Jeep Pickups for Sale near Chesapeake, Virginia
Sort
Filters
973 results
Location
Body Type
Popular Body Types
Price
Mileage
Make, Model, and Trim
Year
Chassis Options
Add-Ons
State
Used 2025 Jeep Gladiator High Crew Cab
$39,003
speed 9,373 mi
sell
Key features
- Gasoline
- Pentastar 3.6L V-6 DOHC, variable valve control, regular gasoline, engine with 285HP
- 4WD
location_on
Ingersoll Auto of Danbury - Chevrolet
Danbury, CT (351.9 mi)
Used 2025 Jeep Gladiator Mojave Crew Cab
$45,997
speed 4,403 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Bowser Chevrolet of Beaver Falls
Beaver Falls, PA (353.8 mi)
Used 2022 Jeep Gladiator Sport Crew Cab
$29,749
speed 58,455 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
Ravenel Ford
Ravenel, SC (355.8 mi)
Used 2023 Jeep Gladiator Sport Crew Cab
$26,315
speed 73,055 mi
sell
Key features
- Gasoline
- 4WD
- Sport S
location_on
Parks GMC Greenville
Greenville, SC (367.8 mi)
Used 2022 Jeep Gladiator Overland Crew Cab
$32,815
speed 45,405 mi
sell
Key features
- Gasoline
- 4WD
- Overland
location_on
Parks GMC Greenville
Greenville, SC (367.8 mi)
Used 2021 Jeep Gladiator Mojave Crew Cab
$30,866
speed 77,140 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Diehl of Grove City
Grove City, PA (369.4 mi)
Used 2022 Jeep Gladiator Sport Crew Cab
$29,499
speed 35,214 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Executive Dodge Jeep Ram
Wallingford, CT (372.9 mi)
Used 2022 Jeep Gladiator Sport Crew Cab
$32,544
speed 21,507 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
Executive Dodge Jeep Ram
Wallingford, CT (372.9 mi)
Used 2022 Jeep Gladiator Mojave Crew Cab
$35,531
speed 36,060 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Executive Dodge Jeep Ram
Wallingford, CT (372.9 mi)
Used 2021 Jeep Gladiator Overland Crew Cab
$29,469
speed 46,806 mi
sell
Key features
- Gasoline
- 3.6L V-6 DOHC, variable valve control, regular gasoline, engine with 285HP
- 4WD
location_on
Richard Chevrolet
Cheshire, CT (373.8 mi)
Used 2022 Jeep Gladiator Overland Crew Cab
$33,537
speed 42,972 mi
sell
Key features
- Gasoline
- 4WD
- Overland
location_on
Shaker's Family Ford
Watertown, CT (374.3 mi)
Used 2021 Jeep Gladiator Rubicon Crew Cab
$39,621
speed 17,011 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
Ken Wilson Ford
Canton, NC (378.6 mi)
Used 2023 Jeep Gladiator Sport Crew Cab
$33,990 List Price
$33,589
speed 40,924 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
Litchfield Ford
Litchfield, CT (381.4 mi)
Used 2021 Jeep Gladiator Mojave Crew Cab
$35,750
speed 34,318 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Fairway Ford of Canfield
Canfield, OH (384.4 mi)
Used 2021 Jeep Gladiator Rubicon Crew Cab
$33,998
speed 48,453 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Herlong Ford
Edgefield, SC (385.1 mi)
Used 2021 Jeep Gladiator Sport Crew Cab
$22,687
speed 90,411 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Papa’s Chrysler Dodge Jeep RAM
New Britain, CT (386.6 mi)
Used 2025 Jeep Gladiator Rubicon Crew Cab
$45,900
speed 12,026 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Sarchione Ford of Alliance
Alliance, OH (389.7 mi)
Used 2020 Jeep Gladiator Rubicon Crew Cab
$29,500
speed 87,665 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Sarchione Ford
Randolph, OH (401.1 mi)
Used 2021 Jeep Gladiator Rubicon Crew Cab
$36,948
speed 44,185 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Sarchione Chevrolet
Randolph, OH (401.1 mi)
Used 2023 Jeep Gladiator Sport Crew Cab
$37,689 List Price
$34,999
speed 18,831 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Mitchell Selig Ford
Windsor, CT (401.2 mi)
Used 2022 Jeep Gladiator Rubicon Crew Cab
$38,899 List Price
$34,999
speed 59,761 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Mitchell Selig Ford
Windsor, CT (401.2 mi)
Used 2026 Jeep Gladiator Rubicon Crew Cab
contact for price
speed 17,350 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Mitchell Selig Ford
Windsor, CT (401.2 mi)
Used 2025 Jeep Gladiator Rubicon Crew Cab
$44,991
speed 15,508 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Gerald Jones Ford
Augusta, GA (401.4 mi)
Used 2023 Jeep Gladiator Sport Crew Cab
$32,050 List Price
$30,398
speed 45,571 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
Hugh White Chevrolet Buick
Lancaster, OH (401.8 mi)
Used 2021 Jeep Gladiator Sport Crew Cab
$34,050 List Price
$24,378
speed 140,531 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Hugh White Chevrolet Buick
Lancaster, OH (401.8 mi)
Used 2020 Jeep Gladiator Rubicon Crew Cab
$26,529
speed 114,950 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Coughlin GMC Newark
Newark, OH (406.4 mi)
Used 2020 Jeep Gladiator Rubicon Crew Cab
$26,529
speed 114,950 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Coughlin Chevrolet Newark
Newark, OH (406.4 mi)
Used 2020 Jeep Gladiator Sport Crew Cab
$44,995 List Price
$39,664
speed 29,483 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
Jeff Wyler Chevrolet Of Columbus
Canal Winchester, OH (413.4 mi)
Used 2025 Jeep Gladiator High Crew Cab
$38,974
speed 7,976 mi
sell
Key features
- Gasoline
- 4WD
- High Tide
location_on
Valley Chrysler Dodge Jeep Ram of Columbus
Pataskala, OH (413.6 mi)
Used 2025 Jeep Gladiator Mojave Crew Cab
$42,829
speed 15,085 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Coughlin Ford of Pataskala
Pataskala, OH (413.6 mi)
