Used Jeep Gladiator for Sale near Winchester, VA

291 results

Winchester, VA

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2020 Jeep Gladiator

Overland Crew Cab 4WD

66,431 miles

$23,899

Good Deal

Springfield, VA

60 mi away

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 Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 66,431
Stock number:: LL155260T
VIN:: 1C6HJTFG9LL155260

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2021 Jeep Gladiator

Mojave Crew Cab 4WD

49,871 miles

$32,982

Good Deal

Elkton, VA

60 mi away

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:: Gray (Granite Crystal Metallic Clearcoat)
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 49,871
Stock number:: 24251A
VIN:: 1C6JJTEG5ML515676

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2021 Jeep Gladiator

Freedom Crew Cab 4WD

51,467 miles

$25,995

Good Deal

Certified Pre-Owned

Frederick, MD

43 mi away

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:: White
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 51,467
Stock number:: 26045A
VIN:: 1C6HJTAG9ML579160

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2021 Jeep Gladiator

Mojave Crew Cab 4WD

38,046 miles

$35,990

Fair Deal

Front Royal, VA

16 mi away

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:: White
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 38,046
Stock number:: 14777
VIN:: 1C6JJTEG0ML574800

2021 Jeep Gladiator

Mojave Crew Cab 4WD

31,512 miles

$33,997

Good Deal

Huntingdon, PA

91 mi away

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:: Gray
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 31,512
Stock number:: 25HT200A
VIN:: 1C6JJTEG5ML525673

2020 Jeep Gladiator

Sport Crew Cab 4WD

93,357 miles

$21,295

Good Deal

Charlottesville, VA

78 mi away

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:: Billet Silver Metallic Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 93,357
Stock number:: S3604B
VIN:: 1C6JJTAG3LL129195

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2021 Jeep Gladiator

High Altitude Crew Cab 4WD

44,997 miles

$27,495

Great Deal

Gaithersburg, MD

51 mi away

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:: 44,997
Stock number:: J250845A
VIN:: 1C6HJTFG9ML578423

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2020 Jeep Gladiator

Rubicon Crew Cab 4WD

33,363 miles

$31,995

Good Deal

Gaithersburg, MD

51 mi away

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:: Billet Silver Metallic Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 33,363
Stock number:: J260016A
VIN:: 1C6JJTBGXLL155307

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2022 Jeep Gladiator

Willys Crew Cab 4WD

71,329 miles

$24,000

Good Deal

Waynesboro, PA

52 mi away

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:: Silver Zynith Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 71,329
Stock number:: B34411
VIN:: 1C6HJTAG7NL145630

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2020 Jeep Gladiator

Sport Crew Cab 4WD

98,031 miles

$20,700

Great Deal

Westminster, MD

69 mi away

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 Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 98,031
Stock number:: MP193235
VIN:: 1C6HJTAG3LL193235

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2024 Jeep Gladiator

NightHawk Crew Cab 4WD

23,347 miles

$32,997

Good Deal

Huntingdon, PA

91 mi away

Year:: 2024
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Blue
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 23,347
Stock number:: HT783
VIN:: 1C6HJTAG2RL125663

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2021 Jeep Gladiator

Rubicon Crew Cab 4WD

75,935 miles

$26,400

Good Deal

Laurel, MD

71 mi away

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:: Bright White Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 75,935
Stock number:: LP436
VIN:: 1C6JJTBGXML509229

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2025 Jeep Gladiator

Mojave X Crew Cab 4WD

7,807 miles

$44,998

Great Deal

Duncansville, PA

90 mi away

Year:: 2025
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: 41
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Green/Black
Transmission:: Automatic
Mileage:: 7,807
Stock number:: 164672
VIN:: 1C6RJTEG2SL514386

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2023 Jeep Gladiator

Rubicon Crew Cab 4WD

26,384 miles

$35,999

Good Deal

Charlottesville, VA

77 mi away

Year:: 2023
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Gray
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 26,384
Stock number:: 40SL1060
VIN:: 1C6JJTBG9PL566106

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2020 Jeep Gladiator

Rubicon Crew Cab 4WD

59,843 miles

$29,995

Good Deal

Manchester, PA

98 mi away

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:: Billet Silver Metallic Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 59,843
Stock number:: M102032
VIN:: 1C6JJTBG7LL102032

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2023 Jeep Gladiator

Sport S Crew Cab 4WD

62,994 miles

$24,000

Good Deal

Waynesboro, PA

52 mi away

Year:: 2023
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Gray (Granite Crystal Metallic Clearcoat)
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 62,994
Stock number:: B34503
VIN:: 1C6HJTAG3PL535157

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2020 Jeep Gladiator

Rubicon Crew Cab 4WD

105,390 miles

$25,525

Good Deal

Madison, VA

57 mi away

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 Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 105,390
Stock number:: 23205A
VIN:: 1C6JJTBG4LL163614

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2023 Jeep Gladiator

Rubicon Crew Cab 4WD

27,508 miles

$36,585

Fair Deal

Thurmont, MD

51 mi away

Year:: 2023
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Gray (Granite Crystal Metallic Clearcoat)
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 27,508
Stock number:: Q260232A
VIN:: 1C6JJTBG7PL559736

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2020 Jeep Gladiator

North Edition 4WD

79,283 miles

$26,995

Good Deal

Charlottesville, VA

73 mi away

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:: Silver
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 79,283
Stock number:: 181948
VIN:: 1C6HJTFG1LL181948

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2024 Jeep Gladiator

Sport S Crew Cab 4WD

10,527 miles

$32,997

Great Deal

Hollidaysburg, PA

88 mi away

Year:: 2024
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:: 10,527
Stock number:: FT6046
VIN:: 1C6HJTAG4RL125714

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2021 Jeep Gladiator

Freedom Crew Cab 4WD

51,467 miles

$25,995

Good Deal

Certified Pre-Owned

Frederick, MD

43 mi away

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:: White
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 51,467
Stock number:: 26045A
VIN:: 1C6HJTAG9ML579160

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2024 Jeep Gladiator

Willys Crew Cab 4WD

11,804 miles

$34,797

Good Deal

Ellicott City, MD

73 mi away

Year:: 2024
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Hydro Blue Pearlcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 11,804
Stock number:: A50345A
VIN:: 1C6HJTAGXRL132098

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2023 Jeep Gladiator

Rubicon Crew Cab 4WD

27,508 miles

$36,585

Fair Deal

Thurmont, MD

51 mi away

Year:: 2023
Make:: Jeep
Model:: Gladiator
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 285 hp 3.6L V6
Exterior color:: Gray (Granite Crystal Metallic Clearcoat)
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 27,508
Stock number:: Q260232A
VIN:: 1C6JJTBG7PL559736

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Overview

Reviews

FAQs

CarGurus recommends the 2021 Jeep Gladiator

## Summary - With 5,475 currently listed for sale on CarGurus and an **average price of $30,763.00**, 34.3% of 2021 Jeep Gladiators for sale on CarGurus are rated as good or great deals. - **Favorably reviewed:** Owners rated the 2021 Jeep Gladiator 4.8 / 5 stars. - **84.4% of 2021 Gladiator models on CarGurus are accident free**. - The 2021 Jeep Gladiator introduced a diesel engine option, enhancing its towing performance and fuel economy with a robust 3.0-liter EcoDiesel V6. ## Why it stands out The 2021 Jeep Gladiator made a bold impression in the midsize truck segment upon its reintroduction, combining the rugged off-road capabilities that Jeep is known for with the practicality of a pickup. Built on the same platform as the Wrangler, it features removable doors and a fold-down windshield, providing a unique open-air driving experience unmatched by competitors. The Gladiator’s off-road prowess is underscored by the Trail Rated badge, showcasing its ability to handle extreme conditions, while the choice of trims caters to both adventurers and those seeking a more refined driving experience. For buyers who value versatility and the ability to tackle challenges off the beaten path, the 2021 Gladiator stands as an appealing choice in the truck market. ## Other model years to consider - **[2020 Jeep Gladiator](https://www.cargurus.com/Cars/l-Used-2020-Jeep-Gladiator-c28934)** - Average price: $28,523.00 - Good/great deal percentage: 35.4% - User rating: 4.72 / 5 - Total listings: 3,847 - **[2022 Jeep Gladiator](https://www.cargurus.com/Cars/l-Used-2022-Jeep-Gladiator-c32007)** - Average price: $32,124.00 - Good/great deal percentage: 33.1% - User rating: 4.4 / 5 - Total listings: 5,412 - **[2023 Jeep Gladiator](https://www.cargurus.com/Cars/l-Used-2023-Jeep-Gladiator-c32473)** - Average price: $33,305.00 - Good/great deal percentage: 33.2% - User rating: 4.84 / 5 - Total listings: 3,994 These recommendations are based on CarGurus' proprietary market data from February 10, 2026, CarGurus experts' opinions, and generative AI.

4.8 Overall rating

(168 reviews)

Customers say

The Jeep Gladiator impresses owners with its off-road capabilities, rugged design, and versatile performance. Many drivers enjoy its powerful feel and smooth ride, appreciating the blend of technology with a tough exterior. However, there are common criticisms regarding the interior space being smaller than expected, the price point relative to features, and concerns about fuel efficiency and comfort. Overall, it's celebrated as a unique vehicle that stands out, especially for those who value ruggedness and off-road performance.

AI generated from the text of customer reviews.

What people say

cargo space interior off-road capability performance ride quality

Anonymous

5.0

Reviewed a 2020 Jeep Gladiator on Feb 11, 2024

This truck is absolutely beautiful inside and out. It’s a surprisingly quiet ride. I love all the bells and whistles the rubicon has to offer. I wouldn’t change a thing.

Anonymous

5.0

Reviewed a 2020 Jeep Gladiator on Apr 13, 2024

Great truck, very roomy inside and it’s fun to drive it, I just love it!

Thomas S

5.0

Reviewed a 2023 Jeep Gladiator on Mar 20, 2024

Wonderful vehicle. This is my second one. Discounts off of MSRP were too good to pass up. Very capable off-road with the ability to be upfitted with over-landing gear.

Anonymous

5.0

Reviewed a 2023 Jeep Mojave Crew Cab 4WD on Sep 20, 2024

This is the third day of ownership. So far so good. This is my second Jeep. The first one was a Jeep Wrangler Rubicon which I had for nine years. I was looking for a truck but test drove a Mojave. I was pleasantly surprised at how much they have improved and how much I fun it was to drive. The suspension is so smooth and it’s much quieter than my old Jeep. I like the mix of truck and Jeep.

Barry j

5.0

Reviewed a 2023 Jeep Gladiator on May 23, 2024

Really love the smooth ride and the way it drives much better than my previous Jeep

Jeep Gladiator FAQs

How much does the Jeep Gladiator cost in Winchester, VA?

The average Jeep Gladiator costs about $32,494.06. The average price has decreased by -6.4% since last year. The 689 for sale near Winchester, VA on CarGurus, range from $20,544 to $209,868 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 4.7/5 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 Winchester, VA have no reported accidents or damage?

689 out of 689 for sale near Winchester, VA 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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