Used Jeep Cherokee for sale near Winsted, CT under $40,000

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.

I had an excellent experience purchasing my BMW X5 with Dennis Smith at BMW of Waterbury. Dennis was professional, knowledgeable, and incredibly patient throughout the entire process. He took the time to answer all my questions, explained every detail about the car, and made sure I felt comfortable with my decision. The buying process was smooth, straightforward, and stress-free thanks to his guidance. I highly recommend Dennis to anyone looking for a seamless and enjoyable car-buying experience!

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.

Great experience the whole process start to finish was mad easy by my salesperson Julie Hoag set up the Toyota app on my Iphone for my new 2025 Rav4 Limited Hybrid

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.

Edwin Guzman of Lia Honda was exceptionally kind and patient with me. I had left another dealer when the salesperson did not acknowledge me in any way and when I asked for help to buy a new gently used car he said “ I have nothing to offer you.” I found Ed to be the opposite. Helpful , polite and courteous, he had three cars to choose from and he made my experience easy and rewarding . Three days later I had my new car , all paperwork completed and I was one happy customer.

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.

Jason and Adam (and the whole crew here) are fantastic! We've been going here for service and all our car purchases for over 20 years and wouldn't go anywhere else. Their name, "Good Guys" isn't just clever, but also very accurate! Highly recommend for all service and if you're looking to purchase a vehicle!

  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.

Buying a car is never easy, Lila and Mark made it smooth. No pressure and understood my needs. Highly recommend Blasius Kia. Thank you!

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.

It’s always a pleasure to make business with Balise Toyota. They services is one of the best if not the best one in the country. Thank you Mike for always providing such a great service. You’re the best!

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

Purchased a truck from Blasius North last night, January 18. Couldn’t ask for a more congenial group of professionals. They prove doing business can be a pleasure. Special thanks to Steve and TJ. Highly recommend this dealership.

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

Thank you so much (Charlie) for helping my husband and I purchase the vehicle we always wanted. I saw how you went above and beyond to get us out of our current loan and always with a smile on and very positive. You kept following up with us several times throughout the day. People like to hear that. You gave us options and hustled for us. Honestly, even if the deal wouldn’t have gone through, I would have been happy because you really tried. I never thought the deal would have gone through because of our credit issues from two years ago and everything but you made it possible. I look forward to working with you again on our next vehicle. I will definitely continue to buy here and I will always recommend you as a sales person. I can continue to say nice things about Shamrock and hope they knows they have a great employee. The Wrangler is absolutely awesome and the modifications are subtle but awesome.

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 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

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

Purchased about 2 months ago. I have taken it on highway trips and driven around town. Very comfortable ride and it looks great. V6 engine is very responsive. I am averaging about 31 mpg so far and am pleasantly surprised by this. Only wish it had a bit more cargo space making it easier to get our 2 bikes inside without having to take the front wheels off. Also, chip shortage cause rear park sensors to be left off of this build. Overall very pleased

I like this car a lot. I gave up a lot of interior space when I traded in my Journey for the Cherokee and the ride is not quite as smooth along with less gas milage but every other way it is far superior. Love the 4x4 and how it handles in snow. The interior design is very nice as is the exterior design. More sleek. It is still a nice comfortable ride, especially on the highway. It is much more reliable than my last car. The seat and steering wheel warmers are an extremely nice touch. Yea, I like the Jeep Cherokee very much.

I live in a different state and I wanted to buy this particular car without even seeing it in person. I had some contact with a salesman but I asked foe a walk around and that never happened. So why put it on a national stage.this would have been an easy sale. Kinda of left me standing...I assumed they were in the business to sell cars..very disappointed 😞..

I have a red 2017 Jeep Cherokee that I bought used, and I love it. I live in the blue ridge mountains of Virginia and this car has been able to deal with everything i've thrown at it. Deep snow, muddy trails, icy roads... You name it. I have the V6 and I can hook up a heavy uHaul trailer and go up and down all the mountains with it. My wife even hit a deer in this car... It obviously had to go to the repair shop, but my wife was safe. The only thing that bothers me a little is that you can't slam on the brakes and throw it in reverse... You need to stop completely, take two seconds and then put it in reverse.

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

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!!!

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

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.

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 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!!!

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:)

I drive a lot my car is a 2014 and it has currently 277,400 miles and still ticking. I’ve had very few maintenance issues overall the basic wear and tear as expected! I didn’t expect it would last as long as it has but I am being pleasantly surprised. It is great on gas compared to most SUVs and overall a comfortable car !

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!!

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.

They serviced my vehicle at unbeatable price and also sold my mother a great vehicle at the lowest price around!!

Great SUV...BOUGHT in 2017...good on gas penalty of zip with V6 engine. The start stop stop working last year and found out why.I needed a new battery as went dead this year...now start stop feature works 100 percent. Have low milage 30000 miles or 50000 kms here in Canada. .

Victoria and Sam were AWSOME to work with. Knowledgeable, personable and professional. I’ll recommend them to my friends and family. Got a great deal on a truck too.

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