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

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.

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.

Worked with my sales rep Luis Moreira to lease a vehicle this weekend. He is very easy to work with, low key, and knowledgeable.

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.

Very good the cars were good and the goodness of the level of good was so good I was like dang. The overall experience was very good

Have owned Jeeps for 35 years. This is the most comfortable ever. Altitude 4x2 L, V6, avg. 19-24 MPG. Tow up to 8,000. 6 passenger with 2 fold downs in back. Paid 34k with 18k miles

The 2012 Gran Cherokee Overland has been my car for over 12 years. I’ve enjoyed every minute of driving it. Have made several road trips with it and never a complaint. It’s plush with features and luxury items. Love the looks, love the ride, love the comfort and love the low cost of ownership. Jeep lives up to its name and fame.

Keyshawn was genuinely the best person to get this deal done with. Helped A lot!

What a great look. I have bought several cars and trucks over the past few years, from 2 trucks for me and helped the family with other cars. I wanted to get something for looks and the 2025 Grand Cherokee fit the bill. Style and looks, 10 out of 10 in my opinion. Good on the mileage and performance. Great dealership and people at Ray's CDJR in Fox Lake. They treat you like you should be, with respect through the entire process.

Every was perfect. Veronica and Vinny helped us from start to finish. We got a Jeep rubicon 392. We absolutely love it. I can’t recommend enough!

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!!!

Keyshawn was awesome! He was patient with me and was able to answer any questions that I had. He had options for me to choose from and honest about the vehicles. I’m happy that I came to shakers to purchase my new jeep. Thank you Keyshawn!

I special ordered my 2021 4 dr Sahara in Feb of 2022 and received it 4/1. I have previously owned 4 JK models over the yrs. The 2021 I just love. the interior appts, the dash layout with the nav. I got the upgraded leather seats and paint color white with One Touch Skyview top. Got the 3.6 with E torque for powerplant. They improved on the brakes vs JK. Much stronger!

Great experience! Veronica was excellent to work with and a great help as well as very knowledgeable!!

Love my 2022 Jeep Grand Cherokee L. Has plenty of room and lots of technology. Plenty of power and is doing great on gas mileage based on its size. Definitely recommend the vehicle!

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.

Nice hellcat red eye jeep Chrysler ram good drive suspension engine and supercharger. Great exhaust 6 seconds on track and review 5 star safety rating

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.

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.

Went in to look for a used car. Salesman was not pushy. Found what I was looking for and immediately walked us out to the car and offered a demo ride. Also offered to get another one I was potentially looking at shipped to local dealer for my review. I did not purchase from them but based on my experience I will definitly go back in the future.

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.

Thanks to CarMax services Team I can now relax and drive my car. They were so helpful and I trust them will never ever ever go to any dealer for my car repair. Special thanks to Carolyn for being so nice and understandable.

Because it a great car because the car has 118k miles on it and its only 15,371 dollars and its used and works very well

Very fair and reasonable. Easy salesperson to deal with. Very knowledgeable.

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.

on 3/3/2021All of what my Used Land Range Rover needed was performed with Great precision I would have damage my vehicle if the facility system were not functioning appropriately . I found out upon entering the facility that my car needed a alignment both front and back, And the service director Michael Laurie and Paul Cardoso did a wonderful Job with seeing that safety and customer satisfaction with regards to the service requested I'm Very HAPPY!

I just love everything about my 2021 80th anniversary edition G/C! I purchased new but now has 81000km. So much enjoy all the style comfort with no issues. So much more reliable and better looking than the new body style that was released later in 2021.

From start to finish a 5 star experience leasing a new Velar from Land Rover Hartford. Thanks to Sean, I’ve never felt more comfortable and confident with a sales process. It was actually fun. Also want to thank Brian, who made my virtual experience the best I’ve encountered from any dealer.

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.

What an experience it was!!!! From the moment we walked through the door to leaving dealership in our new Range Rover. Misha Malchevsky was a tremendous help in showroom which by the way is just beautiful. Misha explained everything to us in details in very friendly and professional way. Great customer experience with Misha. After the initial test drive we knew that Range Rover will be ours in a matter of a few days. The staff of this dealership goes above and beyond to make customer well informed and most of all happy.

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.

My recent purchase of my Range Rover was fantastic! My husband and I did some research online and found what we believed to be our new car. We took a chance as a walk -in without an appointment and Misha did an excellent job at accommodating us in between scheduled appointments with other customers. In addition, I wanted to explicitly highlight the wonderful brokering done by Misha with my insurance company who was having technical issues with sending over the new ID cards. We are delighted with our purchase with Land Rover Hartford and would highly recommend.

My Grand Cherokee Laredo E just turned 50,000 miles a few days ago. Other than routine maintenance, the only money that I have invested in it was for 4 tires last month. Extremely comfortable, capable and reliable. While not delivering Prius-like gas mileage, given the performance it provides in all types of weather.............NO COMPLAINTS !

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.

New Jeep GC owner…about a month in. Bought a ‘23 Grand Cherokee Summit after admiring the looks of it. Was nervous to purchase because I usually drive foreign. I also own a ‘22 Audi and have to say that the quality of my Jeep is comparable. I am pleasantly surprised by the drive as well as the quality of the finishes. The ride is quiet and smooth. The 6 cylinder has plenty of pep and has no trouble getting down the highway. It even has a bit of a growl when you step down on it. I legit smile every time I drive my Jeep.