJHBG1PC539541

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2019 Jeep Grand Cherokee

Overland 4WD

118,071 kilometres

$17,995

Great Deal
Scarborough, ON
54 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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2025 Jeep Grand Cherokee

Altitude 4WD

5,984 kilometres

$56,969

Good Deal
North York, ON
62 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:
Silver
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
5,984
Stock number:
825023-new
VIN:
1C4RJHAG9SC273082

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2019 Jeep Grand Cherokee

Overland 4WD

94,700 kilometres

$27,999

Good Deal
Stouffville, ON
35 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:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
94,700
Stock number:
P1882A
VIN:
1C4RJFCG5KC542518

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2018 Jeep Grand Cherokee

Limited 4WD

110,271 kilometres

$23,200

Good Deal
Caledon, ON
57 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:
White
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
110,271
Stock number:
A406
VIN:
1C4RJFBG1JC417628

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2015 Jeep Grand Cherokee

Limited 4WD

260,800 kilometres

$8,995

Good Deal
Scarborough, ON
57 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:
260,800
Stock number:
260800++ - WE FINANCE EVRYONE
VIN:
1C4RJFBG6FC674467

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2022 Jeep Grand Cherokee

60,459 kilometres

$33,446

Good Deal
Lindsay, ON
43 km away
Year:
2022
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Engine:
293 hp 3.6L V6
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
60,459
Stock number:
25222A
VIN:
1C4RJFAG1NC163619

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2018 Jeep Grand Cherokee

Overland 4WD

154,160 kilometres

$17,995

Good Deal
Scarborough, ON
57 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:
White
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
154,160
Stock number:
154160++ - WE FINANCE EVRYONE
VIN:
1C4RJFCG1JC262612

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2021 Jeep Grand Cherokee

Overland 4WD

58,129 kilometres

$36,497

Good Deal
Richmond Hill, ON
44 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
Transmission:
Automatic
Mileage:
58,129
Stock number:
TY48740A
VIN:
1C4RJFCG1MC839398

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2021 Jeep Grand Cherokee

Limited 4WD

68,829 kilometres

$33,985

Fair Deal
Toronto, ON
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:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
68,829
Stock number:
36886A
VIN:
1C4RJFBG7MC651552

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