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1,612 listings
- $22,998fair price$571 above market
- 35,698 miles
- No accidents, 3 owners, personal use only
- 5 Seats, 20 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from FL to VA*
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Located in Fort Myers, FL / 774 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: Yes
Features and Specs:
23 Combined MPG (20 City/29 Highway)
Listing Information:
VIN: 1C4PJLMX4MD192073
Stock: 27489264
Certified Pre-Owned: No - New Listing$19,998fair price$373 above market
- 56,512 miles
- No accidents, 3 owners, corporate fleet vehicle
- 5 Seats, 19 City / 27 Hwy MPG
- CarMax Raleigh (151 mi away)
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Located in Raleigh, NC / 151 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX6KD461676
Stock: 27574710
Certified Pre-Owned: No - 70,123 miles
- No accidents, 2 owners, personal use
- 5 Seats, 22 City / 31 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Columbus, OH / 430 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/31 Highway)
Listing Information:
VIN: 1C4PJLLB9MD134949
Stock: 2003865398
Certified Pre-Owned: No
Listed since: 07-04-2025- $19,998fair price$551 above market
- 59,886 miles
- No accidents, 3 owners, personal use only
- 5 Seats
- CarMax (In-stock online)
- Transfer available from CA to VA*
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Located in Costa Mesa, CA / 2,344 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: Yes
Features and Specs:
Listing Information:
VIN: 1C4PJLMN9MD120235
Stock: 27271113
Certified Pre-Owned: No - New Listing$22,998good price$822 below market
- 37,279 miles
- 5 Seats, 19 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TN to VA*
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Located in Nashville, TN / 587 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX8MD220219
Stock: 27412733
Certified Pre-Owned: No - New Listing$20,850fair price$296 below market
- 43,220 miles
- 1 accident, 2 owners, personal use
- 5 Seats, 21 City / 29 Hwy MPG
- Easterns Automotive Group of Laurel (167 mi away)
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Located in Laurel, MD / 167 miles away from Chesapeake, VA
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AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 1C4PJMLB7MD161220
Stock: 162820
Certified Pre-Owned: No
Listed since: 06-06-2025 - Price Drop
- 103,184 miles
- No accidents, 2 owners, corporate fleet vehicle
- 5 Seats
- Fayetteville DriveTime (193 mi away)
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Located in Fayetteville, NC / 193 miles away from Chesapeake, VA
Shop at DriveTime: Get started on your personalized car-buying journey today. With no credit impact, you can get approved for your real, personalized ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: 1C4PJLDN5KD353977
Stock: 1190214847
Certified Pre-Owned: No
Listed since: 06-04-2025 - $23,998fair price
- 36,748 miles
- No accidents, 1 owner, personal use
- 5 Seats, 19 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
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Located in Tyler, TX / 1,128 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX4MD243433
Stock: 27242591
Certified Pre-Owned: No - New Listing
- 56,329 miles
- No accidents, 2 owners, personal use only
- 5 Seats, 22 City / 31 Hwy MPG
- CarMax (In-stock online)
- Transfer available from MO to VA*
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Located in Saint Peters, MO / 797 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/31 Highway)
Listing Information:
VIN: 1C4PJLLB0MD155544
Stock: 25833361
Certified Pre-Owned: No - $22,998good price
- 46,018 miles
- 2 accidents, 1 owner, personal use
- 5 Seats, 19 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
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Located in Fort Worth, TX / 1,232 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: Yes
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX3MD226509
Stock: 27600090
Certified Pre-Owned: No - $21,950good price$568 below market
- 51,646 miles
- 1 accident, 1 owner, personal use
- 5 Seats
- Easterns Automotive Group of Sterling / Direct Car Buying (170 mi away)
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Located in Sterling, VA / 170 miles away from Chesapeake, VA
2021 Jeep Cherokee Latitude Lux Granite Crystal Metallic Clearcoat 4WD 9-Speed 948TE Automatic 115V Auxiliary Power Outlet, 7 & 4 Pin Wiring Harness, ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: 1C4PJMMN8MD165785
Stock: 161054
Certified Pre-Owned: No
Listed since: 03-13-2025 - Price Drop$25,590fair price$105 above market
- 33,781 miles
- No accidents, 1 owner, corporate fleet vehicle
- 5 Seats, 18 City / 24 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Buffalo, NY / 444 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 1C4PJMBXXMD218846
Stock: 2003810412
Certified Pre-Owned: No
Listed since: 06-19-2025 - New Listing$16,000fair price$890 below market
- 82,890 miles
- 1 accident, 3 owners, personal use
- 5 Seats
- Ourisman Chevrolet of Rockville (168 mi away)
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Located in Rockville, MD / 168 miles away from Chesapeake, VA
Recent Arrival! This 2019 Bright White Clearcoat Jeep Cherokee Limited FWD is well equipped and includes these features and benefits:.23/31 City/Highw...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: 1C4PJLDN7KD265657
Stock: 272810A
Certified Pre-Owned: No
Listed since: 07-08-2025 - 112,410 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 20 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Atlanta, GA / 506 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: Yes
Features and Specs:
23 Combined MPG (20 City/29 Highway)
Listing Information:
VIN: 1C4PJLMX2MD130834
Stock: 2003760425
Certified Pre-Owned: No
Listed since: 06-04-2025- New Listing$21,590fair price$291 above market
- 62,595 miles
- No accidents, 2 owners, corporate fleet vehicle
- 5 Seats, 19 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Birmingham, AL / 637 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMMX4MD209718
Stock: 2003844772
Certified Pre-Owned: No
Listed since: 07-11-2025 - New Listing$19,452good price$628 below market
- 58,462 miles
- 1 accident, 1 owner, personal use only
- 5 Seats, 21 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Yorkville, NY / 444 miles away from Chesapeake, VA
CarFax 1-Owner,Rare Find,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Lane ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 1C4PJMLB3MD201924
Stock: D201924A
Certified Pre-Owned: No - $21,998fair price$250 above market
- 62,461 miles
- No accidents, 2 owners, personal use
- 5 Seats, 20 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from GA to VA*
Close
Located in Kennesaw, GA / 507 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: Yes
Features and Specs:
23 Combined MPG (20 City/29 Highway)
Listing Information:
VIN: 1C4PJLDX1MD231993
Stock: 27399641
Certified Pre-Owned: No - $23,998fair price$447 above market
- 40,094 miles
- No accidents, 2 owners, corporate fleet vehicle
- 5 Seats, 19 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from AL to VA*
Close
Located in Huntsville, AL / 602 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: Yes
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMMX2MD228798
Stock: 27326720
Certified Pre-Owned: No - 22,402 miles
- No accidents, 2 owners, personal use
- 5 Seats, 18 City / 24 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Minnetonka, MN / 1,065 miles away from Chesapeake, VA
CarFax No Accidents Reported,Low Mileage,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Lan...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 1C4PJMBX2MD162398
Stock: SCU70612AA
Certified Pre-Owned: No- Price Drop$22,999fair price$277 above market
- 52,220 miles
- No accidents, 1 owner, rental vehicle
- 5 Seats, 21 City / 29 Hwy MPG
- Enterprise Car Sales Rockville (172 mi away)
- Home delivery*
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Located in Rockville, MD / 172 miles away from Chesapeake, VA
Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 1C4PJMMBXPD115092
Stock: 7W64DN
Certified Pre-Owned: No
Listed since: 06-10-2025 - $22,998fair price
- 52,812 miles
- No accidents, 3 owners, personal use
- 5 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
Located in El Paso, TX / 1,757 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 1C4PJMDN7MD132664
Stock: 26702007
Certified Pre-Owned: No
Showing 211 - 231 out of 1,612 listings
Consumer Reviews for the Jeep Cherokee
Read recent reviews for the Jeep Cherokee
My new Jeep
bmwcharlie, 02/01/2021
2021 Jeep Cherokee Limited 4dr SUV (3.2L 6cyl 9A)
Time for a new lease as my Tiguan went back. I looked at a new Tiguan, Subaru Outback, Jeep Cherokee and the Volvo X 40. I chose the Jeep Cherokee.
The Jeep felt the most substantial by far. I was surprised by the cheap plastic center in the Subaru and the Volvo. The Tiguan was all plastic but for 289.00 a month all in (including all taxes and fees) the Tiguan Se was the least … expensive vehicle I have ever leased. The same equipped Tiguan was 370.00 a month. I really missed the heated steering wheel from my previous BMW so it was a must for my new lease. A Tiguan with a heated steering wheel was 407.00 a month. I set out for a new compact SUV for 350.00 a month. I never thought of leasing a Jeep but in my budget it kept coming up so I test drove it. I knew instantly this would be my next vehicle. I leased a Jeep Cherokee V6 Limited with Elite Pkg. for 381.00 a month including taxes and all fees. This was the most equipped car I ever had. Cooled seats front and back it even can parallel park. I love the remote start which automatically turns on the heated seats and steering wheel. This Jeep is on par with my X3. Which was 500.00 a month a new one 700. a month to lease. Value wise this is the best vehicle you will find. It took months of tracking prices and negotiating for me to get this price.
The Jeep ride is great, acceleration is great too. The Volvo was slightly better but the Jeep was pretty close. It rides more like the X3. The info entertainment is easy to use intuitive and fast which really makes for a great driving experience. The Jeep is compact unlike the Tiguan which felt like you had so much space in the cabin. Handling is sharp seats are comfortable. Since it mainly me and one other person most of the time I can live with the snug cabin. I took Delivery at the end of November and have had no problems. Fit and finish is great so I am thinking it should be pretty reliable.
Update: I still love my Cherokee. The Adaptive cruise control is amazing. Life changing feature. The stop and go really takes the sting out of heavy traffic. The automatic high beams are amazing. The ride is great it really takes any size pot hole no problem. Well not quite the razor sharp handle of a BMW it’s much more comfortable. The ride, handling, and acceleration strike a great balance. The lane keep assist is the cars big down fall. It’s will pull slightly at the wheel for no reason. Less on the highway than around town. It feels like you hit a piece of ice. I doesn’t bother me as much now but at first it was annoying as hell. I tried to disable it but couldn’t. I just put it on the lowest setting. Hopefully they will use a lane centering on the next update. The car feels so high tech it’s quite unexpected.. I am so glad I got this Jeep. I would have never considered it, if not for the chip shortage. Inventories were starting to get tight and they had the inventory. I got this lease at such a great deal.I am so grateful as prices are skyrocketing on leases. Blown away by the luxury driving experience from a Jeep, Who knew!
Used 2021 Jeep Cherokee in Chesapeake, VA Values
Estimated values
2021 Jeep Cherokee 80th Anniversary Edition 4dr SUV (3.2L 6cyl 9A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $18,355 | $19,810 | $21,268 |
| Clean | $17,964 | $19,378 | $20,793 |
| Average | $17,313 | $18,658 | $20,003 |
| Rough | $16,466 | $17,723 | $18,976 |
The average list price of a used 2021 Jeep Cherokee in Chesapeake, Virginia is $21,585. The average mileage on a used Jeep Cherokee 2021 for sale in Chesapeake, Virginia is 56,037. Based on the average mileage of 56,037 for used 2021 Jeep Cherokee for sale in Chesapeake, VA and using an average vehicle condition rating, which means the vehicle may have a few mechanical and/or cosmetic problems and may require a considerable amount of reconditioning, we appraise the average trade-in value of a used Jeep Cherokee 2021 in Chesapeake, Virginia to be $17,313.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.