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Used Jeep Gladiator for Sale near Winter Haven, FL

218 results

Year:
2021
Make:
Jeep
Model:
Gladiator
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
285 hp 3.6L V6
Exterior color:
Red
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
32,754
Stock #:
ML590152
VIN:
1C6JJTBGXML590152
Red 2021 Jeep Gladiator Rubicon Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic
AutoNation Chevrolet Airport

Sponsored by AutoNation Chevrolet Airport

2021 Jeep Gladiator

Rubicon Crew Cab 4WD

32,754 mi

Orlando, FL
37 mi away
Great Deal

$31,489

Year:
2026
Make:
Jeep
Model:
Gladiator
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
285 hp 3.6L V6
Exterior color:
White
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
668
Stock #:
8770746A
VIN:
1C6RJTBGXTL165743
White 2026 Jeep Gladiator Rubicon X Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2026 Jeep Gladiator

Rubicon X Crew Cab 4WD

668 mi

Tampa, FL
46 mi away
Great Deal
Manufacturer certified

$48,391

Year:
2020
Make:
Jeep
Model:
Gladiator
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
285 hp 3.6L V6
Exterior color:
Black
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
101,362
Stock #:
186353
VIN:
1C6HJTAG7LL186353
Black 2020 Jeep Gladiator Sport S Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic
Price drop

-$2,000

 

2020 Jeep Gladiator

Sport S Crew Cab 4WD

101,362 mi

Kissimmee, FL
24 mi away
Good Deal

$22,900

$20,900

Year:
2022
Make:
Jeep
Model:
Gladiator
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black Clearcoat
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
39,433
Stock #:
L167760A
VIN:
1C6JJTAG9NL175214
Black Clearcoat 2022 Jeep Gladiator Sport Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2022 Jeep Gladiator

Sport Crew Cab 4WD

39,433 mi

Orlando, FL
31 mi away
Great Deal
Manufacturer certified

$29,584

Year:
2021
Make:
Jeep
Model:
Gladiator
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
285 hp 3.6L V6
Exterior color:
Black Clearcoat
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
77,316
Stock #:
26384A
VIN:
1C6JJTEG9ML607261
Black Clearcoat 2021 Jeep Gladiator Mojave Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic
Price drop

-$700

 

2021 Jeep Gladiator

Mojave Crew Cab 4WD

77,316 mi

Winter Haven, FL
2 mi away
Good Deal
Third-party certified

$30,477

$29,777

Year:
2022
Make:
Jeep
Model:
Gladiator
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
285 hp 3.6L V6
Exterior color:
Red
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
33,648
Stock #:
CD25103A
VIN:
1C6HJTAG0NL113814
Red 2022 Jeep Gladiator Sport Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2022 Jeep Gladiator

Sport Crew Cab 4WD

33,648 mi

Lutz, FL
44 mi away
Good Deal

$30,515

Year:
2022
Make:
Jeep
Model:
Gladiator
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
285 hp 3.6L V6
Exterior color:
White
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
83,702
Stock #:
NL123400A
VIN:
1C6JJTBG1NL123400
White 2022 Jeep Gladiator Rubicon Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2022 Jeep Gladiator

Rubicon Crew Cab 4WD

83,702 mi

Lakeland, FL
17 mi away
Fair Deal

$31,184

Year:
2021
Make:
Jeep
Model:
Gladiator
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
285 hp 3.6L V6
Exterior color:
Red Clearcoat
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
54,339
Stock #:
L590308
VIN:
1C6HJTAG4ML590308
Red Clearcoat 2021 Jeep Gladiator Willys Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2021 Jeep Gladiator

Willys Crew Cab 4WD

54,339 mi

Orlando, FL
31 mi away
Good Deal
Manufacturer certified

$28,584

Recommended model year:

2021 Jeep Gladiator

4.8

Shop 2021 Jeep Gladiator »
  • With 4,836 currently listed for sale and an average price of $32,081, 31.7% of 2021 Jeep Gladiators for sale on CarGurus are rated as good or great deals.

  • Favorably reviewed: Owners rated the 2021 Jeep Gladiator 5 / 5 stars.

  • 83.5% of 2021 Gladiator models on CarGurus are accident-free.

  • The 2021 Jeep Gladiator is enhanced with a new diesel-engine option, providing impressive towing capacity and fuel efficiency, combined with robust off-road capabilities and a well-designed interior.

Research summarized using AI

 

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FAQs

How much does the Jeep Gladiator cost in Winter Haven, FL?
The average Jeep Gladiator costs about $34,293.04. The average price has increased by 4.1% since last year. The 218 for sale near Winter Haven, FL on CarGurus, range from $19,054 to $69,890 in price.
Is the Jeep Gladiator a good car?
CarGurus experts gave the 2025 Jeep Gladiator an overall rating of 5.3/10 and Jeep Gladiator owners have rated the vehicle a 4.8/5 stars on average. If a vehicle has both strong expert and owner reviews, you can feel confident in its quality. If either expert reviews, owner reviews, or both are spotty, you might want to do some research to figure out where the car falls short.
How many Jeep Gladiator vehicles in Winter Haven, FL have no reported accidents or damage?
218 out of 218 for sale near Winter Haven, FL have no reported accidents or damage.
Is the Jeep Gladiator safe?
CarGurus experts gave the 2025 Jeep Gladiator a safety rating of 3/10.
What fuel types are available?
Diesel, Gasoline engines are available.

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