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Used
Jeep Gladiator trucks
for sale
near
Greenwich, CT
- 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
2021 Jeep Gladiator Rubicon
Vehicle information
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Reviews
This was a very good experience.
This was a very good experience. North Bay has a straightforward and honest approach to their dealings with clear pricing and costs, good communication, and a friendly/helpful staff.
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
2020 Jeep Gladiator Overland
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Reviews
This is our third car from Nissan Yorktown.
This is our third car from Nissan Yorktown. Maddie was our salesperson each time and our experience was fantastic
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 Rubicon
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Reviews
Happy customer
Very happy with my experience at Autoworld Kia Kia. Jeff was very helpful in getting my car back on the road. This was my first experience with them and will be returning in the future. I would highly recommend to others
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
2023 Jeep Gladiator Sport
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Reviews
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!






Jeep Certified
2021 Jeep Gladiator Sport
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Reviews
Great Experience recommend this dealership.
Our salesman, Ali, and other members of the staff were all knowledgeable, helpful and professional. We are very happy with our new Grand Cherokee Limited.
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!!



Jeep Certified
2021 Jeep Gladiator Overland 4X4
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Reviews
Very smooth transaction
I was shopping around for a car for my wife and the 2 experiences with other city dealers beforehand really turned me off from the whole car buying thing. I was about to give up but saw a 2014 black on black durango R/T from Croton auto. Called on a whim, didn't think I would really purchase but with the staff going beyond how could I say no. Good deal good car and Great experience from financing to test drive. Gave me a couple hundred off the price before I could ask for it, then gave couple more off again when they couldn't find the second key. I was in and out in about 3 hours and that was because of an issue with my insurance company. I didnt mind driving all the way up from long Island because they really showed me they wanted to earn my business. I don't write too many reviews but I had to give xxxxxxto Croton. Thanks guys.
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 Overland
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Reviews
The buying process was easy.
The buying process was easy. I came in and ordered my silverado 1500. The bad part wasn't the dealers fault but I placed the order on December 24, 2024. It came in April 28th , 2025. That was over a 4 month wait. That is way too long .
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 Rubicon
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Reviews
I am very pleased with Stoler.
I am very pleased with Stoler. They treat their customers royally. Their quality of work is excellent. They are always there to help you. Lorenzo, thank you!!
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
2023 Jeep Gladiator Sport S
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Reviews
The entire dealership staff at CPM was incredibly
The entire dealership staff at CPM was incredibly welcoming, making the process smooth, efficient, and completely hassle-free. I got my Jeep Compass Latitude from them, and the experience exceeded my expectations. If you're looking for a top-tier car-buying experience, I highly recommend CPM and working with Jeremy - he made everything seamless and enjoyable.
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
2021 Jeep Gladiator Willys 4x4
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Reviews
Excellent Employees and Dealership
Not that I doubted Brett Saslow but Smith Haven is "The Real Deal" My family has now purchased 5 vehicles from his dealership and we are never, ever disappointed! I was there Friday for a "Free" inspection on my Jeep and as usual I was greeted with a smile by the attendant who was kind, caring & professional. One of the clerks was so kind to these 2 cousins who were with their Grandmother. She gave them papers to color on and her high lighters. That set the tone for all of us in the waiting room. We all talked with one another instead of being glued to our cell phones! The people I met that day, employees and the customers were "Top Notch"! I highly recommend Smith Haven Jeep Ram! Job well done everyone! David Beattie of Blue Point
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
2020 Jeep Gladiator Rubicon
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Features
Reviews
George the manager and Daron the salesman are great!
George the manager and Daron the salesman are great! Took time to understand my car needs and helped me find a vehicle that was right for my needs. No pressure. Also continued to help after the sale. I have leased multiple cars from this dealership and they keep giving me more reasons to keep coming back!
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 !



Jeep Certified
2021 Jeep Gladiator Overland 4X4
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Reviews
El mejor dealer en Nueva York !!
Pedro el Bendedor y el manager de el Jasón me ayudó a sacar un Benz di ayi. Pedro me dio un buen precio y tanto que el iso para ayudar me a sacar este auto bien precioso !!
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
2020 Jeep Gladiator Overland 4X4
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Reviews
I know Tina for many years.
I know Tina for many years. She has sold me four vehicles now. She is a very knowledgeable and personable sales person. Very educated on all the information about the vehicles and the very patient person. The whole experience at the dealership was great. I got a Jeep Grand Cherokee Laredo and I love it. Happy holidays!
Great Truck/Jeep
Love this truck/Jeep! I moved from a SUV to this Gladiator and have never looked back! I have not found anything that I cannot do! If you have any sort of lift, have the fasteners checked every 30,000 miles. Just a FYI, I speak from experience.



Jeep Certified
2023 Jeep Gladiator Willys 4x4
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Reviews
Merrick Dodge Gets it Right
This was my third purchase over the past 11 years which speaks volumes in regards to my satisfaction with the people who work at this dealership. The team of Alfredo Deida (sales) and Scott Froehlich (business manager) made me comfortable with my purchase every step of the way.
Must Love The Jeep Experience
Ecodiesel gladiator is fun to drive and getting good MPG. My second gladiator and no issues. Jeeps aren't for everyone as they are boxy, heavy, noisy in cab at high speeds and not as luxurious as a Lexus. But these things are tanks with body on frame build, Dana 44 axles, real transfer case and mega offroad capability. Plus its easy to modify suspension and its a "jeep thing".






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Reviews
Great experience!
Bought two cars from them, a '66 E-Type in May 2019 and now an Evora GT (2/20). Both are fantastic cars. Had a great experience with Tom and his team. Would not hesitate to by another from Autosport Designs.
Used
2023 Jeep Gladiator Sport
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Reviews
Absolutely first rate service and outstanding customer
Absolutely first rate service and outstanding customer care. I was always kept informed as to the issues of my vehicle repairs.
23 Jeep Gladiator Sport
With the prices of the Gladiator coming way down (because of incentives), it made it an affordable choice. Black on Black, with a tone of options. I love it, and most importantly so does my wife! 🤪
Jeep Certified
2022 Jeep Gladiator Sport
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Reviews
Great experience as always!
Great experience as always! Mike Perez and Mark Ospina always treat us like family when we come in. 4th purchase from town and country and counting
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 Rubicon
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Reviews
I bought two cars from Mike Barrows.
I bought two cars from Mike Barrows. Mike's salesmanship goes unmatched. He did not pressure us at any point and was always willing to do his best on a price for us. The transaction was quick, easy and smooth. Just to top it all off Mike donates $50 dollars for every car he sells to united for the troops and having two grandparents that served this really blew me away. Thanks Big Mike!

Used
2022 Jeep Gladiator High Altitude 4x4
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Features
Reviews
as of any consumer one does have questions about the
as of any consumer one does have questions about the purchase a few days into driving the vehicle. I reached out and my questions were readily resolved.
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
2022 Jeep Gladiator Rubicon
Vehicle information
Features
Reviews
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.
Jeep Gladiator prices by year
Model year | Prices from | Deals |
---|---|---|
2025 Jeep Gladiator | $44,092 | |
2023 Jeep Gladiator | $23,488 | 5 Good deals |
2022 Jeep Gladiator | $24,758 | 7 Good deals |
2021 Jeep Gladiator | $22,995 | 9 Great deals |
2020 Jeep Gladiator | $23,686 | 6 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
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Jeep Gladiator in Greenwich, CT
16 Great Deals out of 56 listings starting at $22,995
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Jeep Gladiator in Cos Cob, CT
13 Great Deals out of 58 listings starting at $23,488
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Jeep Gladiator in Glenville, CT
17 Great Deals out of 60 listings starting at $22,995
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Jeep Gladiator in Pemberwick, CT
17 Great Deals out of 61 listings starting at $22,995
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Jeep Gladiator in Rye Brook, NY
16 Great Deals out of 60 listings starting at $22,995
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Jeep Gladiator in Riverside, CT
14 Great Deals out of 61 listings starting at $23,488
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Jeep Gladiator in Old Greenwich, CT
14 Great Deals out of 61 listings starting at $23,488
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Jeep Gladiator in Port Chester, NY
17 Great Deals out of 62 listings starting at $22,995
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Jeep Gladiator in Byram, CT
17 Great Deals out of 59 listings starting at $22,995
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Jeep Gladiator in Stamford, CT
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Jeep Gladiator in Rye, NY
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Used Jeep Gladiator by body style
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This car is likely to sell soon based on the price, features, and condition.
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