Used Jeep cars for sale near Winterset, IA under $599,963

Very knowledgeable group of folks. I was happy with the experience. I surely would recommend these folks any any automotive question. I enjoy talking with knowledgeable folks

I have never owned a Jeep before and barely even considered an SUV. I've always been a luxury sedan guy, but this Jeep Grand Cherokee L Overland 4x4 has completely changed my mind. The exterior and interior designs are on par with most SUVs and remind me of the luxury sedans I have previously driven. Tech options are better than I've ever had in any other car. The ride and comfort are better than anything I've ever experienced before. Very dependable so far but I'm still under 1000 miles. I'm very pleased with my purchase decision.

I have never had a more pleasurable experience buying a car. Jeremiah Hickenbottom took care of the whole process from Starr to finish. No there was no pressure to buy something that I didn't want. He listened to what I needed and found it. I highly suggest that when someone is looking to buy a new car that you stop here first.

We bought it in 2023 just off lease as a CPO. It’s been a great vehicle. We love it would buy another one in a minute.

When you reply to a car search request for more photos it behoves you too include the vehicle and the dealership identifiers in your email, before demanding identirying info from buyers. This dealer accomplished that miniimum standard. Sadly, across the board dealers are so bad at this that carmax gets 4 stars.

Owning a Jeep is more than just having a car — it’s a lifestyle. The rugged capability, the open-road freedom, and that unmistakable Jeep spirit make every drive an adventure. Whether it’s tackling trails or cruising through town, my Jeep delivers power, comfort, and pure fun every time. Once a Jeeper, always a Jeeper!

Excellent selection of quality used vehicles. Priced very fairly, but low-balled big time when wanting to sell them my current vehicle to the tune of nearly 20% below KBB trade-in value.

It is a GOOD Jeep and I LOVE everything about it the color and EVERYTHING it have in it and the drive and the performance

I worked with Kirk at Deery Waukee and had such a great experience purchasing my 2021 Palisade! Good communication, extremely helpful, and I felt like he really had my best interest in mind. Everyone I spoke to was so kind. I received a follow up call shortly after my purchase to make sure I was loving it. Thank you!!

my grandmother sadly traded in this gladiator i wish she would have kept it . It is very comfortable,reliable,it look great on the outside,it has enough power,and its value is very good.

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.

purchased a new truck from Deery Brothers at the end of January. My experience was exceptional. Elizabeth James was my sales person, and she helped take care of all my needs. When I found the right vehicle she stayed after closing time and made sure I was helped until the end. I would more than recommend her to anyone for a great car Buying experience.

I purchased this Jeep brand new in 2012 as a 2013 Model, I have since put 150,000 miles on. It is a Jeep and can get a little uncomfortable on long highway drives. I took this on a 3 week coast to coast road trip across the US I would know. It does a great job towing my 20foot i/o boat to and from the lake, but wouldn't recommend long trips with that much to tow. Maintenance has been astonishingly low, the only things I needed was regular oil changes, brakes, and a radiator leak that was covered under warranty. This is one of the best all around vehicles, top down cruising in the summer and 4x4 for the snowy PA winters.

Nermin was fantastic to work with. Listened to what we wanted and showed us exactly what we talked about. From test driving to buying our vehicle, everything went smooth. Thank you Nermin for helping us find the right suv for us! Crystal and Rachael H.

Our 22 Wagoneer Series II is awesome. So quiet and the ride quality is like there's a layer of cream cheese between the road and the tires. Totally reliable, nothing but oil/filter changes. Super roomy and comfy interior.

Being 55 I have had dealings with plenty of dealerships in my time. Deery of Waukee, Iowa is different. We ran into some problems with a vehicle purchased and without the long story; I'll say this team stepped up and made it right. Thank you Juju and Jason H. You guys took care of us and made happy, loyal customers.

Very nice vehicle with many hi-tech & comfort features. V-6 engine performs well for a 6 cyl. engine but would prefer a V-8, which is no longer an option. Very happy with over all performance.

Anthony Gladney and Brahim Bouhaik go out of their way to make buyers happy. I challenged Brahim to find me the exact car I was looking for with all the features. He followed up days later delivering beyond my expectations while Anthony spared no expense to ensure the purchase was memorable. These guys are above and beyond

It’s currently summer 2025, I’ve owned my 2020 Wrangler Sahara since spring 2021. I LOVE my jeep and have had ZERO issues with it. This is my 2 nd Wrangler, first one was 2915 New. No issues with it at either. Mine is a 4 cl turbo. I didn’t want that I wanted a 6 cl. My husband convinced me to buy it and I’m glad I did. I have 59,000. Miles currently and I haven’t had to replace anything besides general maintenance.

I set up an appointment on line then the salesman said he would have it ready outside. Our appointment was 3 days out. When we got there the car handnot been processed yet It needed work done and it was dirty. We test drove it and liked the car and the price. Also when we got there the cost of the car had gone up a couple of hundred dollars. Because I copied what we saw on line and our preapproval they gave up the price we first saw. That was nice. The car needed some work done on it and they did it for no cost to us. It took over a week and a couple of phone calls. We now have the car we expected to bring home the day we got it.

I've added aftermarket exhaust and a computer chip and the roar pedal also KNN air filter and bigger tires 35 so far it is a lot of fun to drive

Jeremy Wright went above and beyond for us. He helped us find the right car and right price. When you go there ask for Jeremy Wright. Tell them Aaron Haskin and Angie Butler sent you. The car is amazing.

Bought this 2022 Compass Trail Hawk new for my wife. Earlier this year (2025) we landed a sweetheart deal on a new 2024 Wrangler Sport S. Guess who inherited the Compass ? I stepped down from a Grand Cherokee but I have no regrets. It has had a few electrical teething issues but all have been resolved and have not come back. The handling and fuel economy are much better than the Grand Cherokee. There are only 2 downsides..........the size of the gas tank (13.5 gal vs 24.5) and the cargo space behind the 2nd row seats. I have easily adapted to both ! I want to give a shout-out to our local dealership, Tri-City CDJR. Start to finish, an excellent place to purchase and maintain our Jeeps. BRAVO ZULU !

I have been on a car hunt for a while now, and while I didn’t get a car at Deery, I received a lot of help from all the nice staff. Thank you Derrick for dealing with me and finding me cars even though I’m picky. Would recommend!

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.

Brahim was extremely helpful and professional. Would highly recommend. They were very helping in finding what I was looking for. The whole staff was fantastic and friendly.

I,ve had several Jeeps and Subarus and Chevys and my Compass Latitude 4x4 is as good as any for around the city and my freeway trips. Better than the Subaru for the highway and offroad. I feel safe. posted this as i feel some people are harsh and wrong about Jeeps. Do the required oil and transmission services as requested.

I thoroughly enjoy being able to walk into a car dealership to just look around and sit in vehicles, without being chased around the parking lot by a salesman! That is Carmax. You can go in, walk right out to the cars and browse, and all of them are open, have stickers with pricing and details, and you can get a feel for them without being bothered; no hassle, no haggling. I have purchased one car though them and was happy with the test drive, the buying process and the car has been great. Thanks Carmax!

We have a 2022 Wagoneer Series II rear-wheel drive. It's got nearly 47,000 miles on it now. We absolutely love it. "Silver Zenith" exterior and the two-tone black/Baltic salt interior. It is SO roomy and comfortable, and quiet! Ride quality is smooth as the suspension absorbs just about anything. The exhaust note has an amazingly deep note to it. We love this Wagoneer.

In my many years of car driving and ownership, I have rarely had a better vehicle than my 2019 Jeep Compass Latitude. It has been reliable, comfortable, fun to drive and, for its' size and type, very good on gas. In April, I will have been driving "Lattie"for 5 years. My upkeep has been minimal. She is pretty and still looks new. This vehicle is such a pleasure to drive. Handling and response are excellent. Controls are super easy to manage and absolutely love the heated seat and steering wheel. On a long trip, it is very comfortable (yes, I have ridden in the back seat, too) and fuel economy was just great...fully loaded with air-conditioner on and travelling at highway speeds gave me 30+ mpg. Really can't complain. My Neon didn't do any better. This is a great vehicle. Oh, and I had leased it new, and purchased it when the lease was up..that's how good this car is!

Every Jeep I've owned has been great. I never could understand where the negative reviews come from... I'd buy a Grand Cherokee Limited before any European SUV. The quality surpasses anything the Europeans sell at this price point. So does the service.

Awesome experience Josh was great and was not high pressure like other dealerships will definitely be back

This is the best Jeep Wrangler model ever made. The past YJ, TJ, JK models are great, but this Jeep JL 2018 Wrangler Sahara Automatic V6 is the best one yet. The comfort and modern amenities are top of the line. The 8” infotainment head unit and Alpine sound system is out of this world. The interior fits my family of four and has enough cargo space for a stroller, scooter, Onewheel XR and beach chairs. The exterior needs no introduction with its iconic round headlights and seven slot grill. Followed by a three piece removable top, which I managed to take off and put back on by myself. FYI, don’t try doing this by yourself. My final favorite thing about my Jeep JL is the ability to customize the Jeep with all of the amazing aftermarket parts and pieces. This allows you to take the best looking car on the road and make it your own.

very professional and friendly. answered any questions that I had. They are located in an easy location to get in and out with not a lot of traffic to contend with.

We special ordered a Jeep Galdiato Rubicon in 2021 and loved it. Our only problem was it didn't leave much space in the garage. We decided to trade it for a special ordered Jeep Wrangle 4dr. RubiconX. This new vehicle left us with 34 more inches of space in our garage. We still have our 2021 Jeep GrandCherokee Trailhawk as our long trip vehicle. 2 never gave any problems accept with the Aux, battery after 3 years of own

I love the no hassle car buying experience and my salesman was a good guy that was a veterans car salesman. They took care of getting me set up with a second key very quickly and got me a great interest rate on my loan I quickly paid off within 6 months. I will shop there again and have sent many members of my family there!!

my grandmother sadly traded in this gladiator i wish she would have kept it . It is very comfortable,reliable,it look great on the outside,it has enough power,and its value is very good.