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Used
Jeep Gladiator trucks
for sale
near
Southborough, 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.






Used
2020 Jeep Gladiator Rubicon
Vehicle information
Features
Reviews
THANK YOU!!
Wonderful buying experience!! Thank you Toula and George for your help and kindness...felt like family! We definitely will be back to buy our next car.
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
2020 Jeep Gladiator Sport S
Vehicle information
Features
Reviews
Excellent car purchase experience
I bought my 2016 Audi Q5 sight unseen from Medi at Auto Excellence Group. The vehicle was exactly as advertised and in excellent condition. Medi made the process as easy as possible and always followed up. The entire transaction was seamless. I flew to Boston, picked up the car and drive it home the same day. I highly recommend working with the Auto Excellence Group.
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
2021 Jeep Gladiator Sport S
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Reviews
Found a great car at a great price!
Tony and Justin made the experience of buying a car extremely easy and stress free. The customer service and knowledge that Tony demonstrated was the best I ever worked with. By far, the best car buying experience ever!
We special ordered a Jeep Galdiato Rubicon in 2021 and
We special ordered a Jeep Galdiato Rubicon in 2021 and loved it. Our only problem was it didn't leave much space in the garage. We decided to trade it for a special ordered Jeep Wrangle 4dr. RubiconX. This new vehicle left us with 34 more inches of space in our garage. We still have our 2021 Jeep GrandCherokee Trailhawk as our long trip vehicle. 2 never gave any problems accept with the Aux, battery after 3 years of own






Used
2022 Jeep Gladiator Sport S
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!
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.






Used
2021 Jeep Gladiator Willys 4x4
Vehicle information
Features
Reviews
Great experience buying with Marina !
Great experience buying with Marina ! She helped me get my vehicle traded in, and into my new vehicle in 2 days. Highly recommend seeing Marina for your next purchase.
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
2022 Jeep Gladiator Sport
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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.
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.






Used
2023 Jeep Gladiator Sport S
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.
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
2022 Jeep Gladiator Willys 4x4
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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.
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.






Used
2021 Jeep Gladiator Overland
Vehicle information
Features
Reviews
Great Place
Got exactly what I was looking for. Price was great and staff was very helpful and personable. Definitely recommend to anyone looking for a new vehicle.
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
2022 Jeep Gladiator Altitude 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.
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.






Used
2020 Jeep Gladiator Overland
Vehicle information
Features
Reviews
Optimum quality service
Always courteous, professional and informative. And they do not try to sell you unnecessary services/products. I feel I can trust them having used their services over 4 years.
I have 84,000 miles.
I have 84,000 miles. I don’t hit rod it. I keep it below 2500 rpm unless a must pass happens (rarely). Zero issues with transmission brakes electronics heat or AC. Overland model. It has been a wonderful rig with 19 to 25 mpg. I’m 64 and hoping this and my XJ are my last rides. Both rigs are exceptional. I had a scrambler and loved it, had to have the Gladiator and my 2020 has been far better than expected !






Used
2023 Jeep Gladiator Sport S
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Reviews
North End Motors is the place to go for a car.
North End Motors is the place to go for a car. When you get there be sure to ask for Naf he will help you get the car you need. Naf was amazing
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
2021 Jeep Gladiator Willys 4x4
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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.
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
2024 Jeep Gladiator Nighthawk
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Reviews
Everyone at Tulley was great!
Everyone at Tulley was great! They even took my old car as a trade and gave me a great deal.
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
2021 Jeep Gladiator Willys 4x4
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
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.






Used
2023 Jeep Gladiator Overland
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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
Jeep lifestyle
This is my 3rd Gladiator, I really enjoy the Jeep lifestyle, the Gladiator has been a great addition to my family and we have a ton of fun with it. It’s very versatile we use it for pulling our boat and Travel trailer and for everything else!!



Jeep Certified
2022 Jeep Gladiator Sport S 4x4
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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
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 S
Vehicle information
Features
Reviews
Just bought another Jeep here.
Just bought another Jeep here. Friendly helpful and knowledgeable salesman. Sales manager was also friendly and helpful. The finance manager was helpful and worked with us to assure we were happy with the extended warranty. Service for my other Jeep has been quick an easy. It has been a great experience working with this dealership.






Used
2022 Jeep Gladiator Willys 4x4
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Reviews
Low to no pressure sales.
Low to no pressure sales. Good prices and inventory. I enjoyed the buying process (as much as one can). Thanks George!



Jeep Certified
2022 Jeep Gladiator Mojave 4x4
Vehicle information
Features
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.
Jeep Gladiator prices by year
Model year | Prices from | Deals |
---|---|---|
2025 Jeep Gladiator | $39,758 | |
2021 Jeep Gladiator | $23,995 | 13 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 Southborough, MA
7 Great Deals out of 51 listings starting at $23,995
-
Jeep Gladiator under $99,999 in Cordaville, MA
6 Great Deals out of 52 listings starting at $23,995
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Jeep Gladiator under $99,999 in Marlborough, MA
8 Great Deals out of 47 listings starting at $24,953
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Jeep Gladiator under $99,999 in Ashland, MA
7 Great Deals out of 55 listings starting at $23,995
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Jeep Gladiator under $99,999 in Framingham, MA
9 Great Deals out of 58 listings starting at $23,995
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Jeep Gladiator under $99,999 in Westborough, MA
5 Great Deals out of 44 listings starting at $24,953
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Jeep Gladiator under $99,999 in Hopkinton, MA
6 Great Deals out of 52 listings starting at $23,995
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Jeep Gladiator under $99,999 in Hudson, MA
8 Great Deals out of 48 listings starting at $24,953
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Jeep Gladiator under $99,999 in Northborough, MA
6 Great Deals out of 45 listings starting at $24,953
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Jeep Gladiator under $99,999 in Berlin, MA
7 Great Deals out of 43 listings starting at $24,953
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Jeep Gladiator under $99,999 in Sudbury, MA
9 Great Deals out of 56 listings starting at $23,995
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Jeep Gladiator under $99,999 in Holliston, MA
6 Great Deals out of 56 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.