Used Jeep cars for sale near Winchendon, MA under $99,994

Derek was very friendly, knowledgeable and super humble throughout my whole experience. The whole team there made sure I was very satisfied with the purchase.

Bought this 2022 Compass Trail Hawk new for my wife. Earlier this year (2025) we landed a sweetheart deal on a new 2024 Wrangler Sport S. Guess who inherited the Compass ? I stepped down from a Grand Cherokee but I have no regrets. It has had a few electrical teething issues but all have been resolved and have not come back. The handling and fuel economy are much better than the Grand Cherokee. There are only 2 downsides..........the size of the gas tank (13.5 gal vs 24.5) and the cargo space behind the 2nd row seats. I have easily adapted to both ! I want to give a shout-out to our local dealership, Tri-City CDJR. Start to finish, an excellent place to purchase and maintain our Jeeps. BRAVO ZULU !

Excellent customer service. The overall experience that started with the online customer service team then moved to work with CJ who coordinated the sales process for me until I purchased the car was outstanding. There were no surprises during closing the deal they even matched my bank pre-approval. Definitely will go back for my next purchase!!!

The best vehicle that I've ever owned! It's never needed to go back to the dealer for any work or new vehicle adjustments. I will get another Gladiator after this one!

First time at dealership. Jason was exceptional !! We will be back. Great place. Love my tacoma. Thank you very much. I feel Jason was very upfront and honest. How refreshing. Thanks again the gyles.

ISSUE WITH SUNROOF CLOSING, NEW ONE PUT IN SAME PROBLEM. IN COLD WEATHER SEVERAL DOORS WOULD NOT LOCK AT ALL. AT FIRST I THOUGHT THEY WERE FROZEN THE DEALERSHIP IS STILL NOT SURE WHY THIS HAPPENED. I WAS UNABLE TO DRIVE IT WHEN THIS OCCURRED. JUST HAD THE IGNITION REPLACED - CAR WOULD NOT SHUT OFF. I REALLY LOVED THIS CAR THE SUNROOF IS HUGE, MY FIRST NEW CAR, IT IS A LITTLE SMALL IN THE BACK SEAT FOR PASSENGERS BUT NICE, I LOVE HAVING A HATCH AND NO TRUNK TO MOVE THINGS IF I WANT. I HAVE ALWAYS WANTED A JEEP AND I ABSOLUTELY LOVE THE 4 WHEEL DRIVE AND OPEN FEEL OF THIS CAR. IT DOES VERY WELL ON THE HIGHWAY. THE REAL ISSUE I AM HAVING IS WITH CASTLE JEEP/ RAM IN NAPERVILLE,ILLINOIS COVRING THESE ISSUES WITH MY 100,000 MI WARRANTY.

The service was great and the people were too. I use their services for all my car needs..

Like the look and has plenty of power we have the v6 option The interior is very comfortable with all the bells and whistles you can appreciate. We traded in a Liberty and the ride is so much smoother.

I had an AMAZING experience at Ron Bouchard Honda!! Lethzzy, Eddie, & Shabana were all so helpful and genuine. Lethzzy was so informative and made buying a car feel easy which was very comforting. Anything I needed she was able to help me and even go above and beyond. Plus she is such a sweet and kind person in general! I won’t buy a car anywhere else now! I HIGHLY recommend this dealership!

Overall, pretty decent car. As professional reviews will note, the transmission is a little finicky, but nothing over the top. Learn to work with it, it works with you. Bought this car used last year with 68k and I drive a lot, so I've already put 30k on it. Handling wise, this works great, even in the snow (FWD, not 4x4). Good cargo room, and room for the kiddo's carseat. Now, this is a Jeep, and hasn't been without issue. The front struts have been replaced, probably as part of my driving style and the rough roads in my area. Part of the bumper got pulled off a while back, not a big deal. Mechanically, decently sound, the car has thrown a few check engine lights but for non-issues. It had an issue a while back where it would turn off or restart on its own when stopping (not to be confused with the auto-stop, which is annoying but can be turned off, this car would just flat out turn off), but that fixed itself. Developed an engine tick that does appear in Jeeps, but that has also righted itself. As such, no major maintenance has needed to be done besides my struts. So all in all, it works. If you're in a situation like mine, yeah, buy the 2019.

They did a good job. They also sent pictures as the mechanic did the inspection, showing the trouble spots.

2017 GC Limited 4WD. Bought it 3 years ago with 53k miles and now approaching 108k miles. When we bought it, we went to fill the tank for the first time and the gas pump kept shutting off. Turns out there was a known issue with the fuel filler neck assembly. The selling dealer replaced it under warranty and we literally didn't have another issue until 100k miles. At 100k miles took it in for new spark plugs, which is normal maintenance, and found the radiator leaking. The new radiator was not cheap. Have not had any other issues, just replaced the factory original brakes, they made it almost to 108k! We live in Minnesota and this vehicle is an absolute beast in the snow. Put it in snow mode and it is very stable and feels unstoppable. It is a comfortable long distance cruiser and gets decent mileage on the highway, between 24-27mpg. The UConnect system is very easy to use, and the nav is pretty good, but the whole system operates quite slowly. That's a minor complaint I think. Overall we are pretty happy with our WK2.

My service advisor was great to work with. The only thing is that I see him way more often than I like.

Runs smooth. Very comfortable. Always loved the Jeep brand so this was a natural upgrade. Love the options too. The adaptive cruise control is amazing.

Excellent service and friendly staff! My husband and I were treated like family. We had an issue during the process, but the team supported us every step of the way, and everything worked out perfectly in the end. The entire staff was very professional, and I’d like to especially thank André, Paulo, and Karen, who kept us informed and truly dedicated themselves to achieving a successful outcome — which we did!

We purchased our 2014 Grand Cherokee Overland new and after 11 years and almost 150,000 miles it easily the BEST vehicle we have ever owned. It is comfortable, delivers reasonable mileage, is quiet, well built, incredibly durable and looks as good today as the day we took delivery.

Bought 2 vehicles last Month the service was professional and the negotiations without any problems. When we did not buy the first car we negotiated on they were professional, and we ended up buying another car when it arrived a few days later

bought a new 2022 GC Summit. I wanted the hemi, only found it in Summit pkg at the time. Overall love the vehicle interior is as nice as anything out there. Real wood, lots of leather and nice materials overall on interior. Kicking stereo. Had a 2016 Overland with hemi. Wanted one more new hemi before quit making them. Easy 20-22 mpg at 70 mph. Plenty of power, very quiet and smooth. Biggest complaint all the plastic trim on the outside. First time i shut the door sounded like a rattle or something, not as solid as the 2016, when i shut the door it sounded solid. Nothing i could find wrong just pieces seeming to make a noise. Overall love it. Looks great, rides great, descent mileage, and very nice interior. Did i mention messaging seats are real sweet. Also plenty of towing power which i needed. Excellent in the snow as well.