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1,017 listings
  • Price Drop
    $36,995
    great price
    $8,937 below market
    • 28,678 miles
    • No accidents, 2 owners, personal use only
    • 8 Seats, 22 City / 29 Hwy MPG
    • Glenn Chrysler Dodge Jeep Ram (1 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Crestwood, KY / 1 miles away from Crestwood, KY

    Black 2023 Toyota Highlander Platinum FWD 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed AutomaticMoonroof/Sunroof, Panoramic/Extended...

    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/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH2PS042750
    Stock: AP1532A
    Certified Pre-Owned: No
    Listed since: 05-13-2025

  • New Listing
    $37,998
    great price
    $2,484 below market
    • 31,131 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • CarMax Louisville (11 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Louisville, KY / 11 miles away from Crestwood, KY

    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: Yes

    Features and Specs:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH7PS036649
    Stock: 26845944
    Certified Pre-Owned: No

  • New Listing
    $34,787
    good price
    $1,816 below market
    • 12,323 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 22 City / 29 Hwy MPG
    • Dan Cummins Chrysler Dodge Jeep RAM of Georgetown (50 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Georgetown, KY / 50 miles away from Crestwood, KY

    Discover the 2023 Toyota Highlander L: A Perfect Blend of Power, Comfort, and Style for the Modern AdventurerExperience the ultimate in driving sop...

    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/29 Highway)

    Listing Information:

    VIN: 5TDKDRAHXPS504732
    Stock: 17059
    Certified Pre-Owned: No
    Listed since: 07-24-2025

  • Price Drop
    $14,975
    fair price
    $842 below market
    • 100,273 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 20 City / 25 Hwy MPG
    • Auto Group of Louisville (12 mi away)
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    • USB Inputs
    • Trip Computer
    Close

    Located in Louisville, KY / 12 miles away from Crestwood, KY

    ***LOW MILEAGE***CLEAN CARFAX***SPACIOUS 3-ROW SEATING***BLUETOOTH CONNECTIVITY***KEYLESS ENTRY***Get ready to hit the road in style with this sleek 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:

    22 Combined MPG (20 City/25 Highway)

    Listing Information:

    VIN: 5TDZA3EH4DS043652
    Stock: S043652
    Certified Pre-Owned: No

  • $46,677
    fair price
    $116 below market
    • 10,990 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 21 City / 28 Hwy MPG
    • Toyota of Madison (30 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Madison, IN / 30 miles away from Crestwood, KY

    Midnight Black Metallic 2025 Toyota Highlander XLE AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp Toyota Gold Certified Ce...

    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: 5TDKDRBH7SS577242
    Stock: 577242
    Certified Pre-Owned: No
    Listed since: 07-31-2025

  • $28,665
    fair price
    $433 below market
    • 35,930 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 27 Hwy MPG
    • Auto Group of Louisville (12 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Louisville, KY / 12 miles away from Crestwood, KY

    ***LOWEST MILEAGE2019MODELINTHENATION***HEATED FRONT SEATS***REAR PASSENGER-CLIMATE CONTROL***Climb into the driver's seat of this radiant Blue 2019 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:

    23 Combined MPG (21 City/27 Highway)

    Listing Information:

    VIN: 5TDKZRFH8KS335779
    Stock: 335779
    Certified Pre-Owned: No

  • New Listing
    $36,987
    fair price
    $949 below market
    • 21,397 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Dan Cummins Chrysler Dodge Jeep RAM of Georgetown (50 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Georgetown, KY / 50 miles away from Crestwood, KY

    Discover the 2020 Toyota Highlander Limited: Where Sophistication Meets Performance and Comfort for the Discerning Driver Seeking a Premium Experience...

    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: 5TDDZRBH6LS016669
    Stock: 17096
    Certified Pre-Owned: No
    Listed since: 07-31-2025

  • New Listing
    $37,787
    fair price
    $1,374 below market
    • 41,482 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 28 Hwy MPG
    • Dan Cummins Chrysler Dodge Jeep RAM of Georgetown (50 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Georgetown, KY / 50 miles away from Crestwood, KY

    2023 Toyota Highlander XLE AWD 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed Automatic 4D Sport Utility Wind Chill Pearl 21/28 City/Hig...

    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: 5TDKDRBH9PS038175
    Stock: 16737A
    Certified Pre-Owned: No
    Listed since: 06-17-2025

  • New Listing
    $25,487
    fair price
    $335 below market
    • 117,860 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Dan Cummins Chrysler Dodge Jeep RAM of Georgetown (50 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Georgetown, KY / 50 miles away from Crestwood, KY

    2020 Toyota Highlander XLE AWD 3.5L V6 DOHC 8-Speed Automatic 4D Sport Utility Magnetic Gray Metallic 20/27 City/Highway MPG AWD.Clean CARFAX. CARFA...

    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: 5TDGZRBH7LS510021
    Stock: 9528D
    Certified Pre-Owned: No
    Listed since: 07-14-2025

  • New Listing
    $39,561
    good price
    $837 below market
    • 38,178 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 21 City / 29 Hwy MPG
    • Gary Yeomans Ford Frankfort (36 mi away)
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Frankfort, KY / 36 miles away from Crestwood, KY

    Magnetic Gray Metallic 2021 Toyota Highlander Platinum FWD 8-Speed Automatic 3.5L V6 DOHCTHIS VEHICLE INCLUDES THE FOLLOWING FEATURES AND OPTIONS: P...

    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: 5TDFZRAH4MS047205
    Stock: XP047205
    Certified Pre-Owned: No
    Listed since: 08-04-2025

  • $25,350
    good price
    $1,680 below market
    • 56,532 miles
    • 1 accident, 1 owner, personal use only
    • 8 Seats, 21 City / 27 Hwy MPG
    • Jeff Wyler Toyota of Clarksville (17 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Clarksville, IN / 17 miles away from Crestwood, KY

    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 (21 City/27 Highway)

    Listing Information:

    VIN: 5TDKZRFH7HS517031
    Stock: 31T15941
    Certified Pre-Owned: No
    Listed since: 07-31-2025

  • New Listing
    Stock photo**
    $19,995
    good price
    $1,336 below market
    • 114,210 miles
    • 8 Seats, 20 City / 26 Hwy MPG
    • Glenn Chrysler Dodge Jeep Ram (1 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Crestwood, KY / 1 miles away from Crestwood, KY

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDJZRFH7HS470367
    Stock: AP1662B
    Certified Pre-Owned: No
    Listed since: 08-06-2025

  • Price Drop
    $24,655
    fair price
    $20 above market
    • 94,188 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 21 City / 27 Hwy MPG
    • Jeff Wyler Toyota of Clarksville (17 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Clarksville, IN / 17 miles away from Crestwood, 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 (21 City/27 Highway)

    Listing Information:

    VIN: 5TDKZRFH5KS551153
    Stock: 31215441A
    Certified Pre-Owned: No
    Listed since: 07-29-2025

  • $28,975
    fair price
    $197 below market
    • 42,387 miles
    • 1 accident, 2 owners, personal use only
    • 8 Seats, 20 City / 26 Hwy MPG
    • Auto Group of Louisville (12 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Louisville, KY / 12 miles away from Crestwood, KY

    ***LOW MILEAGE***HEATED/COOLING/POWER FRONT SEATS***JBL AUDIO***AUTOMATED REAR DOOR***Step into luxury and versatility with this sleek Black 2018 Toyo...

    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:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDDZRFH3JS871031
    Stock: 871031
    Certified Pre-Owned: No

    • 81,029 miles
    • No accidents, 2 owners, personal use only
    • 8 Seats, 20 City / 26 Hwy MPG
    • Craig and Landreth Pre-Owned (18 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Clarksville, IN / 18 miles away from Crestwood, KY

    WE ARE THE LARGEST LUXURY PRE-OWNED DEALER IN KENTUCKIANA WITH 49 YEARS OF EXPERIENCE, A+ BBB RATING! THIS TOYOTA HIGHLANDER XLE IS CERTIFIED BY CARFA...

    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 (20 City/26 Highway)

    Listing Information:

    VIN: 5TDJZRFH4KS621267
    Stock: MU20014
    Certified Pre-Owned: No
    Listed since: 07-03-2025

  • Price Drop
    $22,198
    fair price
    $742 above market
    • 118,950 miles
    • 2 accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 29 Hwy MPG
    • Jeff Wyler Toyota of Clarksville (17 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Clarksville, IN / 17 miles away from Crestwood, KY

    Recent Arrival! CARFAX One-Owner. 21/29 City/Highway MPGAwards: * ALG Residual Value Awards, Residual Value Awards 18" Painted Alloy Wheels, 3.003...

    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

  • $22,484
    fair price
    $453 above market
    • 113,820 miles
    • 1 accident, 2 owners, personal use
    • 7 Seats, 18 City / 24 Hwy MPG
    • Mike's Car Store (28 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Georgetown, IN / 28 miles away from Crestwood, KY

    The 2016 Toyota Highlander Limited Platinum is a top-tier family SUV that checks all the boxes for comfort, safety, and capability. Every vehicle on o...

    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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDDKRFH1GS312722
    Stock: P1611
    Certified Pre-Owned: No

  • New Listing
    $12,985
    fair price
    $923 below market
    • 115,871 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 18 City / 24 Hwy MPG
    • Louisville Cars & Trucks (25 mi away)
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    • Third-row seating
    Close

    Located in Louisville, KY / 25 miles away from Crestwood, 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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDZK3EH6CS068421
    Stock: 2374
    Certified Pre-Owned: No

  • New Listing
    • 95,593 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 20 City / 26 Hwy MPG
    • CarMax Louisville (11 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Louisville, KY / 11 miles away from Crestwood, KY

    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:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDJZRFH3JS859075
    Stock: 27392628
    Certified Pre-Owned: No

  • Price Drop
    $34,675
    good price
    $1,044 below market
    • 43,925 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 22 City / 29 Hwy MPG
    • Neil Huffman Chevrolet Buick GMC of Frankfort (36 mi away)
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Frankfort, KY / 36 miles away from Crestwood, 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/29 Highway)

    Listing Information:

    VIN: 5TDKDRAHXPS004599
    Stock: N3138A
    Certified Pre-Owned: No

  • Price Drop
    $28,780
    good price
    $1,025 below market
    • 103,136 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Herb Jones Chevrolet Buick GMC (48 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Elizabethtown, KY / 48 miles away from Crestwood, 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: 5TDGZRBHXMS526506
    Stock: 30421
    Certified Pre-Owned: No

Showing 1 - 21 out of 1,017 listings
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