Used Jeep Cherokee for sale near Winsted, CT

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 love my Cherokee overall. This is my 3rd one. Sadly I've noticed the quality slipping. Jeep no longer provides a spare tire - WHAT? The floor mats are now of lesser quality and no longer have the Jeep emblem embroidered on them. The transmission is still a little iffy but not as bad as my '15. The tail lights fill with condensation but the dealership tells me it is normal to do so - WHAT? Additionally you're never gonna be able to find a V6 anymore. I had to go down a year to a '22 in order to get one. They are pushing EVs and Hybrids. All this being said I'm still Jeep girl and still love my Cherokee.

This is my 2nd HRV that I am buying from Hoffman Honda!!! Kim the sales person was wonderful!! Love everything about this dealership!!! Very happy!!!

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.

Thorough and courteous. Great customer service. Oil changed and issue checked out and repaired.

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.

The customer service was good. Car buying process was also good. Great prices and clean cars. Had a problem with my car the day after driving buying it and driving it home and had to have it towed back to J and F's shop. They ended up fixing the vehicle and paying for my tow bill and rental car charges. Needless to say they made it right, although I would expect nothing less. Only thing I wasn't happy with was their mechanic shop. I don't know how they could sale and send out a truck that breaks down the following day BUT they were very apologetic and ultimately made up for it. I will definitely go back.

I purchased recently a used 2020 Cherokee Limited and it has turned out excellent, I have no problems or issues. The only minor issue that I have is the location of the cup holderss.

Was at dealership shopping and this new Jeep Cherokee Lattitude came in on transport. Wanted it the minute I saw it. Jeep dealership had ordered it custom with every option I wanted. Blackout package, V6 a true dual exhaust, sport, power everthing, 4x4 etc. The 4x4 is excellent and never failed me! Its been flawless, aftermarket tuning has turned it into a screaming black speed machine. 112,000 miles so far. No issues with anything! Would buy another if they still made this Cherokee Latitude Special! One very satisfied customer!!!

I buy a ford and by now love it thank you so much. Good dealer

Purchased new in 2015. Have only done 1 repair in 129k, which was fixing oil leak at oil filter housing. Solid car, great in rain and snow. Thoroughly enjoy this car

Absolutely amasing dealership. When I reached out to them about a vehicle they had, I had some very strict guidelines for what I wanted, what I could spend and what i had to put down. All of which was far outside the realm of possibility, considering my credit was not so great. Or so I thought. Milton was not discouraged in the least and put in serious work to make it happen for me. I was never pressured to consider another vehicle, tho he did offer a couple of options. He was great at communicating throughout the whole process about his attempts with different lenders and what documents I would need to provide him with. I have to say, he was far more confident than I was! And in the end, I only had to pay a slightly higher down payment, but got lower monthly payments and got the truck I wanted! Everyone at the dealership was very professional, yet welcoming. There was never any pressure, at all. We drove 2 hours to finalise the deal and actually had to wait awhile because MIlton wouldn't let the truck go until it was clean and had had a more than thorough final inspection and servicing. It is also obvious from their inventory, when you're there, that they handpick only the best. I have never had a more pleasant experience buying a car! We will be replacing another car next year, and I won't consider going anywhere else! Thank you Milton! And all your associates who helped make this happen!

I bought my 2019 Cherokee new in July 2019. I have had it for 4 and a half years now and I have had no problems at all. I have over 61k miles on it. I do worry about the warranty being up that something might happen but it has not given me any issues so I shouldn't really be letting it bother me. This is the longest I have had a vehicle. I usually keep a car and trade it in around 3 years but I have loved driving this car so much that I have no desire in letting it go. I hate that Jeep is no longer producing more of these.

It was a pleasure to deal with Zach, Patrick and Mike. The car was as Zach described, and I am very happy with it. The purchase was made easy by these guys and they were very accommodating:)

Would recommend this vehicle. Overall very good value and has proven very reliable. Sorry to hear it is being discontinued Jeep had a winner and what I thought was a great tweeter between the Compass and Grand Cherokee.

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.

Go with the 3.2 V 6 it has plenty of power. The Auto engine stop/start is terrible even if it does save gas it is too jerky

Great Quick Lane service. Helpful and easy. Dropped me off at work and offered to pick up as well. Very convenient. Fast Overall, a Good value.

We bought it in 2023 just off lease as a CPO. It’s been a great vehicle. We love it would buy another one in a minute.

Great guys to work with. Just the truck I was looking for in excellent condition. The first hour I had it I stopped to get gas and several people at the gas station commented on how nice the truck was.

I have been looking at new Jeeps for awhile was needing a new vehicle was driving a 2005 dodge grand caravan sxt drove it everywhere kid's learned how to drive in it. But I'm a jeep guy have a 1979Jeepcj7 since brand new drive it daily. Seen the jeep cherokee trailhawk at my local dealership talked to them about it took it for a test drive and fell in love with it. Had to take it home. Very comfortable all the buttons are in the right places. Display screen is very simple to navigate easy-to-use app's phone linked right up no need to look at it. Mics are in right places above head everyone I call or calls me has no problem hearing me. Has alot of safety features to get use to but not hard. I have had other cherokee in the past but love this one. If you are interested in a Jeep check out the Cherokee line like I said I'am a Jeep guy test drive and you will see what I mean.

I have been very happy with everyone at Prime Wheels. Everyone is very friendly and helpful. I purchased one car in February and returned to purchase another in April. I have been very happy with the service and the fact that they honor what hey say. I would definitely recommend them to anyone looking for a used car.

  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.

Great dealer. No hassle. In my new vehicle the same day. Smooth transaction. Very happy with whole experience.

A great looking car. We will probably never learn all of the features the car has. Dealer was excellent and no problems working with them. Only one thing not to like was the location of the Emergency Brake lever. Things seem to get set there, and locking the lever.

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.

We purchased the same night a wrangler sport JLU 3.6 manual trans and this Cherokee Limited with the same engine and the 9-speed automatic. And oh boy, these cars were completely different despite having the same 3.6 Pentastar engine. Launching the Wrangler was never an issue. Launching the Cherokee and even more reaccelerating was truly painful and required a lot of preparation. Sometimes, the transmission would take few seconds before downshifting making the throttle response slow at best. Other than that, the car proved to be reliable and was extremely silent and very well equipped. I would recommend that car as a commuter for someone who is not seeking any driving fun. For families who enjoy long trips, there are better and more responsive options out there.

I had an outstanding experience purchasing my Cadillac Lyriq from Blasius Cadillac. Despite having researched the vehicle extensively through YouTube videos, sales representative Rich Noble took the time to thoroughly explain every detail during my test drive, ensuring I fully understood all the features. When I arrived late due to travel delays from Boston and a previous dealership appointment, the team was incredibly accommodating and flexible with my schedule. The pricing process was refreshingly transparent—we negotiated the complete out-the-door price entirely through email with no hidden fees or last-minute surprises. Most impressively, they coordinated with the Massachusetts RMV and delivered my vehicle directly to my home with plates and registration paperwork already completed, saving me an additional trip back to the dealership. Blasius Cadillac demonstrated professionalism, transparency, and genuine customer care throughout the entire process. Highly recommended!

the car is largest enough to haul baseball equipment around, yet easy parking and handling. i like the interior and the room. the seats are very comfortable

Was contacted by Zach from Waterbury dealership. Right off the bat I felt like he understood my needs and wanted to work a fair deal for the sale of my truck. We got it done and myself into new Colorado. Staff was very helpful and patient. I would recommend this dealership team to anyone. Thanks!!

The vehicle is perfect for me....This is my second time buying a car through Music City Autoplex and each time I have driven away completely satisfied. David Beasley has made the purchasing process seamless and smooth. There was no gimmick or trickery like most dealerships...just pure honesty and me driving away knowing that I got a great deal. I bought this red Equinox a year ago with David's assistance and this Jeep, Chocolate, two days ago, again with David's assistance. Many places prey on woman purchasers and try to force us into deals that will hurt us in the long run. Not Music City Autoplex. If you are looking for a great deal and good people to help you purchase your dream car....stop by and ask for David...let him know that me and Chocolate are getting along just fine. Happy Shopping!!!

I got a good deal on the car. Tyler was great to work with. If there was one thing to complain about, it was the time it took to work things out. I was there for four hours, just wish we could’ve cut down on the time.

Love everything about the car the color the room in the interior the pick up the ride and the options are just excellent I am so excited to be able to take a road trip soon

Ordered new , love it so far , I went with the 2.0 turbo , far more responsive than expected , this coming from a life long V-8 driver . Went with the Lattude Lux model , came with many standard feature & we added everything else on the option list , the sun & sound package with the panoramic sunroof and this premium Alpine sound system is awesome . Just wish they would offer more interior colors , had money added in the deal so we could install a differnet color Katzkin leather interior

I went here and had the best service and it was priced excellent I've been in the business for years my mechanic bailed on me and was directed here and it was a plus

I met the owner and he was a tremendous guy. He was very kind and fair and in a separate situation I offered him money for a favor he had granted me and he would not accept it. This is real American charm.

Overall very capable vehicle. 3.2L with 4wd/factory trailer tow. Silly things show up like the service 4wd light that comes/goes and radio/controller that resets after replacement. Solid car with a good pedigree.