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Used
Jeep cars
for sale
near
Chestertown, MD
- Down Payment
- $0
- Net trade-in value
- $0
- Months
- 72
- APR
- 7.0%
- Sales tax
- 0.0%
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
Used
2020 Jeep Grand Cherokee Overland
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Shane was very helpful in getting us into a new vehicle ;
Shane was very helpful in getting us into a new vehicle ; I would highly recommend their service
Snow commuter
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.
Used
2021 Jeep Grand Cherokee Laredo
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Still Smiling
I purchased my first Jeep, a modified 2-door Wrangler Sport, From Adam's 2 weeks ago. Scott Cheuvront and Thomas Stiles were both very Helpful. I was allowed to take the vehicle on an extended test ride to show my wife before purchasing which was unexpected and very helpful as it allowed me to judge its highway driving characteristics. I was smiling as I left and can't help but smile every time I drive it; especially after getting in the mud for the first time.
I just love everything about my 2021 80th anniversary
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.
Used
2019 Jeep Grand Cherokee Limited
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Jason Schaffer was a great salesman and very
Jason Schaffer was a great salesman and very knowledgeable about the various models and trim packages found on all of the Silverado's we test drove and had a chance to look at. He was also easy to talk to and honest without any of the typical games most others play. Financing was great as well to find the option and warranties that worked best for my situation. I never felt pressured at any step of the way and enjoyed my experience.
The 2019 Grand Cherokee Limited was the Jeep I had my eye
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.
Used
2022 Jeep Grand Cherokee Limited
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Jaime Christopher was Awesome with my visit today for my
Jaime Christopher was Awesome with my visit today for my needs for my 2019 Toyota Camry. She was very Cutomer Friendly and Experienced 👍🏾
My opinion of 2022 Jeep Grand Cherokee
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.
Used
2022 Jeep Grand Cherokee Overland
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Hello John, I'm so glad that you're back with Heritage
Hello John, I'm so glad that you're back with Heritage VW. Thanks for doing a GREAT job getting me into my 2024 Atlas yesterday. You really made my day. You've always worked with my family in getting us an payment that we can afford monthly. My sister is going to be seeing you soon. Please keep up the good work with your excellent customer service. *********
2022 Grand Cherokee Overland. great car.
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.
Used
2021 Jeep Wrangler Sport S
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Brian Perry and Jeff Bejna provided excellent service.
Brian Perry and Jeff Bejna provided excellent service. They were very honest, accommodating, and I felt at ease during the whole buying process. I highly recommend Heritage MileOne!
I love my jeep
I love my jeep Sahara I put a 2in lift in it and 20 in rims with 35 in wide tires , I took it on a 5000 mile road trip it did great on the highway and over the mountains of Colorado I hit a lot of snow and rain on the trip to the west coast and back to Oklahoma I loved the drive it does not drive like a sport car but better then my work truck does , for the whole trip I avg 20 miles to the gal even with the over size tires on it and the off road is just what you think a jeep would be , if you want a good on and off road then I say this is a good jeep for you
Used
2019 Jeep Grand Cherokee Limited X
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Best experience !
Best experience !!!! Thank you eastern !!! Wendell you were great !!! Jesus santos thank you and Walid thank you for your service you guys are the best. ! We truly appreciate you very much !!!!
We love our new Jeep
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.
Used
2016 Jeep Wrangler Sport
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Great experience!
Great experience! Reilly especially was so help and informative. Then entire process was made easier and more efficient, they made sure to keep my best interest in mind!
great with oil leak
Great vehicle. mine is a soft top and the noise was expected Have to be aware of oil leak at the oil cooler. Chrysler uses a plastic material that over time will warp and not seal. The after market ones are aluminum and since you have to remove to of intake, the coils and spark plugs are accessible as well on the drivers side. Other than that it is awesome
Used
2024 Jeep Grand Cherokee Altitude
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I had the pleasure of working with Karla Araujo at
I had the pleasure of working with Karla Araujo at Ourisman in Dundalk, and I couldn’t be more impressed with her exceptional service. From the moment I walked in, Karla was incredibly professional, knowledgeable, and attentive to my needs. She made the entire process of purchasing my 2018 Jeep Renegade smooth and enjoyable. Karla went above and beyond to ensure I was fully informed, answered all my questions, and made sure I was comfortable with every step. Her flexibility and willingness to accommodate my schedule and preferences truly set her apart. It’s clear that she genuinely cares about her customers and strives to make the experience as seamless as possible. I highly recommend Karla Araujo to anyone looking for a stress-free car-buying experience. Her dedication and outstanding service make her a true asset to Ourisman at Dundalk!
Have owned Jeeps for 35 years.
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
Used
2018 Jeep Grand Cherokee Altitude
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I went in last week to check out a 2019 Honda Accord
I went in last week to check out a 2019 Honda Accord EX-L, only because it was close to another car I was scheduled to test down the road in Pasadena. May sales rep was Mark and he's awesome. He is extremely helpful and knowledgeable and even better, showed me with minimal research that the other car I was going to see had TWO previous accidents (shame on me for not seeing that) and they met me at the price I needed. So I ended up buying the Accord (very low mileage) at a great price. The best part was how easy Mark made the experience. My wife is on the loan but she didn't even have to be there. I drove the car off the lot about 2 hours after I arrived. They let me keep my old Honda in the lot until we were able to return that afternoon to pick it up. Overall the best car buying experience we've ever had. Thanks Mark and JBA Auto!
I initially leased my Grand Cherokee Limited but ended up
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!
Used
2025 Jeep Wrangler 4-Door Sahara 4x4
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Great place to purchase a car.
Great place to purchase a car.George did a great job.He was very helpful and had the car ready to go the day I had a appointment.I would buy from Hertz again.
Incredible vehicle.
Incredible vehicle. Especially if you put a manufacturer 3 inch lift on it and aftermarket wheels and tires and running boards. A total beast if you can’t afford the Renegade or if you are too upside down on your trade. If you don’t know the Jeep go get one. It’s life-changing.
Used
2021 Jeep Grand Cherokee Laredo
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Great Experience
Terri Anistead was a warm, professional and wonderful salesman. I was impressed with the no mess no fuss flow of the overall process. I was able to say what I want to put down, what price range I want to stay in. Terri followed my ques and not the other way around. What a pleasure. I had a family member go through drive time and I was not sure if it was a good choice. I can see why they picked Drive Time. Thumbs up!
Perfect New England Vehicle !
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 !
Used
2022 Jeep Grand Cherokee Laredo
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I had an AMAZING experience!
I had an AMAZING experience! I worked with Morgan and she was wonderful-super patient, not pushy, very knowledgeable and super nice. Highly recommend reaching out to her if you are looking to buy a Buick or GMC at Anderson Buick GMC Of Abingdon ? I am absolutely in love with my 2025 Fully Loaded Buick Encore GX
2022 Summit Reserve Comfort m, Performace and Luxu
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.
Used
2021 Jeep Grand Cherokee Laredo
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William goes all out for his customers and above and
William goes all out for his customers and above and beyond, I appreciate the hard work and dedication that he did.
GREAT SUV - GOES ANYWHERE
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.
Used
2020 Jeep Grand Cherokee Overland
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Mark was very pleasant to deal with would buy from them
Mark was very pleasant to deal with would buy from them again easy and quick
Make the Two Hands on Wheel feature stand a lone.
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).
Used
2023 Jeep Grand Cherokee Limited
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Sharon Kensler-White
I purchased a Nissan rouge, told the dealer what I want in my rouge and they found it for me. I also purchased a camero. Professional staff. I will always get my cars from Carmax in Whitemarsh
Natural upgrade choice
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.
Used
2023 Jeep Grand Cherokee Altitude
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The teamwork of the sales team was outstanding.
The teamwork of the sales team was outstanding. Can’t say enough about how seamless the process was.
Great overall
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.
Used
2021 Jeep Grand Cherokee Limited
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Great Service, They picked up my car from work and
Great Service, They picked up my car from work and delivered it back to me within a few hours. Everything I needed done was fixed quickly.
Frustrated but happy
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!
Used
2020 Jeep Wrangler Unlimited Rubicon
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It was another good experience at Car Max White Marsh.
It was another good experience at Car Max White Marsh. I bought a car back in 2001, which was a good experience, so this time I returned again to Car Max. Everyone was friendly and knowledgeable. Thanks Carmax...keep up the good work. Peace, Jan
Lots of fun
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.
Used
2021 Jeep Grand Cherokee Laredo
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Perfect service experience!
I brought my SUV from another dealership (not even one of their brands) in for service on what I knew was going to be an expensive bit of work. The service team was fantastic from start to finish. Communication was consistent and complete. They managed my expectations as they related to time and budget and delivered in my favor on both. I would highly recommend giving them the opportunity to help you with your vehicle. Kudos to TJ on their team as a great representative and a consiment professional.
Best Jeep Ever!
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!!
About Jeep
What is the cheapest Jeep vehicle available?
The Jeep Liberty is the cheapest available vehicle by average Cars.com listing price in Jeep's lineup, with an average listing price of $6,262.
Which Jeep vehicle has the best MPG?
The hybrid Jeep Grand Cherokee 4xe can reach up to 23 combined MPG. The Jeep Renegade with traditional internal combustion engine offers up to 24 MPG city and 31 MPG highway for a combined rating of 27 MPG.
These figures are based on EPA mileage ratings and are for comparison purposes only. The actual mileage will vary depending on the selected vehicle model year, trim, driving conditions, driving habits, vehicle maintenance, and other factors.
Which Jeep vehicle has the longest range?
The electric Jeep Wagoneer S can travel up to 300 miles on a single charge depending on electric motor and battery options. The plug-in hybrid Jeep Grand Cherokee 4xe can travel up to 26 electric-only miles before the gas engine kicks on.
EPA-estimated range is the distance, or predicted distance, a new plug-in vehicle will travel on electric power before its battery charge is exhausted. Actual range will vary depending on model year, driving conditions, driving habits, elevation changes, weather, accessory usage (lights, climate control), vehicle condition and other factors.
Which Jeep vehicle has the most deals?
The Jeep Grand Cherokee has the most available deals on Cars.com with 4261 great deals out of 14805 listings starting at $204.
Where can I find the most Jeep deals?
The most Jeep deals can be found near Edgemere, MD with 248 great deals out of 858 listings starting at $3,000.
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
Used Jeep by price
- Jeep for sale under $15,000 in Chestertown, MD
- Jeep for sale under $20,000 in Chestertown, MD
- Jeep for sale under $25,000 in Chestertown, MD
- Jeep for sale under $30,000 in Chestertown, MD
- Jeep for sale under $40,000 in Chestertown, MD
- Jeep for sale under $50,000 in Chestertown, MD
- Jeep for sale under $100,000 in Chestertown, MD
Used Jeep by city
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Used Jeep in Kingstown, MD
100 Great Deals out of 426 listings starting at $3,000
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Used Jeep in Fairlee, MD
131 Great Deals out of 501 listings starting at $3,000
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Used Jeep in Church Hill, MD
32 Great Deals out of 148 listings starting at $3,000
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Used Jeep in Rock Hall, MD
156 Great Deals out of 574 listings starting at $3,000
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Used Jeep in Centreville, MD
24 Great Deals out of 104 listings starting at $3,000
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Used Jeep in Millington, MD
18 Great Deals out of 114 listings starting at $5,500
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Used Jeep in Galena, MD
58 Great Deals out of 331 listings starting at $5,500
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Used Jeep in Queenstown, MD
61 Great Deals out of 204 listings starting at $3,000
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Used Jeep in Cecilton, MD
69 Great Deals out of 370 listings starting at $2,500
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Used Jeep in Aberdeen Proving Ground, MD
117 Great Deals out of 474 listings starting at $2,500
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Used Jeep in Bowleys Quarters, MD
203 Great Deals out of 728 listings starting at $3,000
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Used Jeep in Edgewood, MD
182 Great Deals out of 647 listings starting at $3,000
Used Jeep in Chestertown, MD by model
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Jeep Grand Cherokee in Chestertown, MD
23 Great Deals out of 118 listings starting at $12,000
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Jeep Compass in Chestertown, MD
21 Great Deals out of 65 listings starting at $5,500
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Jeep Grand Cherokee L in Chestertown, MD
18 Great Deals out of 65 listings starting at $20,777
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Jeep Wrangler Unlimited in Chestertown, MD
6 Great Deals out of 62 listings starting at $10,997
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Jeep Cherokee in Chestertown, MD
17 Great Deals out of 50 listings starting at $6,995
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Jeep Wrangler in Chestertown, MD
10 Great Deals out of 38 listings starting at $9,995
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Jeep Gladiator in Chestertown, MD
9 Great Deals out of 24 listings starting at $27,497
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Jeep Grand Cherokee 4xe in Chestertown, MD
6 Great Deals out of 24 listings starting at $25,901
Used Jeep by body style
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This vehicle is currently in high demand given its competitive price, desirable features, and overall condition, and may have a higher chance of selling quickly.
