Skip to FiltersReport abuse
747 listings
- $39,999fair price$1,464 above market
- 19,743 miles
- No accidents, 1 owner, personal use only
- 5'0” bed, 3.6l, 6cyl
- Sullivan Auto Trading (131 mi away)
Close
Located in Fredericksburg, VA / 131 miles away from Chesapeake, VA
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6JJTBGXLL125191
Stock: 143059
Certified Pre-Owned: No
Listed since: 11-20-2024 - Price Drop$29,992good price$3,351 below market
- 79,031 miles
- No accidents, 2 owners, corporate fleet vehicle
- 5'0” bed, 3.6l, 6cyl
- Driveway (In-stock online)
- Home delivery*
Close
Located in Wappingers Falls, NY / 358 miles away from Chesapeake, VA
CarFax No Accidents Reported,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Leather Seats,R...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6JJTBG4LL198329
Stock: WTP8235
Certified Pre-Owned: No - New Listing$29,590fair price$1,523 below market
- 58,294 miles
- No accidents, 3 owners, personal use
- 5'0” bed, 3.6l, 6cyl
- Carvana (In-stock online)
- Home delivery*
Close
Located in Tampa, FL / 707 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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTAG6LL121185
Stock: 2003522519
Certified Pre-Owned: No
Listed since: 04-06-2025 
See my car’s valueSelling or trading in?
Know what your car is worth while you shop for your next vehicle.
- Price Drop$30,990good price$2,282 below market
- 29,714 miles
- 1 accident, 1 owner, personal use
- 5'0” bed, 3.6l, 6cyl
- Carvana (In-stock online)
- Home delivery*
Close
Located in Indianapolis, IN / 579 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: 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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTAGXLL119357
Stock: 2003683454
Certified Pre-Owned: No
Listed since: 04-29-2025 - $39,987fair price$735 above market
- 38,376 miles
- 1 accident, 2 owners, personal use only
- 5'0” bed, 3.6l, 6cyl
- Lynchburg Mazda (172 mi away)
Close
Located in Forest, VA / 172 miles away from Chesapeake, VA
Hydro Blue Pearlcoat 2022 Jeep Gladiator Mojave 4WD 8-Speed Automatic 3.6L V6 24V VVT ***WE HAVE GUARANTEED CREDIT APPROVAL*** ***WE HAVE 4 LOCATIONS ...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6JJTEG6NL105907
Stock: Z11015
Certified Pre-Owned: No
Listed since: 04-01-2025 - $34,487fair price$46 above market
- 34,493 miles
- No accidents, 1 owner, rental vehicle
- 5'0” bed, 3.6l, 6cyl
- 1st Choice Motors (167 mi away)
Close
Located in Madison Heights, VA / 167 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. This vehicle is located at 1st Choice Motors. 4799 S Amherst Hwy, Madison Heights, VA 24572., Black 3-Piece Hard Top, ...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTFG5NL138782
Stock: J5384
Certified Pre-Owned: No
Listed since: 04-07-2025 - New Listing$30,143fair price$240 below market
- 62,630 miles
- No accidents, 4 owners, personal use only
- 5'0” bed, 3.6l, 6cyl
- Williamsburg Hyundai (53 mi away)
Close
Located in Williamsburg, VA / 53 miles away from Chesapeake, VA
Priced below KBB Fair Purchase Price! 2020 Jeep Gladiator Overland *CLEAN HISTORY...NO ACCIDENTS REPORTED*, *RECENT TRADE IN*, *BACKUP CAMERA*, *ALUMI...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTFG2LL147520
Stock: HOH6049U
Certified Pre-Owned: No
Listed since: 04-18-2025 - New Listing$27,786good price$1,618 below market
- 85,378 miles
- 2 accidents, 1 owner, personal use
- 5'0” bed, 3.6l, 6cyl
- Baltimore Auto Group (178 mi away)
Close
Located in Baltimore, MD / 178 miles away from Chesapeake, VA
2020 Jeep Gladiator Overland Pickup 4D 5 ft1 Owner, No Accidents, CarFax CertifiedLoaded with Options See Window Sticker in the PhotosOverland Edition...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTFG7LL170369
Stock: LL170369
Certified Pre-Owned: No
Listed since: 04-16-2025 - Price Drop$38,104fair price$737 below market
- 36,127 miles
- No accidents, 1 owner, personal use only
- 5'0” bed, 3.6l, 6cyl
- Safford Chrysler Jeep Dodge Ram of Warrenton (162 mi away)
Close
Located in Warrenton, VA / 162 miles away from Chesapeake, VA
Priced below KBB Fair Purchase Price! 2022 Jeep Gladiator Mojave CARFAX One-Owner.240 Amp Alternator, 4.10 Rear Axle Ratio, Air Conditioning, Apple ...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6JJTEG7NL153612
Stock: Z0131
Certified Pre-Owned: No
Listed since: 04-23-2025 - Price Drop$25,892fair price$242 above market
- 83,559 miles
- No accidents, 1 owner, personal use only
- 5'0” bed, 3.6l, 6cyl
- CMA's Rocky Mount Toyota (103 mi away)
Close
Located in Rocky Mount, NC / 103 miles away from Chesapeake, VA
Thank you for choosing CMA's Rocky Mount Toyota, this Black Clearcoat 2020 Jeep Gladiator Sport S is a great choice! Check out the following: No Acci...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTAG2LL129185
Stock: ALL129185
Certified Pre-Owned: No
Listed since: 02-04-2025 - $25,499fair price$439 below market
- 69,312 miles
- 1 accident, 1 owner, personal use only
- 5'0” bed, 3.6l, 6cyl
- Westgate Chrysler Dodge Jeep Ram of Burgaw (179 mi away)
Close
Located in Burgaw, NC / 179 miles away from Chesapeake, VA
Bright White Clearcoat 2020 Jeep Gladiator Sport SportThe 2020 Jeep Gladiator Sport is everything you love about a Jeep, but with the added bonus of b...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTAG4LL188836
Stock: 2391XP
Certified Pre-Owned: No
Listed since: 01-04-2025 - New Listing$26,931fair price
- 81,918 miles
- No accidents, 3 owners, corporate fleet vehicle
- 5'0” bed, 3.6l, 6cyl
- Driveway (In-stock online)
- Home delivery*
Close
Located in Corpus Christi, TX / 1,380 miles away from Chesapeake, VA
CarFax No Accidents Reported,Rare Find,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Tow Hitch,4-Wheel Disc Brakes,6-Speed M/T,8-Speed A/T,A/C,A...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6JJTAG4LL213073
Stock: LL213073
Certified Pre-Owned: No - $35,595fair price$152 above market
- 61,670 miles
- No accidents, 1 owner, personal use only
- 5'0” bed, 3.6l, 6cyl
- County Ford (182 mi away)
Close
Located in Graham, NC / 182 miles away from Chesapeake, VA
ABS BRAKES. ALLOY WHEELS. GPS NAVIGATION. HEATED FRONT SEATS. HEATED STEERING WHEEL. COMPASS. SPEED CONTROL. PUSH BUTTON START. TRAILER TOW PACKAGE. F...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6JJTBG3LL142530
Stock: 252035A
Certified Pre-Owned: No
Listed since: 04-05-2025 - 21,463 miles
- Frame damage reported, 1 owner, corporate fleet vehicle
- 5'0” bed, 3.6l, 6cyl
- Timeless Motorcars (136 mi away)
Close
Located in Stafford, VA / 136 miles away from Chesapeake, VA
Timeless Motorcars we Thrive on our Customer Service and the capability to Provide cars to the community at a Fair Price. When you buy from Timeless M...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Issue reported
Salvage Vehicle: No
Frame Damage: Yes
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6JJTEG6NL149471
Stock: 149471
Certified Pre-Owned: No- Price Drop$34,900fair price$539 above market
- 24,354 miles
- No accidents, 1 owner, corporate fleet vehicle
- 5'0” bed, 3.6l, 6cyl
- Lindsay Manassas Chrysler Dodge Jeep Ram (156 mi away)
Close
Located in Manassas, VA / 156 miles away from Chesapeake, VA
*LOW MILEAGE*, *WELL MAINTAINED*, SOFT TOP, APPLE CARPLAY/ANDROID AUTO, UCONNECT 8.4 NAV, BLUETOOTH, ALPINE PREMIUM SOUND SYSTEM, PUSH-BUTTON START, R...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTFG6NL138189
Stock: MD1402
Certified Pre-Owned: Yes
Listed since: 04-25-2025 - New Listing$32,998fair price$807 above market
- 42,098 miles
- No accidents, 1 owner, personal use only
- 5'0” bed, 3.6l, 6cyl
- CarMax (In-stock online)
- Transfer available from FL to VA*
Close
Located in Pompano Beach, FL / 758 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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTFG2LL157190
Stock: 27309759
Certified Pre-Owned: No - Price Drop$28,990good price$1,878 below market
- 78,720 miles
- No accidents, 1 owner, personal use only
- 5'0” bed, 3.6l, 6cyl
- Carvana (In-stock online)
- Home delivery*
Close
Located in Chicago, IL / 746 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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTFG2LL107406
Stock: 2003697371
Certified Pre-Owned: No
Listed since: 05-01-2025 - $28,990fair price$168 below market
- 78,347 miles
- No accidents, 1 owner, personal use only
- 5'0” bed, 3.6l, 6cyl
- Carvana (In-stock online)
- Home delivery*
Close
Located in Cleveland, OH / 440 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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6JJTAG8LL154528
Stock: 2003674636
Certified Pre-Owned: No
Listed since: 04-28-2025 - 91,913 miles
- No accidents, 2 owners, personal use
- 5'0” bed, 3.6l, 6cyl
- 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: No
Features and Specs:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTFG5LL185940
Stock: 2003671786
Certified Pre-Owned: No
Listed since: 04-29-2025- $23,814fair price$529 above market
- 112,171 miles
- No accidents, 1 owner, personal use
- 5'0” bed, 3.6l, 6cyl
- Bob Bell Ford (170 mi away)
Close
Located in Glen Burnie, MD / 170 miles away from Chesapeake, VA
2020 Jeep Gladiator Sport **BACKUP CAMERA**, **BLUETOOTH**, **BED LINER**, **FOUR WHEEL DRIVE**, **CLEAN VEHICLE HISTORY**, **PUSH-BUTTON START**, **T...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTAG0LL122414
Stock: 255491A
Certified Pre-Owned: No
Listed since: 05-04-2025 - Price Drop$37,988fair price$1,495 above market
- 48,296 miles
- No accidents, 1 owner, personal use only
- 5'0” bed, 3.6l, 6cyl
- Sullivan Auto Trading (131 mi away)
Close
Located in Fredericksburg, VA / 131 miles away from Chesapeake, VA
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6JJTBG4LL168537
Stock: 142794
Certified Pre-Owned: No
Listed since: 01-08-2025
Showing 169 - 189 out of 747 listings
Consumer Reviews for the Jeep Gladiator
Read recent reviews for the Jeep Gladiator
Finally -the Best of Both Worlds
AJ, 02/29/2020
2020 Jeep Gladiator Overland 4dr Crew Cab 4WD SB (3.6L 6cyl 6M)
Look, this will be my third Wrangler-style vehicle (JK, CJ5 & Gladiator in that order) and my 6th Jeep product overall so my post is obviously a bit biased. That being said, when you buy a Jeep, you probably know what you are getting into; they ride and look different. If you are looking for a vehicle that rides like a Bentley on the road, look elsewhere. If however you can accept … reasonable creature comforts, ride, and noise while benefiting from extreme versatility, ruggedness, freedom, stable value and the timeless "cool" factor then this is the vehicle for you. Taking off the top and doors gets you as close to the freedoms of riding a motorcycle without having to wear a helmet. It really is a great time. Also, no other vehicle is as customizable as a Jeep. There are entire magazines devoted to it so you can make each one into your own. I've loved Jeeps but always needed a truck, now I can have both. My only two critiques are 1- the keyfob is the size of of a Zippo lighter which is unnecessarily large and 2- the soft top version of the Gladiator simply looks "off" -like something out of World War 2 which is perhaps why they are not selling well. Small concessions for what you get in return. The hard top is the way to go anyway for heat and noise. The new hardtop material is feather light and I can lift everything off by myself. Go buy one and don't look back. I will drive this thing until it or I are dead.
Used 2020 Jeep Gladiator in Chesapeake, VA Values
Estimated values
2020 Jeep Gladiator Rubicon 4dr Crew Cab 4WD SB (3.6L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $27,083 | $29,036 | $30,926 |
| Clean | $26,587 | $28,480 | $30,306 |
| Average | $25,761 | $27,551 | $29,273 |
| Rough | $24,687 | $26,345 | $27,929 |
The average list price of a used 2020 Jeep Gladiator in Chesapeake, Virginia is $31,740. The average mileage on a used Jeep Gladiator 2020 for sale in Chesapeake, Virginia is 58,934. Based on the average mileage of 58,934 for used 2020 Jeep Gladiator 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 Gladiator 2020 in Chesapeake, Virginia to be $25,761.
Filters
Skip to ResultsApplied Filters4Active
Make & Model
Year
New / Used
Price & Payments
Price Rating
Trim
Truck Details
Mileage
Accidents & History
Engine & Drivetrain
Exterior Color
Interior Color
Total Seating
Edmunds Review
Features
Options & Packages
MPG
* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.