Used Jeep cars for sale near Middlebury, CT under $899,990

Jason was an amazing salesman to work with- again! He was incredibly patient, genuinely helpful, and truly cared about our needs throughout the entire process. It's clear he puts his customers first, and we couldn't have asked for a better experience. Highly recommended.

I've been driving for 43 years now and have owned an array of different vehicles, however I've never been financially fortunate to purchase a luxury model - until now! I was looking for a mid size vehicle that would check many boxes for my snowy Michigan commutes, along with distant travel comfort to and from my cabin and some towing capacity. I have only had this for roughly 1500 miles and wow.. My first impression was luxury. So many base options included in a mid sized and mid priced SUV that pleasantly surprised me. Secondly was the ride quality. Both smooth and quiet and handling. I've read other reviews discussing power inadequacy, but not at all. Plenty of passing and get tup to speed power. Next was the snow. I have Michelin defender tires and wow - what have I been missing? The snow 4x4 duaratac features combined with these tires make this a beast in the snow, slush and rain. It definitely gives me a much more safety reassurance while driving in these conditions. I have not tried the towing yet and have not had any "reliable" issues to report, but we are very fortunate with our pick and one very capable snow commuter.

I had THE best experience at Carmax...the salespeople were non-pressuring, helpful and just amazing (especially Daniel!). They went out of their way to make every step comfortable and unpainful. I will most definitely go there when I need to buy my daughter a car and when I need to upgrade in a few years!

I purchased it used in 2022, it had 76k and now has 96 in 2025. It's 4wd with the 5.7 Hemi in the Overland trim. It hasn't given me any trouble.

Thank You Norbit and Thank Steve for crunching those numbers for making it happen. Nor you wanted me in that Cadillac Escalade and I am. Once again thank you J&M Automotive for looking for me.

  I have the Trailhawk trim, the serious off-road version.  Finally, a car that I can confidently drive in and out of rough construction sites, and not be afraid that I'll break it or get it stuck.   It is possessed by a powerful spirit of wanderlust, and frequently demands that I take it on drives just to see places it hasn't yet been, preferably places that normal cars cannot go.   If Don Quixote de La Mancha lived in our time, he would surely drive a vehicle like this one; a vehicle truly fit for a modern Knight Errant.   I didn't know until a few days after I bought it, and I don't think the dealership knew either, but this one has about a 2" aftermarket lift, and slightly larger tires than stock.

Always reliable and outstanding customer service. Waiting area well stocked and comfortable. Staff friendly and informative, attentive to details and future needs. Service department used modern diagnostic equipment that can be reviewed while waiting

Best vehicle I’ve ever owned, fuel savings combined with functionality! Highly recommend for outdoor enthusiasts who want to decrease their dependency on gasoline! Get one!

Great experience all around, gave me a a fair trade in valve, would highly recommend.

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

extremely helpful met all our needs worked with us on pricing while finding the vechicle we wanted would recommend to everyone

My dream car since a teenager was a grand Cherokee and when I finally got one in 2021, I’ve loved it the same ever since. They are bold in appearance and look like a strong vehicle. It has always run beautifully and I have had no issues thus far since 2021 and now it’s 2024. Very comfortable interior and attractive to the eye. Love love love my car.

OMG !!! This was my 3rd time there. I had a very pleasant experience. Keep up the good work and wonderful staff. Not more to say.

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.

I purchased a 2009 Nissan Rogue on 10-11-12. It was an easy, actually fun experience. The sales man was not pushy, it was an easy process and everyone was very helpful. I love my new car. I would recomend carmax to anyone who wants a stress free car buying experience.

I love my 2019 Jeep Wrangler. It looks and drives great and is a good value for the money. Try it…You might like it!! The Jeep Wrangler Sport S is like no other…with the exception of another style of Jeep Wrangler!!

I had a wonderful experience buying my Jeep from Mitchell Chrysler Dodge Ram. I highly recommend working with Rakib!

I purchased a special ordered Jeep Wrangler RubiconX with the 3.6 engine from our local Dealership! When I first drove this this vehicle I knew it may be rough riding, but after having this for for over 6 months it now is our main vehicle for getting around town. I get 17.1-18.3mpg. It's a 4dr and we enjoy it every day for shopping and other chores. We had it on the main highway and do between 65 and 70mph. It handles great and the ride is actually pretty good. Has great passing power as it has 4:56 gearing! We just recently took our vehicle to Keene Dodge/Jeep to have the tires rotated and were very impressed with the service and the entire staff as they treated us very special.

We purchased a new car from Crowley and found them to be most helpful and not pushy. We brought our car in for service and found everyone to be helpful and friendly.

This is my first Jeep I have ever owned. I always liked the looks of the Grand Cherokee. I’m happy with the vehicle. No complaints except it does like to drink gasoline. My previous 4 vehicles were all 8 cylinder full size pickup trucks. The Jeep being a 6 cylinder eats more gas. The Other than that, I’m very happy with my purchase of my 2022 Jeep Grand Cherokee. Good looks, drives well, comfortable and safe.

Donald Jones from Crowley Chrysler Jeep Dodge Ram did a great job helping me throughout the buying process...no hassle, just hustle!

I have a 2018 Cherokee latitude plus. More than 140k miles. Very nice SUV. I think most of this bad reviews are not fair. I will buy a new one in the near future.

ask for Heidie, she goes above and beyond to get you in a new car !! whole process was fast and smooth like butter. loved it

Approaching 25,000 miles and we haven’t had any issues. I actually enjoy choosing whether to run on electric or gas based on what my journey is. If you just put it in hybrid mode, you’re not utilizing the efficiency of the engine. My advice, think about your journey. If I’m jumping on the highway to then head into the city, I run it on gas on the highway then switch to all electric in the city -no point wasting the electric with highway driving! Then I use up the last of my electric when google tells me I’m X miles from home when I still have X miles of electric remaining to use it all up. When we just do local drives less than 25 miles (grocery, day care pick up etc.) we can literally run off electric only for days, even weeks. It just takes thinking about what your journey involves. Crawling traffic for a 5 mile slow down ahead, I’m on gas until I hit that traffic, then switch to electric. We’ve taken this Jeep (Willys) through plenty of winter storms with feet of snow and ice, never needed to use chains with its AWD or 4WD to choose from. Hopefully the great reliability continues.

On Saturday, June 7, my daughter and I had an outstanding experience at XXX Chevrolet. While my initial intent was simply to support her in purchasing her first vehicle, I ended up trading in my own car and driving away in a brand-new 2026 Equinox — while she purchased a 2025 Colorado. Both vehicles impressed us during the test drive. The safety features, interior design, storage space, and overall aesthetics sealed the deal for both of us. While comfort and safety were top priorities, what truly set this experience apart was the exceptional service we received. Steven connected us with Brian, an outstanding sales specialist who was both highly knowledgeable and incredibly personable. He built immediate rapport, listened carefully to our needs, and guided us to the right vehicles without any pressure. The process was smooth and efficient — we were both driving off the lot the same day! The dealership itself was clean, welcoming, and even treated us to a delicious lunch during our visit — a thoughtful touch that made the day feel even more special. I’ve purchased several vehicles over the years, but nothing compares to the level of service we received from Steven and Brian. I highly recommend them to anyone looking for a car-buying experience that’s professional, honest, and genuinely enjoyable. Judi and Jackie T.

I have a 2021, 2 door, Jeep Wrangler Rubicon. Is it a decent vehicle - yes. Is it for everyone? Probably not. But if you like to drive with the roof off, don't mind bouncing around on the road a little bit....and it is bouncing around, ok with the wind noise, then this is the vehicle for you. The V6 engine is decent. Do the maintenance and it will be fine long term. I have the manual transmission. Works fine and makes it more enjoyable to drive. It is a very nimble vehicle, no problem on the highway, comfortable, and the noise is not that bad when travelling. Is it a vehicle I would drive in bitterly cold winters and icy roads - I am in Canada where winter is winter and -40 is real....nope I would not. However there are thousands of people around here that do. This vehicle is an acquired taste with a variety of uses, applications, and lots of strengths. Does it have many weaknesses - no not really. But you need to be sure why you have it, accept its nuances - which are not that bad, and enjoy it!! It is a fun vehicle to have especially in the summer when the sun is blazing!!!

The Sahara high altitude with the sky one touch roof is awesome. The one touch opens or closed in 15 seconds. This is a game changer as we do not hesitate to open the roof in all different weather conditions. Reason is if bad weather or hot weather gets us we can have the roof closed in little time. The ride is very smooth. Noise is low at highway speeds. Overall, we really all the accessories and sound system. Definitely, recommend.

This is my 2nd Jeep Wrangler. I absolutely love it!!!! I ordered it new, so I have all the bells and whistles I wanted. The SOT is fabulous. It is so fun to drive and I get compliments all the time about how beautiful it is. Receiving ducks and giving out ducks is a blast. The Jeep wave is awesome, too. Wranglers also keep their value.

Over the last 17 years we have purchased four cars from the Crowley Dealership in Bristol. Each of those cars has been serviced at the dealership. Very satisfied.

This review is for a 2023 Jeep Wrangler 4 door Willys. I had traded in my 2008 Jeep Wrangler 4 door Sahara. So I know these Jeep’s not only last a long time, but are reliable. The new Jeep is beautiful, runs well, and is fun to drive. Exceptional on road and off road performer. Snow, rain, sleet, or mud, this Jeep can handle pretty much any conditions.

Easy, friendly, and low pressure buying experience. Offered a good price and then was open to an even better price. Delivered car to my home.

i recently had a 2023 for explorer it was a good truck never a problem but not a comfortable as the jeep grand Cherokee l front seating is amazing no issues at all i did my research and made sure i bought one with the German transmission its a good idea to check that only thing i can say on the down side seam to be a little under powered but i can live with it decent milage 20 around town.

Jon Bryant and team were highly professional and made my recent purchase a pleasant experience.

I love my vehicle. It's a 2023 model year Jeep Grand Cherokee L in the Summit Reserve trim with the 5.7 liter HEMI V8 engine. Overall sleek exterior design of the vehicle is nice. As for the interior, it's great! Nice and comfortable interior. Palermo leather seats, massaging front seats and power folding rear seats. Heated/ventilated seats for both the first and second rows. Front passenger infotainment screen, interior camera, night vision camera, ambient lighting and a 19-speaker premium audio system. More importantly is the excellent performance. This V8 engine comes with 357 horsepower and 390 pound feet of torque. It'll go from 0-60 in 6.1 seconds. Very good acceleration for sure. A recommended vehicle for performance, enjoying features, hauling passengers and carrying big loads when seats are folded. 👍👍

Recently bought a used Lincoln from Blasius. Great experience! Ken McKay is a great guy. Took car of everything. Great car, great price, great experience. Wouldn't hesitate to go back. And thanks to Chris in finance as well. Another great job.

Visibility and size are what I need. 4WD, clearance for snow. Rather tight interior, not suitable for more than two. Auto Park is very confusing. Not auto parallel Park. Car will stop while backing out of parking space, won't move if a somewhat complex procedure is not followed.

I had a routine service call scheduled with Mitchell Jeep for my 2023 Jeep Grand Wagoneer. When I drove up to service I immediately was greeted by a service representative and the service and timing were discussed,The service area, the showroom and the waiting area were all spotless. The service and timing were as promised. Overall an excellent experience and my service representative was Eric Calica, Great Job !!

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!!