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1,324 listings
  • Price Drop
    $21,995
    great price
    $4,081 below market
    • 35,438 miles
    • No accidents, 1 owner, personal use
    • 5 Seats, 18 City / 24 Hwy MPG
    • Glenn Chrysler Dodge Jeep Ram (74 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Crestwood, KY / 74 miles away from Winchester, KY

    Billet Silver Metallic Clearcoat 2022 Jeep Cherokee Trailhawk 4WD 3.2L V6 9-Speed 948TE AutomaticTHIS VEHICLES FEATURES INCLUDE:, 4x4/ Four Wheel Dr...

    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: 1C4PJMBX6ND513413
    Stock: AP1579
    Certified Pre-Owned: No
    Listed since: 05-15-2025

  • $11,321
    great price
    $3,126 below market
    • 91,141 miles
    • No accidents, 2 owners, personal use only
    • 5 Seats, 22 City / 31 Hwy MPG
    • Jeff Wyler Honda in Florence (75 mi away)
    • Back-up camera
    • Bluetooth
    • Upgraded Headlights
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Florence, KY / 75 miles away from Winchester, KY

    WYLER CERTIFIED, ACCIDENT FREE CARFAX, BLUETOOTH HANDS FREE, REAR BACKUP CAMERA, LOCAL TRADE IN, 17" x 7" Painted Aluminum Wheels, 4-Wheel Disc Brakes...

    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: 1C4PJLCB2KD144462
    Stock: 2255251A
    Certified Pre-Owned: No
    Listed since: 06-02-2025

  • Price Drop
    $16,150
    great price
    $2,948 below market
    • 46,566 miles
    • No accidents, 4 owners, corporate fleet vehicle
    • 5 Seats, 22 City / 31 Hwy MPG
    • Piles Chevrolet (53 mi away)
    • Back-up camera
    • Bluetooth
    • Upgraded Headlights
    • Blind Spot Monitorin...
    • Tire Pressure Warnin...
    Close

    Located in Dry Ridge, KY / 53 miles away from Winchester, KY

    Velvet Red Pearlcoat 2020 Jeep CherokeeLatitude FWD 9-Speed 948TE Automatic 2.4L I4Odometer is 8405 miles below market average! 22/31 City/Highway...

    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:

    25 Combined MPG (22 City/31 Highway)

    Listing Information:

    VIN: 1C4PJLCB5LD514627
    Stock: 05755A
    Certified Pre-Owned: No
    Listed since: 07-16-2025

  • Stock photo**
    $17,800
    great price
    $3,134 below market
    • 57,703 miles
    • No accidents, 2 owners, personal use
    • 5 Seats
    • Performance Kings Honda (90 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Cincinnati, OH / 90 miles away from Winchester, KY

    This *2019 Jeep Cherokee Latitude Plus* is loaded with convenient features like: Backup Camera, Heated Seats, Tow Pkg, Apple CarPlay, Voice Controls, ...

    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: 1C4PJMLXXKD351456
    Stock: KD351456B
    Certified Pre-Owned: No
    Listed since: 07-26-2025

  • Price Drop
    $24,500
    great price
    $2,384 below market
    • 14,372 miles
    • No accidents, 1 owner, personal use
    • 5 Seats
    • Glenn Chrysler Dodge Jeep Ram (74 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Crestwood, KY / 74 miles away from Winchester, KY

    Bright White Clearcoat 2022 Jeep Cherokee Limited 4WD 2.0L I4 DOHC 9-Speed 948TE AutomaticTHIS VEHICLES FEATURES INCLUDE:, Clean CARFAX, 4x4/ Four W...

    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: 1C4PJMDN9ND505110
    Stock: AP1594
    Certified Pre-Owned: No
    Listed since: 05-22-2025

  • Price Drop
    $10,999
    great price
    $2,577 below market
    • 124,177 miles
    • 2 accidents, 3 owners, personal use
    • 5 Seats, 21 City / 29 Hwy MPG
    • Jeff Wyler Honda of Colerain (89 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Cincinnati, OH / 89 miles away from Winchester, KY

    Jeff Wyler Honda of Colerain is proud to offer this gorgeous 2017 Jeep Cherokee Overland in Bright White Clearcoat. Well equipped with: Quick Order Pa...

    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: 1C4PJMJS0HW633934
    Stock: 27T9139
    Certified Pre-Owned: No
    Listed since: 05-31-2025

  • $20,987
    great price
    $2,124 below market
    • 51,754 miles
    • No accidents, 1 owner, rental vehicle
    • 5 Seats, 21 City / 29 Hwy MPG
    • Dan Cummins Chrysler Dodge Jeep RAM of Georgetown (25 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Georgetown, KY / 25 miles away from Winchester, KY

    2023 Jeep Cherokee Altitude 4WD 2.4L I4 9-Speed 948TE Automatic 4D Sport Utility Bright White Clearcoat 21/29 City/Highway MPG**THIS VEHICLE HAS BEEN ...

    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: 1C4PJMMB9PD111454
    Stock: 16834
    Certified Pre-Owned: No
    Listed since: 06-09-2025

  • Price Drop
    $4,900
    good price
    $1,172 below market
    • 199,576 miles
    • No accidents, 4 owners, rental vehicle
    • 5 Seats
    • Dan Cummins Chrysler Dodge Jeep Ram of Paris (16 mi away)
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    • Upgraded Engine
    Close

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

    This 2015 Jeep Cherokee Latitude is being offered to you as an alternative to us taking to the auction. This Cherokee is a spacious, well desired vehi...

    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: 1C4PJLCB3FW683585
    Stock: 17574A
    Certified Pre-Owned: No
    Listed since: 06-07-2025

  • New Listing
    Stock photo**
    $9,450
    great price
    $2,016 below market
    • 118,252 miles
    • 1 accident, 2 owners, personal use only
    • 5 Seats
    • Lincoln of Cincinnati (86 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Cincinnati, OH / 86 miles away from Winchester, KY

    Recent Arrival!Granite Crystal Metallic Clearcoat 2016 Jeep Cherokee Limited 3.2L V6 9-Speed 948TE AutomaticAlthough every reasonable effort has been ...

    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: 1C4PJMDS4GW262805
    Stock: GW262805
    Certified Pre-Owned: No
    Listed since: 07-23-2025

  • New Listing
    $22,990
    fair price
    $499 below market
    • 36,716 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5 Seats, 19 City / 27 Hwy MPG
    • Carvana - Louisville (87 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Louisville, KY / 87 miles away from Winchester, KY

    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: 1C4PJMDX7MD161194
    Stock: 2003833082
    Certified Pre-Owned: No
    Listed since: 06-26-2025

  • Price Drop
    $15,998
    good price
    $2,044 below market
    • 88,617 miles
    • No accidents, 2 owners, rental vehicle
    • 5 Seats, 18 City / 24 Hwy MPG
    • Jeff Wyler Superior Hyundai (83 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Cincinnati, OH / 83 miles away from Winchester, KY

    Jeff Wyler Superior Hyundai is pleased to offer this superb-looking 2019 Jeep Cherokee Trailhawk in Bright White Clearcoat. Well equipped with: Quick ...

    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: 1C4PJMBX2KD298625
    Stock: 6113506A
    Certified Pre-Owned: No
    Listed since: 05-25-2025

  • $9,850
    fair price
    $1,221 below market
    • 131,611 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 22 City / 31 Hwy MPG
    • Jeff Wyler Nissan of Cincinnati (89 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Cincinnati, OH / 89 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:

    25 Combined MPG (22 City/31 Highway)

    Listing Information:

    VIN: 1C4PJLDB6FW760478
    Stock: 25T3507
    Certified Pre-Owned: No
    Listed since: 07-19-2025

  • $9,500
    good price
    $860 below market
    • 125,052 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 21 City / 28 Hwy MPG
    • Glenn Chevrolet (60 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Eminence, KY / 60 miles away from Winchester, KY

    Bright White Clearcoat 2016 Jeep Cherokee Altitude 4WD 2.4L 4-Cylinder SMPI SOHC 9-Speed 948TE AutomaticTHIS VEHICLES FEATURES INCLUDE:.

    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/28 Highway)

    Listing Information:

    VIN: 1C4PJMAB2GW375298
    Stock: 176305B
    Certified Pre-Owned: No
    Listed since: 07-05-2025

  • $9,995
    good price
    $897 below market
    • 145,052 miles
    • No accidents, 2 owners, personal use only
    • 5 Seats, 19 City / 25 Hwy MPG
    • Cincinnati Used Auto Sales (75 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Upgraded Headlights
    • Tire Pressure Warnin...
    Close

    Located in Cincinnati, OH / 75 miles away from Winchester, KY

    *TRAILHAWK EDITION* THIS 2017 JEEP CHEROKEE 4X4 IS IN GREAT CONDITION IN AND OUT! INCLUDES A 3 MONTH/4500 MILE WARRANTY! ASK ABOUT OUR GREAT FINANCE O...

    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/25 Highway)

    Listing Information:

    VIN: 1C4PJMBB2HW530500
    Stock: 16179
    Certified Pre-Owned: No

  • Price Drop
    $18,590
    fair price
    $785 above market
    • 33,040 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats
    • Carvana - Cincinnati (79 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Upgraded Headlights
    • Tire Pressure Warnin...
    Close

    Located in Cincinnati, OH / 79 miles away from Winchester, KY

    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: 1C4PJMCB2HD226951
    Stock: 2003820334
    Certified Pre-Owned: No
    Listed since: 06-17-2025

  • Price Drop
    $22,987
    good price
    $1,741 below market
    • 31,882 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 21 City / 29 Hwy MPG
    • Dan Cummins Chrysler Dodge Jeep Ram 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

    Adventure Awaits with the 2023 Jeep Cherokee Altitude: Embrace the Granite Crystal Metallic Clearcoat and Conquer Every Road with Confidence and Style...

    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: 1C4PJMMB8PD107718
    Stock: 17884
    Certified Pre-Owned: No
    Listed since: 06-12-2025

  • Price Drop
    $15,339
    fair price
    $856 below market
    • 67,698 miles
    • No accidents, 2 owners, personal use only
    • 5 Seats
    • Performance Kings Honda (90 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Cincinnati, OH / 90 miles away from Winchester, KY

    This *2017 Jeep Cherokee Limited* is loaded with convenient features like: GPS, 4X4, Backup Camera, Navigation, Heated Seats, Voice Controls, Heated-S...

    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: 1C4PJMDB3HW594042
    Stock: HW594042
    Certified Pre-Owned: No
    Listed since: 07-01-2025

  • $23,647
    fair price
    $726 above market
    • 51,912 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5 Seats, 18 City / 24 Hwy MPG
    • Bob Allen Nissan (40 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

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

    Hydro Blue Pearlcoat 2022 Jeep Cherokee Trailhawk 4WD 9-Speed 948TE Automatic 3.2L V6

    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: 1C4PJMBX4ND513474
    Stock: CP1520
    Certified Pre-Owned: No
    Listed since: 06-25-2025

  • New Listing
    $15,987
    fair price
    $936 below market
    • 32,905 miles
    • No accidents, 2 owners, personal use only
    • 5 Seats, 21 City / 28 Hwy MPG
    • Dan Cummins Chrysler Dodge Jeep RAM of Georgetown (25 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Georgetown, KY / 25 miles away from Winchester, KY

    Adventure Awaits: Discover the 2016 Jeep Cherokee Sport, the Perfect Companion for Thrill-Seekers and Outdoor Enthusiasts Who Crave Rugged Reliability...

    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/28 Highway)

    Listing Information:

    VIN: 1C4PJMAB9GW290121
    Stock: 17005
    Certified Pre-Owned: No
    Listed since: 07-14-2025

  • $10,991
    fair price
    $659 below market
    • 117,997 miles
    • No accidents, 4 owners, rental vehicle
    • 5 Seats, 21 City / 28 Hwy MPG
    • BMW of Louisville (76 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Power Driver Seat
    Close

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

    2015 Jeep Cherokee Limited Billet Silver Metallic Clearcoat Recent Arrival!Quick Order Package 24G.BMW of Louisville is Louisville's First Choice for ...

    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/28 Highway)

    Listing Information:

    VIN: 1C4PJMDB8FW773142
    Stock: XB05939A
    Certified Pre-Owned: No
    Listed since: 07-19-2025

  • $23,734
    fair price
    $362 below market
    • 30,532 miles
    • No accidents, 2 owners, personal use
    • 5 Seats, 19 City / 27 Hwy MPG
    • Driveway (11 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    Close

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

    Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Lane Keeping Assist,Leather Seats,Premium So...

    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: 1C4PJMDX2MD209510
    Stock: MD209510A
    Certified Pre-Owned: No

Showing 1 - 21 out of 1,324 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.