What if you want a Jeep but in pickup truck form? That’s where this iconic American off-roader brand has read your mind. They’ve been offering a model called the Gladiator since 2020 that is a midsize pickup truck with the face and underpinnings of a Wrangler. You’ve got all those unique attributes such as the removable doors and top, paired with a versatile cargo bed out back. If that sounds like your kind of vehicle, we’ve got a 41,189-mile 2020 Jeep Gladiator Overland for sale from Wilbraham, Massachusetts. Notably, the current owner says that this vehicle has completed its clutch and transmission recall, so you don’t have to worry about those issues.
Dressed in a Gator clear coat, this 2020 Jeep Gladiator Overland 4x4 looks like nothing but a Jeep. The front and passenger cabin are quintessentially Wrangler, but as you move rearwards, the distinctive pickup truck style quickly becomes apparent. This vehicle rolls on an attractive set of double-five-spoke alloy wheels, and comes with a premium black Sunrider soft top. It’s also got black tubular side steps by Mopar to aid entry and exit. Meanwhile, theres’s a spray-in bedliner, and the vehicle has been specified with the Trailer Tow Package too. The interior of this 2020 Jeep Gladiator Overland comes in Dark Saddle Brown, and includes amenities such as all weather slush mats, dual-zone automatic climate control with rear passenger vents, and premium wrapped instrument panel bezels. You’ve also got Jeep’s uConnect infotainment system, power locks, power mirrors and power windows. You’ve also got power sockets inside the cabin, automatic headlamps, and a multifunction steering wheel with cruise control.
Powering this 2020 Jeep Gladiator Overland is a 3.6-liter Pentastar naturally aspirated V6 that reportedly makes a factory-rated 285hp and 262lb-ft. Notably in this vehicle, it’s paired with a 6-speed manual transmission that makes off-road driving truly pleasurable for those who enjoy a more connected experience. You’ve also got a two-speed transfer case, and can engage rear-wheel drive for better fuel economy when driving on tarmac. When the going gets tough, slot it in to 4WD high or 4WD low and make your merry way across the terrain.
2020 Jeep Gladiator Overland 4x4
3.6L V6
6–Speed Manual
RWD w/ 4x4
Gator Clear Coat Exterior
Black/Dark Saddle Interior
Leather–Trimmed Bucket Seats
Trailer–Tow Package
Spray-In Bedliner
All–Weather Slush Mats
Premium Black Sunrider Soft Top
Black Tubular Side Steps by Mopar®
Premium Wrapped Instrument Panel Bezels
Clutch & Transmission Recall Completed as Per Current Owner
The Jeep Gladiator is a pickup truck based on Jeep’s popular Wrangler off-roader. Thanks to being heavily based on the Wrangler, this midsize pickup truck looks much the same as its sibling from the front three quarters, comes with the same powertrain choices, and the same off-road hardware too. But it swaps the rear cargo compartment for a five-foot truck bed. That’s all well and good for most, but what if you want a Wrangler with some serious capabilities in case, you know, the world ends as we know it? That’s where a build like this 2023 Jeep Gladiator Apocalypse Hellfire 6x6 enters the scene. Built by SoFlo Customs, this mean machine is up for grabs in Utah with just 1,710 miles. It’s got a 3.0-liter turbodiesel, a custom leather interior and more. Oh, and it’s a true 6x6, meaning all six wheels are powered!
Jeep’s Gladiator offers all those fun features of the Wrangler such as the removable doors and roof in a midsize pickup truck package. Yes, for those who need a Jeep with a cargo bed, this American off-roader maker has got you covered. The current generation of Gladiator is the JT which was sold from 2020 onwards, based on the Wrangler JL which preceded it by one model year. Today’s Gladiator is no regular one, though. It’s a 2022 Jeep Gladiator Hellcat Powered AMW 707 with the AMW 707 Hellcat conversion package. That includes a monster 6.2-liter HEMI with a supercharger tacked on, while you and your passengers luxuriously lounge upon a premium Tuscany leather interior. All this awaits you in Scappoose, Oregon with just 22,500 miles done so far. Tempted? Give in and call us.
The Jeep Gladiator is a pickup truck that’s heavily based on Jeep’s famous Wrangler off-roader. This means that the Gladiator is probably the only pickup truck available today with removable doors and a pop-off roof. Introduced in 2020, it’s a midsize truck that can carry between 1,000 and 1,700 pounds depending on trim. It’s also got the same off-road hardware and software as the Wrangler, which means its nearly as capable in the rough stuff. Today, we have a 2020 Jeep Gladiator Sport for sale from Milan, Ohio, with some significant upgrades. The things added to this 48,833-mile machine include a full body Armor coating, a heavy-duty lift kit, a custom leather interior and many more goodies.
The 1973 Jeep CJ-5 stands as a true symbol of classic American off-road culture, and this particular example takes that legacy to an entirely different level with a heavily built, trail-focused setup. Showing just 7,635 miles, it has clearly been maintained as a purpose-driven machine rather than a daily driver. What makes this CJ-5 especially compelling is the depth of its upgrades—from the V8 swap to reinforced axles, steering improvements, and a fully outfitted recovery and lighting system. It’s not just visually aggressive; it’s engineered to perform in serious off-road environments, making it an excellent option for enthusiasts who want a vintage Jeep that’s already been built right instead of starting from scratch.
The 2022 Jeep Wrangler Unlimited Sahara Black Widow Edition takes the already capable Wrangler platform and elevates it into a purpose-built off-road machine with aggressive styling and premium customization. Showing just 16,110 miles, this example blends factory comfort and technology from the Sahara trim with SCA Performance’s renowned Black Widow package. With its lifted stance, FOX suspension, and 35-inch all-terrain tires, this Jeep is equally at home crawling trails or commanding attention on city streets. The addition of features like a WARN winch, Gorilla Glass windshield, and cold weather amenities make it a well-rounded, turnkey build that stands out both visually and functionally.
Most off-road machines don't have any road manners; they can be tough to control, and you eventually may get tired and resort to a car that doesn't have any soul for daily driving and your purpose-built off-road for the weekends. Don't settle on the soulless daily and unreliable weekenders, cut out the trouble and get yourself this 2024 Jeep Wrangler Sport we have today. Hailing from El Paso, Texas and with a reported 21,007 miles run since new, this machine comes with a Customer Preferred Package 22S, Trailer Tow & Auxiliary Switch Group, Convenience Group, Jeep trail-rated kit and makes for a daily driver that is more than capable when the road stops.
If you’re looking for the ultimate combination of heavy-duty capability and premium comfort, this 2024 Ford F-450 Super Duty King Ranch checks every box. Designed as Ford’s top-tier dually pickup, the F-450 is built to handle serious towing and commercial-grade workloads while surrounding occupants with upscale materials and advanced tech. This example shows just 10,480 miles, making it a lightly used, near-new truck with a strong presence and even stronger capability. Finished in the deep and sophisticated Antimatter Blue over a signature Java leather interior, it carries the unmistakable King Ranch identity. With desirable options like the FX4 Off-Road Package, 360-degree camera system, and onboard power generation, this truck is equally suited for demanding job sites or long-distance hauling in comfort.
The 2022 RAM 1500 TRX Crew Cab 4x4 is the definition of a modern supertruck, combining extreme power with cutting-edge off-road engineering. Showing just 50 miles, this example is essentially brand new and presents a rare opportunity to own one of the most capable and aggressive trucks ever produced. Built to dominate both pavement and desert terrain, the TRX redefined what a factory pickup could do by pairing supercar-level performance with rugged durability. Finished in Bright White over a bold Black and TRX Red interior, this truck delivers presence, capability, and exclusivity in one package.
The Ford F-150 has long been America’s best-selling truck, but this 2022 Ford F-150 XLT Rocky Ridge Edition takes that proven platform and elevates it into something far more aggressive and distinctive. Showing 54,575 miles, this SuperCrew 4x4 blends factory capability with a full Rocky Ridge upfit, transforming it into a head-turning off-road machine. Powered by the sought-after 5.0L V8, this truck delivers classic naturally aspirated performance paired with modern technology and everyday usability. With its lifted stance, upgraded wheels and tires, and exclusive Rocky Ridge touches, this is not your average F-150—it’s built to stand out both on and off the road.
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