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Used
Jeep Gladiator trucks
for sale
near
Medfield, MA
under $99,999
- 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.






Jeep Certified
2022 Jeep Gladiator Sport S






Used
2021 Jeep Gladiator Mojave






Used
2021 Jeep Gladiator Willys 4x4
Vehicle information
Features
Reviews
Great store overall
my experience here was great. my sales person Matt Waters could not have been better. He made the entire experience efficient. The finance team was ok even though I had to go back in to sign the paperwork but it was still a great experience overall. I love my MDX.
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
2023 Jeep Gladiator Overland
Vehicle information
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Reviews
Great experience always!
We bought three Cars in past from Rajeev Arora "Ricky" every time was great experience. He is true professional, respectful and Knowledgeable. We enjoyed his service
MOST importantly it is a JEEP.
MOST importantly it is a JEEP. If you want a luxury vehicle, buy one, if you want a full-size truck, buy one, if you want a sports car, buy one, the Jeep Gladiator is none of these. It is designed to be a mid-sized pick-up yet still be a Jeep, it does this PERFECTLY. I have owned 9 Jeeps over the years, as early as 1978 up through 2006; the Jeeps today are full of more amenities and comfort than they ever have been in history. I have 2 Gladiators; a '23 Mojave, and a '23 Diesel Overland, both of them are INCREDIBLE vehicles on and off road, and MORE than fit the bill for a light duty pick-up, superseding most others on the market, and I am even comparing to any of the 5 Tacoma's I have owned. If you are in the market for a light duty pick-up, you can't beat it; whether it is a loaded up graded model, or even the base model, it is still a truck with 4WD, straight axles, and still available with a manual transmission. VERY happy with both of mine!






Used
2024 Jeep Gladiator Rubicon
Vehicle information
Features
Reviews
One of the Best Buying Experiences!
I recently purchased a pre-owned vehicle at the AutoMax in Framingham. I have bought many cars in my lifetime but I can honestly say, this was one of the best car buying experiences I've had in a long time. This was my first time at AutoMax of Framingham and I was able to find the right vehicle, with the right options and at a fair price (compared to your competitors). However, what really made the experience worthwhile and very appreciable was the salesperson Matheus. "Matt" is really a great salesperson. Much different from others I have met and dealt with. Matt is extremely Knowledgeable and professional - Great Hire and Asset! I will continue to do future business with AutoMax and will refer my family and friends as well. Mark
It’s a Jeep, so people who buy this understand what it’s
It’s a Jeep, so people who buy this understand what it’s all about, great off road performance, reliable and fun to drive. The Gladiator is unique because it’s a pickup and gives you more flexibility on abilities to carry more, but doesn’t hamper performance in any way, also, priced well compared to similar vehicles.






Used
2022 Jeep Gladiator Sport S
Vehicle information
Features
Reviews
Just picked up my (new to me) truck.
Just picked up my (new to me) truck. I worked with Flori. He was very attentive to my questions and found answers quickly. Went the extra mile to get me the deal I was comfortable with. Would definitely work with him again.
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
2021 Jeep Gladiator Sport S 4x4
Vehicle information
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Reviews
MY new challenger
Bought my new 2023 challenger here and they did anything I asked mainly being keeping it wrapped up for me. But otherwise while waiting who can't say no to the free Chick-fil-A they have to offer.
mojave
I have a jeep gladiator mojave, 2021, great vehicle , the best i have ever owned, great for offroading and the suspension is great, designed for higher speed offroading and it does a great jjob at this and just regular off roading. also fun just to drive around town. Highly recommend this vehicle, i also love the xtras, led lights, safety features, (blind spot and ADC, etc), aux swithes . This just a great vehicle.






Used
2021 Jeep Gladiator High Altitude 4X4
Vehicle information
Features
Reviews
awesome service awesome team awesome dealership!
the staff is amazing and they are very knowledgeable and i truly trust they are doing what is best for me and my vehicles life! highly recommend to anyone!
Definitely a fan!
I bought my 2021 Overland new. I love it!!! It is fun to drive. Handles well in the snow. This is a well made vehicle. I love the leather seating. The best heated seats and steering wheel I have owned. I’m definitely a fan!!






Used
2022 Jeep Gladiator Willys 4x4
Vehicle information
Features
Reviews
While many dealerships say they really care about making
While many dealerships say they really care about making customers happy, Albrecht CDJR is a gold standard dealership for customer satisfaction. They agreed to fix a problem with my Durango that was not their fault because it was an OEM issue. Stellantis should have issued a recall on my radio but they haven't yet. Making me happy was more important to them than pointing fingers, and they fixed the issue at no charge. They are the type of dealership that you can trust because they play the long game, and they really do want customers for life. It's too bad that there aren't more dealerships like them.
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 Willys 4x4
Vehicle information
Features
Reviews
Amazing Service
Laura Spinola is the always there for me when my car needs service. She gives me The Best service and She is an Expert at her job. I don't know what I would do without out her help. She always schedule me an appointment. She explains the work being done on my car. She is wonderful. Thank you
MOHAVE ride makes for good daily driver
Mojave trim gives a smooth ride. A big improvement over the 2012 Rubicon Unlimited that I had. 17-18 mpg around suburbs and 20-21 on trips. At 13,000 miles no reliability issues. 8-Speed transmission coupled with the 3.6 v6 works well. Great in SNOW. Recommend the AWD optional transfer case.



Jeep Certified
2021 Jeep Gladiator 80th Anniversary 4x4
Vehicle information
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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.



Jeep Certified
2021 Jeep Gladiator Sport S 4x4
Vehicle information
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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.



Jeep Certified
2022 Jeep Gladiator Sport S 4x4
Vehicle information
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Reviews
I just purchased my first JEEP from Andy Sanchez of Jeep
I just purchased my first JEEP from Andy Sanchez of Jeep 24~ Andy was fabulous, very easy to deal with no high pressure sales just a really NICE guy! If your thinking of buying a Jeep go see Andy at Jeep 24 Brockton MA! You will not be disappointed! Cheers to you Andy it was pleasure working with you!
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.



Jeep Certified
2021 Jeep Gladiator Willys 4x4
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Reviews
Ner 2023 Ram 2500
I bought my 7th new truck from Harr and again the sale went smooth. Danielle and Adrian make it very easy to purchase a new vehicle.



Jeep Certified
2022 Jeep Gladiator Mojave 4x4
Vehicle information
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Reviews
Experience was very professional
Bought 2 vehicles last Month the service was professional and the negotiations without any problems. When we did not buy the first car we negotiated on they were professional, and we ended up buying another car when it arrived a few days later
Gladiator will be the next Jeep superstar.
I am a old school jeep owner, what they have come up with in the Gladiator is a hit. The ride along with rugged styling and performance and a usable pickup bed is fantastic.
Used
2022 Jeep Gladiator Sport
Vehicle information
Features
Reviews
This review is about services provided by Nicholas
This review is about services provided by Nicholas Almeida. My daughter has been going to Parkway Honda for all her car needs because they are simply the best—we already knew that. But what happened recently exceeded our wildest expectations. She had an issue that required a substantial payment from the insurance company to fix. Nicholas Almeida (Nick) took charge of the situation, and from the very beginning, he was incredible. He contacted our insurance company, patiently explained the problem, and for THREE WEEKS, he handled everything. He worked with not one but two appraisers, engaged in multiple conversations with the insurance company, filled out the forms they insisted on, emailed documentation and test results, and kept us informed every step of the way. Thanks to him our insurance company covered the cost of the repairs. We have never seen such exceptional customer care and professionalism, especially when dealing with a difficult insurance company. We are absolutely blown away by Nick’s dedication to his work and his commitment to his customers. We only wish there were more people as proud and passionate about doing an excellent job as Nick is.
Used
2023 Jeep Gladiator High Altitude 4x4
Vehicle information
Features
Reviews
My experience at Imperial chrysler dodge jeep ram was
My experience at Imperial chrysler dodge jeep ram was very good. I worked with Ahmad Al-Jallad and Khalil Mansour and both were very attentive and explained everything clearly. They answered all my questions and gave me the best deal possible. If you are looking for a new or used car, I would recommend Imperial dealerships for your next purchase.
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
2024 Jeep Gladiator Sport S
Vehicle information
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Reviews
I recently purchased a used Subaru from Imperial and had
I recently purchased a used Subaru from Imperial and had a wonderful experience with Laith. He was kind, courteous and very efficient. Highly recommend.
Reliable and great looking truck!
Reliable and great looking truck! Love the way it rides and how many options they have to customize this great mid size vehicle. Love the color options
Used
2021 Jeep Gladiator Sport
Vehicle information
Features
Reviews
Service
Went in for tires and inspection sticker.The technician noticed the front and rear brakes needed to be replaced or I would not pass the inspection . They had the parts in stock and told them to repair the brakes so I would not have to comeback another day so they did.
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Used
2020 Jeep Gladiator Rubicon
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Used
2022 Jeep Gladiator Overland
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Used
2022 Jeep Gladiator Mojave
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Used
2022 Jeep Gladiator Rubicon
Vehicle information
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Used
2021 Jeep Gladiator Mojave 4X4
Vehicle information
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Jeep Certified
2022 Jeep Gladiator Altitude 4x4
Vehicle information
Features






Used
2021 Jeep Gladiator Willys 4x4
Vehicle information
Features






Used
2021 Jeep Gladiator Sport
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Used
2021 Jeep Gladiator Mojave
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Used
2022 Jeep Gladiator Altitude 4x4
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Features
Jeep Gladiator prices by year
Model year | Prices from | Deals |
---|---|---|
2025 Jeep Gladiator | $39,758 | |
2021 Jeep Gladiator | $23,995 | 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
Jeep Gladiator under $99,999 by city
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Jeep Gladiator under $99,999 in Medfield, MA
11 Great Deals out of 57 listings starting at $23,995
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Jeep Gladiator under $99,999 in Millis-Clicquot, MA
11 Great Deals out of 56 listings starting at $23,995
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Jeep Gladiator under $99,999 in Millis, MA
11 Great Deals out of 56 listings starting at $23,995
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Jeep Gladiator under $99,999 in Walpole, MA
11 Great Deals out of 55 listings starting at $23,995
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Jeep Gladiator under $99,999 in Dover, MA
11 Great Deals out of 56 listings starting at $23,995
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Jeep Gladiator under $99,999 in Norfolk, MA
11 Great Deals out of 59 listings starting at $23,995
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Jeep Gladiator under $99,999 in Sherborn, MA
11 Great Deals out of 59 listings starting at $23,995
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Jeep Gladiator under $99,999 in Westwood, MA
9 Great Deals out of 52 listings starting at $23,995
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Jeep Gladiator under $99,999 in Norwood, MA
9 Great Deals out of 54 listings starting at $23,995
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Jeep Gladiator under $99,999 in Medway, MA
11 Great Deals out of 55 listings starting at $23,995
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Jeep Gladiator under $99,999 in Holliston, MA
10 Great Deals out of 56 listings starting at $23,995
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Jeep Gladiator under $99,999 in Natick, MA
9 Great Deals out of 55 listings starting at $23,995
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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.