Used Jeep cars for sale near Winchester, MA under $899,990

I had an exceptional experience purchasing a vehicle from Highline Group. Upon expressing interest in a test drive, Sales Manager Ted promptly contacted me to arrange the appointment. During the test drive, Salesperson Robert exhibited remarkable enthusiasm and provided a comprehensive overview of the vehicle’s features, addressing all of my questions and concerns. The vehicle was in impeccable condition, as Robert explained that Highline Group maintains an in-house service facility to ensure rigorous quality control. The dealership’s showroom was impressively stocked with a diverse collection of Ferrari, Ducati, and other high-performance vehicles. I promptly finalized the purchase, secured by Highline Group’s competitive loan rate that surpassed offerings from other institutions. I collected the vehicle within one week and have been thoroughly satisfied with the experience. I look forward to returning for future purchases and will confidently recommend this dealership to my associates.

Been a jeep guy for 35years. 2 Cherokees always wanted a wrangler bought a 02 sahara in good condition 193000. It's a 4.0 5spd enough said. No leaks body in great shape,paid 8200.00. After rebuilding the frame that broke due to knuckle head engineers who put drain holes on the side of the frame instead of on the bottom the frame rusted out. 5000 both sides & front anyway after all that I upgraded almost everything on my beloved jeep , new power strip bosch platinum plugs kn filters bilstein 5100 shocks magnaflow exhaust system revolver style rims good year wrangler tires front grill protector tail light guards plus a power chip so from my point of view I have a classic tj better than new these classic TJ s are fun to drive my jeep goes topless 6 mos a year. My advice is to inspect the frame!!!. I didn't know to look, but it all worked out I wouldn't trade my jeep for a Lamborghini, there's only one, to top it off I added a US Navy Anchor ⚓ tire cover to show my pride of my service to my country as both of my sons have and are serving I'll keep this jeep until it's over the engine will outlast me!!! Jeep should've kept the 4.0 5spd the 3.6 is a great engine too

Amazing dealership experience overall. Nick and the entire team from Albrecht CDJR were excellent both during negotiation as well as during the delivery of our new Jeep Wagoneer S

So beautiful and so comfy and so cute and so speedy and so tough and so perfectly green like kermit the frog or nice fresh lettuce.

Car five provides wonderful service, I will recommend them to all my friends. Great experience

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.

Really satifisfied amazing service. The guy at the dealer was really approachable and friendly. People like that is the people you need for dealers great guy.

Jeep passing jobs have been corroding at welds & hinges due to 2 diff. Metals built together. Issue for 15+ years!, recalled opens need to be addressed, my 3 rd wrangler and loved it! Great freedom ride, sport driven, outdoorsy attitude, love Jeep Wrangler the makers need to fix this cheap paint job causing our jeeps to rust prematurely!

I had a good experience. Traded in my old car and bought a used Honda. Been driving it for around two years no problem. Big fan of CarMax.

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 really liked Honda I chose. car was incredibly clean and exactly what I was looking for. Finance process was quick easy and honestly smoothest experience I’ve ever had at a dealership. I definitely recommend them to everyone

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

Thank you to Brian and auto factory for selling my 2019 Chevy Silverado it was very stress free and made the experience wonderful. -Justin E.

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.

Great experience with Copeland Hudson! The sales staff was super helpful and informative, answered all questions right away and just great to work with. I would highly recommend Copeland Chevy Hudson.

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.

Love my Sierra AT4, the team there was great! 5 stars! Only wish is, that I would have done this sooner.

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 recently purchased a vehicle from Mirak Chev , and I couldn?t be happier with the entire process. The staff was professional, patient, and informative. (Oshane Scott) took the time to answer all my questions and made sure I felt confident in my choice. Thank you

Bought my used 2 door at about a year old, with 17,000 miles. Had a couple issues initially: passenger seat got stuck, and airbag light was on. But once I had those fixed, the car has been completely reliable. And I found out that the 2 problems were related. So really it was only 1 problem. The stuck seat has impacted the air bag sensor or something. Loads of fun driving this thing through the snow. 1 foot, 2 feet. Fluffy, or packed by the snow plow. It didn’t matter. Shift it into 4wd and point it where you want it to go. It just went over all of it, and without any drama. Nice and slow. No need for momentum. It just went right through the snow . Can’t wait to take it off road with some friends. As for everyday driving, I love it. You just have to know what you’re getting into. It’s not designed to be a comfortable or sporty car. It’s loud, rather uncomfortable on the bumps, the 2 liter engine sounds like a dish washer, etc. But, those are also all the quirks I love about it. It’s not pretending to be something it’s not. I would’ve gotten the manual roll down windows if I had the choice. It’s just the opposite of my other car, a Macan turbo. It’s just a good old fashioned, honest vehicle. The engine and transmission combo make for a pretty quick team. I’d say 0-60 in about 6 seconds. That’s pretty xxxx quick for a 4000 pound truck designed to go off road. Rarely do I push it that fast of course. I like to drive nice and slow in this car. This is my car to go slow and smell all the roses. I love it. I’m averaging just under 20 mpg driving mostly in NYC. Not bad. Best mpg I’ve had from all my suvs. The hardtop only takes 10 minutes to take off. But it’s still a pain in the xxx. It’s definitely a 2 person job. And then there the issue of where to store this big thing. It’s not like NYC houses have big garages. We’ll see how often I take it off once the summer comes around.

I had a fantastic experience buying my vehicle at Cadillac of Norwood. My sales professional Al was fantastic to deal with. Highly recommend.

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.

Today was one of the best deals of my life. The ease of completion surprised me. They went over the pros and cons of the car with me from start to finish, which is not expected from any other dealer. They run their business with honesty and integrity. I will buy my family's next car from here. Thank you.

I've owned 3 Jeep products (2 Cherokees, and 1 Wrangler) and bought Cherokees 3 for my kids. Now they bought their own. Reliable, durable, and affordable. I love my 2017 Altitude. Looks great. The only thing I had to replace was a water pump at 80,000 miles.

John at Drum Hill is the best buying experience I have had in years. He is very professional, his office manager is very responsive to her customers. They shipped my Mini Cooper to Maryland thru the snow. My Wife has since taken it from me. Their prices are very fair and the vehicle was in excellent condition!! We are very happy with Them and will buy another car from them in the future and can count on a wonderful buying experience. From Massachusetts to Maryland with an understanding and honest dealership!!! Fantastic

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.

My car repair took longer than expected as the ordered part was delayed, but the service team went above and beyond to expedite and resolve.

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 friendly and informative place, staff approachable and knowledgeable. Good selection of vehicles. Prices competitive.

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.

My Experience with Chelmsford Street Auto Sales was Excellent! Both Matt and Ross went above and beyond to help secure the deal I wanted. Very professional and went out their way to make sure I got what I wanted. This is my first Range Rover and it is Awesome. I am very happy with my purchase and nothing drives like a Range Rover 😀

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.

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 had the best experience buying my car with Done Deal! The dealership was very easy to work with, the entire process was very smooth. They have a high quality vehicles and excellent service;no price changing, no hidden fees or costs. Oliver was so nice and helpful, she answered all my questions and I really appreciate that. Truly Five star business and people!

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.

The most stress free and enjoyable buying experience ever! Shant (our Salesperson) was upfront about everything. No games here, and we purchased a truck we are most happy with. And, it checked out perfectly with our Mechanic.

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).

Bought one for my son for college. Had 108K, now as 190K. Can't complaint. Safe, reliable and very comfortable. Did have to replace the oil cooler assembly, but that's a given on a 3.6. Other than that, tires, brake pads, the usual. It's been a winner.