Used Jeep Grand Cherokee for sale near Winfield, IN under $60,000

I want to humbly thank Mario and Neville for their friendliness and professionalism. I wasn't able to purchase a vehicle but the dealership was clean and all working there were very professional. Thank you, thank you.

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.

They were excellent!! Quick and easy and very knowledgeable. Traveled two hours and it was worth the drive

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.

JSON helped me out today t south oak and personally edge my vehicle thank you

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

Jacques was an absolute pleasure to work with. Coming into the day we test drove at Webb Hyundai Merrillville, we were leaning towards a luxury mid-size with BMW and Infiniti at the top of our list, and we closed out the day by driving home in a 2026 Hyundai Palisade Calligraphy. Jacques was very knowledgeable, easy to work with, not too pushy but also stayed on us once he saw our interest increasing. Much of the reason why we ended up choosing the Palisade Calligraphy was due to his approach, as the many the dealerships we went to within our test-drives did not provide a good experience. It also helped that the dealership itself was nice with responsive parts and service employees, free car washes, and a comfortable service area given how long it can sometimes take getting your car serviced at a dealership. Very happy with our decision to purchase from Jacques and Webb Hyundai Merrillville. Highly recommend!

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

Was ok . just couldnt find what was in my budget . needed something for around 1500 cash without a lot of major issues. Since my credit needs help getting cleared up and the fact im not working i wouldnt be able to afford payments

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.

Just purchased our third vehicle from Fieldhouse. Every experience has been too notch, no pressure. Dennis took great care of us and made the whole experience painless and quick. Anytime we need a vehicle Demotte is where we will be heading

This is my 2nd Jeep Grand Cherokee (previous one was a 2016), and I absolutely love it. Gives a very smooth ride. The vehicle feels very sturdy and solid, which to me is another plus. Disappointed that it didn't come with a cargo cover though!

Working with Castle Jeep was simply awesome. I have never had a better experience at a dealership. Josh and Tony did such a great job working with me. I don’t have enough good things to say about them.

2022 Grand Cherokee Overland. Beautiful inside and out. Love the extras that the Overland package provide. Beats EPA milage estimates easily. ride comfort is very good, even in the rear seats.

Process was incredibly simple and Blayne (salesman) and the finance group were awesome. I was coming from out of state and they were able to accommodate me and I drove my truck home within 45 minutes of getting there. I can’t recommend them enough!

The 2019 Grand Cherokee Limited was the Jeep I had my eye on for a while. I've owned a 2012 Laredo X, and a 2018 Limited Anniversary/Heritage Edition. I was specifically looking for Limited trim without the 20" rims, although, I love the look of the Altitude versions, I just didn't really care/want to deal with less side-wall, nicer-looking rims. I avoided the Overland and Trailhawk because of the air-suspension. Overall the interior is fine, it's comfortable and familiar for me, since I've owned them before, but that's also the only issue/complaint I would have. The interior is updated from the 2012, however, basically it's a very light update, U-Connect, Gauges, Shifter, and possibly a few other items here and there. But essentially, the dashboard is the same dashboard I've seen since 2012. While owning the previous (2) I never experienced any mechanical issues that left me stranded. One had a weird issue with blowing lights in the tailgate, but it would just randomly decide to burn out, replace one it would blow another. No other major issues. The 2019 leather on the steering wheel feels smooth and buttery like they always have. The suspension feels great, still solid and tight. Brakes are strong and grippy, pedal feel is nice and firm. So far I'm super satisfied with this Jeep, I got the perfect combination of all the features I wanted, Memory Seats, Sunroof, power trunk, heated-seats and wheel. Not sure if I'd be willing to sell this one and get a newer model, but, I'd possibly get another WK2.

I took my Audi in for an oil change, and the service I received was phenomenal! Blake McCarty went above to assure I had a great experience. Once my vehicle was done he walked me out and opened the door for me. Now that's top notch service. Thank you Blake for the best customer service ever! Keep up the good work.

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.

Most seamless purchase EVER. Adam Rausei is competent and decent, as is manager Matt Monix. You won't regret working with them!

I initially leased my Grand Cherokee Limited but ended up buying it outright at lease end. It has been an awesome vehicle for the 6 years I've had it. I have only had two minor things that have needed work, one was AC needed more coolant and leaking rear strut which must be a fairly common issue as my mom's Durango has had the same problem. Super comfortable ride and plenty of room. My only beef is the halogen factory lights are horrendous but swapping the bulbs out for LED made a big difference for under $200. I normally don't keep a vehicle for longer than 2 years, but after 6 I love this vehicle just as much today as did the day I ordered it!

Cheyenne Fontanez is the best! This process started back in March of 2025 when I was gone for the winter and she stayed in contact with me until we got a deal done on 10/8! It was a seamless process and I couldn’t be happier!

This is the 3rd Jeep product we have owned over the years, first was a Grand Cherokee Laredo, then most recently a 2012 Jeep Liberty Sport. We just purchased the 2019 Jeep Grand Cherokee Ltd in Febrary 2023. This Jeep is the most luxuary we've ever had in a vehicle, it has everything but the cooling seats which would be nice as we live in FL. This will be a dinghy towed vehicle behind our Class A motorhome. We also towed the Liberty Sport.

Excellent experience at DriveTime everybody was top-notch it also I sales guy Brian Johnson thanks very much yes I would recommend this place to anybody but like I said top-notch people go there enjoy

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 !

It was a very smooth experience, Nick Marzullo was extremely helpful - even off of the clock!

We are very happy with our '21 GC Limited. It is well appointed, with many options, drives nice, comfortable and still sits higher, unlike a lot of other "car" SUV's. We use this as our only vehicle, and flat tow behind our motorhome. Jeeps are the best vehicles made to flat tow!! We have climbed dirt trails in the West and cruised coastal waterways. Love it.

My husband and I love our Grand Jeep Cherokee we purchased from Chrysler, Dodge, Jeep of Winter Haven. We love everything about this vehicle. Matt is our Salesman, and he did everything he could to get us in a Jeep we would like. I highly recommend this company.

Great place to deal with answered all the questions and made the right price for the purchase and everyone there was very helpful

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.

I had one of the best experiences with this dealership, I recommend it 100% . I drove one hour and half , but it’s was worth the trip

Love my jeep. They have come a long way baby!! I am now a Jeep girl for life and recommend them highly. No matter the weather my Grand Cherokee gets me there in comfort and safety.

Sam and Scott were able to help me with a service issue. A pleasure and timely assistance.

Love my GC 80th Anniversary Edition. A little over 15K miles and she’s been in the shop 2 times now with a squeaking coming from the engine. Tensioner rod and idle sensor were replaced first, they had it for almost a month. alternator was just replaced, they had it for a week. Picked her up last night, drove her this morning and it’s still squeaking! Very frustrated but hoping to get her fixed!

I could not get a decent car any were CarMax put me back into the drivers seat i will recommend CarMax to anyone Andrea and his team in Tinley Park are truly number one in car sales . Marcel Potvin.

This is third Jeep I have leased and best yet. Summit Reserve Trim is amazing. Great performance and many comfort features. Performance from the v8 Hemi is amazing.

Awesome service from Jose!!! Very patient and kind. Explained every detail. All dealerships need a Jose!

The turning radius is the best for the size of this suv. The brakes are quick to respond. The 4x4 is a must. The only downside is that they aren't all standard with a trailer hitch. Love the sunroof, the all leather interior.

Syed, and staff worked very diligently to connect us to a car that we wanted from the available stock and to finalize the purchase.

Bought a 2010 Jeep Grand Cherokee 6 cylinder. One owner , very clean, well maintained at 91,000 miles. This Jeep drives better than some of the newest suvs I have driven. Previously owed a 2011 with a hemi that I drove til about 220,000 and it was one repair after another. I think the 2010 is much more reliable as long as you maintain it.