CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
  • Sell
    • Sell my car
    • Car values
  • Research
    • Test drive reviews
    • Price trends
    • Compare cars
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

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

330 results
Odessa, ON
2024 Jeep Grand Cherokee Limited 4WD Belanger Chrysler Dodge Jeep Ram

2024 Jeep Grand Cherokee

Limited 4WD

25,500 kilometres

$48,999

Fair Deal
Clarence-Rockland, ON
156 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:
Automatic
Mileage:
25,500
Stock number:
P3412
VIN:
1C4RJHBG0RC250993

Sponsored

2017 Jeep Grand Cherokee Laredo 4WD

2017 Jeep Grand Cherokee

Laredo 4WD

167,475 kilometres

$14,999

Fair Deal
Barrie, ON
235 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 (Burgundy)
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
167,475
Stock number:
762318
VIN:
1C4RJFAG7HC762318

Sponsored

2021 Jeep Grand Cherokee Summit 4WD

2021 Jeep Grand Cherokee

Summit 4WD

78,500 kilometres

$35,737

Fair Deal
Ottawa, ON
125 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:
78,500
Stock number:
A9627A
VIN:
1C4RJFJG9MC866528

Sponsored

2018 Jeep Grand Cherokee Altitude 4WD

2018 Jeep Grand Cherokee

Altitude 4WD

120,543 kilometres

$19,900

Great Deal
Papineauville, QC
193 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
Combined gas mileage:
11 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
120,543
Stock number:
25-178a
VIN:
1C4RJFAG8JC292452

2015 Jeep Grand Cherokee Laredo 4WD

2015 Jeep Grand Cherokee

Laredo 4WD

136,816 kilometres

$9,888

Great Deal
Newmarket, ON
222 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

2017 Jeep Grand Cherokee Trailhawk 4WD

2017 Jeep Grand Cherokee

Trailhawk 4WD

160,000 kilometres

$18,995

Great Deal
Ottawa, ON
98 km away
Year:
2017
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Transmission:
Automatic
Mileage:
160,000
Stock number:
8013
VIN:
1C4RJFLG0HC621135

Preparing for a close up...

Photos coming soon

2019 Jeep Grand Cherokee

Altitude 4WD

186,231 kilometres

$13,888

Great Deal
Toronto, ON
239 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
Interior colour:
Black
Transmission:
Automatic
Mileage:
186,231
Stock number:
R60420
VIN:
1C4RJFAG4KC762641

Preparing for a close up...

Photos coming soon

2018 Jeep Grand Cherokee

Overland 4WD

154,160 kilometres

$17,995

Great Deal
Scarborough, ON
215 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

Preparing for a close up...

Photos coming soon

2020 Jeep Grand Cherokee

Altitude 4WD

64,402 kilometres

$25,995

Great Deal
Embrun, ON
134 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:
64,402
Stock number:
U3354
VIN:
1C4RJFAG2LC257599

Preparing for a close up...

Photos coming soon

2015 Jeep Grand Cherokee

Limited 4WD

134,259 kilometres

$12,888

Great Deal
North York, ON
238 km away
Year:
2015
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Interior colour:
Black
Transmission:
Automatic
Mileage:
134,259
Stock number:
200887
VIN:
1C4RJFBG2FC876260

Preparing for a close up...

Photos coming soon

2017 Jeep Grand Cherokee

Overland 4WD

149,684 kilometres

$18,994

Great Deal
Barrie, ON
237 km away
Year:
2017
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Gray
Transmission:
Automatic
Mileage:
149,684
Stock number:
39430B
VIN:
1C4RJFCGXHC848851

Preparing for a close up...

Photos coming soon

2024 Jeep Grand Cherokee

Altitude 4WD

26,005 kilometres

$41,988

Great Deal
Peterborough, ON
131 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:
Automatic
Mileage:
26,005
Stock number:
728HPUAA
VIN:
1C4RJHAG8RC205964

Preparing for a close up...

Photos coming soon

2016 Jeep Grand Cherokee

Limited 4WD

234,929 kilometres

$9,499

Great Deal
Newmarket, ON
223 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

Preparing for a close up...

Photos coming soon

2015 Jeep Grand Cherokee

Limited 4WD

240,908 kilometres

$7,990

Great Deal
Etobicoke, ON
248 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

Preparing for a close up...

Photos coming soon

2019 Jeep Grand Cherokee

Altitude 4WD

95,339 kilometres

$20,995

Great Deal
Scarborough, ON
223 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

Preparing for a close up...

Photos coming soon

2011 Jeep Grand Cherokee

Limited 4WD

183,920 kilometres

$8,498

Great Deal
Vaughan, ON
247 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:
Blue
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
183,920
Stock number:
537670
VIN:
1J4RR4GG6BC537670

Preparing for a close up...

Photos coming soon

2022 Jeep Grand Cherokee

73,701 kilometres

$36,300

Great Deal
Etobicoke, ON
248 km away
Year:
2022
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
Gray
Transmission:
8-Speed Automatic
Mileage:
73,701
Stock number:
OP3328
VIN:
1C4RJFAG8NC142315

Preparing for a close up...

Photos coming soon

2019 Jeep Grand Cherokee

Limited 4WD

112,700 kilometres

$21,999

Great Deal
North York, ON
239 km away
Year:
2019
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Transmission:
Automatic
Mileage:
112,700
Stock number:
10072503
VIN:
1C4RJFBG2KC664982

Preparing for a close up...

Photos coming soon

2023 Jeep Grand Cherokee

38,724 kilometres

$39,998

Great Deal
Pickering, ON
208 km away
Year:
2023
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Exterior colour:
Red
Transmission:
8-Speed Automatic
Mileage:
38,724
Stock number:
JC26013A
VIN:
1C4RJHAG6PC619533

Preparing for a close up...

Photos coming soon

2021 Jeep Grand Cherokee

Limited X 4WD

97,587 kilometres

$31,500

Great Deal
Huntsville, ON
211 km away
Year:
2021
Make:
Jeep
Model:
Grand Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
97,587
Stock number:
T70MA012
VIN:
1C4RJFBG6MC711207

Preparing for a close up...

Photos coming soon

2017 Jeep Grand Cherokee

Limited 4WD

197,828 kilometres

$10,888

Great Deal
Newmarket, ON
226 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

Preparing for a close up...

Photos coming soon

2015 Jeep Grand Cherokee

Summit 4WD

206,323 kilometres

$10,998

Great Deal
Pickering, ON
208 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

Preparing for a close up...

Photos coming soon

2019 Jeep Grand Cherokee

Overland 4WD

118,071 kilometres

$17,995

Great Deal
Scarborough, ON
223 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

Preparing for a close up...

Photos coming soon

2024 Jeep Grand Cherokee

Limited 4WD

74,764 kilometres

$39,995

Fair Deal
Clarington, ON
174 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:
74,764
Stock number:
R06A6470
VIN:
1C4RJHBG9RC148253

Sponsored

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

  • 2011 Jeep Grand Cherokee Overland in Sydenham ON

  • 2009 Jeep Grand Cherokee Overland in Sydenham ON

  • 2007 Jeep Grand Cherokee Overland in Sydenham ON

  • 2006 Jeep Grand Cherokee Overland in Sydenham ON

  • All Used Cars

  • Cheap Cars

  • Manual Transmission Cars

  • Sports Cars

  • Hybrid Cars

  • Red Interior Cars

  • Electric Cars

  • Small Cars

  • AWD Cars

  • Cheap Automatic Transmission Cars

  • Classic Trucks

  • Conversion Vans

  • Three Quarter Ton Trucks

  • Diesel Trucks

  • Small Trucks

  • Chevrolet Diesel Trucks

  • Manual Diesel Trucks

  • One Ton Trucks

  • Cheap Trucks

  • Ford Trucks

  • Cheap SUVs

  • Mercedes-Benz Convertibles

  • Ford Diesel Trucks

  • Mercedes-Benz SUVs

  • BMW Convertibles

  • Chevrolet SUVs

  • Toyota SUVs

  • Nissan SUVs

  • Used Cars Under $10,000

  • Used Cars Under $5,000

  • Used Sedans for Sale with Low Mileage in Sydenham

  • Used SUVs / Crossovers for Sale with Low Mileage in Sydenham

  • Used Hatchbacks for Sale with Low Mileage in Sydenham

  • Used Convertibles for Sale with Low Mileage in Sydenham

  • Used Vans for Sale with Low Mileage in Sydenham

  • Used Minivans for Sale with Low Mileage in Sydenham

  • Used Pickup Trucks for Sale with Low Mileage in Sydenham

  • Used Coupes for Sale with Low Mileage in Sydenham

  • Used Wagons for Sale with Low Mileage in Sydenham

  • Kingston Dodge Chrysler Ltd

  • McKeown Motor Sales

  • Beattie Dodge Chrysler Ltd

  • Hinton Dodge Chrysler Jeep

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2026 CarGurus, Inc., All Rights Reserved.