Used Jeep Pickup Trucks for Sale in Windermere, FL

575 results

Napleton Chrysler Jeep Dodge Ram Kissimmee

2022 Jeep Gladiator

Altitude Crew Cab 4WD

30,107 miles

$30,097

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Silver Zynith Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 30,107
Stock #:: L162806A
VIN:: 1C6HJTAG4NL162806

Sponsored by Napleton Chrysler Jeep Dodge Ram Kissimmee

2022 Jeep Gladiator

Willys Sport Crew Cab 4WD

41,439 miles

$30,394

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Hydro Blue Pearlcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 41,439
Stock #:: NL171593
VIN:: 1C6HJTAG3NL171593

2023 Jeep Gladiator

Mojave Crew Cab 4WD

39,884 miles

$37,874

Year:: 2023
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: High Velocity Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 39,884
Stock #:: P547554
VIN:: 1C6JJTEG2PL547554

2020 Jeep Gladiator

Sport Crew Cab 4WD

63,113 miles

$23,995

Year:: 2020
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Sting-Gray Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 63,113
Stock #:: 164547T
VIN:: 1C6HJTAG9LL164547

2023 Jeep Gladiator

Sport S Crew Cab 4WD

16,863 miles

$32,787

Good Deal

$623/mo est.

Manufacturer certified

Davenport, FL

19 mi away

Year:: 2023
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Hydro Blue Pearlcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 16,863
Stock #:: U763245B
VIN:: 1C6HJTAG3PL541184

2022 Jeep Gladiator

Overland Crew Cab 4WD

43,989 miles

$29,536

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Hydro Blue Pearlcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 43,989
Stock #:: 26H1147A
VIN:: 1C6HJTFG2NL154342

2021 Jeep Gladiator

Overland Crew Cab 4WD

59,996 miles

$27,948

Good Deal

$540/mo est.

Third-party certified

Dade City, FL

40 mi away

Year:: 2021
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Bright White Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 59,996
Stock #:: C630205A
VIN:: 1C6HJTFG3ML623050

2025 Jeep Gladiator

NightHawk Crew Cab 4WD

22,114 miles

$34,646

Year:: 2025
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Anvil Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 22,114
Stock #:: SL512455
VIN:: 1C6PJTAG0SL512455

2023 Jeep Gladiator

Willys Crew Cab 4WD

17,570 miles

$34,484

Year:: 2023
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Blue
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 17,570
Stock #:: PL555600
VIN:: 1C6HJTAG6PL555600

2025 Jeep Gladiator

Mojave Crew Cab 4WD

9,089 miles

$43,442

Year:: 2025
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Gray
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Green
Transmission:: Automatic
Mileage:: 9,089
Stock #:: SL524005
VIN:: 1C6RJTEG3SL524005

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2022 Jeep Gladiator

Rubicon Crew Cab 4WD

44,302 miles

$34,677

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Black Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 44,302
Stock #:: NL122805
VIN:: 1C6JJTBG0NL122805

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2021 Jeep Gladiator

Sport Crew Cab 4WD

64,450 miles

$24,999

Year:: 2021
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Bright White Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 64,450
Stock #:: 1T26285A
VIN:: 1C6HJTAG4ML508321

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2021 Jeep Gladiator

Sport Crew Cab 4WD

49,998 miles

$27,925

Year:: 2021
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Black Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 49,998
Stock #:: ML576859
VIN:: 1C6HJTAG4ML576859

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2025 Jeep Gladiator

NightHawk Crew Cab 4WD

24,928 miles

$37,907

Fair Deal

$708/mo est.

Manufacturer certified

Fruitland Park, FL

33 mi away

Year:: 2025
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: 41
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 24,928
Stock #:: C512397
VIN:: 1C6PJTAG1SL512397

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2020 Jeep Gladiator

Sport Crew Cab 4WD

44,961 miles

$26,999

Year:: 2020
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Gray (Granite Crystal Metallic Clearcoat)
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 44,961
Stock #:: 6T26526A
VIN:: 1C6HJTAG6LL161976

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2022 Jeep Gladiator

Rubicon Crew Cab 4WD

21,792 miles

$35,394

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Hydro Blue Pearlcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 21,792
Stock #:: NL101271
VIN:: 1C6JJTBG5NL101271

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2021 Jeep Gladiator

Rubicon Crew Cab 4WD

17,995 miles

$38,094

Year:: 2021
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Black
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 17,995
Stock #:: M2Y33117B
VIN:: 1C6JJTBG2ML615027

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2023 Jeep Gladiator

Mojave Crew Cab 4WD

40,228 miles

$37,565

Good Deal

$712/mo est.

Manufacturer certified

Fruitland Park, FL

33 mi away

Year:: 2023
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Sarge Green Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 40,228
Stock #:: L166429A
VIN:: 1C6JJTEGXPL501003

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2021 Jeep Gladiator

High Altitude Crew Cab 4WD

28,623 miles

$34,677

Good Deal

$672/mo est.

Manufacturer certified

Titusville, FL

46 mi away

Year:: 2021
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Bright White Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 28,623
Stock #:: ML562791
VIN:: 1C6HJTFG2ML562791

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2022 Jeep Gladiator

Altitude Crew Cab 4WD

30,107 miles

$30,097

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Silver Zynith Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 30,107
Stock #:: L162806A
VIN:: 1C6HJTAG4NL162806

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2022 Jeep Gladiator

Rubicon Crew Cab 4WD

33,691 miles

$36,231

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Black
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Manual
Mileage:: 33,691
Stock #:: NL137518
VIN:: 1C6JJTBG6NL137518

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2024 Jeep Gladiator

Mojave Crew Cab 4WD

30,567 miles

$40,084

Great Deal

$754/mo est.

Manufacturer certified

Orlando, FL

8 mi away

Year:: 2024
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Hydro Blue Pearlcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 30,567
Stock #:: L129856
VIN:: 1C6JJTEG6RL129856

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2021 Jeep Gladiator

Sport Crew Cab 4WD

46,084 miles

$27,295

Year:: 2021
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Black Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 46,084
Stock #:: ML598785A
VIN:: 1C6JJTAGXML598785

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2022 Jeep Gladiator

Rubicon Crew Cab 4WD

70,546 miles

$28,110

Year:: 2022
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Sarge Green Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 70,546
Stock #:: T0226
VIN:: 1C6JJTBG5NL177914

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Used Jeep Pickup Trucks for Sale in Windermere, FL

2022 Jeep Gladiator

$30,097

2022 Jeep Gladiator

$30,394

2023 Jeep Gladiator

$37,874

2020 Jeep Gladiator

$23,995

2023 Jeep Gladiator

$32,787

2022 Jeep Gladiator

$29,536

2021 Jeep Gladiator

$27,948

2025 Jeep Gladiator

$34,646

2023 Jeep Gladiator

$34,484

2025 Jeep Gladiator

$43,442

2022 Jeep Gladiator

$34,677

2021 Jeep Gladiator

$24,999

2021 Jeep Gladiator

$27,925

2025 Jeep Gladiator

$37,907

2020 Jeep Gladiator

$26,999

2022 Jeep Gladiator

$35,394

2021 Jeep Gladiator

$38,094

2023 Jeep Gladiator

$37,565

2021 Jeep Gladiator

$34,677

2022 Jeep Gladiator

$30,097

2022 Jeep Gladiator

$36,231

2024 Jeep Gladiator

$40,084

2021 Jeep Gladiator

$27,295

2022 Jeep Gladiator

$28,110

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