2,206 New Jeep Gladiator for Sale Near Winter Haven, FL
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2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG4TL189545
$49,463
Phillips Chrysler Dodge Jeep Ram
Ocala, FL
4.4
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG9TL189542
$49,463
Phillips Chrysler Dodge Jeep Ram
Ocala, FL
4.4
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG0TL189543
$49,463
Phillips Chrysler Dodge Jeep Ram
Ocala, FL
4.4
2026 Jeep Gladiator 85th Anniversary Edition Auto
4 mi.
26 days on market
1C6PJTAG9TL185474
$50,578
Fair Deal
Chrysler Dodge Jeep Ram Of Seminole County
Sanford, FL
4.6
2026 Jeep Gladiator Mojave X Auto
26 days on market
1C6RJTEG7TL189638
$59,330
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Rubicon Auto
26 days on market
1C6RJTBG2TL189633
$55,086
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Rubicon Auto
26 days on market
1C6RJTBG6TL189635
$56,253
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG9TL189668
$39,716
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG5TL189666
$40,251
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG8TL189662
$40,251
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG7TL189670
$39,716
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG0TL189669
$39,716
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG7TL189667
$40,251
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG0TL189672
$40,251
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG3TL189665
$40,251
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG1TL189664
$40,251
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Shadow OPS Auto
26 days on market
1C6RJTBG7TL179163
$67,359
Cdjr Brooksville
Brooksville, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG2TL189544
$48,868
Phillips Chrysler Dodge Jeep Ram
Ocala, FL
4.4
2026 Jeep Gladiator Mojave Auto
27 days on market
1C6RJTEG5TL189069
$55,261
Napletons South Orlando Chrysler Jeep Dodge
Kissimmee, FL
4.5
2026 Jeep Gladiator Shadow OPS Auto
10 mi.
27 days on market
1C6RJTBG8TL179124
$63,529
Fair Deal
Lake City Chrysler Dodge Jeep Ram
Lake City, FL
4.3
2026 Jeep Gladiator 85th Anniversary Edition Auto
27 days on market
1C6PJTAGXTL186259
$44,789
Gator Chrysler Dodge Jeep Ram
Melbourne, FL
4.2
2026 Jeep Gladiator Sport S Auto
5 mi.
27 days on market
1C6PJTAG8TL189211
$41,515
Great Deal
Cape Coral Chrysler Dodge Jeep Ram
Cape Coral, FL
4.5
2026 Jeep Gladiator Sport S Auto
5 mi.
27 days on market
1C6PJTAG8TL188916
$41,215
Great Deal
Cape Coral Chrysler Dodge Jeep Ram
Cape Coral, FL
4.5
2026 Jeep Gladiator Sahara Auto
5 mi.
27 days on market
1C6PJTAG1TL188921
$45,315
Great Deal
Cape Coral Chrysler Dodge Jeep Ram
Cape Coral, FL
4.5
2026 Jeep Gladiator Willys Auto
27 days on market
1C6PJTAG8TL189323
$58,674
Griffin Chrysler Dodge Jeep Ram Valdosta
Valdosta, GA
4.2
2020 Jeep Gladiator Sport S
27 days on market
1C6HJTAG9LL128907
$29,995
Verena Automotive Inc
Clearwater, FL
4.4
2026 Jeep Gladiator Sport S Auto
10 mi.
27 days on market
1C6PJTAG1TL188403
$41,209
Great Deal
Brickell Chrysler Dodge Jeep Ram
Miami, FL
4.7
2026 Jeep Gladiator Sport S Auto
10 mi.
27 days on market
1C6PJTAG6TL188400
$41,209
Great Deal
Brickell Chrysler Dodge Jeep Ram
Miami, FL
4.7
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG4TL189545
$49,463
Phillips Chrysler Dodge Jeep Ram
Ocala, FL
4.4
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG9TL189542
$49,463
Phillips Chrysler Dodge Jeep Ram
Ocala, FL
4.4
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG0TL189543
$49,463
Phillips Chrysler Dodge Jeep Ram
Ocala, FL
4.4
2026 Jeep Gladiator 85th Anniversary Edition Auto
4 mi.
26 days on market
1C6PJTAG9TL185474
$50,578
Fair Deal
Chrysler Dodge Jeep Ram Of Seminole County
Sanford, FL
4.6
2026 Jeep Gladiator Mojave X Auto
26 days on market
1C6RJTEG7TL189638
$59,330
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Rubicon Auto
26 days on market
1C6RJTBG2TL189633
$55,086
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Rubicon Auto
26 days on market
1C6RJTBG6TL189635
$56,253
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG9TL189668
$39,716
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG5TL189666
$40,251
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG8TL189662
$40,251
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG7TL189670
$39,716
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG0TL189669
$39,716
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG7TL189667
$40,251
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG0TL189672
$40,251
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG3TL189665
$40,251
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG1TL189664
$40,251
Hollywood Chrysler Jeep
Hollywood, FL
4.3
2026 Jeep Gladiator Shadow OPS Auto
26 days on market
1C6RJTBG7TL179163
$67,359
Cdjr Brooksville
Brooksville, FL
4.3
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG2TL189544
$48,868
Phillips Chrysler Dodge Jeep Ram
Ocala, FL
4.4
2026 Jeep Gladiator Mojave Auto
27 days on market
1C6RJTEG5TL189069
$55,261
Napletons South Orlando Chrysler Jeep Dodge
Kissimmee, FL
4.5
2026 Jeep Gladiator Shadow OPS Auto
10 mi.
27 days on market
1C6RJTBG8TL179124
$63,529
Fair Deal
Lake City Chrysler Dodge Jeep Ram
Lake City, FL
4.3
2026 Jeep Gladiator 85th Anniversary Edition Auto
27 days on market
1C6PJTAGXTL186259
$44,789
Gator Chrysler Dodge Jeep Ram
Melbourne, FL
4.2
2026 Jeep Gladiator Sport S Auto
5 mi.
27 days on market
1C6PJTAG8TL189211
$41,515
Great Deal
Cape Coral Chrysler Dodge Jeep Ram
Cape Coral, FL
4.5
2026 Jeep Gladiator Sport S Auto
5 mi.
27 days on market
1C6PJTAG8TL188916
$41,215
Great Deal
Cape Coral Chrysler Dodge Jeep Ram
Cape Coral, FL
4.5
2026 Jeep Gladiator Sahara Auto
5 mi.
27 days on market
1C6PJTAG1TL188921
$45,315
Great Deal
Cape Coral Chrysler Dodge Jeep Ram
Cape Coral, FL
4.5
2026 Jeep Gladiator Willys Auto
27 days on market
1C6PJTAG8TL189323
$58,674
Griffin Chrysler Dodge Jeep Ram Valdosta
Valdosta, GA
4.2
2020 Jeep Gladiator Sport S
27 days on market
1C6HJTAG9LL128907
$29,995
Verena Automotive Inc
Clearwater, FL
4.4
2026 Jeep Gladiator Sport S Auto
10 mi.
27 days on market
1C6PJTAG1TL188403
$41,209
Great Deal
Brickell Chrysler Dodge Jeep Ram
Miami, FL
4.7
2026 Jeep Gladiator Sport S Auto
10 mi.
27 days on market
1C6PJTAG6TL188400
$41,209
Great Deal
Brickell Chrysler Dodge Jeep Ram
Miami, FL
4.7
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.