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Used
Jeep Gladiator trucks
for sale
near
Old 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
Features
Reviews
Very helpful service from Petar and extreme transparency
Very helpful service from Petar and extreme transparency very truthful and genuine 👏 looking forward to purchasing from this dealership
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
2021 Jeep Gladiator Willys 4x4
Vehicle information
Features
Reviews
Found the exact truck I was looking for called Security
Found the exact truck I was looking for called Security Dodge to make sure it was available and off I went to the easiest car buying experience I've ever had. Everyone I met at the dealer was extremely helpful and guided me into the seat of my new truck.Special thanks to Elvis my salesman,love my truck!
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 Overland
Vehicle information
Features
Reviews
Vehicle was sold before I was able to speak to a sales
Vehicle was sold before I was able to speak to a sales person. No problem! They were working on it before I inquired about it.
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.



Jeep Certified
2021 Jeep Gladiator Overland 4X4
Vehicle information
Features
Reviews
Excellent Deal
This dealership give me very good deal my sales person Pedro and general sales manager Jason did a very good job explaining everything to me and get me approved and a very nice truck.
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.






Jeep Certified
2020 Jeep Gladiator Sport
Vehicle information
Features
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.
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 Rubicon
Vehicle information
Features
Reviews
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
2023 Jeep Gladiator Rubicon
Vehicle information
Features
Reviews
Excellent service!
Excellent service! The sales person spent a lot of time with me. They were excellent showing me all the features.
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 Overland 4X4
Vehicle information
Features
Reviews
2010 Dodge challenger
Jessica and Vinnie were very helping in the buying process. I would recommend them to anyone.
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
Vehicle information
Features
Reviews
Shopping for a new vehicle
Spoke to your dealer Derek B he was incredibly helpful and and was a huge help in making this process easier than I thought I would highly recommend him.Great experience buying a new vehicle from Derek B
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 Willys 4x4
Vehicle information
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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






Vehicle information
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Reviews
great response to the gentleman to the 599
Tom Papadopoulos you have a excellent reputation with exotic imports . You did the right thing. Good for you . Time Bandits are just that. You deserve better .






Jeep Certified
2022 Jeep Gladiator Sport
Vehicle information
Features
Reviews
Mr Perez , was Awsome !
Mr Perez , was Awsome ! Handled my needs from a to z . Highly recommended ! Great place to buy a car . Excellent customer service and plenary of used cars and trucks to choose from !!
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
2022 Jeep Gladiator Sport
Vehicle information
Features
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.

Jeep Certified
2023 Jeep Gladiator Sport
Vehicle information
Features
Reviews
Service was done on time and with quality results.
Service was done on time and with quality results. Service cost was the same as quoted
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
2020 Jeep Gladiator Rubicon
Vehicle information
Features
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.
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.
Used
2023 Jeep Gladiator Sport
Vehicle information
Features
Reviews
Fast and efficient, Everyone at the service department
Fast and efficient, Everyone at the service department was extremely nice and helpful , thank you
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!!
Used
2022 Jeep Gladiator Rubicon
Vehicle information
Features
Reviews
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 Rubicon
Vehicle information
Features
Reviews
Thank you so much Andrew & Alex for setting me up in my
Thank you so much Andrew & Alex for setting me up in my preowned certifed Kia sorento!
Best vehicle I’ve ever owned. And I’ve owned many
Went to the dealership in August of 2020 to get a 2 door Willy. They did not have any and due to COVID did not know when they were getting any in. I had just purchased a grand Cherokee from same dealership about a year prior but needed a jeep wrangler as I previously owned one. They had a 2020 Jeep Gladiator sport on the showroom floor with a ton of extras (2 inch lift kit, all Fox shocks, coated bed liner, custom bed cover (hard shell), 34” all terrain tires, Matt black 18” wheels, led light bar mounted right in front of the front windshield, 2 led lights at front on either side, custom soundproofing on the inside hard shell top and I think the beefed up tow package but not sure. Within the first 2000 miles loaded a 35’ tv weighing 5800 pounds and headed out to Utah from Chicago driving through Colorado. The thing was phenomenal towing this heavy rv up and down the mountain pass on I 70. At a gas station some guy with a fifth wheel and a Ford F350 asked me what I was doing towing such a big rv with such a small truck. Kinda laughed. Saw him on the road later going up a mountain pass and blew right past him in my small truck. This truck has been nothing short of amazing. The dealership I purchased from is the best I’ve ever dealt with (Fields Chrysler/Jeep in Glenview, Il). They always have a loaner if needed. They are awesome. I bought in August of 2020 and today I have just shy of 70k miles on it and still running strong. I do not know why everyone says these things top off at 97 mph. I have gotten mine up to 110mph with a bit of room to spare. Gets to over a 100mph rather quickly. Maybe I just lucked out on a good one. I’ve read a lot of people complaining about a little water run off from the front door design. They are not wrong but you bought a freakin jeep, you’re not going to melt. Grow a set. Best vehicle I have ever owned. Best part with all the extras that came with it I got it for 49k with 15 miles on it. That same gladiator was there when I bought my grand Cherokee. I guess they were sick of it sitting on their showroom floor because back then it was listed for a tad over 60k.
Used
2021 Jeep Gladiator Willys 4x4
Vehicle information
Features
Reviews
I had a great experience at Blasius South.
I had a great experience at Blasius South. The staff was friendly, knowledgeable, and genuinely helpful throughout the entire process especially Luis, Veronica, Jay, and Mike L. They made buying my car easy and stress-free, answering all my questions and offering great advice, and went above and beyond to make sure everything was taken care of. Highly recommend this dealership for anyone looking for a smooth and pleasant car-buying experience!
Used
2021 Jeep Gladiator Rubicon
Vehicle information
Features
Reviews
Great experience and service!
Great experience and service!! Prior to pickup everything was explained and verified in order to have a seamless delivery experience. Sharon was great at going over everything and Mike took it home with no hiccups. Definitely great customer service and experience!! Would recommend and buy another vehicle!
Jeep Gladiator prices by year
Model year | Prices from | Deals |
---|---|---|
2025 Jeep Gladiator | $44,568 | |
2023 Jeep Gladiator | $24,988 | 5 Good deals |
2022 Jeep Gladiator | $26,822 | 6 Good deals |
2021 Jeep Gladiator | $24,795 | 14 Good deals |
2020 Jeep Gladiator | $25,178 | 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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Used Jeep Gladiator by city
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Jeep Gladiator in Old Greenwich, CT
8 Great Deals out of 62 listings starting at $24,795
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Jeep Gladiator in Riverside, CT
8 Great Deals out of 62 listings starting at $24,795
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Jeep Gladiator in Cos Cob, CT
8 Great Deals out of 60 listings starting at $24,795
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Jeep Gladiator in Greenwich, CT
10 Great Deals out of 57 listings starting at $22,995
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Jeep Gladiator in Pemberwick, CT
9 Great Deals out of 63 listings starting at $22,995
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Jeep Gladiator in Byram, CT
9 Great Deals out of 61 listings starting at $22,995
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Jeep Gladiator in Glenville, CT
9 Great Deals out of 62 listings starting at $22,995
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Jeep Gladiator in Port Chester, NY
10 Great Deals out of 63 listings starting at $22,995
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Jeep Gladiator in Stamford, CT
5 Great Deals out of 45 listings starting at $24,795
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Jeep Gladiator in Darien, CT
5 Great Deals out of 53 listings starting at $24,795
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Jeep Gladiator in Rye Brook, NY
9 Great Deals out of 61 listings starting at $22,995
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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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