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550 listings
  • Price Drop
    $37,987
    great price
    $6,211 below market
    • 12,112 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Dan Cummins Chrysler Dodge Jeep Ram of Paris (17 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Paris, KY / 17 miles away from Winchester, KY

    Conquer Every Terrain with the 2024 Jeep Gladiator Sport: Adventure Awaits in this Rugged, Black Clearcoat Crew Cab with Unmatched Off-Road Prowess...

    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:

    18 Combined MPG (16 City/21 Highway)

    Listing Information:

    VIN: 1C6JJTAG6RL115624
    Stock: 17727
    Certified Pre-Owned: No
    Listed since: 05-09-2025

  • $38,899
    great price
    $4,573 below market
    • 13,133 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Louisville INFINITI (79 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Louisville, KY / 79 miles away from Winchester, KY

    2023 Jeep Gladiator High Altitude CARFAX One-Owner. Clean CARFAX. Hydro Blue Pearlcoat 2023 Jeep Gladiator High Altitude 4WD 8-Speed Automatic 3.6L V6...

    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: 1C6HJTFG1PL538941
    Stock: 250151A
    Certified Pre-Owned: No
    Listed since: 05-09-2025

  • New Listing
    $37,000
    great price
    $7,786 below market
    • 3,725 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Jake Sweeney Express (91 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Cincinnati, OH / 91 miles away from Winchester, KY

    Jake Sweeney Is the only Chrysler Dodge Jeep Ram dealer in the Cincinnati metro area to offer a complementary Lifetime Mechanical Protection with a $0...

    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:

    18 Combined MPG (16 City/21 Highway)

    Listing Information:

    VIN: 1C6HJTAG8RL115817
    Stock: E11989
    Certified Pre-Owned: No
    Listed since: 06-17-2025

  • Price Drop
    $33,425
    great price
    $6,506 below market
    • 7,998 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Jeff Wyler Chrysler Jeep Dodge Ram Of Lawrenceburg (86 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Tire Pressure Warnin...
    Close

    Located in Lawrenceburg, IN / 86 miles away from Winchester, KY

    Jeff Wyler Chrysler Dodge Jeep of Lawrenceburg is proud to offer this handsome-looking 2023 Jeep Gladiator Sport in Black Clearcoat. 8.4" Radio & Prem...

    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: 1C6HJTAG3PL546840
    Stock: 2811249A
    Certified Pre-Owned: No
    Listed since: 06-03-2025

  • New Listing
    $24,587
    great price
    $6,107 below market
    • 113,199 miles
    • No accidents, 2 owners, corporate fleet vehicle
    • 5'0” bed, 3.6l, 6cyl
    • Dan Cummins Chevrolet Buick of Paris (16 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Paris, KY / 16 miles away from Winchester, KY

    **THIS VEHICLE HAS BEEN INSPECTED by our ASE technicians who performed a lube and oil change, mounted and balanced 4 new tires, replaced front brake p...

    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: 1C6HJTFG0LL185473
    Stock: 123961A
    Certified Pre-Owned: No
    Listed since: 06-06-2025

  • New Listing
    $30,898
    great price
    $5,588 below market
    • 27,170 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Jeff Wyler Chrysler Dodge Jeep Ram (77 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • Upgraded Stereo
    Close

    Located in Batavia, OH / 77 miles away from Winchester, KY

    Only 27,170 Miles! Scores 22 Highway MPG and 17 City MPG! This Jeep Gladiator delivers a Regular Unleaded V-6 3.6 L/220 engine powering this Automatic...

    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: 1C6HJTAG4ML516516
    Stock: 11T10108A
    Certified Pre-Owned: No
    Listed since: 06-20-2025

  • $35,468
    good price
    $2,633 below market
    • 11,400 miles
    • No accidents, 2 owners, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Driveway (11 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Lexington, KY / 11 miles away from Winchester, KY

    Low Mileage,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Leather Seats,4-Wheel Disc Brakes,6-Speed M/T,8-Speed A/T,A/C,A/T,ABS,Ad...

    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: 1C6HJTAG2NL132171
    Stock: NL132171P
    Certified Pre-Owned: Yes

  • Price Drop
    $34,934
    good price
    $2,824 below market
    • 26,720 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Jeff Wyler Chrysler Dodge Jeep Ram (77 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Batavia, OH / 77 miles away from Winchester, KY

    Only 26,720 Miles! Boasts 22 Highway MPG and 17 City MPG! This Jeep Gladiator delivers a Regular Unleaded V-6 3.6 L/220 engine powering this Automatic...

    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: 1C6HJTFG9NL152264
    Stock: 11T10089
    Certified Pre-Owned: No
    Listed since: 05-19-2025

  • New Listing
    $36,987
    good price
    $3,506 below market
    • 20,619 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Dan Cummins Chrysler Dodge Jeep RAM of Georgetown (26 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Georgetown, KY / 26 miles away from Winchester, KY

    Conquer Every Terrain with the 2022 Jeep Gladiator Rubicon: Bold, Rugged, and Ready for Adventure in Sting-Gray ClearcoatStep into the world of advent...

    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: 1C6JJTBG9NL174949
    Stock: 8691A
    Certified Pre-Owned: No
    Listed since: 06-19-2025

  • $41,988
    good price
    $2,867 below market
    • 8,486 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Jake Sweeney Express (91 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Cincinnati, OH / 91 miles away from Winchester, KY

    Jake Sweeney Is the only Chrysler Dodge Jeep Ram dealer in the Cincinnati metro area to offer a complementary Lifetime Mechanical Protection with a $0...

    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: 1C6JJTBG1PL567167
    Stock: E11981
    Certified Pre-Owned: No
    Listed since: 06-12-2025

  • $29,000
    fair price
    $961 below market
    • 40,725 miles
    • No accidents, 1 owner, rental vehicle
    • 5'0” bed, 3.6l, 6cyl
    • Driveway (11 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Lexington, KY / 11 miles away from Winchester, KY

    Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,WiFi Hotspot,4-Wheel Disc Brakes,6-Speed M/T,8-Speed A/T,A/C,A/T,ABS,Adjustable Stee...

    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: 1C6HJTAG7PL541818
    Stock: PL541818P
    Certified Pre-Owned: Yes

  • $42,000
    good price
    $2,557 below market
    • 3,625 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Lincoln of Cincinnati (87 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Cincinnati, OH / 87 miles away from Winchester, KY

    Firecracker Red Clearcoat 2023 Jeep Gladiator Mojave 3.6L V6 24V VVT 8-Speed AutomaticCARFAX One-Owner. Clean CARFAX.Although every reasonable effort ...

    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: 1C6JJTEG9PL581104
    Stock: PL581104
    Certified Pre-Owned: No
    Listed since: 04-15-2025

  • Price Drop
    $29,780
    fair price
    $51 below market
    • 29,133 miles
    • No accidents, 2 owners, personal use
    • 5'0” bed, 3.6l, 6cyl
    • Jake Sweeney Express (91 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Cincinnati, OH / 91 miles away from Winchester, KY

    Jake Sweeney Is Here to Help! If you are in need of a new or used vehicle, we are offering you the ability to shop online and have your vehicle delive...

    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: 1C6HJTAG6ML510538
    Stock: D79844
    Certified Pre-Owned: No
    Listed since: 05-14-2025

  • Price Drop
    Stock photo**
    $37,987
    good price
    $3,099 below market
    • 25,688 miles
    • No accidents, 2 owners, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Dan Cummins Chrysler Dodge Jeep Ram of Paris (17 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Paris, KY / 17 miles away from Winchester, KY

    Conquer Any Terrain with the 2020 Jeep Gladiator Rubicon: Rugged Performance Meets Modern Adventure in Granite Crystal Metallic ClearcoatStep into ...

    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: 1C6JJTBG1LL207181
    Stock: 102661C
    Certified Pre-Owned: No
    Listed since: 04-27-2025

  • Price Drop
    $28,332
    good price
    $2,595 below market
    • 64,796 miles
    • No accidents, 1 owner, personal use
    • 5'0” bed, 3.6l, 6cyl
    • Jeff Wyler Honda in Florence (76 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Florence, KY / 76 miles away from Winchester, KY

    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: 1C6HJTAGXLL151502
    Stock: 2255365A
    Certified Pre-Owned: No
    Listed since: 06-08-2025

  • Price Drop
    $35,976
    good price
    $5,455 below market
    • 6,701 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Neil Huffman Chevrolet Buick GMC of Frankfort (38 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Tire Pressure Warnin...
    Close

    Located in Frankfort, KY / 38 miles away from Winchester, KY

    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:

    18 Combined MPG (16 City/21 Highway)

    Listing Information:

    VIN: 1C6HJTAG4RL105074
    Stock: C8363A
    Certified Pre-Owned: No

  • $42,882
    fair price
    $446 below market
    • 8,478 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Bob Allen Nissan (40 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Danville, KY / 40 miles away from Winchester, KY

    CARFAX One-Owner. Clean CARFAX. Sarge Green Clearcoat 2023 Jeep Gladiator Rubicon 4WD 8-Speed Automatic 3.6L V6 24V VVT *Bluetooth*, Special Financing...

    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: 1C6JJTBG0PL586079
    Stock: MP8373A
    Certified Pre-Owned: No
    Listed since: 06-11-2025

  • $33,987
    good price
    $2,811 below market
    • 57,730 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Dan Cummins Chrysler Dodge Jeep Ram of Paris (17 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Paris, KY / 17 miles away from Winchester, KY

    Conquer the Wild in Style: 2021 Jeep Gladiator Rubicon with Granite Crystal Metallic Finish and Rugged 3.6L V6 EngineStep into the world of adventu...

    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: 1C6JJTBG5ML538038
    Stock: 17829
    Certified Pre-Owned: No
    Listed since: 06-18-2025

  • $35,989
    good price
    $2,260 below market
    • 40,998 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • McCluskey Chevrolet (91 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Cincinnati, OH / 91 miles away from Winchester, KY

    Call McCluskey Chevrolet at 513-741-1111 to schedule your Free 48 Hour Test Drive.MCCLUSKEY CHEVROLET'S FREE LIFETIME MECHANICAL WARRANTY Unlimited ...

    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: 1C6JJTBG1NL109223
    Stock: A57108HT
    Certified Pre-Owned: No
    Listed since: 06-15-2025

  • $49,777
    fair price
    $695 below market
    • 8,242 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Don Franklin Bardstown Chevrolet Buick (72 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    Close

    Located in Bardstown, KY / 72 miles away from Winchester, KY

    Certified. CARFAX One-Owner. Freshly Detailed, Ready for immediate delivery. Clean CARFAX. Priced below KBB Fair Purchase Price! Bright White Clearcoa...

    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:

    18 Combined MPG (16 City/21 Highway)

    Listing Information:

    VIN: 1C6JJTBG8RL120984
    Stock: RL120984
    Certified Pre-Owned: No
    Listed since: 05-01-2025

  • New Listing
    $36,500
    fair price
    $1,359 below market
    • 27,274 miles
    • No accidents, 2 owners, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Glenn Chevrolet (61 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Eminence, KY / 61 miles away from Winchester, KY

    Black Clearcoat 2022 Jeep Gladiator Overland 4WD 3.6L V6 24V VVT 8-Speed AutomaticTHIS VEHICLES FEATURES INCLUDE:, Black 3-Piece Hard Top, Cold Weat...

    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: 1C6HJTFG3NL159324
    Stock: 333338A
    Certified Pre-Owned: No
    Listed since: 06-22-2025

Showing 1 - 21 out of 550 listings
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.

** This image is a stock photo and may not reflect the model year or color of, and/or equipment offered on, the advertised vehicle.