Used Jeep Grand Cherokee for sale near Winter Park, FL under $50,000

Found the car I?ve been looking for at their Winter Park Location. From the moment I connected by email with the dealership to the moment I drove off with the car, everything was smooth! Christian and Gerald were courteous, professional and kind, a pleasure to do business with! Absolutely recommendable.

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.

They had a Tesla that was the exact color and miles I wanted They gave me videos, pictures even a FaceTime with someone driving since I was buying out of state. Easy process E signed and they transported the vehicle to my driveway can't say enough about this place!

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.

I really like the service! Thank you Andris for very helpful service today for your advice I will come back to get the car

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.

I traded in a 6 month old Lexus hybrid for a Mitsibushi lancer. I paid $20k for the lexus and my 16 year old pretended to like it but he hated it. It was a lame hybrid and his friends laughed at him. So before he even got his license and had only added 400 miles to the car I took it back. Eliot got me a deal on a Mitsibushi with 19,000 miles. The trade in came back at $14,000. Eliot WENT BACK AND GOT ME A BETTER DEAL! because I was a previous Carmax customer. I ended up with a 5 year warranty on the Mitsubishi and a $700 refund... You cannot beat Carmax. If you buy cars from this dealership THEY LOOK AFTER YOU. Genuine customer.

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.

This is an after the fact review. In fact the last vehicle I night was a year ago. Anyway, I have bought at least 6 vehicles at this dealer. Fantastic place to buy and great detail from start to finish. The only problem is that we moved away and just bought a vehicle in the Tampa area. Not the same experience! I really miss VW Orlando. Probably will be back to buy as an out of towner we next time.

One of the best vehicles I have ever owned! Dependable, lots of features, stylish, fun to drive on and off road. A vehicle you can enjoy and be proud of!

So far I have bought (12) vehicles from this dealership if I’m not forgetting one or two. The last a 2023 power wagon - I love coming here everyone here is very polite and helpful. I deal mostly with Tarek and Bill and they are both very professional. I have never had a problem at the service center that I didn’t get resolved. If you give these guys a chance I think you will be very happy in the in.

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

Great experience! Hope to do business with them someday again. A+ professional and very thorough!

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.

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.

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 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.

Very good experience! My daughter was looking for two specific used car models, and we had spent the entire day driving from one dealership to another. Winter Park Auto Mall was our last stop, and we weren't hopeful, because the price was lower than any we had seen advertised, and the vehicle had 20,000 fewer miles. However, it turned out to be exactly what she was looking for. The trunk liner was missing, but the dealership ordered one and had it sent to my daughter in MD as promised. Also, there was a small stain on one of the seats, so they gave the whole car a steam cleaning and detailing while we waited. If you are looking for a shiny dealership with free coffee, this is not your place. If you are looking for a no-nonsense car purchase with lower-than-average dealer fees, this is your place! Thank you for your help, Tim!

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.

Very friendly, courteous and accommodating. I was helping my grandson car shop but he made a decision on a different vehicle. I liked the car so much that I almost bought it for myself.

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 !

Josh was great. The loan process took a little bit and my tires on my car needed to be rebalanced. But everything was fixed promptly as soon as I notified them what the problems were.

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.

I would like to express my appreciation for the outstanding service provided by Felipe, a Chevrolet sales representative. He was extremely attentive, professional, and patient throughout the entire process. Felipe demonstrated extensive knowledge about the vehicles and was always willing to answer my questions with clarity and kindness. My purchasing experience was much smoother and more positive thanks to his excellent support.

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.

Manny was a pleasure to work with! Andrew was very quick and through with the finance team! Aside from a little miscommunication on the front end my experience was very good.

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.

If you need a new car. Greenway Ford is the place to go. Our salesman was Jack Starkey. He's knowledgeable polite helpful patient and very attentive. He is an asset to Greenway Ford. We give Jack 10 stars!!!

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.

Great price for a reliable, used vehicle. Minimal dealer fees. Fair, honest, and quick buying process. Great communication, and even delivered the car to my home.

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.

Eric was my salesman was easy to work with. Made it a pleasure to go to buy a car. Wasn't pressured into making a buy. Please let Eric help you make a great decision in buying your new ride.

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.

Today, I visited the Sun State Collision Center with a detached back-up sensor. With no appointment, I expected a complex evaluation and a need to return for the actual repair at a later date. Surprise! A very courteous manager introduced me to a very courteous tech who took my keys for an on the spot repair! All done in about an hour. This is simply the best customer service I have experienced in years! Well Done and thanks!

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!

A very good experience dealing with Greenway Dodge and especially my salesman. Would recommend this car dealership to anyone looking for a new car. Highly recommend using my salesman for getting the best deal and good buying experience.

We special ordered the 2021 Jeep Grand Cherokee Trailhawk. The vehicle is all black inside and out. The paint is a Diamond Gloss Black Metalic. The day after delivery we had the entire finish done with Ceramic Coating. We've had this vehicle for a year and the fit and finish is like new. The Ride is tight and still handles great. Fuel mileage is now 21 City. We're sorry to see they will no longer produce this vehicle!!