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Used
Jeep Gladiator trucks
for sale
near
Winchester, MA
under $899,990
- Down Payment
- $0
- Net trade-in value
- $0
- Months
- 72
- APR
- 7.0%
- Sales tax
- 0.0%
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
Used
2023 Jeep Gladiator Sport S
Used
2022 Jeep Gladiator Mojave 4x4
Vehicle information
Features
Reviews
Lease expiration options
Met with Anthony R. to discuss my upcoming lease expiration. He worked out all the options I had, and was very supportive. I also had to get my Jeep inspected at the same time. It was a very pleasant experience.
The best vehicle that I've ever owned!
The best vehicle that I've ever owned! It's never needed to go back to the dealer for any work or new vehicle adjustments. I will get another Gladiator after this one!
Used
2022 Jeep Gladiator Altitude 4x4
Vehicle information
Features
Reviews
Post Covid
Nothing big, just having regular maintenance. This has been a great car. I leased then purchased it from Colonial and have been happy that I did. All set now.
My Gladiator is 3 years old.
My Gladiator is 3 years old. Driving in Alaska and what a great vehicle. Starts every morning with no issues. Drives great in deep snow thanks to the ground clearance. The ride is stiff-it’s a Jeep.
Jeep Certified
2022 Jeep Gladiator Sport S 4x4
Vehicle information
Features
Reviews
We walked onto the lot matt was there to greet us
We had a great experience it was a 5 star experience. Matt Deleo our sales person was great answered all questions and helped us out with what ever we needed.
What’s Not to Like
This is a.rock solid vehicle that defines “utility” better than all the rest. You have tons of ways to configure the vehicle every day. Open air roof, doors off, entire top off, pick-up truck uses, off roading, climbing, travel, snowshoeing, skiing, snow driving, trails and dirt roads, hiking, carry bed loads, trailering, ATVs, etc, etc, etc. No way to ever find it boring. Plus, the extra bonus of the culture, friendliness, the wave, jeep groups, and the way it promotes and nurtures getting outdoors and getting active. No issues. Alpine stereo is great. Nav is great. Heat is great. comfort great, carrying fun loads great, towing to 4K lbs great. No complaints.
Jeep Certified
2023 Jeep Gladiator Sport S 4x4
Vehicle information
Features
Reviews
Amazing Service
I needed service for my car today. Laura always takes good care of me and my car. She is the Best and the team did a great job repairing my car. Nobody knows my car like she does.
Always go to Pilson auto, we always use the same
Always go to Pilson auto, we always use the same salesman. Always have a good experience! The salesman always answers calls and texts even if he is not at work! Everyone there has always been extremely friendly and helpful!
Used
2022 Jeep Gladiator Sport
Vehicle information
Features
Reviews
Worked with Brian Villuannueva on a recent purchase of a
Worked with Brian Villuannueva on a recent purchase of a Jeep Wrangler 2021 Rubicon. Brian was a pleasure to work with. He was straight forward, addressed any questions I ad in a timely manner, followed up and made the whole experience a pleasant one. I would highly recommend recommend seeking out Brian when looking for a car at Kelly.
Great vehicle poor local warranty service
I think my 2022 Gladiator is one of the top vehicles I have owned The only drawback is the lack of warranty service from my local Jeep dealer.
Jeep Certified
2021 Jeep Gladiator Overland
Vehicle information
Features
Reviews
very casual and easy-going experience working with our
very casual and easy-going experience working with our salesman Brian, Kayla, Josh and Tim
Have driven Jeeps in the military and loved the
Have driven Jeeps in the military and loved the performance and easy maintenance. Have 2 Jeeps now and looking to replace one of my Jeep with another one. Love Jeeps!!
Used
2020 Jeep Gladiator Sport S
Vehicle information
Features
Reviews
Beautiful showroom gorgeous used cars.
Beautiful showroom gorgeous used cars. I was taken aback by how awesome the service is.
my grandmother sadly traded in this gladiator i wish she
my grandmother sadly traded in this gladiator i wish she would have kept it . It is very comfortable,reliable,it look great on the outside,it has enough power,and its value is very good.
Used
2022 Jeep Gladiator Mojave 4x4
Vehicle information
Features
Reviews
Mike treated me fairly no pressure.
Mike treated me fairly no pressure. Ease of working with personalized care buying experience. Very helpful, knowledgeable and honest.
Explore New Areas
Great vehicle for enjoying the outdoors in being able to explore new places other vehicles could not go. Looks like a vehicle that can take you into areas safely.
There are additional matching cars outside your search area.
Partial matches are generated by applying your search criteria to a larger search area. Our goal is to help you discover additional cars that match your search preferences.
As a benefit to some of our dealer customers, we display their listings first.
Used
2021 Jeep Gladiator Overland
Vehicle information
Features
Used
2020 Jeep Gladiator Rubicon
Vehicle information
Features
Used
2023 Jeep Gladiator High Altitude 4x4
Vehicle information
Features
Used
2021 Jeep Gladiator Overland
Vehicle information
Features
Used
2021 Jeep Gladiator Rubicon
Vehicle information
Features
Used
2022 Jeep Gladiator Willys 4x4
Vehicle information
Features
Used
2020 Jeep Gladiator Rubicon
Vehicle information
Features
Jeep Certified
2021 Jeep Gladiator Sport S
Vehicle information
Features
Used
2022 Jeep Gladiator Altitude
Vehicle information
Features
Used
2021 Jeep Gladiator Overland
Vehicle information
Features
Jeep Gladiator prices by year
| Model year | Average price | Deals |
|---|---|---|
| 2026 Jeep Gladiator | $52,138 | |
| 2022 Jeep Gladiator | $33,329 | 12 Good deals |
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
Used Jeep Gladiator by price
Compare the Jeep Gladiator
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Jeep Gladiator under $899,990 in Winchester, MA
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This vehicle is certified pre-owned, backed by a manufacturer warranty, and typically undergoes a rigorous multi-point inspection to ensure quality and reliability.
This vehicle is currently in high demand given its competitive price, desirable features, and overall condition, and may have a higher chance of selling quickly.
