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Used Jeep Grand Cherokee for Sale near Windermere, ON

448 results
Windermere, ON
2012 Jeep Grand Cherokee Overland 4WD Credit Auto Sales

2012 Jeep Grand Cherokee

Overland 4WD

199,885 kilometres

$11,999

Fair Deal
Toronto, ON
155 km away
Year:
2012
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Transmission:
Automatic
Mileage:
199,885
Stock number:
100888
VIN:
1C4RJFCT8CC100888

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2014 Jeep Grand Cherokee Summit 4WD

2014 Jeep Grand Cherokee

Summit 4WD

253,598 kilometres

$10,988

Fair Deal
Concord, ON
150 km away
Year:
2014
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
241 hp 3L V6 Diesel
Exterior colour:
Gray
Combined gas mileage:
10 L/100km
Fuel type:
Diesel
Transmission:
Automatic
Mileage:
253,598
Stock number:
P3742
VIN:
1C4RJFJM2EC333136

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2020 Jeep Grand Cherokee Limited 4WD

2020 Jeep Grand Cherokee

Limited 4WD

112,145 kilometres

$29,088

Fair Deal
Markham, ON
143 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:
112,145
Stock number:
2948
VIN:
1C4RJFBG5LC106982

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2020 Jeep Grand Cherokee Limited 4WD

2020 Jeep Grand Cherokee

Limited 4WD

77,796 kilometres

$26,995

Great Deal
Mississauga, ON
169 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:
77,796
Stock number:
17261A
VIN:
1C4RJFBG5LC343150

2022 Jeep Grand Cherokee Limited 4WD

2022 Jeep Grand Cherokee

Limited 4WD

103,823 kilometres

$29,995

Great Deal
Cambridge, ON
208 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:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
103,823
Stock number:
s3790
VIN:
1C4RJHBG9N8550819

2015 Jeep Grand Cherokee Laredo 4WD

2015 Jeep Grand Cherokee

Laredo 4WD

89,518 kilometres

$12,788

Great Deal
Newmarket, ON
119 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:
89,518
Stock number:
P0686
VIN:
1C4RJFAG8FC636533

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2021 Jeep Grand Cherokee

Altitude 4WD

124,410 kilometres

$22,488

Great Deal
Mississauga, ON
175 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
White
Transmission:
Automatic
Mileage:
124,410
Stock number:
L7170
VIN:
1C4RJFAG8MC685744

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2022 Jeep Grand Cherokee

Summit Reserve 4WD

80,500 kilometres

$43,988

Great Deal
Barrie, ON
94 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:
Red
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
80,500
Stock number:
A0500C
VIN:
1C4RJHET9N8501550

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2022 Jeep Grand Cherokee

Limited 4WD

60,641 kilometres

$33,888

Great Deal
Newmarket, ON
122 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:
Silver
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
60,641
Stock number:
28166P
VIN:
1C4RJHBG1N8602685

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2019 Jeep Grand Cherokee

Limited 4WD

112,700 kilometres

$22,800

Great Deal
North York, ON
153 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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2021 Jeep Grand Cherokee

Limited 4WD

79,474 kilometres

$28,990

Great Deal
171 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
Interior colour:
Black
Transmission:
Automatic
Mileage:
79,474
Stock number:
72609
VIN:
1C4RJFBG0MC504425

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2023 Jeep Grand Cherokee

Limited 4WD

36,678 kilometres

$38,495

Great Deal
Store transfer to North Bay, ON
281 km away • Price includes $0 shipping Price includes $0 shipping
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:
8-Speed Automatic
Mileage:
36,678
Stock number:
251613
VIN:
1C4RJHBG8PC526320

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2023 Jeep Grand Cherokee

Limited 4WD

59,293 kilometres

$34,999

Great Deal
Toronto, ON
161 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:
Silver
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
59,293
Stock number:
43740A
VIN:
1C4RJHBG2PC632262

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2025 Jeep Grand Cherokee

11,000 kilometres

$48,884

Great Deal
Woodstock, ON
247 km away
Year:
2025
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Engine:
293 hp 3.6L V6
Exterior colour:
Bright White Clearcoat
Fuel type:
Gasoline
Interior colour:
Global Black w/Global Black
Transmission:
Automatic
Mileage:
11,000
Stock number:
114WNNA
VIN:
1C4RJHAG5SC351258

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2023 Jeep Grand Cherokee

Altitude 4WD

96,000 kilometres

$30,888

Great Deal
Woodbridge, ON
153 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:
96,000
Stock number:
33327125
VIN:
1C4RJHAG3PC551482

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2023 Jeep Grand Cherokee

Limited 4WD

76,285 kilometres

$32,542

Great Deal
Mississauga, ON
168 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:
76,285
Stock number:
U5405
VIN:
1C4RJHBG0PC627142

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2023 Jeep Grand Cherokee

Limited 4WD

88,347 kilometres

$31,699

Great Deal
Barrie, 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:
Red
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
88,347
Stock number:
K0324
VIN:
1C4RJHBGXPC539313

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2021 Jeep Grand Cherokee

Altitude 4WD

100,321 kilometres

$24,922

Great Deal
Brampton, ON
166 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
Gray
Transmission:
Automatic
Mileage:
100,321
Stock number:
635454
VIN:
1C4RJFAG2MC635454

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2021 Jeep Grand Cherokee

Limited X 4WD

99,318 kilometres

$30,999

Great Deal
Kitchener, ON
208 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
Interior colour:
Black
Transmission:
Automatic
Mileage:
99,318
Stock number:
4751
VIN:
1C4RJFBGXMC820995

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2022 Jeep Grand Cherokee

Limited 4WD

71,341 kilometres

$31,298

Great Deal
Kitchener, ON
209 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:
Black
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
71,341
Stock number:
176690AX
VIN:
1C4RJFBG8NC140952

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2025 Jeep Grand Cherokee

Summit Reserve 4WD

1,200 kilometres

$71,995

Great Deal
Mississauga, ON
179 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:
8-Speed Automatic
Mileage:
1,200
Stock number:
250788 (BRENDA)DMO
VIN:
1C4RJHEGXS8751006

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2019 Jeep Grand Cherokee

Overland 4WD

118,071 kilometres

$19,995

Great Deal
Scarborough, ON
151 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

Laredo 4WD

23,060 kilometres

$45,760

Fair Deal
Uxbridge, ON
120 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:
8-Speed Automatic
Mileage:
23,060
Stock number:
W9161
VIN:
1C4RJHAG2RC205989

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

4.4 Overall rating

(5 reviews)
maria r
5.0
Reviewed a 2007 Jeep Overland 4WD on Aug. 12, 2012

I love this car, great on and off the road, handles great, very reliable in the snow, great power and great sound system. We bought this car brand new from the dealer and had no problems. The metallic paint still looks brand new.

Anonymous
4.0
Reviewed a 2007 Jeep Overland on Sep. 16, 2008

Great vehicle overall. It is a Jeep so it can get up the mountain like no other. However. It has so many gadgets in it that cost so much to replace that I am scared to take it on anything other then the asphalt. Have had just a couple of problems with it, but nothing major that wasn't my fault. :)

Gary H
5.0
Reviewed a 2007 Jeep Overland on Feb. 28, 2009

Really it is the best four wheel vehicle I've ever owned. It goes anywhere, has ever feature I've ever wanted, especially like the back up camera when hooking up the trailer, and the satellite radio. If you keep it under 60mph, you'll get almost 20mpg or so. If you need to pass, it will kick in like a vette and toss you back in your seat. I'm trying to think of something negative about it but just can't at the moment. Oh maybe a power rear hatch would be a nice addition

Mathew W
4.0
Reviewed a 2007 Jeep Overland on Mar. 22, 2008

For the amount of money you pay for this vehicle i think there are a few cut backs, but i love it

Paul V
4.0
Reviewed a 2007 Jeep Overland on May 10, 2009

Older american design suspension slightly dissappointing when compared to European SUV makes but the grant of 500 Nm of torque will see you through most sticky situations. Although suspention is noisy which I dislike. The 5.7 litre V8 is a blast though. Also has a smooth transmission although do not like the sequential in low range.

  • 2009 Jeep Grand Cherokee Overland in Windermere ON

  • 2008 Jeep Grand Cherokee Overland in Windermere ON

  • 2006 Jeep Grand Cherokee Overland in Windermere ON

  • 2004 Jeep Grand Cherokee Overland in Windermere ON

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