Used Jeep cars for sale near Winfield, IN under $1,000,000

Brandon and the Manager were very helpful in helping me finding the right car for me.

Visibility and size are what I need. 4WD, clearance for snow. Rather tight interior, not suitable for more than two. Auto Park is very confusing. Not auto parallel Park. Car will stop while backing out of parking space, won't move if a somewhat complex procedure is not followed.

Go see Joe, he is the best salesman!! cares about his customers he is kind and knows his stuff. If I ever bought a car again I would go back to see Joe. They gave me an IOU for things that needed to be fixed two little things and when I went in Joe was right there ready to help

I purchased a special ordered Jeep Wrangler RubiconX with the 3.6 engine from our local Dealership! When I first drove this this vehicle I knew it may be rough riding, but after having this for for over 6 months it now is our main vehicle for getting around town. I get 17.1-18.3mpg. It's a 4dr and we enjoy it every day for shopping and other chores. We had it on the main highway and do between 65 and 70mph. It handles great and the ride is actually pretty good. Has great passing power as it has 4:56 gearing! We just recently took our vehicle to Keene Dodge/Jeep to have the tires rotated and were very impressed with the service and the entire staff as they treated us very special.

What an amazing time I had buying my first car! I believed that my time with Michael Darge was going to be hectic, but it ended up being the most relaxed and educational period of my life. Michael made this transaction enjoyable and stress free in addition to being nice and willing to teach me everything there was to know about this new car. Michael being a Marine Corps Veteran and coming from a family of veterans, Michael and the Garber Chevy staff treated me with the utmost respect. I strongly advise anyone looking to purchase a vehicle to visit Michael Darge. Thank you so much once again!

It is a great car, my uncle drove it in the west hamptons in New York to the beach. Very fun when the roof is not there.

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!

Absolutely LOVE my 392 20th Yr edition!! She’s a stingray grey beast, that is just as powerful and fun to drive as my Ftype Jaguar! The detail and design is comfortable and I am addicted to the powerful exhaust rumble on her! Puts any previous year Wrangler in a different class- my opinion, after having other Rubicon’s. Well worth taking the leap and spending the +$100k on her! No regrets!

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!

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

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.

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

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!

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.

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.

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.

Thank you, Imperial Jeep and Hany Arian, for the recent great car buying experience; I got a Jeep Wrangler which was very competitively priced, and I got a very fair price for my trade-in. Also, thanks to Sales Manager Bob Baillargeon for supporting and developing significant car-buying solutions. Hany went above and beyond to ensure we were satisfied with the car-buying experience and wrapped the paperwork seamlessly. I recommend this car dealership. A big thank you to Bob and Hany!

Alexandra help us solved our problem, We had to sell Grandmas Car without a title in short time in town. They gave us what we wanted without a title in a few hours at CarMax. This was an unimageable process that Alexandra help us through....Alexandra was Calm with Great Compassion. We Appreciate Alexandra and CarMax Thanks again..

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.

My experience at this dealership was nothing short of exceptional. From the moment I walked in, I felt supported and guided through every step of the process. They made it seamless, transparent, and genuinely enjoyable to purchase a vehicle. Jaguar Land Rover South Shore has earned my trust, and I won’t buy a vehicle anywhere else!

Bought a ‘23 Wrangler 4 cylinder with High Altitude package, upsized my tires to 275/70-17. Rides great, and getting 23 mpg Highway. Very happy with my purchase.

Second lease on a Grand Cherokee. Different than my 2021 in many ways. The all wheel drive makes the steering more sensitive. Tricky parking brake and much smaller layout of gauges in dash. No Sirius satilitte radio. Seats are harder. Overall better than the 2021.

Went very smoothly The is the fifth vechicle we have purchased from this dealer and really appreciate the process of the purchase We plan taking this vechical back for service for the entire time we own it

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 !

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!

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!!!

The service staff are always a pleasure to work with. I send all my friends to Homewood Chevy for sales and service. Give them a try, you won?t be disappointed!!!

Just purchased my Jeep in late March 2023. Rides good, looks good and handles good. Mine is stock. Looking to get some new wheels and tires.

I ended up buying a 2019 Ford Fusion. I absolutely love the car. I would buy it again tomorrow. Ran into a few glitches on a few issues which I was confused about but they were promptly handled much to my satisfaction. My car was cleaned to perfection, received a complete checkup, oil changed at my request, met the service dept which I intend to use for all needs in the future. I met the General Manager Greg and my salesman was Blake who I highly recommend This was my first experience with Michigan City Ford and they will be my dealer moving forward for all future needs. I highly recommend Michigan City Ford, they go the extra mile. Patricia L Mason

Bought a brand new Subaru Forester Hybrid Sport from them. Andre was great at showing us both the regular gas and hybrid versions. They didn’t have the color we liked in the hybrid, so they found it from another dealer for us within a day and gave us a good fair price. Very friendly staff there who do not try to pressure you into buying vehicle extras like some others do.

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.

Excellent customer service! We've been a customer for several years and they never disappoint

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.

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.

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.

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

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.