Used Jeep Grand Cherokee for sale near New Fairfield, CT under $899,990

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.

Absolutely amasing dealership. When I reached out to them about a vehicle they had, I had some very strict guidelines for what I wanted, what I could spend and what i had to put down. All of which was far outside the realm of possibility, considering my credit was not so great. Or so I thought. Milton was not discouraged in the least and put in serious work to make it happen for me. I was never pressured to consider another vehicle, tho he did offer a couple of options. He was great at communicating throughout the whole process about his attempts with different lenders and what documents I would need to provide him with. I have to say, he was far more confident than I was! And in the end, I only had to pay a slightly higher down payment, but got lower monthly payments and got the truck I wanted! Everyone at the dealership was very professional, yet welcoming. There was never any pressure, at all. We drove 2 hours to finalise the deal and actually had to wait awhile because MIlton wouldn't let the truck go until it was clean and had had a more than thorough final inspection and servicing. It is also obvious from their inventory, when you're there, that they handpick only the best. I have never had a more pleasant experience buying a car! We will be replacing another car next year, and I won't consider going anywhere else! Thank you Milton! And all your associates who helped make this happen!

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 work with Casandra she is very professional person She make all proses nice and smooth

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.

Luiz was my salesman. He was very personable, knowledgeable and made the overall experience easy and stress free

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.

Veronica was very helpful and clear and made the process smooth. I would consider this dealership again.

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.

I just bought a Grand Cherokee from Hudson Valley Chrysler Dodge Jeep. My saleswoman, Debbie Pignotti was very helpful throughout the process. I will definitely recommend Debbie to my family and friends!

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

It was a great experience from start to finish. Veronica was very knowledgeable and accommodating to help us buy the car we wanted. Would 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

Debbi and John are amazing ! They made the experience so easy and smooth. Highly recommend buying from them !! Can’t thank them enough

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 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).

Highly recommend Brewster Ford. I walked in and customer service introduced me to my sales rep Tim. He was funny, knowledgeable, just a really relatable guy. He walked me through their inventory, and we began test drives. He worked with me on the price to meet my budget. We submitted the paperwork and within 48 hrs I received a call from Brian in the finance department. Another great employee, he was knowledgeable and patient. He explained every option and choice I had to make very well. I felt no pressure and picked the options that worked best for me. From the time I walked in to the day I drove away in my car was 3 days. They did everything, got me the best financing, handled my insurance, they even detailed a car I already thought was perfect. When I went to pick it up it somehow looked even better. Great group of people working at this location, if you are looking for excellent quality cars and a friendly environment you should really check out Brester Ford.

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.

Carmen was GREAT! Celine got us up on the road quick and we drove a loooong way. Thanks guys, love our Jeep! The facility is amazing!

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!

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.

Worked with my sales rep Luis Moreira to lease a vehicle this weekend. He is very easy to work with, low key, and knowledgeable.

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 !

I bought two cars from Mike Barrows. Mike's salesmanship goes unmatched. He did not pressure us at any point and was always willing to do his best on a price for us. The transaction was quick, easy and smooth. Just to top it all off Mike donates $50 dollars for every car he sells to united for the troops and having two grandparents that served this really blew me away. Thanks Big Mike!

Bought my first Jeep Grand Cherokee in January of 2022. I was in a wreck where another vehicle hit me and threw me off the road into a ditch. I went airborne and came down hard. It was a miracle I did not flip. All of my driver-side airbags deployed (front and back) and I walked away with minor injuries. This vehicle kept me safe and I will have another one to replace the totaled Jeep from my wreck.

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.

I just bought a new vehicle from Fitzpatrick's. They are not a "pushy" dealership at all, so you feel very comfortable. I was very specific with what I wanted in my car, and they had no problems finding exactly what I was looking for (they had to bring it in from out of state). They also gave me a great price on my vehicle, as well as a great price on my trade (beating the prices of surrounding dealerships by a large amount). This was my first new vehicle, and they made the process very smooth for me. I couldn't be happier!

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 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.

My buying experience, exceeded all of my expectations. From the moment I arrived at Bill Volz Westchester CDJRAM /CPO, until Brian showed me my Cherokee latitude plus, It was a Five Star experience. Thanks to Mike and his Team

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!

Excellent service! Quick and easy process. Very professional and friendly.

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.

Our salesman, Ali, and other members of the staff were all knowledgeable, helpful and professional. We are very happy with our new Grand Cherokee Limited.

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.