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Used
Jeep Gladiator trucks
for sale
near
Windsor, CT
under $50,000
- 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
Special ordered and delivered more than promised.
Special ordered a new Mustang. Dealt directly with the owner to ensure order was perfect. We had an agreement but not a deal on trade. When the car arrived a month sooner than expected I was offered more than we agreed on trade, a nice rebate and MSRP was lower than when I ordered. Salesman John is honest, straight forward, and zero sales tactics. Couldn't be happier with my experience.
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 S
Vehicle information
Features
Reviews
It was very easy with them.
It was very easy with them. I bought a Ford transit 250 from them, and when I saw that my odometer was not working, they quickly repaired it. Thank you.
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
2022 Jeep Gladiator Rubicon
Vehicle information
Features
Reviews
Drive away with confidence and happy!
I am a returning customer who bought several Jeeps from Barry Pinto. Barry is not only a true professional but also very approachable, friendly, attends to requests promptly and always returns a call. Everyone at Bolles is helpful, providing a stress-free experience. Their service department over the years has been beyond reproach; the customer service is excellent. It is refreshing to know there is a caring car dealership that has kept car buying stress free with confidence. I shall never go anywhere else and hope Barry Pinto will be there as long as I'm buying cars.
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
2023 Jeep Gladiator Willys 4x4
Vehicle information
Features
Reviews
very good .
very good . the pm's that werte compleated were checked off and not everey box was checked off like last time . it i see a box checked off and that service was not required or compleated i will go somplace other than your location. a good pm programhave has certain guidelines to fallow. the person compleating the pm's should not check of a pm that he did not comcomplete, and checked off after completion. i hav worked with vehicle pm programe in the U,S MARINES AND U.S Army and U.S Air Force . alos for the city of chicopee for 30 years. it was unacceptable and quite shocking when i picked up my truck to find all pm check boxed checked . this was not my last pm with you but the one befor. ,
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
Bought remotely from a couple states away.
Bought remotely from a couple states away. Opted to arrange my own financing. Ken & Joe were very patient, holding the vehicle (with minimal deposit) while lender rqmts. for availability of funds were met. They made it EZ. An all around awesome experience! When I went to get the vehicle I purchased, the only distraction was their impressive inventory!
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
2024 Jeep Gladiator Sport
Vehicle information
Features
Reviews
Worked with Steve, didn't end up buying but he was super
Worked with Steve, didn't end up buying but he was super nice and upfront with us. A much better experience than some of the dealers we talked to on this journey.
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.






Jeep Certified
2023 Jeep Gladiator Overland
Vehicle information
Features
Reviews
Great service every time
I bring my fleet vehicle here for repairs/maintenance. Other dealerships have treated me like a second class customer because the fleet company pays for everything. I have never once felt that way at Sullivan's. They are always kind and have gone above and beyond for me at times. My husband became a loyal customer here because of their great customer 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!!






Used
2021 Jeep Gladiator Sport
Vehicle information
Features
Reviews
I have been doing business with this company since 2002 .
I have been doing business with this company since 2002 . Best dealer , they are conscientious , pleasant and take good care of their customers. They do know their stuff . Whether purchasing or servicing ur car . Expect the best !
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






Jeep Certified
2022 Jeep Gladiator Mojave 4x4
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Reviews
Dodge dart
This is my second car from Troiano I just bought an AMAZING new Dart, Dave is super.
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
2023 Jeep Gladiator Sport S
Vehicle information
Features
Reviews
Very easy to work with
Edwin was great to work with from the beginning. He reached out shortly after I inquired about the car and scheduled a time the next day to take a test drive. They were able to complete the purchase that day so I could take the car home. Overall, both Edwin and their Finance department were easy to work with.
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".






Used
2020 Jeep Gladiator Sport
Vehicle information
Features
Reviews
Had a great buying experience here at terryville chevy.
Had a great buying experience here at terryville chevy. My salesman Peter was great and very knowledgeable. I highly recommend going here!
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 Overland
Vehicle information
Features
Reviews
Todd was our salesman.
Todd was our salesman. Our car buying experience was handled very professionally and with great care. Todd did not rush us through the process. He was very prompt while we tested the vehicles. His manager closed the deal and showed the same level of care. We will definitely return with our family on future car purchases.
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
Vehicle information
Features
Reviews
Every person I dealt with were very professional and good
Every person I dealt with were very professional and good communicators. This was a factor in my decision to purchase my car. It was a positive experience. Definitely recommend.
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
2023 Jeep Gladiator Sport
Vehicle information
Features
Reviews
Champagne and Fernando made the entire process seamless
Champagne and Fernando made the entire process seamless and were very accommodating with me while being many states away. Couldn't ask for a better experience!



Jeep Certified
2023 Jeep Gladiator Sport S 4x4
Vehicle information
Features
Reviews
Jeep Cherokee limited
Very good customer service, very good support throughout the process. Shout out to John in sales.... thank you so much for your time and patience!






Jeep Certified
2022 Jeep Gladiator Willys 4x4
Vehicle information
Features
Reviews
Warranty work
I would like to thank Andy Keleher and Trioano Auto Group for providing excellent warranty service on my '09 Challenger RT while 1000 miles from home. I brought the car in at 8:00 AM Monday morning with the transmission in "limp-in" mode. I did not have an appointment but they worked me in and diagnosed the problem as a failed speed sensor inside the transmission before 10:00 AM. They located the part in another town and sent a driver to pick it up. I had my car back by 3:00 PM. Troiano's fast service literally saved the rest of my vacation. I have put over 1000 miles on the car since with no problems. This is the way warranty service is supposed to work.
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
Great experience - painless transaction from out of state
Great experience - painless transaction from out of state - Fernando helped out at every step to keep us informed and answered every question -






Jeep Certified
2022 Jeep Gladiator Willys 4x4
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Reviews
Great Dealership - Even better Salesmen
This was my first Jeep Wrangler purchase and it was very pleasant and my salesman Henry went above and beyond! I was astonished with how much Henry really cared about me and how much he actively assisted me with purchasing my vehicle.






Jeep Certified
2021 Jeep Gladiator Sport
Vehicle information
Features
Reviews
Great dealer
Great sales and excellent service departments! Have leased two jeeps and have always been happy going here. I would recommend to go here to others!
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
2021 Jeep Gladiator Mojave 4X4
Vehicle information
Features
Reviews
Got my answer in very short time just what I needed ok
Got my answer in very short time just what I needed ok fine job but
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.
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About the Jeep Gladiator
How much does the Jeep Gladiator cost?
The Jeep Gladiator price depends on several factors, including the trim level, optional features, mileage, vehicle history and location. The nationwide average price for the Gladiator is $34,702, with pricing starting at $15,480.
What is the MPG of the Jeep Gladiator?
The Jeep Gladiator with traditional internal combustion engine offers up to 17 MPG city and 22 MPG highway for a combined rating of 19 MPG.
These figures are based on EPA mileage ratings and are for comparison purposes only. The actual mileage will vary depending on the selected vehicle model year, trim, driving conditions, driving habits, vehicle maintenance, and other factors.
What are some similar vehicles and competitors of the Jeep Gladiator?
The Jeep Gladiator compares to and/or competes against the following vehicles:
What trim levels are available for the Jeep Gladiator?
The Jeep Gladiator is available in the following trim levels:
What model years are available for the Jeep Gladiator?
Available model years for Jeep Gladiator inventory range from 2020 to 2025.
*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 $50,000 by city
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Jeep Gladiator under $50,000 in Windsor, CT
3 Great Deals out of 35 listings starting at $25,422
-
Jeep Gladiator under $50,000 in Bloomfield, CT
5 Great Deals out of 43 listings starting at $21,995
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Jeep Gladiator under $50,000 in Windsor Locks, CT
3 Great Deals out of 31 listings starting at $25,422
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Jeep Gladiator under $50,000 in Blue Hills, CT
5 Great Deals out of 43 listings starting at $21,995
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Jeep Gladiator under $50,000 in Tariffville, CT
3 Great Deals out of 31 listings starting at $25,422
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Jeep Gladiator under $50,000 in South Windsor, CT
3 Great Deals out of 32 listings starting at $25,422
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Jeep Gladiator under $50,000 in East Windsor, CT
3 Great Deals out of 33 listings starting at $25,422
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Jeep Gladiator under $50,000 in East Granby, CT
3 Great Deals out of 28 listings starting at $25,422
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Jeep Gladiator under $50,000 in Simsbury Center, CT
4 Great Deals out of 33 listings starting at $21,995
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Jeep Gladiator under $50,000 in Broad Brook, CT
3 Great Deals out of 33 listings starting at $25,422
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Jeep Gladiator under $50,000 in Hartford, CT
5 Great Deals out of 45 listings starting at $21,995
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Jeep Gladiator under $50,000 in Simsbury, CT
5 Great Deals out of 36 listings starting at $21,995
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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.