Used Jeep Pickup Trucks for Sale inWinchester, VA
685 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Blue Pearl
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 40,535
- Stock #:
- P6310B
- VIN:
- 1C6JJTEG1RL119297
Sponsored by Ourisman Chevrolet of Rockville
2024 Jeep Gladiator
Mojave Crew Cab 4WD
40,535 mi
Rockville, MD
56 mi away
Good Deal
$39,500
- 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:
- Red
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 37,874
- Stock #:
- BJ1411R
- VIN:
- 1C6HJTFG1LL138176
Sponsored Listing
2020 Jeep Gladiator
Overland Crew Cab 4WD
37,874 mi
Westminster, MD
70 mi away
Fair Deal
$30,299
- 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:
- Crystal Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 56,211
- Stock #:
- 31005P
- VIN:
- 1C6HJTAG0PL539389
Sponsored Listing
2023 Jeep Gladiator
Sport Crew Cab 4WD
56,211 mi
Glen Burnie, MD
83 mi away
Good Deal
$27,999
- 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:
- 43,458
- Stock #:
- NL139743
- VIN:
- 1C6HJTAG1NL139743
2022 Jeep Gladiator
Willys Crew Cab 4WD
43,458 mi
Winchester, VA
4 mi away
Good Deal
$29,899
- 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:
- 95,114
- Stock #:
- PML510778
- VIN:
- 1C6HJTAG4ML510778
2021 Jeep Gladiator
80th Anniversary Edition Crew Cab 4WD
95,114 mi
Martinsburg, WV
22 mi away
Good Deal
$23,494
- 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:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 62,637
- Stock #:
- 3082342B
- VIN:
- 1C6JJTBG1LL136600
2020 Jeep Gladiator
Rubicon Crew Cab 4WD
62,637 mi
Glen Burnie, MD
83 mi away
Great Deal
$26,799
- 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:
- Red
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 34,565
- Stock #:
- 28990947
- VIN:
- 1C6JJTEG9ML607597
2021 Jeep Gladiator
Mojave Crew Cab 4WD
34,565 mi
Store transfer to Sterling, VA
Price includes $1,999 shipping
Good Deal
$34,997
- 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:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 46,837
- Stock #:
- ZLL170264
- VIN:
- 1C6HJTAG5LL170264
2020 Jeep Gladiator
Sport S Crew Cab 4WD
46,837 mi
Chambersburg, PA
60 mi away
Good Deal
$25,978
- 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:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 21,200
- Stock #:
- TNL131943
- VIN:
- 1C6HJTAG2NL131943
2022 Jeep Gladiator
Willys Sport Crew Cab 4WD
21,200 mi
Martinsburg, WV
22 mi away
Good Deal
$30,390
- Year:
- 2021
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 260 hp 3L V6 Diesel
- Exterior color:
- Sting-Gray Clearcoat
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 71,595
- Stock #:
- UP534982
- VIN:
- 1C6JJTBM5ML534982
2021 Jeep Gladiator
Rubicon Crew Cab 4WD
71,595 mi
Mc Connellsburg, PA
55 mi away
Fair Deal
$35,485
- 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:
- Bright White Clear Coat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 51,800
- VIN:
- 1C6HJTAG4PL533921
2023 Jeep Gladiator
Sport S Crew Cab 4WD
51,800 mi
Sterling, VA
41 mi away
Good Deal
$26,945
- 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:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 13,545
- Stock #:
- BW81998B
- VIN:
- 1C6HJTAG7RL131250
2024 Jeep Gladiator
Sport Crew Cab 4WD
13,545 mi
Suitland, MD
71 mi away
Fair Deal
$33,495
- 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:
- Gray (Granite Crystal Metallic Clearcoat)
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 50,151
- Stock #:
- L26446A
- VIN:
- 1C6JJTAG6NL150402
2022 Jeep Gladiator
Sport Crew Cab 4WD
50,151 mi
Leesburg, VA
34 mi away
Fair Deal
$29,495
- 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:
- 16,100
- Stock #:
- 28737A
- VIN:
- 1C6RJTBG6SL503458
New arrival
2025 Jeep Gladiator
Rubicon Crew Cab 4WD
16,100 mi
Harrisonburg, VA
65 mi away
Great Deal
$40,594
- 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:
- Mojito
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 7,054
- Stock #:
- 26625A
- VIN:
- 1C6PJTAG9SL541260
2025 Jeep Gladiator
High Tide Crew Cab 4WD
7,054 mi
Glen Burnie, MD
83 mi away
Fair Deal
$39,699
- 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:
- Black Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 77,047
- Stock #:
- D20135
- VIN:
- 1C6JJTBGXLL211066
2020 Jeep Gladiator
Rubicon Crew Cab 4WD
77,047 mi
Fredericksburg, VA
73 mi away
Great Deal
$27,495
- 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:
- Gray (Granite Crystal Metallic Clearcoat)
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 38,989
- Stock #:
- 26GT126B
- VIN:
- 1C6HJTAG7NL159107
2022 Jeep Gladiator
Sport S Crew Cab 4WD
38,989 mi
Altoona, PA
91 mi away
Good Deal
$28,987
- 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:
- Firecracker Red Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 50,591
- Stock #:
- CRL122883A
- VIN:
- 1C6HJTAG1RL122883
2024 Jeep Gladiator
Sport Crew Cab 4WD
50,591 mi
Chantilly, VA
42 mi away
Good Deal
$30,724
- 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:
- Brown (Gobi Clearcoat)
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 78,416
- Stock #:
- LL200712A
- VIN:
- 1C6JJTBG4LL200712
New arrival
2020 Jeep Gladiator
Rubicon Crew Cab 4WD
78,416 mi
Chantilly, VA
42 mi away
Fair Deal
$29,949
- 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:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 6,458
- Stock #:
- 4599A
- VIN:
- 1C6PJTAG2SL540922
2025 Jeep Gladiator
High Tide Crew Cab 4WD
6,458 mi
Cockeysville, MD
84 mi away
Fair Deal
$39,791
- 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:
- Billet Silver Metallic Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 29,933
- Stock #:
- N1L0103
- VIN:
- 1C6HJTAG6ML523967
Price drop
-$2,400
2021 Jeep Gladiator
Sport Crew Cab 4WD
29,933 mi
Derwood, MD
54 mi away
Good Deal
$29,800
$28,200
- 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:
- Black Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 46,237
- Stock #:
- B476217A
- VIN:
- 1C6HJTFG6PL573443
2023 Jeep Gladiator
High Altitude Crew Cab 4WD
46,237 mi
Suitland, MD
71 mi away
Good Deal
$33,300
- 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:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 58,264
- Stock #:
- B34974
- VIN:
- 1C6HJTFG3PL560813
Price drop
-$1,202
2023 Jeep Gladiator
Overland Crew Cab 4WD
58,264 mi
Waynesboro, PA
52 mi away
Great Deal
$30,590
$29,388
- Year:
- 2026
- 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:
- 19,234
- Stock #:
- BC1035
- VIN:
- 1C6RJTEG6TL160678
Price drop
-$5,200
Sponsored Listing
2026 Jeep Gladiator
Mojave Crew Cab 4WD
19,234 mi
Clarksville, MD
66 mi away
Good Deal
$46,700
$41,500
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