2,206 New Jeep Gladiator for Sale Near Winter Haven, FL
Save search
2026 Jeep Gladiator 85th Anniversary Edition Auto
1 mi.
22 days on market
1C6PJTAG0TL185363
$44,985
Great Deal
Jacksonville Chrysler Jeep Dodge Ram Westside
Jacksonville, FL
4.0
2026 Jeep Gladiator 85th Anniversary Edition Auto
1 mi.
22 days on market
1C6PJTAG4TL185365
$44,449
Great Deal
Jacksonville Chrysler Jeep Dodge Ram Westside
Jacksonville, FL
4.0
2026 Jeep Gladiator 85th Anniversary Edition Auto
1 mi.
22 days on market
1C6PJTAG9TL185362
$44,985
Great Deal
Jacksonville Chrysler Jeep Dodge Ram Westside
Jacksonville, FL
4.0
2026 Jeep Gladiator Mojave Auto
23 days on market
1C6RJTEG0TL188377
Contact Dealer
Fitzgeralds Countryside Chrysler Jeep
Clearwater, FL
4.6
2026 Jeep Gladiator Shadow OPS Auto
11 mi.
23 days on market
1C6RJTBG1TL179224
$60,112
Good Deal
Chrysler Dodge Jeep Ram Fiat Of Fort Myers
Fort Myers, FL
4.3
2026 Jeep Gladiator Shadow OPS Auto
5 mi.
23 days on market
1C6RJTBGXTL178590
$67,460
Fair Deal
Wallace Chrysler Jeep Dodge Ram
Stuart, FL
4.5
2026 Jeep Gladiator Mojave Auto
11 mi.
23 days on market
1C6RJTEG8TL188059
$50,729
Good Deal
Brickell Chrysler Dodge Jeep Ram
Miami, FL
5.0
2026 Jeep Gladiator 85th Anniversary Edition Auto
5 mi.
23 days on market
1C6PJTAG2TL188524
$50,388
Fair Deal
Central Florida Chrysler Dodge Jeep Ram
Orlando, FL
4.1
2026 Jeep Gladiator Rubicon X Auto
2 mi.
23 days on market
1C6RJTBG3TL187597
$52,145
Great Deal
Arrigo Cdjr Of Fort Pierce
Fort Pierce, FL
4.4
2026 Jeep Gladiator Sport S Auto
24 days on market
1C6PJTAG1TL189602
$48,618
Hanania Chrysler Dodge Jeep Ram
St. Augustine, FL
4.5
2026 Jeep Gladiator Mojave Auto
24 days on market
1C6RJTEG1TL186783
$58,362
Vaden Chrysler Dodge Jeep Ram Of Brunswick
Brunswick, GA
4.2
2026 Jeep Gladiator Sport Auto
24 days on market
1C6RJTAG1TL189317
$40,768
Chrysler Dodge Jeep Ram Of Leesburg
Fruitland Park, FL
4.1
2026 Jeep Gladiator 85th Anniversary Edition Auto
1 mi.
25 days on market
1C6PJTAG4TL185382
$48,170
Great Deal
Garber Chrysler Dodge Jeep Ram Green Cove Springs
Green Cove Springs, FL
4.8
2026 Jeep Gladiator Shadow OPS Auto
5 mi.
25 days on market
1C6RJTBG3TL179063
$59,940
Great Deal
Sarasota Chrysler Dodge Jeep Ram
Sarasota, FL
4.3
2026 Jeep Gladiator Sport S Auto
25 days on market
1C6PJTAG8TL189600
$48,618
Hanania Chrysler Dodge Jeep Ram
St. Augustine, FL
4.5
2025 Jeep Gladiator Sport S Auto
2 mi.
25 days on market
1C6RJTAG8SL516844
$41,309
Great Deal
Dayton Andrews Dodge Chrysler Jeep Ram
St. Petersburg, FL
4.4
2026 Jeep Gladiator Mojave Auto
25 days on market
1C6RJTEG1TL189070
$61,635
Napletons South Orlando Chrysler Jeep Dodge
Kissimmee, FL
4.5
2026 Jeep Gladiator Sport S Auto
25 days on market
1C6PJTAGXTL189601
$48,023
Hanania Chrysler Dodge Jeep Ram
St. Augustine, FL
4.5
2026 Jeep Gladiator Mojave Auto
25 days on market
1C6RJTEG2TL189675
$63,835
Jenkins Chrysler Dodge Jeep Ram Of Homosassa
Homosassa, FL
4.5
2026 Jeep Gladiator Sport S Auto
25 days on market
1C6PJTAGXTL186696
$50,085
Jenkins Chrysler Dodge Jeep Ram Of Homosassa
Homosassa, FL
4.5
2026 Jeep Gladiator Sahara Auto
5 mi.
25 days on market
1C6PJTAG3TL189620
$40,181
Great Deal
Taverna Chrysler Dodge Jeep Ram Of Fort Lauderdale
Pompano Beach, FL
4.3
2026 Jeep Gladiator Mojave X Auto
26 days on market
1C6RJTEG3TL189636
$59,330
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Rubicon Auto
26 days on market
1C6RJTBG4TL189634
$55,745
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG2TL189673
$40,251
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG4TL189674
$39,716
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG9TL189671
$39,716
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG4TL188153
$55,687
Deland Chrysler Dodge Jeep Ram
DeLand, FL
4.1
2026 Jeep Gladiator Rubicon X Auto
18 mi.
26 days on market
1C6RJTBG9TL189404
$50,993
Great Deal
Spitzer Chrysler Dodge Jeep Ram Homestead
Homestead, FL
4.3
2026 Jeep Gladiator 85th Anniversary Edition Auto
1 mi.
22 days on market
1C6PJTAG0TL185363
$44,985
Great Deal
Jacksonville Chrysler Jeep Dodge Ram Westside
Jacksonville, FL
4.0
2026 Jeep Gladiator 85th Anniversary Edition Auto
1 mi.
22 days on market
1C6PJTAG4TL185365
$44,449
Great Deal
Jacksonville Chrysler Jeep Dodge Ram Westside
Jacksonville, FL
4.0
2026 Jeep Gladiator 85th Anniversary Edition Auto
1 mi.
22 days on market
1C6PJTAG9TL185362
$44,985
Great Deal
Jacksonville Chrysler Jeep Dodge Ram Westside
Jacksonville, FL
4.0
2026 Jeep Gladiator Mojave Auto
23 days on market
1C6RJTEG0TL188377
Contact Dealer
Fitzgeralds Countryside Chrysler Jeep
Clearwater, FL
4.6
2026 Jeep Gladiator Shadow OPS Auto
11 mi.
23 days on market
1C6RJTBG1TL179224
$60,112
Good Deal
Chrysler Dodge Jeep Ram Fiat Of Fort Myers
Fort Myers, FL
4.3
2026 Jeep Gladiator Shadow OPS Auto
5 mi.
23 days on market
1C6RJTBGXTL178590
$67,460
Fair Deal
Wallace Chrysler Jeep Dodge Ram
Stuart, FL
4.5
2026 Jeep Gladiator Mojave Auto
11 mi.
23 days on market
1C6RJTEG8TL188059
$50,729
Good Deal
Brickell Chrysler Dodge Jeep Ram
Miami, FL
5.0
2026 Jeep Gladiator 85th Anniversary Edition Auto
5 mi.
23 days on market
1C6PJTAG2TL188524
$50,388
Fair Deal
Central Florida Chrysler Dodge Jeep Ram
Orlando, FL
4.1
2026 Jeep Gladiator Rubicon X Auto
2 mi.
23 days on market
1C6RJTBG3TL187597
$52,145
Great Deal
Arrigo Cdjr Of Fort Pierce
Fort Pierce, FL
4.4
2026 Jeep Gladiator Sport S Auto
24 days on market
1C6PJTAG1TL189602
$48,618
Hanania Chrysler Dodge Jeep Ram
St. Augustine, FL
4.5
2026 Jeep Gladiator Mojave Auto
24 days on market
1C6RJTEG1TL186783
$58,362
Vaden Chrysler Dodge Jeep Ram Of Brunswick
Brunswick, GA
4.2
2026 Jeep Gladiator Sport Auto
24 days on market
1C6RJTAG1TL189317
$40,768
Chrysler Dodge Jeep Ram Of Leesburg
Fruitland Park, FL
4.1
2026 Jeep Gladiator 85th Anniversary Edition Auto
1 mi.
25 days on market
1C6PJTAG4TL185382
$48,170
Great Deal
Garber Chrysler Dodge Jeep Ram Green Cove Springs
Green Cove Springs, FL
4.8
2026 Jeep Gladiator Shadow OPS Auto
5 mi.
25 days on market
1C6RJTBG3TL179063
$59,940
Great Deal
Sarasota Chrysler Dodge Jeep Ram
Sarasota, FL
4.3
2026 Jeep Gladiator Sport S Auto
25 days on market
1C6PJTAG8TL189600
$48,618
Hanania Chrysler Dodge Jeep Ram
St. Augustine, FL
4.5
2025 Jeep Gladiator Sport S Auto
2 mi.
25 days on market
1C6RJTAG8SL516844
$41,309
Great Deal
Dayton Andrews Dodge Chrysler Jeep Ram
St. Petersburg, FL
4.4
2026 Jeep Gladiator Mojave Auto
25 days on market
1C6RJTEG1TL189070
$61,635
Napletons South Orlando Chrysler Jeep Dodge
Kissimmee, FL
4.5
2026 Jeep Gladiator Sport S Auto
25 days on market
1C6PJTAGXTL189601
$48,023
Hanania Chrysler Dodge Jeep Ram
St. Augustine, FL
4.5
2026 Jeep Gladiator Mojave Auto
25 days on market
1C6RJTEG2TL189675
$63,835
Jenkins Chrysler Dodge Jeep Ram Of Homosassa
Homosassa, FL
4.5
2026 Jeep Gladiator Sport S Auto
25 days on market
1C6PJTAGXTL186696
$50,085
Jenkins Chrysler Dodge Jeep Ram Of Homosassa
Homosassa, FL
4.5
2026 Jeep Gladiator Sahara Auto
5 mi.
25 days on market
1C6PJTAG3TL189620
$40,181
Great Deal
Taverna Chrysler Dodge Jeep Ram Of Fort Lauderdale
Pompano Beach, FL
4.3
2026 Jeep Gladiator Mojave X Auto
26 days on market
1C6RJTEG3TL189636
$59,330
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Rubicon Auto
26 days on market
1C6RJTBG4TL189634
$55,745
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG2TL189673
$40,251
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG4TL189674
$39,716
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG9TL189671
$39,716
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG4TL188153
$55,687
Deland Chrysler Dodge Jeep Ram
DeLand, FL
4.1
2026 Jeep Gladiator Rubicon X Auto
18 mi.
26 days on market
1C6RJTBG9TL189404
$50,993
Great Deal
Spitzer Chrysler Dodge Jeep Ram Homestead
Homestead, FL
4.3
Find New Jeep Gladiator in Winter Haven, FL
The Jeep Gladiator is offered in the U.S. lineup in the Pickup configuration. Differences mainly come down to trim, features, and drivetrain.