Skip to Main Content

Used Jeep Overland for Sale

12 Matches
Sort By:
Sort By

2015 Jeep Grand Cherokee Overland

$21,998* 62K Miles


CarMax Dulles In stock

Key Features
Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Harman Kardon Sound, Satellite Radio Ready, Parking Sensors
Location: CarMax Dulles in Dulles, Virginia 20165
Description: Used 2015 Jeep Grand Cherokee Overland for sale - $21,998, 61,465 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Harman Kardon Sound, Satellite Radio Ready, Parking Sensors
Transmission: Automatic Color:Silver Interior Color: Black Average Vehicle Review: (4.655 reviews) Most SUV's now make you feel like you are in a cockpit, the front is soooo small. The Patriot has plenty of room not only in front but plenty of room in back to load larger items. I drive hundreds of miles each month and find the SUV maneuvers well, but rides a bit bumpy. Seat heaters are fantastic!
New Arrival

2017 Jeep Grand Cherokee Overland

$29,998* 39K Miles


CarMax Dulles In stock

Key Features
Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Alpine Sound System, Satellite Radio Ready
Location: CarMax Dulles in Dulles, Virginia 20165
Description: Used 2017 Jeep Grand Cherokee Overland for sale - $29,998, 38,590 miles with Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Alpine Sound System, Satellite Radio Ready
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (4.5 reviews) High quality leather bucket seats. It feels very safe inside and very solid. It runs on a powerful 3.7L V6. Has a truck type body frame making the ride very smooth and quiet. The car also has a quiet transmission that switches gears very smoothly. This car is what a real jeep feels like!
New Arrival

2018 Jeep Grand Cherokee Overland

$35,899* 4K Miles


CarMax Gaithersburg Free shipping • MD to VA

Key Features
Power Liftgate/DeckLid, Auto Cruise Control, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Location: CarMax Gaithersburg in Gaithersburg, Maryland 20877
Description: Used 2018 Jeep Grand Cherokee Overland for sale - $35,899, 3,328 miles with Power Liftgate/DeckLid, Auto Cruise Control, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Transmission: Automatic Color:Brown Interior Color: Brown Average Vehicle Review: (4.667 reviews) Not very roomy or fast and it likes fuel (only around 18 mpg hwy) but a solid SUV that with proper tires will get you almost anywhere. My Jeep has the manual transmission which in my opinion is better than the auto on 2007-2011 models and helps a bit with the mileage. It,s a ton of fun with the soft top down and you always get waves from other Jeepers. But they do stand out a bit so if you would rather not be seen you might want to look elsewhere, however if you want a vehicle that works hard and plays harder you will be pleased. Not to mention the HUGE variety of aftermarket accessories available to make it your own!

2016 Jeep Grand Cherokee Overland

$25,899* 40K Miles


CarMax Frederick Shipping not available

Key Features
Technology Package, Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Harman Kardon Sound
Location: CarMax Frederick in Frederick, Maryland 21704
Description: Used 2016 Jeep Grand Cherokee Overland for sale - $25,899, 39,932 miles with Technology Package, Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Harman Kardon Sound
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (5 reviews) The high altitude package is the ultimate especially with the Boston Acoustic speaker package on it! This was presented as a value package on both the Compass and Patriot which included on the 4x2, partial leather, sunroof, special grill, and satellite radio. The only knock is that you can't get it on a 4x4 but you get a lot of goodies at a reasonable price.

2017 Jeep Grand Cherokee Overland

$27,899* 44K Miles


CarMax White Marsh Free shipping • MD to VA

Key Features
Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Alpine Sound System, Satellite Radio Ready
Location: CarMax White Marsh in White Marsh, Maryland 21162
Description: Used 2017 Jeep Grand Cherokee Overland for sale - $27,899, 43,522 miles with Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Alpine Sound System, Satellite Radio Ready
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (4.5 reviews) Still rides like a jeep, still goes where I want to go but now I have enough room for a couple of our kids, dogs and gear. You don't buy a jeep because they are cheap, quiet or have a smooth ride. You buy them because they do what you want to do, no matter the terrain or the weather. This is my 4th jeep and I love it!

2017 Jeep Grand Cherokee Overland

$30,899* 24K Miles


CarMax White Marsh Free shipping • MD to VA

Key Features
Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Harman Kardon Sound, Satellite Radio Ready
Location: CarMax White Marsh in White Marsh, Maryland 21162
Description: Used 2017 Jeep Grand Cherokee Overland for sale - $30,899, 23,542 miles with Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Harman Kardon Sound, Satellite Radio Ready
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4.5 reviews) I would not recommend this car to a friend because I find it hard to drive. It has larger blind spots than I realized when I test drove the car. A bigger issue is its reliability. It seems to have electronic issues. It's been in the shop 3 weeks out of the 14 that I have owned the car. If I hadn't bought the warranty, I would have been walking for those 3 weeks. The warranty entitles me to a loaner car when my car is in the shop, but it has sometimes been a hassle to get the loaner car. Eventually I get a loaner, but I traded in an 11 year old car because of dependability issues. At this point I miss my old car. I'm not sure I will be keeping this car very long, and I'm sure I'm going to be out quite a bit when I trade it.

2017 Jeep Grand Cherokee Overland

$30,998* 26K Miles


CarMax King of Prussia Free shipping • PA to VA

Key Features
Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors
Location: CarMax King of Prussia in Philadelphia, Pennsylvania 19406
Description: Used 2017 Jeep Grand Cherokee Overland for sale - $30,998, 25,023 miles with Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors
Transmission: Automatic Color:Brown Interior Color: Black Average Vehicle Review: (4.5 reviews) It has been a good value since it is a nice roomy vehicle with over 110k and I paid under 30k for it. Roomy, spacious, car like ride and handling. I have taken good care of the car (body, interior, mechanically) and has a lot more life left in it. Has 4.7 V8 and wish I would have had the Hemi engine. I have done some heavy towing over he years and recently had to replace engine due to broken connecting rod. Good for another 100k now.

2017 Jeep Grand Cherokee Overland

$32,998* 13K Miles


CarMax Turnersville Free shipping • NJ to VA

Key Features
Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Alpine Sound System, Satellite Radio Ready, Parking Sensors
Location: CarMax Turnersville in Sicklerville, New Jersey 08081
Description: Used 2017 Jeep Grand Cherokee Overland for sale - $32,998, 12,674 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Alpine Sound System, Satellite Radio Ready, Parking Sensors
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (4.5 reviews) The compass is sluggish its very sluggish and the speakers are horrible. But if your a new driver or it your first car and you don't want to tear it up its perfect because u won't be distracted by loud music or speeding. It takes 30 seconds to go from 0 to 60

2015 Jeep Grand Cherokee Overland

$26,998* 34K Miles


CarMax Virginia Beach $99 Shipping • VA to VA

Key Features
Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Harman Kardon Sound, Satellite Radio Ready
Location: CarMax Virginia Beach in Virginia Beach, Virginia 23452
Description: Used 2015 Jeep Grand Cherokee Overland for sale - $26,998, 33,061 miles with Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Harman Kardon Sound, Satellite Radio Ready
Transmission: Automatic Color:Red Interior Color: Black Average Vehicle Review: (4.655 reviews) Appears to be reliable. Fuel economy bearable. Capable of modest towing. Sure footed (can do mild off-roading). In a nutshell, it is quite a bit of vehicle for the price I paid in today's market. While I'm not a fan of electronic automatics, this one seems to shift in a sensible fashion and with no strange anomalies so far. I have already taken the vehicle on a 3k mile road trip, camping out of the back of it for 4 of the 7 days I was on the road and it performed admirably. With 1000 pounds of me and my gear in it and ON it (I've added rood racks), I got 16mpg overall, including some dirt driving and HARD pushing it hard interstates. In normal use with just me and my lady aboard it gets every bit of the 23mpg claimed by Jeep.

2017 Jeep Grand Cherokee Overland

$27,998* 45K Miles


CarMax Easton $99 Shipping • PA to VA

Key Features
Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Alpine Sound System, Satellite Radio Ready, Parking Sensors
Location: CarMax Easton in Philadelphia, Pennsylvania 18045
Description: Used 2017 Jeep Grand Cherokee Overland for sale - $27,998, 44,921 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Alpine Sound System, Satellite Radio Ready, Parking Sensors
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (4.5 reviews) Love my jeep, loved my last one too. TERRIBLE gas mileage, but so much fun. Has the newer soft top mechanism which allows me to have fingernails (female jeep issues), but leaks. Leaks in the rear behind the back seat and passenger seat, but I don't sit there. Keep my extra raincoat, hat and first aid kit in a space bag now.

2016 Jeep Grand Cherokee Overland

$28,998* 13K Miles


CarMax Virginia Beach $99 Shipping • VA to VA

Key Features
Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Location: CarMax Virginia Beach in Virginia Beach, Virginia 23452
Description: Used 2016 Jeep Grand Cherokee Overland for sale - $28,998, 12,163 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (5 reviews) Inside interior room is adequate and storage in rear works fine for what I need it for. Interior design is eye catching and comfort is good. Love the blue tooth technology. There is also adequate storage up front for the drivers convenience and enough ports to support a few electronic devices. Here are my complaints concerning the vehicle. I hate the way it drives in the snow. I have an incline for my driveway and on snowy/icy days, I cannot stop and then start to make it up my driveway, I must back down to the road and then start again without stopping to be successful and that does not always work. The radio reception is awful! I owned a Nissan Versa before this vehicle and it drove way better in all aspects!!!

2018 Jeep Grand Cherokee Overland

$33,998* 22K Miles


CarMax Raleigh $99 Shipping • NC to VA

Key Features
Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Location: CarMax Raleigh in Raleigh, North Carolina 27612
Description: Used 2018 Jeep Grand Cherokee Overland for sale - $33,998, 21,994 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Transmission: Automatic Color:Silver Interior Color: Black Average Vehicle Review: (4.667 reviews) I was so excited, I had a grand years ago and thought this was sporty lower cost option. I was so wrong. It rattles everywhere. I have had more recalls then I could have imagined, and overall it just seems small. I want to love it, and at the end of the day it's a car so I will keep driving it but it's not my favorite car I have ever owned. The nose is a huge blind spot I never noticed in the test drive but have caught myself almost hitting things because it's got a huge blind spot in the front.

Reviews for Jeep

Overall Rating

4.4 out of 5(2,317 reviews)

OK Vehicle

Inside interior room is adequate and storage in rear works fine for what I need it for. Interior design is eye catching and comfort is good. Love the blue tooth technology. There is also adequate storage up front for the drivers convenience and enough ports to support a few electronic devices. Here are my complaints concerning the vehicle. I hate the way it drives in the snow. I have an incline for my driveway and on snowy/icy days, I cannot stop and then start to make it up my driveway, I must back down to the road and then start again without stopping to be successful and that does not always work. The radio reception is awful! I owned a Nissan Versa before this vehicle and it drove way better in all aspects!!!

- Kelly Coats, 2014 Jeep Cherokee

So-so car.

I would not recommend this car to a friend because I find it hard to drive. It has larger blind spots than I realized when I test drove the car. A bigger issue is its reliability. It seems to have electronic issues. It's been in the shop 3 weeks out of the 14 that I have owned the car. If I hadn't bought the warranty, I would have been walking for those 3 weeks. The warranty entitles me to a loaner car when my car is in the shop, but it has sometimes been a hassle to get the loaner car. Eventually I get a loaner, but I traded in an 11 year old car because of dependability issues. At this point I miss my old car. I'm not sure I will be keeping this car very long, and I'm sure I'm going to be out quite a bit when I trade it.

- C. O., 2014 Jeep Cherokee

Great for work or play, not quick or flashy but it will get you there.

Not very roomy or fast and it likes fuel (only around 18 mpg hwy) but a solid SUV that with proper tires will get you almost anywhere. My Jeep has the manual transmission which in my opinion is better than the auto on 2007-2011 models and helps a bit with the mileage. It,s a ton of fun with the soft top down and you always get waves from other Jeepers. But they do stand out a bit so if you would rather not be seen you might want to look elsewhere, however if you want a vehicle that works hard and plays harder you will be pleased. Not to mention the HUGE variety of aftermarket accessories available to make it your own!

- Anonymous, 2008 Jeep Wrangler

This price does not include tax, title, and tags. Additional fees may also apply depending on the state of purchase.