Jeep Pickups for Sale near Chesapeake, Virginia
Sort
Filters
975 results
Location
Body Type
Popular Body Types
Price
Mileage
Make, Model, and Trim
Year
Chassis Options
Add-Ons
State
Used 2022 Jeep Gladiator Sport Crew Cab
$30,995 List Price
$27,797
speed 86,076 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
Long-Lewis Chevrolet of the Shoals
Tuscumbia, AL (662.3 mi)
(256) 978-2346
Used 2023 Jeep Gladiator Overland Crew Cab
$34,275 List Price
$28,989
speed 79,042 mi
sell
Key features
- Gasoline
- 4WD
- Overland
location_on
Long-Lewis Chevrolet of the Shoals
Tuscumbia, AL (662.3 mi)
(256) 978-2346
Used 2024 Jeep Gladiator Mojave Crew Cab
$46,850 List Price
$42,999
speed 26,824 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Long-Lewis Chevrolet of the Shoals
Tuscumbia, AL (662.3 mi)
(256) 978-2346
Used 2023 Jeep Gladiator Overland Crew Cab
$35,925 List Price
$34,933
speed 30,925 mi
sell
Key features
- Gasoline
- 4WD
- Overland
location_on
Long-Lewis Chevrolet of the Shoals
Tuscumbia, AL (662.3 mi)
(256) 978-2346
Used 2025 Jeep Gladiator Sport Crew Cab
$36,547
speed 14,000 mi
sell
Key features
- Gasoline
- Regular Gasoline V-6 3.6 L/220
- 4WD
location_on
Michigan City Ford
Michigan City, IN (663.7 mi)
Used 2025 Jeep Gladiator Sport Crew Cab
$37,169
speed 9,546 mi
sell
Key features
- Gasoline
- 4WD
- Sport S
location_on
Vatland Chrysler Dodge Jeep Ram
Vero Beach, FL (678 mi)
(772) 247-6240
Used 2025 Jeep Gladiator Sport Crew Cab
$34,203
speed 23,577 mi
sell
Key features
- Gasoline
- 4WD
- Nighthawk
location_on
Vatland Chrysler Dodge Jeep Ram
Vero Beach, FL (678 mi)
(772) 247-6240
Used 2021 Jeep Gladiator Sport Crew Cab
$25,634
speed 105,784 mi
sell
Key features
- Diesel
- 4WD
- Willys
location_on
Preferred Ford
Grand Haven, MI (679.7 mi)
(616) 207-1972
Used 2022 Jeep Gladiator Overland Crew Cab
$39,575 List Price
$32,485
speed 39,316 mi
sell
Key features
- Gasoline
- 4WD
- Overland
location_on
Sunrise Ford
Fort Pierce, FL (691.1 mi)
(772) 773-1856
Used 2023 Jeep Gladiator Overland Crew Cab
$36,514 List Price
$31,997
speed 13,038 mi
sell
Key features
- Gasoline
- 3.6L V6 24V MPFI DOH
- 4WD
location_on
Sunrise Ford
Fort Pierce, FL (691.1 mi)
(772) 773-1856
Used 2024 Jeep Gladiator Sport Crew Cab
$35,006
speed 3,886 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Arrigo Dodge Chrysler Jeep Ram - Fort Pierce
Fort Pierce, FL (691.1 mi)
(855) 785-1062
Used 2022 Jeep Gladiator Sport Crew Cab
$28,078
speed 64,163 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Arrigo Dodge Chrysler Jeep Ram - Fort Pierce
Fort Pierce, FL (691.1 mi)
(855) 785-1062
Used 2022 Jeep Gladiator Rubicon Crew Cab
contact for price
speed 29,468 mi
sell
Key features
- Diesel
- Intercooled Turbo Diesel V-6 3.0 L/182
- 4WD
location_on
Stingray Chevrolet
Plant City, FL (694.4 mi)
(813) 981-1089
Used 2023 Jeep Gladiator Sport Crew Cab
$33,783
speed 45,399 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Taylor Chrysler Jeep Dodge
Bourbonnais, IL (694.8 mi)
Used 2025 Jeep Gladiator Mojave Crew Cab
$41,599
speed 17,656 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Gator Ford
Seffner, FL (700.2 mi)
(813) 592-3352
Used 2023 Jeep Gladiator Rubicon Crew Cab
$36,841
speed 21,305 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Chrysler Dodge Jeep Ram of Tampa Bay
Tampa, FL (701.5 mi)
(813) 548-3762
Used 2024 Jeep Gladiator Sport Crew Cab
$35,198
speed 31,611 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
Ferman Chevrolet on North Dale Mabry
Tampa, FL (702 mi)
(813) 212-3768
Used 2025 Jeep Gladiator Rubicon Crew Cab
contact for price
speed 14,907 mi
sell
Key features
- Gasoline
- 3.6L V6 Cylinder Engine
- 4WD
location_on
Ford Square of Mount Vernon
Mt. Vernon, IL (702 mi)
(618) 432-1575
Used 2025 Jeep Gladiator Rubicon Crew Cab
$46,990
speed 9,617 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Bettenhausen CDJR of Tinley Park
Tinley Park, IL (702.7 mi)
(815) 524-1446
Used 2021 Jeep Gladiator Sport Crew Cab
$26,087
speed 70,253 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
Ferman Chevrolet
Tampa, FL (707.5 mi)
(813) 412-6451
Used 2024 Jeep Gladiator Sport Crew Cab
$55,625 List Price
$34,764
speed 32,265 mi
sell
Key features
- Gasoline
- Regular Gasoline V-6 3.6 L/220
- 4WD
location_on
Brandon Ford
Tampa, FL (707.5 mi)
(813) 981-1471
Used 2023 Jeep Gladiator Sport Crew Cab
$29,387
speed 63,878 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
Ferman Chevrolet
Tampa, FL (707.5 mi)
(813) 412-6451
Used 2023 Jeep Gladiator Sport Crew Cab
$28,609
speed 25,217 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
Jerry Ulm Chrysler Dodge Jeep Ram
Tampa, FL (710.2 mi)
(813) 548-3648
Used 2024 Jeep Gladiator Mojave Crew Cab
$39,400
speed 17,594 mi
sell
Key features
- Gasoline
- Regular Gasoline V-6 3.6 L/220
- 4WD
location_on
Jerry Ulm Chrysler Dodge Jeep Ram
Tampa, FL (710.2 mi)
(813) 548-3648
Used 2025 Jeep Gladiator High Crew Cab
$37,643
speed 16,327 mi
sell
Key features
- Gasoline
- Regular Gasoline V-6 3.6 L/220
- 4WD
location_on
Jerry Ulm Chrysler Dodge Jeep Ram
Tampa, FL (710.2 mi)
(813) 548-3648
Used 2023 Jeep Gladiator Rubicon Crew Cab
$30,310
speed 65,360 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
Jerry Ulm Chrysler Dodge Jeep Ram
Tampa, FL (710.2 mi)
(813) 548-3648
Used 2023 Jeep Gladiator Sport Crew Cab
$35,198
speed 30,469 mi
sell
Key features
- Diesel
- Intercooled Turbo Diesel V-6 3.0 L/182
- 4WD
location_on
Jerry Ulm Chrysler Dodge Jeep Ram
Tampa, FL (710.2 mi)
(813) 548-3648
Used 2024 Jeep Gladiator Sport Crew Cab
$33,786
speed 14,147 mi
sell
Key features
- Gasoline
- Regular Gasoline V-6 3.6 L/220
- 4WD
location_on
Jerry Ulm Chrysler Dodge Jeep Ram
Tampa, FL (710.2 mi)
(813) 548-3648
Used 2023 Jeep Gladiator Mojave Crew Cab
$35,986
speed 37,792 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Gilbert Ford
Okeechobee, FL (711.6 mi)
(863) 220-9536
Used 2022 Jeep Gladiator Sport Crew Cab
$28,098
speed 54,219 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Gilbert Ford
Okeechobee, FL (711.6 mi)
(863) 220-9536
