Used Jeep Gladiator for Sale near Winchester, IN
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
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.
Great truck, very roomy inside and it’s fun to drive it, I just love it!
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.
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.
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, IN?
The average Jeep Gladiator costs about $32,494.06. The average price has decreased by -6.4% since last year. The 694 for sale near Winchester, IN on CarGurus, range from $19,880 to $209,971 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, IN have no reported accidents or damage?
582 out of 694 for sale near Winchester, IN 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.
-
Used Jeep Gladiator for Sale Under $10,000 Near Winchester
-
Used Jeep Gladiator for Sale Under $15,000 Near Winchester
-
Used Jeep Gladiator for Sale Under $20,000 Near Winchester
-
Used Jeep Gladiator for Sale Under $25,000 Near Winchester
-
Used Jeep Gladiator for Sale Under $30,000 Near Winchester
-
Used Jeep Gladiator for Sale Under $40,000 Near Winchester
-
Small Trucks for Sale in Winchester IN
-
Shop cars from Fast & Furious 9 for sale in Winchester IN
-
Jeep SUVs & Crossovers for Sale near Winchester IN
-
American Made Trucks For Sale in Winchester IN
-
Best Pickup Trucks For Sale in Winchester IN
-
Used Jeep Gladiator for Sale with Low Mileage
-
Used Pickup Trucks for Sale with Low Mileage
-
All Used Cars
-
Manual Transmission Cars
-
Luxury Cars
-
Cars with Red Interior
-
Cheap Manual Cars
-
Hybrid Cars
-
Sports Cars
-
Electric SUVs
-
Cheap Trucks
-
Small Cars
-
Third Row SUVs
-
Three Quarter Ton Trucks
-
Lifted Trucks
-
Manual Transmission Trucks
-
Diesel Trucks
-
Hybrid SUVs
-
Dually Trucks
-
One Ton Trucks
-
Cheap SUVs
-
Lifted Ford Trucks
-
4x4 Trucks
-
Work Trucks
-
AWD SUVs
-
Ford Trucks
-
Chevrolet Trucks
-
Toyota Trucks
-
Trucks Under $10,000
-
Cars Under $15,000
-
Sports Cars Under $20,000
-
Trucks Under $20,000
-
Used Sedans for Sale with Low Mileage
-
Used SUVs / Crossovers for Sale with Low Mileage
-
Used Hatchbacks for Sale with Low Mileage
-
Used Convertibles for Sale with Low Mileage
-
Used Vans for Sale with Low Mileage
-
Used Minivans for Sale with Low Mileage
-
Used Pickup Trucks for Sale with Low Mileage
-
Used Coupes for Sale with Low Mileage
-
Used Wagons for Sale with Low Mileage
-
Russ Hubler Chrysler Dodge Jeep Ram
-
Erwin Chrysler Dodge Jeep
-
Bud's Chrysler Dodge Jeep
-
SVG Chrysler Dodge Jeep Ram
-
Bill Gaddis Chrysler Dodge Jeep Ram
-
Mike Anderson Chrysler Dodge Jeep RAM Fiat of Marion
-
Riedman Motors Company Incorporated
-
Glass Capital Chrysler Dodge Jeep RAM
-
St Marys Chrysler Dodge Jeep Incorporated
-
Ed Martin Chrysler Dodge Jeep RAM