2,219 New Jeep Gladiator for Sale Near Winter Haven, FL
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2026 Jeep Gladiator Sport Auto
16 days on market
1C6RJTAG9TL189890
$50,246
Napleton Northlake Chrysler Dodge Jeep Ram
Lake Park, FL
4.4
2026 Jeep Gladiator Sport S Auto
16 days on market
1C6PJTAG2TL189883
$56,281
Napleton Northlake Chrysler Dodge Jeep Ram
Lake Park, FL
4.4
2026 Jeep Gladiator Sport Auto
16 days on market
1C6RJTAG0TL189972
$47,845
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator Sport Auto
16 days on market
1C6RJTAG6TL189975
$49,930
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator Sport S Auto
16 days on market
1C6PJTAG2TL189981
$55,810
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator Willys Auto
16 days on market
1C6PJTAG6TL190079
$56,570
Cass Burch Chrysler Dodge Jeep Ram
Quitman, GA
4.6
2026 Jeep Gladiator Mojave Auto
16 days on market
1C6RJTEG8TL188840
$53,270
Coastal Jeep Ram Of Quincy
Quincy, FL
4.3
2026 Jeep Gladiator Shadow OPS Auto
16 days on market
1C6RJTBG1TL191471
$63,075
Airport Chrysler Dodge Jeep Ram
Orlando, FL
4.1
2026 Jeep Gladiator Sport S Auto
16 days on market
1C6PJTAG7TL190012
$49,398
Schumacher Chrysler Dodge Jeep Ram Of Delray
Delray Beach, FL
4.3
2026 Jeep Gladiator Sport S Auto
16 days on market
1C6PJTAG5TL190011
$49,993
Schumacher Chrysler Dodge Jeep Ram Of Delray
Delray Beach, FL
4.3
2026 Jeep Gladiator Sport S Auto
16 days on market
1C6PJTAG6TL189885
$55,686
Napleton Northlake Chrysler Dodge Jeep Ram
Lake Park, FL
4.4
2026 Jeep Gladiator Sport Auto
10 mi.
16 days on market
1C6RJTAG4TL189974
$43,335
Fair Deal
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator Sport S Auto
10 mi.
16 days on market
1C6PJTAG9TL189976
$65,510
Fair Deal
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator Sport S Auto
10 mi.
16 days on market
1C6PJTAG4TL189979
$65,510
Fair Deal
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator Sport S Auto
16 days on market
1C6PJTAG0TL189980
$54,915
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator 85th Anniversary Edition Auto
17 days on market
1C6PJTAG6TL185769
$56,750
Tallahassee Chrysler Dodge Jeep Ram Fiat
Tallahassee, FL
4.3
2026 Jeep Gladiator Sport S Auto
17 days on market
1C6PJTAG8TL189886
$55,686
Napleton Northlake Chrysler Dodge Jeep Ram
Lake Park, FL
4.4
2026 Jeep Gladiator Sport S Auto
17 days on market
1C6PJTAGXTL189887
$55,686
Napleton Northlake Chrysler Dodge Jeep Ram
Lake Park, FL
4.4
2026 Jeep Gladiator Sport Auto
2 mi.
17 days on market
1C6PJTAG6TL170141
$34,278
Great Deal
Arrigo Chrysler Dodge Jeep Ram Of Margate
Margate, FL
4.3
2026 Jeep Gladiator Sport Auto
17 days on market
1C6PJTAG0TL189171
$43,053
Phillips Chrysler Dodge Jeep Ram
Ocala, FL
4.4
2026 Jeep Gladiator Shadow OPS Auto
17 days on market
1C6RJTBG3TL191438
$58,537
Walker Jones Chrysler Jeep Dodge Ram
Waycross, GA
4.3
2026 Jeep Gladiator Sport S Auto
10 mi.
17 days on market
1C6PJTAG0TL189977
$65,510
Fair Deal
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator Sport Auto
19 days on market
1C6PJTAG9TL189170
$44,948
Phillips Chrysler Dodge Jeep Ram
Ocala, FL
4.4
2026 Jeep Gladiator Mojave Auto
138 mi.
20 days on market
1C6RJTEG6TL173432
$58,043
Fair Deal
Chrysler Dodge Jeep Ram Fiat Of Fort Myers
Fort Myers, FL
4.3
2026 Jeep Gladiator Mojave X Auto
110 mi.
20 days on market
1C6RJTEG4TL181352
$57,246
Fair Deal
Chrysler Dodge Jeep Ram Fiat Of Fort Myers
Fort Myers, FL
4.3
2026 Jeep Gladiator Shadow OPS Auto
6 mi.
21 days on market
1C6RJTBG7TL179003
$63,505
Fair Deal
Morgan Auto Group
Tampa, FL
2.6
2026 Jeep Gladiator Sport Auto
15 mi.
21 days on market
1C6PJTAG0TL188585
$47,041
Fair Deal
Chrysler Dodge Jeep Ram Of Seminole County
Sanford, FL
4.6
2026 Jeep Gladiator Rubicon Auto
21 days on market
1C6RJTBG9TL188544
Contact Dealer
Fitzgeralds Countryside Chrysler Jeep
Clearwater, FL
4.6
2026 Jeep Gladiator Sport Auto
16 days on market
1C6RJTAG9TL189890
$50,246
Napleton Northlake Chrysler Dodge Jeep Ram
Lake Park, FL
4.4
2026 Jeep Gladiator Sport S Auto
16 days on market
1C6PJTAG2TL189883
$56,281
Napleton Northlake Chrysler Dodge Jeep Ram
Lake Park, FL
4.4
2026 Jeep Gladiator Sport Auto
16 days on market
1C6RJTAG0TL189972
$47,845
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator Sport Auto
16 days on market
1C6RJTAG6TL189975
$49,930
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator Sport S Auto
16 days on market
1C6PJTAG2TL189981
$55,810
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator Willys Auto
16 days on market
1C6PJTAG6TL190079
$56,570
Cass Burch Chrysler Dodge Jeep Ram
Quitman, GA
4.6
2026 Jeep Gladiator Mojave Auto
16 days on market
1C6RJTEG8TL188840
$53,270
Coastal Jeep Ram Of Quincy
Quincy, FL
4.3
2026 Jeep Gladiator Shadow OPS Auto
16 days on market
1C6RJTBG1TL191471
$63,075
Airport Chrysler Dodge Jeep Ram
Orlando, FL
4.1
2026 Jeep Gladiator Sport S Auto
16 days on market
1C6PJTAG7TL190012
$49,398
Schumacher Chrysler Dodge Jeep Ram Of Delray
Delray Beach, FL
4.3
2026 Jeep Gladiator Sport S Auto
16 days on market
1C6PJTAG5TL190011
$49,993
Schumacher Chrysler Dodge Jeep Ram Of Delray
Delray Beach, FL
4.3
2026 Jeep Gladiator Sport S Auto
16 days on market
1C6PJTAG6TL189885
$55,686
Napleton Northlake Chrysler Dodge Jeep Ram
Lake Park, FL
4.4
2026 Jeep Gladiator Sport Auto
10 mi.
16 days on market
1C6RJTAG4TL189974
$43,335
Fair Deal
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator Sport S Auto
10 mi.
16 days on market
1C6PJTAG9TL189976
$65,510
Fair Deal
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator Sport S Auto
10 mi.
16 days on market
1C6PJTAG4TL189979
$65,510
Fair Deal
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator Sport S Auto
16 days on market
1C6PJTAG0TL189980
$54,915
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator 85th Anniversary Edition Auto
17 days on market
1C6PJTAG6TL185769
$56,750
Tallahassee Chrysler Dodge Jeep Ram Fiat
Tallahassee, FL
4.3
2026 Jeep Gladiator Sport S Auto
17 days on market
1C6PJTAG8TL189886
$55,686
Napleton Northlake Chrysler Dodge Jeep Ram
Lake Park, FL
4.4
2026 Jeep Gladiator Sport S Auto
17 days on market
1C6PJTAGXTL189887
$55,686
Napleton Northlake Chrysler Dodge Jeep Ram
Lake Park, FL
4.4
2026 Jeep Gladiator Sport Auto
2 mi.
17 days on market
1C6PJTAG6TL170141
$34,278
Great Deal
Arrigo Chrysler Dodge Jeep Ram Of Margate
Margate, FL
4.3
2026 Jeep Gladiator Sport Auto
17 days on market
1C6PJTAG0TL189171
$43,053
Phillips Chrysler Dodge Jeep Ram
Ocala, FL
4.4
2026 Jeep Gladiator Shadow OPS Auto
17 days on market
1C6RJTBG3TL191438
$58,537
Walker Jones Chrysler Jeep Dodge Ram
Waycross, GA
4.3
2026 Jeep Gladiator Sport S Auto
10 mi.
17 days on market
1C6PJTAG0TL189977
$65,510
Fair Deal
Chrysler Dodge Jeep Ram Of Tampa Bay
Tampa, FL
4.4
2026 Jeep Gladiator Sport Auto
19 days on market
1C6PJTAG9TL189170
$44,948
Phillips Chrysler Dodge Jeep Ram
Ocala, FL
4.4
2026 Jeep Gladiator Mojave Auto
138 mi.
20 days on market
1C6RJTEG6TL173432
$58,043
Fair Deal
Chrysler Dodge Jeep Ram Fiat Of Fort Myers
Fort Myers, FL
4.3
2026 Jeep Gladiator Mojave X Auto
110 mi.
20 days on market
1C6RJTEG4TL181352
$57,246
Fair Deal
Chrysler Dodge Jeep Ram Fiat Of Fort Myers
Fort Myers, FL
4.3
2026 Jeep Gladiator Shadow OPS Auto
6 mi.
21 days on market
1C6RJTBG7TL179003
$63,505
Fair Deal
Morgan Auto Group
Tampa, FL
2.6
2026 Jeep Gladiator Sport Auto
15 mi.
21 days on market
1C6PJTAG0TL188585
$47,041
Fair Deal
Chrysler Dodge Jeep Ram Of Seminole County
Sanford, FL
4.6
2026 Jeep Gladiator Rubicon Auto
21 days on market
1C6RJTBG9TL188544
Contact Dealer
Fitzgeralds Countryside Chrysler Jeep
Clearwater, FL
4.6
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.