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145 listings
  • Price Drop
    $27,995
    good price
    $1,406 below market
    • 88,762 miles
    • No accidents, 3 owners, personal use
    • 7 Seats, 21 City / 29 Hwy MPG
    • A+ Auto Sales (92 mi away)
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in West Chester, OH / 92 miles away from Winchester, KY

    Recent Arrival! Clean CARFAX. Red 2021 Toyota Highlander XSE FWD 8-Speed Automatic 3.5L V6 DOHCHighlander XSE, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed...

    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: 5TDLZRAH0MS053960
    Stock: AT5871
    Certified Pre-Owned: No
    Listed since: 07-11-2025

  • Price Drop
    $33,225
    good price
    $739 below market
    • 55,055 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Jeff Wyler Eastgate Auto Mall (76 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Batavia, OH / 76 miles away from Winchester, KY

    ALG Residual Value Awards, Residual Value Awards. Boasts 27 Highway MPG and 20 City MPG! This Toyota Highlander delivers a Regular Unleaded V-6 3.5 L/...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDLZRBH8MS102790
    Stock: 11671024A
    Certified Pre-Owned: No
    Listed since: 07-06-2025

  • Price Drop
    $32,625
    fair price
    $304 below market
    • 62,808 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • Bob Allen Nissan (40 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

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

    Black 2021 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC AWD.Odometer is 8485 miles below market average! 20/27 City/Highway MPGAwards:* AL...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH1MS536759
    Stock: C25432A
    Certified Pre-Owned: No
    Listed since: 08-05-2025

  • Price Drop
    $26,995
    good price
    $1,607 below market
    • 95,213 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • A+ Auto Sales (92 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in West Chester, OH / 92 miles away from Winchester, KY

    CARFAX One-Owner. Gray 2021 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC**New Tires**, Fresh Oil Change, Highlander XLE, 4D Sport Utility,...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH5MS547649
    Stock: AT5841
    Certified Pre-Owned: No
    Listed since: 06-25-2025

  • Price Drop
    $27,373
    good price
    $1,003 below market
    • 101,155 miles
    • 1 accident, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Dutch Miller Hyundai (97 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Huntington, WV / 97 miles away from Winchester, KY

    Vehicle DetailsDiscover the perfect blend of style, performance, and reliability with the 2021 Toyota Highlander XLE AWD. This SUV is designed to elev...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDHZRBH3MS523967
    Stock: H45365A
    Certified Pre-Owned: No
    Listed since: 07-17-2025

  • $34,975
    fair price
    $284 above market
    • 56,334 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Bob Allen Nissan (40 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

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

    Black 2021 Toyota Highlander XSE AWD 8-Speed Automatic 3.5L V6 DOHC AWD.Odometer is 6670 miles below market average! 20/27 City/Highway MPGAwards:* AL...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDJZRBH4MS152612
    Stock: C25304A
    Certified Pre-Owned: No
    Listed since: 07-31-2025

  • Price Drop
    $34,980
    fair price
    $707 below market
    • 56,388 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • Jeff Wyler Eastgate Auto Mall (76 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Batavia, OH / 76 miles away from Winchester, KY

    ALG Residual Value Awards, Residual Value Awards. Scores 27 Highway MPG and 20 City MPG! This Toyota Highlander delivers a Regular Unleaded V-6 3.5 L/...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDDZRBH3MS552156
    Stock: 11T10370
    Certified Pre-Owned: No
    Listed since: 07-27-2025

  • Price Drop
    $29,990
    good price
    $773 below market
    • 100,084 miles
    • No accidents, 3 owners, corporate fleet vehicle
    • 7 Seats, 20 City / 27 Hwy MPG
    • Carvana - Cincinnati (79 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    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: 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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDDZRBH5MS527047
    Stock: 2003937792
    Certified Pre-Owned: No
    Listed since: 08-05-2025

  • Price Drop
    $33,980
    fair price
    $548 below market
    • 47,739 miles
    • No accidents, 1 owner, personal use
    • 8 Seats, 20 City / 27 Hwy MPG
    • Jeff Wyler Eastgate Auto Mall (76 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Batavia, OH / 76 miles away from Winchester, KY

    ALG Residual Value Awards, Residual Value Awards. Only 47,739 Miles! Delivers 27 Highway MPG and 20 City MPG! This Toyota Highlander boasts a Regular ...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDHZRBH2MS072210
    Stock: 1160019A
    Certified Pre-Owned: No
    Listed since: 08-22-2025

  • Price Drop
    $35,990
    fair price
    $235 below market
    • 70,840 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Carvana - Cincinnati (79 mi away)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDFZRBH5MS145478
    Stock: 2003943794
    Certified Pre-Owned: No
    Listed since: 08-15-2025

  • $21,395
    fair price
    $565 below market
    • 118,953 miles
    • 2 accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 29 Hwy MPG
    • Jeff Wyler Toyota of Clarksville (89 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Clarksville, IN / 89 miles away from Winchester, KY

    CARFAX One-Owner. 21/29 City/Highway MPGAwards: * ALG Residual Value Awards, Residual Value Awards 18" Painted Alloy Wheels, 3.003 Axle Ratio, 3rd...

    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: 5TDCZRAHXMS041590
    Stock: 31T15958A
    Certified Pre-Owned: No
    Listed since: 07-26-2025

  • New Listing
    Stock photo**
    $34,988
    fair price
    $604 below market
    • 28,963 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Jake Sweeney Express (91 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH0MS125949
    Stock: G19012
    Certified Pre-Owned: No
    Listed since: 08-28-2025

  • New Listing
    $29,777
    fair price
    $234 above market
    • 91,895 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Stuart Powell Mazda (42 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Danville, KY / 42 miles away from Winchester, KY

    AWD, 18 Machined Alloy Wheels, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes, 6 Speakers, ABS brakes, Air Conditioning, Alloy whee...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH0MS550118
    Stock: T11343A
    Certified Pre-Owned: No
    Listed since: 08-30-2025

  • $32,779
    fair price
    $455 above market
    • 71,579 miles
    • 1 accident, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Bob Allen Nissan (40 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    Close

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

    CARFAX One-Owner. Silver 2021 Toyota Highlander Limited AWD 8-Speed Automatic 3.5L V6 DOHC *Bluetooth*, Special Financing Available!, **Apple CarPlay*...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDDZRBH8MS530184
    Stock: M25688B
    Certified Pre-Owned: No
    Listed since: 06-30-2025

  • Price Drop
    $32,990
    fair price
    $74 above market
    • 58,912 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • Carvana - Cincinnati (79 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDHZRBH0MS550320
    Stock: 2003928859
    Certified Pre-Owned: No
    Listed since: 08-26-2025

  • Price Drop
    $31,206
    fair price
    $174 above market
    • 73,972 miles
    • No accidents, 2 owners, personal use
    • 8 Seats, 20 City / 27 Hwy MPG
    • Jeff Wyler Honda of Colerain (89 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

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

    Jeff Wyler Honda of Colerain is honored to offer this superb-looking 2021 Toyota Highlander XLE in Blizzard Pearl. Well equipped with: 18" Machined Al...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH1MS101059
    Stock: 2748154B
    Certified Pre-Owned: No
    Listed since: 08-06-2025

  • Price Drop
    • 46,852 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • Kings Mazda (91 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

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

    CARFAX One-Owner. SUNROOF/ MOONROOF PACKAGE, HEATED FRONT SEATS, BACK UP CAMERA, HANDS FREE BLUETOOTH, LANE DEPATURE WARNING, LANE MONITOR ASSIST, CRU...

    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: Yes

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDJZRBH1MS140269
    Stock: MS140269
    Certified Pre-Owned: No
    Listed since: 06-27-2025

    • 83,378 miles
    • 2 accidents, 2 owners, personal use
    • 7 Seats, 21 City / 29 Hwy MPG
    • Dan Cummins Chevrolet Buick of Paris (15 mi away)
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Paris, KY / 15 miles away from Winchester, KY

    **THIS VEHICLE HAS BEEN INSPECTED by our ASE technicians who performed a lube and oil change, mounted and balanced 3 new tires, replaced front brake r...

    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: 5TDGZRAH0MS532316
    Stock: 122144B
    Certified Pre-Owned: No
    Listed since: 08-09-2025

  • Price Drop
    $31,235
    fair price
    $78 below market
    • 72,338 miles
    • 1 accident, 2 owners, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Dutch Miller Hyundai (97 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Huntington, WV / 97 miles away from Winchester, KY

    Vehicle DetailsExperience the perfect blend of style, performance, and advanced technology with this exceptional 2021 Toyota Highlander XLE AWD! This ...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDHZRBH8MS125718
    Stock: H45305AAA
    Certified Pre-Owned: No
    Listed since: 08-21-2025

    • 47,830 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 7 Seats, 20 City / 27 Hwy MPG
    • Jake Sweeney Express (91 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

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

    Free Lifetime Mechanical Protection! Recent Arrival!Our One Owner, No Accidents Reported 2021 Toyota Highlander XLE AWD has fantastic family appeal in...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH3MS125962
    Stock: A31198
    Certified Pre-Owned: No
    Listed since: 07-21-2025

  • $32,980
    fair price
    $539 above market
    • 60,860 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • EZ Car Connection (38 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH1MS102499
    Stock: F13897C
    Certified Pre-Owned: No

Showing 1 - 21 out of 145 listings
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