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

On Saturday, June 7, my daughter and I had an outstanding experience at XXX Chevrolet. While my initial intent was simply to support her in purchasing her first vehicle, I ended up trading in my own car and driving away in a brand-new 2026 Equinox — while she purchased a 2025 Colorado. Both vehicles impressed us during the test drive. The safety features, interior design, storage space, and overall aesthetics sealed the deal for both of us. While comfort and safety were top priorities, what truly set this experience apart was the exceptional service we received. Steven connected us with Brian, an outstanding sales specialist who was both highly knowledgeable and incredibly personable. He built immediate rapport, listened carefully to our needs, and guided us to the right vehicles without any pressure. The process was smooth and efficient — we were both driving off the lot the same day! The dealership itself was clean, welcoming, and even treated us to a delicious lunch during our visit — a thoughtful touch that made the day feel even more special. I’ve purchased several vehicles over the years, but nothing compares to the level of service we received from Steven and Brian. I highly recommend them to anyone looking for a car-buying experience that’s professional, honest, and genuinely enjoyable. Judi and Jackie T.

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.

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

driving now 1 1/2 years. still love it. 59,000 mi. rec. chang rear end oil. mine had broken bits of gear. much better now. leaks from windsheld area, gotta work on that. overall still jeep'n--- please stop putting ducks on my jeep

Mark, Damian and my ring lady were all amazing. Thank you for being so great and giving me a great experience. I look forward for my future car

Love my 2022 Jeep Grand Cherokee L. Has plenty of room and lots of technology. Plenty of power and is doing great on gas mileage based on its size. Definitely recommend the vehicle!

Purchased new in 2015. Have only done 1 repair in 129k, which was fixing oil leak at oil filter housing. Solid car, great in rain and snow. Thoroughly enjoy this car

Curtis was incredibly smart and efficient throughout our process purchasing a car. Our trade in was handled fairly and easily, and we left with the new car on the same day. Can’t thank the entire team at Napoli for the excellent customer service and even better results! We loved working with them and would do so again in a heartbeat.

  I have the Trailhawk trim, the serious off-road version.  Finally, a car that I can confidently drive in and out of rough construction sites, and not be afraid that I'll break it or get it stuck.   It is possessed by a powerful spirit of wanderlust, and frequently demands that I take it on drives just to see places it hasn't yet been, preferably places that normal cars cannot go.   If Don Quixote de La Mancha lived in our time, he would surely drive a vehicle like this one; a vehicle truly fit for a modern Knight Errant.   I didn't know until a few days after I bought it, and I don't think the dealership knew either, but this one has about a 2" aftermarket lift, and slightly larger tires than stock.

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!

I have been wanting a Jeep for a while and very happy that I was finally able to purchased the Jeep and it seems like a nice car.

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!

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.

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

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.

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!

Approaching 25,000 miles and we haven’t had any issues. I actually enjoy choosing whether to run on electric or gas based on what my journey is. If you just put it in hybrid mode, you’re not utilizing the efficiency of the engine. My advice, think about your journey. If I’m jumping on the highway to then head into the city, I run it on gas on the highway then switch to all electric in the city -no point wasting the electric with highway driving! Then I use up the last of my electric when google tells me I’m X miles from home when I still have X miles of electric remaining to use it all up. When we just do local drives less than 25 miles (grocery, day care pick up etc.) we can literally run off electric only for days, even weeks. It just takes thinking about what your journey involves. Crawling traffic for a 5 mile slow down ahead, I’m on gas until I hit that traffic, then switch to electric. We’ve taken this Jeep (Willys) through plenty of winter storms with feet of snow and ice, never needed to use chains with its AWD or 4WD to choose from. Hopefully the great reliability continues.

This has been the most fun car I have ever owned. You can do so many things with it. Very comfortable and reliable. If you like adventure I recommend a jeep wrangler.

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.

I was pleased with my purchase. I was pleased with the salesman knowledge while showing the instructions on the various things about the 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).

I was looking for a change for a lease and choose to go with a Jeep Renegade. The first dealership I visited was Milford Auto Group and they took excellent care of me, exceeding my expectations. My salesman, Mark Setaro went above and beyond to get me an extraordinary deal on a loaded Renegade, even though my intention was to go with a base model, they made a great deal possible for my means and for that I am very grateful. I look forward to building a relationship with this dealership. very good feeling all around. Thank you again! ~mike

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.

This is simply the finest dealership anywhere. First of all it is family owned and every member of the family actually works there. One of the owners, Bob Fedor, personally oversaw the purchase of our new Ram. He was 100% available and was in the background throughout our entire experience making sure everything went perfectly. He is honest, caring, and completely forthright. By the time we picked up our new Ram we felt like we were a part of his family. Our salesman, Mark Setaro, couldn't have been more professional or helpful. Mark was knowledgeable about every aspect of our purchase and helped me from start to finish making himself available at all times even when he wasn't working. Buying a new vehicle can be extremely stressful, however, when you have a professional such as Mark guiding you through the process it is anything but. The purchase of our 2022 Ram Rebel was a surprise gift for my wife and Mark and Bob went to great lengths to make it all happen. I can not express how appreciative I am to them both or what a great experience this has been.

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 just purchase a Jeep Compass Gregory was my sale representative. Gregory went above & beyond to help me. He went over the entire car from top to bottom! AWESOME!!!***** One other thing I came in when the shop was about to close and he still help me.

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.