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786 listings
  • Price Drop
    $34,998
    fair price
    $668 above market
    • 14,018 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • CarMax (In-stock online)
    • Transfer available from NC to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Tire Pressure Warnin...
    Close

    Located in Asheville, NC / 364 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: 1C6HJTAG0PL566124
    Stock: 27678009
    Certified Pre-Owned: No

  • $29,995
    fair price
    $416 below market
    • 51,881 miles
    • No accidents, 1 owner, rental vehicle
    • 5'0” bed, 3.6l, 6cyl
    • Wake Auto Sales (147 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Raleigh, NC / 147 miles away from Chesapeake, VA

    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: 1C6HJTAG7PL522783
    Stock: 522783
    Certified Pre-Owned: No
    Listed since: 02-13-2025

  • $30,806
    good price
    $2,434 below market
    • 43,640 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Cape Coral, FL / 776 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: 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 (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTFGXPL524018
    Stock: 7V8T1V
    Certified Pre-Owned: No
    Listed since: 08-04-2025

  • $31,279
    fair price
    $32 below market
    • 46,787 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5'0” bed, 3.6l, 6cyl
    • AnyoneRides.com (183 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Kingsville, MD / 183 miles away from Chesapeake, VA

    Thank you to all of our new and returning customers for continuing to choose Anyonerides.com for all of your vehicle needs! To check vehicle availabil...

    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: 1C6HJTAG9PL542629
    Stock: 18180
    Certified Pre-Owned: No
    Listed since: 07-11-2025

  • $26,998
    fair price
    $685 below market
    • 56,238 miles
    • No accidents, 1 owner, rental vehicle
    • 5'0” bed, 3.6l, 6cyl
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Oklahoma City, OK / 1,184 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:

    19 Combined MPG (16 City/23 Highway)

    Listing Information:

    VIN: 1C6HJTAG9PL523871
    Stock: 7V3BM3
    Certified Pre-Owned: No
    Listed since: 04-22-2025

  • $28,498
    fair price
    $383 below market
    • 67,000 miles
    • No accidents, 1 owner, rental vehicle
    • 5'0” bed, 3.6l, 6cyl
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Saint Louis, MO / 779 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:

    19 Combined MPG (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTFG3PL523583
    Stock: 7VR6Q2
    Certified Pre-Owned: No
    Listed since: 05-09-2025

  • New Listing
    $36,999
    fair price
    $736 above market
    • 7,383 miles
    • 5'0” bed, 3.6l, 6cyl
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Tire Pressure Warnin...
    Close

    Located in Waukesha, WI / 763 miles away from Chesapeake, VA

    CarFax 1-Owner,Low Mileage,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Satellite Radio,WiFi H...

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    19 Combined MPG (16 City/23 Highway)

    Listing Information:

    VIN: 1C6HJTAG6PL546346
    Stock: PL546346S
    Certified Pre-Owned: Yes

  • Stock photo**
    $31,650
    fair price
    $944 below market
    • 43,455 miles
    • No accidents, 1 owner, rental vehicle
    • 5'0” bed, 3.6l, 6cyl
    • Starr Motors (19 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Suffolk, VA / 19 miles away from Chesapeake, VA

    Dealer What sets us apart from a huge dealer group, is that we have deep roots in Suffolk as an entire family. If you don?t see one of the owners wal...

    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: 1C6HJTAG6PL542667
    Stock: CP11928
    Certified Pre-Owned: No
    Listed since: 08-14-2025

  • Price Drop
    $39,989
    fair price
    $1,264 above market
    • 18,004 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • HoneyCar (192 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Winchester, VA / 192 miles away from Chesapeake, VA

    Discover your next ride at HoneyCar Winchester Adventure-ready and built for the Shenandoah lifestyle, this 2023 Jeep Gladiator Rubicon blends rugged ...

    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: 1C6JJTBG8PL521691
    Stock: PL521691
    Certified Pre-Owned: No
    Listed since: 08-21-2025

  • $29,508
    fair price
    $1,329 below market
    • 46,182 miles
    • No accidents, 1 owner, rental vehicle
    • 5'0” bed, 3.6l, 6cyl
    • Westgate Triad Mitsubishi (182 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Graham, NC / 182 miles away from Chesapeake, VA

    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 (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTFG0PL523735
    Stock: 3787P
    Certified Pre-Owned: No
    Listed since: 04-05-2025

  • New Listing
    Stock photo**
    $28,086
    fair price
    $1,044 below market
    • 84,120 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Koons Annapolis Toyota (151 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Annapolis, MD / 151 miles away from Chesapeake, VA

    **ONE OWNER CARFAX**, **LEATHER SEATING**, **NAVIGATION**, **BLUETOOTH**, **BACK-UP CAMERA**, 8.4" Touchscreen Display, ABS brakes, Alloy wheels, Appl...

    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: 1C6HJTFG9ML556759
    Stock: KAT260963A
    Certified Pre-Owned: No
    Listed since: 08-26-2025

  • $28,998
    fair price
    $36 below market
    • 65,563 miles
    • No accidents, 1 owner, rental vehicle
    • 5'0” bed, 3.6l, 6cyl
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Saint Charles, MO / 791 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:

    19 Combined MPG (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTFG2PL550581
    Stock: 7WWSL0
    Certified Pre-Owned: No
    Listed since: 06-01-2025

    • 24,265 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    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:

    19 Combined MPG (16 City/23 Highway)

    Listing Information:

    VIN: 1C6JJTEGXPL525205
    Stock: 2003906855
    Certified Pre-Owned: No
    Listed since: 08-08-2025

  • New Listing
    • 39,008 miles
    • 5'0” bed, 3.6l, 6cyl
    • CarMax (In-stock online)
    • Transfer available from TX to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in El Paso, TX / 1,755 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:

    19 Combined MPG (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTAG2PL517488
    Stock: 27445317
    Certified Pre-Owned: No

  • $32,977
    good price
    $1,773 below market
    • 30,420 miles
    • 1 accident, 1 owner, corporate fleet vehicle
    • 5'0” bed, 3.6l, 6cyl
    • Off Lease Motors (133 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Stafford, VA / 133 miles away from Chesapeake, VA

    English & Spanish Speaking?? Hablamos Español We Sell BRAND NEW & Used! Financiamos a Todos ? <--Click Para Aplicar Ahora (Click To Apply No...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    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 (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTFGXPL520678
    Stock: 520678
    Certified Pre-Owned: No

  • Price Drop
    $29,399
    fair price
    $469 above market
    • 72,450 miles
    • No accidents, 2 owners, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Lindsay Chevrolet (137 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    Close

    Located in Woodbridge, VA / 137 miles away from Chesapeake, VA

    Bright White Clearcoat 2021 Jeep Gladiator High Altitude High Altitude1-Year SiriusXM Guardian Trial, 110 mph Vehicle Max Speed Calibration, 3.73 Re...

    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 (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTFG0ML579217
    Stock: HP9198A
    Certified Pre-Owned: No
    Listed since: 06-18-2025

    • 28,323 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Dallas, TX / 1,193 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: 1C6JJTEG6PL589631
    Stock: 2003947011
    Certified Pre-Owned: No
    Listed since: 08-06-2025

  • New Listing
    $27,587
    fair price
    $1,034 below market
    • 67,300 miles
    • 5'0” bed, 3.6l, 6cyl
    • Fayetteville Dodge Ram (192 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Fayetteville, NC / 192 miles away from Chesapeake, VA

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    19 Combined MPG (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTFGXPL523757
    Stock: RPL523757
    Certified Pre-Owned: No
    Listed since: 08-29-2025

  • $30,000
    fair price
    $541 above market
    • 66,932 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Mercedes-Benz of Catonsville (174 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Baltimore, MD / 174 miles away from Chesapeake, VA

    Recent Arrival! CARFAX One-Owner. 2021 Jeep Gladiator Willys, 4D Crew Cab, 3.6L V6 24V VVT, 8-Speed Automatic, 4WD, Bright White Clearcoat, Black Clot...

    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: 1C6HJTAG1ML576124
    Stock: KMBS210015
    Certified Pre-Owned: No
    Listed since: 08-21-2025

  • Price Drop
    $33,900
    fair price
    $1,130 below market
    • 50,434 miles
    • 1 accident, 1 owner, personal use
    • 5'0” bed, 3.6l, 6cyl
    • Lindsay Manassas Chrysler Dodge Jeep Ram (151 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    Close

    Located in Manassas, VA / 151 miles away from Chesapeake, VA

    *WELL MAINTAINED*, HARD TOP, GPS/ NAVIGATION, APPLE CARPLAY/ANDROID AUTO, UCONNECT 8.4 NAV, BLUETOOTH, ALPINE PREMIUM SOUND SYSTEM, PUSH-BUTTON START,...

    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 (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTFG8ML535885
    Stock: MP9056
    Certified Pre-Owned: Yes
    Listed since: 07-26-2025

  • $34,590
    fair price
    $169 above market
    • 64,634 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3l, 6cyl
    • Carvana - Richmond (95 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Richmond, VA / 95 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:

    Listing Information:

    VIN: 1C6JJTFM7ML570912
    Stock: 2003961721
    Certified Pre-Owned: No
    Listed since: 08-20-2025

Showing 190 - 210 out of 786 listings

Consumer Reviews for the Jeep Gladiator

Read recent reviews for the Jeep Gladiator
Overall Consumer Rating
4.1 out of 5 stars38 Reviews
Write a vehicle reviewSee all 38 reviews
  • 5 star
    (68%)
  • 4 star
    (11%)
  • 3 star
    (0%)
  • 2 star
    (5%)
  • 1 star
    (16%)
5 out of 5 stars

Perfect for me

Dan Hirvi, 04/22/2022
2022 Jeep Gladiator Sport S 4dr Crew Cab 4WD SB (3.6L 6cyl 6M)
I highly recommend the Sport S with the Max Tow Package. Torquey and smooth, the automatic 8-speed transmission is pretty nice with the trusty 3.6 L V6. It's a real hauler or puller when I need it, it's articulation is great for some off road adventures and is comfortable on the highway. Plus, the sticker on my door has a rated payload of 1465 lbs! Don't let them tell you it's not "Jeep" … enough or it's not "truck" enough or it's not comfy enough. Get the customer preferred package with hard top and stick with the M+S rated all terrains for smooth and quiet daily driving. This is a perfect niche vehicle for some people!
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Used 2023 Jeep Gladiator in Chesapeake, VA Values

Estimated values
2023 Jeep Gladiator Sport S 4dr Crew Cab 4WD SB (3.6L 6cyl 8A) with no options
ConditionTrade-InPrivate PartyDealer Retail
Outstanding$25,025$26,348$27,838
Clean$24,742$26,030$27,481
Average$24,271$25,500$26,887
Rough$23,658$24,812$26,114

The average list price of a used 2023 Jeep Gladiator in Chesapeake, Virginia is $32,592. The average mileage on a used Jeep Gladiator 2023 for sale in Chesapeake, Virginia is 47,049. Based on the average mileage of 47,049 for used 2023 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 2023 in Chesapeake, Virginia to be $24,271.

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