Jeep Pickups for Sale near Cheshire, Connecticut
Sort
Filters
979 results
Location
Body Type
Popular Body Types
Price
Mileage
Make, Model, and Trim
Year
Chassis Options
Add-Ons
State
Used 2024 Jeep Gladiator Sport Crew Cab
$35,995
speed 16,899 mi
sell
Key features
- Gasoline
- V6, 3.6L
- 4WD
location_on
Red River Chrysler Dodge Jeep Ram of Heber Springs
Heber Springs, AR (1,110.8 mi)
(501) 302-4084
Used 2026 Jeep Gladiator Sport Crew Cab
$39,950
speed 1,316 mi
sell
Key features
- Gasoline
- V6, 3.6L
- 4WD
location_on
Red River Chrysler Dodge Jeep Ram of Heber Springs
Heber Springs, AR (1,110.8 mi)
(501) 302-4084
Used 2024 Jeep Gladiator Sport Crew Cab
$34,875
speed 47,245 mi
sell
Key features
- Gasoline
- V6, 3.6L
- 4WD
location_on
Red River Chrysler Dodge Jeep Ram of Heber Springs
Heber Springs, AR (1,110.8 mi)
(501) 302-4084
Used 2024 Jeep Gladiator Sport Crew Cab
$35,677
speed 18,318 mi
sell
Key features
- Gasoline
- Pentastar 3.6L V-6 DOHC, variable valve control, regular unleaded, engine with 285HP
- 4x4
location_on
Pete Moore Chevrolet
Pensacola, FL (1,112 mi)
(850) 805-8546
Used 2023 Jeep Gladiator Sport Crew Cab
$36,000 List Price
$26,199
speed 50,439 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
Cox Chevrolet
Bradenton, FL (1,115.8 mi)
(941) 315-6080
Used 2022 Jeep Gladiator Sport Crew Cab
$34,660 List Price
$29,199
speed 29,532 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
Cox Chevrolet
Bradenton, FL (1,115.8 mi)
(941) 315-6080
Used 2021 Jeep Gladiator Sport Crew Cab
$26,266
speed 54,814 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Grieco Ford of Delray Beach
Delray Beach, FL (1,116.6 mi)
(561) 933-9349
Used 2026 Jeep Gladiator Mojave Crew Cab
contact for price
speed 14,843 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Schumacher Chrysler Dodge Jeep Ram of Delray
Delray Beach, FL (1,116.6 mi)
Used 2020 Jeep Gladiator Overland Crew Cab
$26,708
speed 27,235 mi
sell
Key features
- Gasoline
- 4WD
- Overland
location_on
Grieco Ford of Delray Beach
Delray Beach, FL (1,116.6 mi)
(561) 933-9349
Used 2022 Jeep Gladiator Sport Crew Cab
$24,999
speed 65,569 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
Grieco Ford of Delray Beach
Delray Beach, FL (1,116.6 mi)
(561) 933-9349
Used 2020 Jeep Gladiator Sport Crew Cab
contact for price
speed 58,983 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Schumacher Chrysler Dodge Jeep Ram of Delray
Delray Beach, FL (1,116.6 mi)
Used 2021 Jeep Gladiator Sport Crew Cab
$28,500
speed 64,582 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
Sarasota Ford
Sarasota, FL (1,121.8 mi)
(941) 207-0662
Used 2023 Jeep Gladiator Overland Crew Cab
contact for price
speed 53,093 mi
sell
Key features
- Gasoline
- 4WD
- Overland
location_on
Matthews-Currie Ford
Nokomis, FL (1,129.3 mi)
(941) 294-3005
Used 2021 Jeep Gladiator Mojave Crew Cab
$28,184
speed 81,098 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Gettel Chrysler Dodge Jeep Ram
Punta Gorda, FL (1,134.9 mi)
(941) 676-9509
Used 2023 Jeep Gladiator Sport Crew Cab
$29,219
speed 44,917 mi
sell
Key features
- Gasoline
- 4WD
- Sport S
location_on
Gettel Chrysler Dodge Jeep Ram
Punta Gorda, FL (1,134.9 mi)
(941) 676-9509
Used 2022 Jeep Gladiator Overland Crew Cab
$30,261
speed 57,264 mi
sell
Key features
- Gasoline
- 4WD
- Overland
location_on
Gettel Chrysler Dodge Jeep Ram
Punta Gorda, FL (1,134.9 mi)
(941) 676-9509
Used 2024 Jeep Gladiator Rubicon Crew Cab
$39,439
speed 34,872 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Gettel Chrysler Dodge Jeep Ram
Punta Gorda, FL (1,134.9 mi)
(941) 676-9509
Used 2023 Jeep Gladiator Sport Crew Cab
$31,925 List Price
$28,600
speed 54,186 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Molle Chevrolet
Blue Springs, MO (1,135.9 mi)
Used 2023 Jeep Gladiator Rubicon Crew Cab
$42,725 List Price
$33,808
speed 43,869 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Molle Chevrolet
Blue Springs, MO (1,135.9 mi)
Used 2023 Jeep Gladiator Mojave Crew Cab
$32,222
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4x4
location_on
Arrigo Chrysler Dodge Jeep Ram of Sawgrass
Tamarac, FL (1,137.2 mi)
(954) 206-1231
Used 2023 Jeep Gladiator Sport Crew Cab
$33,308
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4x4
location_on
Arrigo Chrysler Dodge Jeep Ram of Sawgrass
Tamarac, FL (1,137.2 mi)
(954) 206-1231
Used 2021 Jeep Gladiator Sport Crew Cab
$27,294
speed 47,418 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Sam Galloway Ford
Fort Myers, FL (1,151.7 mi)
(239) 266-2393
Used 2023 Jeep Gladiator Sport Crew Cab
$31,789
speed 20,361 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
Sam Galloway Ford
Fort Myers, FL (1,151.7 mi)
(239) 266-2393
Used 2025 Jeep Gladiator Sport Crew Cab
$38,193
speed 14,080 mi
sell
Key features
- Gasoline
- 4WD
- Nighthawk
location_on
Chrysler Dodge Jeep Ram Fiat of Fort Myers
Fort Myers, FL (1,152.5 mi)
(239) 790-4635
Used 2026 Jeep Gladiator Mojave Crew Cab
$41,419
speed 14,697 mi
sell
Key features
- Gasoline
- 4WD
- Mojave 4x4
location_on
Chrysler Dodge Jeep Ram Fiat of Fort Myers
Fort Myers, FL (1,152.5 mi)
(239) 790-4635
Used 2021 Jeep Gladiator Rubicon Crew Cab
$48,964
speed 45,120 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon 4x4
location_on
Chrysler Dodge Jeep Ram Fiat of Fort Myers
Fort Myers, FL (1,152.5 mi)
(239) 790-4635
Used 2025 Jeep Gladiator Sport Crew Cab
$37,416
speed 19,472 mi
sell
Key features
- Gasoline
- 4WD
- Nighthawk
location_on
Chrysler Dodge Jeep Ram Fiat of Fort Myers
Fort Myers, FL (1,152.5 mi)
(239) 790-4635
Used 2022 Jeep Gladiator Overland Crew Cab
$36,496
speed 31,001 mi
sell
Key features
- Diesel
- 4WD
- Overland 4x4
location_on
Chrysler Dodge Jeep Ram Fiat of Fort Myers
Fort Myers, FL (1,152.5 mi)
(239) 790-4635
Used 2024 Jeep Gladiator Sport Crew Cab
$29,963
speed 29,123 mi
sell
Key features
- Gasoline
- 4WD
- Nighthawk
location_on
Chrysler Dodge Jeep Ram Fiat of Fort Myers
Fort Myers, FL (1,152.5 mi)
(239) 790-4635
Used 2026 Jeep Gladiator Sport Crew Cab
$33,683
speed 2,671 mi
sell
Key features
- Gasoline
- 4WD
- Sport 4x4
location_on
Chrysler Dodge Jeep Ram Fiat of Fort Myers
Fort Myers, FL (1,152.5 mi)
(239) 790-4635
