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Used
Jeep Gladiator trucks
for sale
near
Windermere, FL
under $400,000
- 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.






Jeep Certified
2021 Jeep Gladiator Sport S






Jeep Certified
2024 Jeep Gladiator Sport S






Used
2020 Jeep Gladiator Overland
Vehicle information
Features
Reviews
Steve B and arturo reyes made my car buying experience
Steve B and arturo reyes made my car buying experience great i was scare but they explained me everything and help me get a good deal
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
Salesman Michael Martinez was fantastic to deal with in
Salesman Michael Martinez was fantastic to deal with in trading in my vehicle and purchasing another. He was knowledgeable and a pleasure to work with. Everyone else in dealership was professional and easy to work with. Highly recommend Posner Park Dodge ram.
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
2021 Jeep Gladiator High Altitude 4X4
Vehicle information
Features
Reviews
Extremely profesional and knowledgeable!
Extremely profesional and knowledgeable! No xx dealership! I highly recommend them!! I visited the dealership and appraised (based on milage and real condition of the car), once I had the correct value for the car and interest rate for financing, I made my offer, and once they confirmed the numbers, we made the deal in less than 15 minutes! I did visit a few dealerships were I wasted my time! Some dealerships don’t take the time to look at garbage they are selling. They go by time on the lot, the make and models and average market sale price not really looking into the real condition of the car. All the information I needed is easily accessible, if you know where to look. I deal with facts not averages!
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 Sport S
Vehicle information
Features
Reviews
This is the best dealership I've ever worked with.
This is the best dealership I've ever worked with. Very friendly staff and beautiful facility. Would highly recommend!
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
2020 Jeep Gladiator Rubicon
Vehicle information
Features
Reviews
There is a Solid inventory of beautiful Porsche vehicles
There is a Solid inventory of beautiful Porsche vehicles to peruse while service is being performed. Waiting facilities are Top notch and the service reps listen to your concerns.
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
2022 Jeep Gladiator Sport
Vehicle information
Features
Reviews
Drew in parts is very helpful and knowledgeable.
Drew in parts is very helpful and knowledgeable. I got the right parts to fit my car on the first trip.Will definitely recommend him to everyone
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 Sport S
Vehicle information
Features
Reviews
Shopping experience
I found the truck I wanted to purchase online. I called the dealership and they were kind enough to hold the truck for me since I couldn't get there for about five days. Upon arrival, I was meet by Mr. Ron Stepp and he was very professional throughout the buying process. In just a couple of hours I was driving home in the truck I wanted. Great buying experience. I will be shop the dealership again. Thanks, Ron for the outstanding help.
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 Sport S
Vehicle information
Features
Reviews
Really liked the car and staff was great to work with.
Really liked the car and staff was great to work with. Good variety and salesperson was very helpful. They followed up and made sure everything was good. Did everything they said they would.
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
2022 Jeep Gladiator Sport S
Vehicle information
Features
Reviews
correction to previous review
I wrote an earlier review about some misunderstadings concerning a car i bought from Falcon. The review wasn't particularly flattering. The dealership reached out to me (prior to the review even being published) and handled the problem.
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
2020 Jeep Gladiator Rubicon
Vehicle information
Features
Reviews
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 Willys 4x4
Vehicle information
Features
Reviews
Thank you Sunny for working so hard to find what I
Thank you Sunny for working so hard to find what I wanted! Your patience and kindness and perseverance were appreciated. You relentlessly worked so hard for us and it was noticed and I will refer you to my family members as well. Thank you, we will be using you again in the future.
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
2025 Jeep Gladiator Sport
Vehicle information
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Reviews
..................................................
after 13 years looking to buy a truck, I went to Sam Boswell GMC. I got a 1500 Sierra GMC a very nice ride. sales person Trent Rice was the best made sure I was well aware of truck I was buying , and explaining everything inside the truck. I have recommended Trent Rice to family members.






Certified
2023 Jeep Gladiator Sport
Vehicle information
Features
Reviews
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 Sport S
Vehicle information
Features
Reviews
I would like to express my appreciation for the
I would like to express my appreciation for the outstanding service provided by Felipe, a Chevrolet sales representative. He was extremely attentive, professional, and patient throughout the entire process. Felipe demonstrated extensive knowledge about the vehicles and was always willing to answer my questions with clarity and kindness. My purchasing experience was much smoother and more positive thanks to his excellent support.
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.






Certified
2020 Jeep Gladiator Overland
Vehicle information
Features
Reviews
If you need a new car.
If you need a new car. Greenway Ford is the place to go. Our salesman was Jack Starkey. He's knowledgeable polite helpful patient and very attentive. He is an asset to Greenway Ford. We give Jack 10 stars!!!
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 Overland
Vehicle information
Features
Reviews
Mario was very honest and professional, helped me get
Mario was very honest and professional, helped me get into a car that I could afford. The whole staff was nice and tried to get us in and out as fast as possible and I certainly appreciated that!
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
2022 Jeep Gladiator Overland
Vehicle information
Features
Reviews
Edgar is great at customer service.
Edgar is great at customer service. He always keeps me informed about my car , and how it?s doing. He always gets me a ride to and from my house without any problem.
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
2024 Jeep Gladiator Willys
Vehicle information
Features
Reviews
Great place!
We Love our new 2021 Challenger! We Had the pleasure of working with Nicholas. He actually made it fun to shop for a new car!!!
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
2022 Jeep Gladiator Rubicon
Vehicle information
Features
Reviews
Mr. Michael Losardo assisted us while our 2019 Subaru was
Mr. Michael Losardo assisted us while our 2019 Subaru was being service om July 3rd, Our radio had gone out on us and needed to be replace. Michael went all out to assisted us to a point of amazing, We are very great ful to him.In another occasion there was another issue with a DCM. The issue was resolved in a timely matter. Thanks Michael you went out far beyond the call of duty.






Used
2022 Jeep Gladiator Rubicon
Vehicle information
Features
Reviews
Central Florida Toyota is awesome.
Central Florida Toyota is awesome. Johana was a pleasure to work with. She was very knowledgeable and professional. We will certainly recommend this dealership to our friends and family.
Jeep Gladiator prices by year
Model year | Average price | Deals |
---|---|---|
2025 Jeep Gladiator | $44,706 |
*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 $400,000 by city
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Jeep Gladiator under $400,000 in Windermere, FL
18 Great Deals out of 79 listings starting at $20,555
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Jeep Gladiator under $400,000 in Lake Butler, FL
18 Great Deals out of 79 listings starting at $20,555
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Jeep Gladiator under $400,000 in Gotha, FL
18 Great Deals out of 79 listings starting at $20,555
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Jeep Gladiator under $400,000 in Bay Hill, FL
17 Great Deals out of 77 listings starting at $20,555
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Jeep Gladiator under $400,000 in Winter Garden, FL
18 Great Deals out of 83 listings starting at $20,555
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Jeep Gladiator under $400,000 in Doctor Phillips, FL
17 Great Deals out of 77 listings starting at $20,555
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Jeep Gladiator under $400,000 in Ocoee, FL
18 Great Deals out of 83 listings starting at $20,555
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Jeep Gladiator under $400,000 in Orlovista, FL
18 Great Deals out of 79 listings starting at $20,555
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Jeep Gladiator under $400,000 in Horizon West, FL
17 Great Deals out of 76 listings starting at $20,555
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Jeep Gladiator under $400,000 in Tangelo Park, FL
17 Great Deals out of 77 listings starting at $20,555
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Jeep Gladiator under $400,000 in Oakland, FL
18 Great Deals out of 84 listings starting at $20,555
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Jeep Gladiator under $400,000 in Pine Hills, FL
19 Great Deals out of 83 listings starting at $20,555
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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.