Used Jeep Grand Cherokee for sale near Winfield, IN under $20,000

They went 400 miles to get my van couldn?t ask for a better experience. The best Ford dealer in the area and one of the best dealerships of any kind. Ask for Tin Heineken.

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.

I HATE is the warning 'Place Two Hands On Wheel' as it goes off even when I have both hands on the wheel - No matter where I place my hands on the wheel it goes off. Since it is connected to the Lane Departure feature in order to not have to hear a constant warning alarm for Two Hands on Wheel I have to turn off the Lane Departure feature (which I love).

This is the fourth Subaru we have bought from Castle Subaru. Dave set us up with Cheyene who helped us get exactly what we wanted. This will primarily be my wife’s car and they did everything to make her happy. Then we got to work with Stephanie who worked with us so we could creatively pay for the car without a loan. We are extremely happy with this team effort. There is a reason our family has bought all of their Subarus from Castle!

Bought my 2017 Overland 2WD preowned with 74k miles. It’s now Feb of 2024 my Jeep’s got 135k on the odometer and I’ve never once had an issue. I occasionally get car fever, start looking at cars online, but the second I jump behind the wheel of my Grand Cherokee I smile and decide to keep it for a little longer. I still love the look, it’s super comfortable, has plenty of power, all the bells and whistles I want (and beyond), and I love the fact not every single thing is touch screen as most modern vehicles. I love I can turn up the volume, operate the AC and many features with good ‘ole KNOBS without taking my eyes off the road.

TY was and amazing help to me! He is in fact a real like rockstar who made this complicated process the easiest it could’ve been!

We purchased our 2014 Grand Cherokee Overland new and after 11 years and almost 150,000 miles it easily the BEST vehicle we have ever owned. It is comfortable, delivers reasonable mileage, is quiet, well built, incredibly durable and looks as good today as the day we took delivery.

Had a great experience working with Dave W. to bring home my new Golf GTI 380 Autobachn

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.

Real curtious and knowledgeable staff I would tell my friends and family about this car lot

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.

Great team, great service, highly recommend them! Go purchase your next vehicle with them! Ask for Sam

I've owned 3 Jeep products (2 Cherokees, and 1 Wrangler) and bought Cherokees 3 for my kids. Now they bought their own. Reliable, durable, and affordable. I love my 2017 Altitude. Looks great. The only thing I had to replace was a water pump at 80,000 miles.

This is the best car we've ever had! Before my wife passed away, we bought this car (pre-owned), she fell in love with it and insisted on driving everywhere! Since she passed in Sept, 2021, I've been driving it and I LOVE IT TOO! I have some issues with programming/memory, but the dealer assures me they can fix this problem

Triple M motors was incredibly helpful. I was able to get rid of my broken down piece of junk and trade it in for a newer model. Danny provided me with very useful information that made my decision easy.

I have that car and I’m happy with it. Yes it have some problems, need some care, you can just go to speedway and fuel up it would be your last fuel up with diesel on speedway. To previous review: I bought the car with 185000 miles. After I fuel up at speedway 😁, I sen car to dealership. They replace entire emission system with brand new. No problems after that. Just fuel up at good stations, I prefer Sheetz or BP or shell. About $300 oil changes: I do my oil changes by my self: 2, 5 quart oil canisters and $25 filter and it’s don for $75. I change oil every 5k miles. About fuel filters: I do it by myself too. So 2 filters on Amazon for $17-25 and you have done it for $35-50. I change them every 20k miles.

We bought this car for our daughter. Elvis could not have been any better. He was so patient with us and I would recommend anyone looking for a vehicle to go see Elvis. He was a rock star. I was in the car business for 30 years and he exceeded our expectations of how we wanted to be treated. Five Star Dealership and sales person.

Andrew was great!!! Very friendly with great customer service. We are very very happy with our new car!!

I bought my used 2017 limited around christmas of 2022. Its now may of 23 and i cannot believe how much i like this thing. Always been a ford truck guy but for a great all arounder....this jeep cannot be beat. I got the 3.6L V6, has alot more giddy up then you would expect, tows my 4200lb trailer with ease, and in my daily driving i average around 22mpg. Snow/off road performance is excellent...its not a 78 Bronco but for a modern SUV its very capable. 10inches of slushy snow riding on street tires it ate it up and asked for more. Its comfortable, drives good, and ive put 7000mi on since december with not so much as a hiccup. Reccommend to anyone looking for an SUV.

I was looking for a CPO Jeep Grand Cherokee and Pearl had just the one! Nick was so helpful in answering any questions I had, and Jim made the purchase process so smooth and quick!

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.

Mike R was amazing. He even traveled to Chicago to bring our car to a different locations so we could see it. I would highly recommend this location.

Very friendly staff . Not bad prices Would recommend to friends to come here and check out the inventory Thank you again Moe for the great service

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.

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!

I want to thank Joe Collins for the wonderful service I received today. From the time I arrived I was welcomed with a smile and knowledgeable service. Joe and the technicians that serviced my Caravan today I want to say Thank you. Someone asked me why I bring my vehicle here for service this is why! I would recommend Castle Chrysler Dodge Ram of Chesterton. I have been a customer now for over 5yrs. and they have always been top notch. You have earned a 5star from me. That's why I'll always return. Happy Holidays to the entire staff and especially to Joe Collins for all your kindness 🥰

Great looking vehicle. Very comfortable and fun to drive. Great for traveling. Controls are easy to use and do a wonderful job. Would definitely purchase again.

5 stars – Honest, efficient, and the reason I came back This was my second time working with Josh Hendrix, and I specifically came back because of how straightforward he is. We were buying a car for my daughter, and I appreciated that Josh didn’t push, didn’t upsell, and didn’t waste our time. He gave us a fair offer from the start and made the process easy. After dealing with salespeople at other dealerships who overtalk or dodge questions, Josh is someone I trust. If you’re buying a car, especially for family, he’s the one to work with.

Bought the vehicle with 30,000 miles. Turned over 100,000 this week after four years. ZERO unplanned visits to the dealership. Just normal oil, filters, wipers. Since we tow a 3500-pound boat, decided to replace the brakes at 80,000 miles, turns out there was still plenty of material left. Infotainment screen developed minor delamination this spring. Was still working fine but decided to replace it anyway. Easy replacement job for $350 with YouTube help. Lowest maintenance vehicle we have ever owned.

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

This my 5th and best Grand Cherokee. I ordered this one with the diesel engine and love it. We get 28 to 30MPG on the highway and almost as much in city. Range is 600 to 700 miles. I have the Overland Summit model. If I had a negative I'd say the sound system is not up to pay. The U Connect system is very intuitive however.

Bas was my salesman and he did an excellent job. He educated me and made sure that I understood the process. Very satisfied!

As I read, don't buy unless you can work on it. Plenty of things broke, but the parts are cheap if you can work on it. All four interior door handles broken, but all four replacements were $40, I put them in. Starter motor bad, $160 and very difficult to install, but did it. Exhaust manifold to engine gasket bad. $20 and very difficult to install. Rubber gators over CV joints, cheap, but very hard to install. Advice: watch Youtube video's, take your time, and don't get aggravated, I told you its difficult...Plus all the plastic fasteners and parts are dry and brittle after 17 years.

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!

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.