Used Jeep Pickup Trucks for Sale in Winchester, ON

226 results

2023 Jeep Gladiator

Rubicon Crew Cab 4WD

39,187 km

$51,999

CarGurus partner

Year:: 2023
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: High Velocity
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Interior colour:: BLACK, LEATHER-FACED SEATS W/RUBICON & UTILITY GRI
Transmission:: Automatic
Mileage:: 39,187
Stock #:: T00188A
VIN:: 1C6JJTBG1PL568612

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2022 Jeep Gladiator

Willys Crew Cab 4WD

37,302 km

$40,995

CarGurus partner

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Red
Combined gas mileage:: 13 L/100km
Fuel type:: Gasoline
Interior colour:: Black
Transmission:: 6-Speed Manual
Mileage:: 37,302
Stock #:: 26-046
VIN:: 1C6HJTAG0NL125297

2021 Jeep Gladiator

Mojave Crew Cab 4WD

45,729 km

$43,934

CarGurus partner

Year:: 2021
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Gray
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Interior colour:: Black
Transmission:: Automatic
Mileage:: 45,729
Stock #:: 241441
VIN:: 1C6JJTEGXML552657

2024 Jeep Gladiator

NightHawk Crew Cab 4WD

13,347 km

$50,440

Great Deal

$799/mo est.

Home delivery from Terrebonne, QC

Price includes $145 shipping

CarGurus partner

Year:: 2024
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: White
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Interior colour:: Black
Transmission:: Automatic
Mileage:: 13,347
Stock #:: A-8264
VIN:: 1C6HJTAG5RL125639

2021 Jeep Gladiator

Rubicon Crew Cab 4WD

100,410 km

$36,495

CarGurus partner

Year:: 2021
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Red
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 100,410
Stock #:: HH26-246A
VIN:: 1C6JJTBGXML593813

Home delivery

2023 Jeep Gladiator

High Altitude Crew Cab 4WD

26,054 km

$50,288

Good Deal

$796/mo est.

Home delivery from Guelph, ON

Price includes $500 shipping

CarGurus partner

Year:: 2023
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Gray
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Interior colour:: Black
Transmission:: Automatic
Mileage:: 26,054
Stock #:: PL500256
VIN:: 1C6HJTFG5PL500256

Home delivery

2026 Jeep Gladiator

Willys '41 4dr Crew Cab 4WD

1,032 km

$60,030

Good Deal

$951/mo est.

Home delivery from Dollard-des-Ormeaux, QC

Price includes $250 shipping

CarGurus partner

Year:: 2026
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Black
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 1,032
Stock #:: D-260074
VIN:: 1C6PJTAG9TL155973

Home delivery

2022 Jeep Gladiator

High Altitude Crew Cab 4WD

125,211 km

$38,283

Good Deal

$606/mo est.

Home delivery from Mississauga, ON

Price includes $395 shipping

CarGurus partner

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Black
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Interior colour:: Black
Transmission:: Automatic
Mileage:: 125,211
Stock #:: um32796
VIN:: 1C6HJTFG8NL132796

Home delivery

2026 Jeep Gladiator

Sport S Crew Cab 4WD

1,100 km

$57,125

Good Deal

$905/mo est.

Home delivery from Dollard-des-Ormeaux, QC

Price includes $250 shipping

CarGurus partner

Year:: 2026
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Black
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 1,100
Stock #:: D-260169
VIN:: 1C6PJTAG0TL155974

Home delivery

2023 Jeep Gladiator

Mojave Crew Cab 4WD

34,444 km

$47,088

Good Deal

$746/mo est.

Home delivery from Guelph, ON

Price includes $500 shipping

CarGurus partner

Year:: 2023
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Gray
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Interior colour:: Black
Transmission:: Automatic
Mileage:: 34,444
Stock #:: PL532929
VIN:: 1C6JJTEGXPL532929

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Home delivery

2025 Jeep Gladiator

Sport S Crew Cab 4WD

1,352 km

$57,143

Good Deal

$905/mo est.

Home delivery from Mascouche, QC

Price includes $148 shipping

CarGurus partner

Year:: 2025
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Red
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 1,352
Stock #:: MW15126
VIN:: 1C6PJTAG3SL512627

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2022 Jeep Gladiator

Willys Crew Cab 4WD

37,302 km

$40,995

CarGurus partner

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Red
Combined gas mileage:: 13 L/100km
Fuel type:: Gasoline
Interior colour:: Black
Transmission:: 6-Speed Manual
Mileage:: 37,302
Stock #:: 26-046
VIN:: 1C6HJTAG0NL125297

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Home delivery

2023 Jeep Gladiator

Sport S Crew Cab 4WD

20,291 km

$42,440

Good Deal

$672/mo est.

Home delivery from Terrebonne, QC

Price includes $145 shipping

CarGurus partner

Year:: 2023
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: White
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Interior colour:: Black
Transmission:: Automatic
Mileage:: 20,291
Stock #:: A-8121
VIN:: 1C6JJTAG8PL541666

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2022 Jeep Gladiator

Sport S Crew Cab 4WD

134,042 km

$30,587

CarGurus partner

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Black
Combined gas mileage:: 13 L/100km
Fuel type:: Gasoline
Transmission:: Manual
Mileage:: 134,042
Stock #:: 67356A
VIN:: 1C6JJTAGXNL136289

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2022 Jeep Gladiator

Overland Crew Cab 4WD

65,541 km

$38,995

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Bright White
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 65,541
Stock #:: PR0140A
VIN:: 1C6HJTFG4NL178626

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2022 Jeep Gladiator

Sport S Crew Cab 4WD

53,770 km

$38,995

CarGurus partner

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Black
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Interior colour:: Black
Transmission:: Automatic
Mileage:: 53,770
Stock #:: 26-112
VIN:: 1C6JJTAG2NL109023

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2020 Jeep Gladiator

Sport Crew Cab 4WD

82,000 km

$32,995

CarGurus partner

Year:: 2020
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Gray
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 82,000
Stock #:: A2E3ED
VIN:: 1C6HJTAG0LL104267

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2026 Jeep Gladiator

Willys '41 4dr Crew Cab 4WD

9,000 km

$56,996

Year:: 2026
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Black
Fuel type:: Gasoline
Interior colour:: CLOTH LOW-BACK BUCKET SEATS
Transmission:: Automatic
Mileage:: 9,000
Stock #:: 26-065
VIN:: 1C6PJTAG5TL160992

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Home delivery

2020 Jeep Gladiator

Sport S Crew Cab 4WD

85,318 km

$30,840

Good Deal

$489/mo est.

Home delivery from Terrebonne, QC

Price includes $145 shipping

CarGurus partner

Year:: 2020
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Gray
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Interior colour:: Black
Transmission:: Automatic
Mileage:: 85,318
Stock #:: A-7924A
VIN:: 1C6HJTAGXLL104275

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Home delivery

2021 Jeep Gladiator

Mojave Crew Cab 4WD

78,045 km

$44,488

Fair Deal

$705/mo est.

Home delivery from Guelph, ON

Price includes $500 shipping

CarGurus partner

Year:: 2021
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Red
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Interior colour:: Gray
Transmission:: Automatic
Mileage:: 78,045
Stock #:: ML598683
VIN:: 1C6JJTEGXML598683

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Home delivery

2022 Jeep Gladiator

Overland Crew Cab 4WD

30,000 km

$43,476

Fair Deal

$689/mo est.

Home delivery from Québec, QC

Price includes $1,081 shipping

CarGurus partner

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Black
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Interior colour:: Brown (Beige)
Transmission:: Automatic
Mileage:: 30,000
Stock #:: 1t110a
VIN:: 1C6HJTFG6NL109419

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Home delivery

2021 Jeep Gladiator

Rubicon Crew Cab 4WD

54,603 km

$44,319

Fair Deal

$702/mo est.

Home delivery from Innisfil, ON

Price includes $1,419 shipping

CarGurus partner

Year:: 2021
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Granite Crystal Metallic
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Interior colour:: Black
Transmission:: Automatic
Mileage:: 54,603
Stock #:: 21-13212WFC
VIN:: 1C6JJTBG9ML613212

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Home delivery

2022 Jeep Gladiator

Sport S Crew Cab 4WD

41,000 km

$42,124

Fair Deal

$667/mo est.

Home delivery from Mississauga, ON

Price includes $699 shipping

CarGurus partner

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Gray
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Interior colour:: Black
Transmission:: Automatic
Mileage:: 41,000
Stock #:: T11522
VIN:: 1C6HJTAG1NL100652

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2021 Jeep Gladiator

Rubicon Crew Cab 4WD

100,410 km

$36,495

CarGurus partner

Year:: 2021
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior colour:: Red
Combined gas mileage:: 12 L/100km
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 100,410
Stock #:: HH26-246A
VIN:: 1C6JJTBGXML593813

Used Jeep Pickup Trucks for Sale in Winchester, ON

2023 Jeep Gladiator

$51,999

2022 Jeep Gladiator

$40,995

2021 Jeep Gladiator

$43,934

2024 Jeep Gladiator

$50,440

2021 Jeep Gladiator

$36,495

2023 Jeep Gladiator

$50,288

2026 Jeep Gladiator

$60,030

2022 Jeep Gladiator

$38,283

2026 Jeep Gladiator

$57,125

2023 Jeep Gladiator

$47,088

2025 Jeep Gladiator

$57,143

2022 Jeep Gladiator

$40,995

2023 Jeep Gladiator

$42,440

2022 Jeep Gladiator

$30,587

2022 Jeep Gladiator

$38,995

2022 Jeep Gladiator

$38,995

2020 Jeep Gladiator

$32,995

2026 Jeep Gladiator

$56,996

2020 Jeep Gladiator

$30,840

2021 Jeep Gladiator

$44,488

2022 Jeep Gladiator

$43,476

2021 Jeep Gladiator

$44,319

2022 Jeep Gladiator

$42,124

2021 Jeep Gladiator

$36,495

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