Used Toyota Highlander for Sale in Winchester, KY
Shop for a versatile Toyota Highlander in the seat of Clark County
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1,375 listings
- $29,999good price$1,402 below market
- 57,827 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Kelsey Chevrolet (86 mi away)
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Located in Greendale, IN / 86 miles away from Winchester, KY
Priced below KBB Fair Purchase Price! Highlander LE, 4D Sport Utility, 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp, 8-Speed Automatic, FWD, A...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH2PS505065
Stock: C5872JR
Certified Pre-Owned: No
Listed since: 04-14-2025 - Price Drop$28,750fair price$303 below market
- 35,930 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Auto Group of Louisville (77 mi away)
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Located in Louisville, KY / 77 miles away from Winchester, 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$15,500good price$691 below market
- 182,702 miles
- 3 accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Dan Cummins Chrysler Dodge Jeep Ram of Paris (16 mi away)
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Located in Paris, KY / 16 miles away from Winchester, KY
This 2018 Toyota Highlander LE is being offered to you as an alternative to us taking to the auction. This Highlander is a spacious, family friendly v...
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: 5TDBZRFH1JS859502
Stock: 103744A
Certified Pre-Owned: No
Listed since: 07-21-2025 - Price Drop$30,250good price$968 below market
- 58,095 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Jeff Wyler Chrysler Jeep Dodge Ram Of Lawrenceburg (85 mi away)
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Located in Lawrenceburg, IN / 85 miles away from Winchester, KY
Jeff Wyler Chrysler Dodge Jeep of Lawrenceburg is honored to offer this good-looking 2019 Toyota Highlander Limited in Black. AWD, ABS brakes, Active ...
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: 5TDDZRFH1KS737426
Stock: 2811222B
Certified Pre-Owned: No
Listed since: 07-08-2025 - $35,987fair price$124 below market
- 54,413 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Dan Cummins Chrysler Dodge Jeep RAM of Georgetown (25 mi away)
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Located in Georgetown, KY / 25 miles away from Winchester, KY
2022 Toyota Highlander XLE AWD 3.5L V6 DOHC 8-Speed Automatic 4D Sport Utility Wind Chill Pearl 20/27 City/Highway MPG AWD.**THIS VEHICLE HAS BEEN INS...
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: 5TDHZRBH8NS236366
Stock: 17016
Certified Pre-Owned: No
Listed since: 07-16-2025 - Price Drop$13,241fair price$819 below market
- 103,475 miles
- 1 accident, 2 owners, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Jeff Wyler Nissan of Cincinnati (89 mi away)
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Located in Cincinnati, OH / 89 miles away from Winchester, 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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDZK3EH5CS056633
Stock: 2511962B
Certified Pre-Owned: No
Listed since: 07-16-2025 - $15,776good price$375 below market
- 124,687 miles
- 1 accident, 4 owners, personal use
- 8 Seats, 20 City / 25 Hwy MPG
- Gates Ford Lincoln (17 mi away)
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Located in Richmond, KY / 17 miles away from Winchester, 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:
22 Combined MPG (20 City/25 Highway)
Listing Information:
VIN: 5TDZARFH5ES006211
Stock: 006211
Certified Pre-Owned: No
Listed since: 06-30-2025 - $32,213good price$1,860 below market
- 39,600 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Kings Toyota (90 mi away)
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Located in Cincinnati, OH / 90 miles away from Winchester, KY
Certified. CARFAX One-Owner. Odometer is 8345 miles below market average! 20/27 City/Highway MPG Clean CARFAX. Midnight Black Metallic 2022 Toyota 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRBH3NS238256
Stock: NS238256
Certified Pre-Owned: Yes
Listed since: 07-17-2025 - New Listing$35,937fair price$370 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)
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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$25,487fair price$473 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 (25 mi away)
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Located in Georgetown, KY / 25 miles away from Winchester, 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. CARFAX ...
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 - Price Drop$35,854fair price$318 below market
- 53,674 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Jeff Wyler Honda in Florence (75 mi away)
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Located in Florence, KY / 75 miles away from Winchester, KY
CARFAX One-Owner. ONE OWNER ACCIDENT FREE CARFAX, REAR BACKUP CAMERA, THIRD ROW SEATING, ALL WHEEL DRIVE, PASSED OUR SAFETY INSPECTION, SERVICE RECORD...
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: 5TDGZRBH0NS581306
Stock: 2255650A
Certified Pre-Owned: No
Listed since: 07-06-2025 - $35,500good price$961 below market
- 51,986 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Kings Kia (91 mi away)
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Located in Cincinnati, OH / 91 miles away from Winchester, KY
CARFAX One-Owner. Sunroof / Moonroof, Local Trade, AWD All Wheel Drive, Heated Seats, Bluetooth, Rear View Camera, Alloy wheels, Apple CarPlay/Android...
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: 5TDGZRBH4NS229748
Stock: NS229748
Certified Pre-Owned: No
Listed since: 05-24-2025 - $28,995fair price$425 below market
- 88,762 miles
- No accidents, 3 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- A+ Auto Sales (92 mi away)
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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$15,000fair price$538 above market
- 166,463 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 24 Hwy MPG
- Kings Toyota (90 mi away)
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Located in Cincinnati, OH / 90 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:
22 Combined MPG (20 City/24 Highway)
Listing Information:
VIN: 5TDZARFH0HS031988
Stock: HS031988
Certified Pre-Owned: No
Listed since: 06-30-2025 - Price Drop$25,787fair price$268 above market
- 93,806 miles
- No accidents, 2 owners, corporate fleet vehicle
- 7 Seats, 21 City / 27 Hwy MPG
- Dan Cummins Chrysler Dodge Jeep Ram of Paris (16 mi away)
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, replaced engine air filter, replaced wiper blades, and v...
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 (21 City/27 Highway)
Listing Information:
VIN: 5TDYZRFH7KS324623
Stock: 17931
Certified Pre-Owned: No
Listed since: 06-20-2025 - Price Drop
- 40,386 miles
- No accidents, 2 owners, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Dan Cummins Chevrolet Buick of Paris (15 mi away)
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Located in Paris, KY / 15 miles away from Winchester, KY
Discover the 2023 Toyota Highlander LE: Where Sophistication Meets Performance in a Magnetic Gray Metallic Finish, Perfect for the Modern Adventurer...
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: Yes
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH3PS521743
Stock: 64084
Certified Pre-Owned: No
Listed since: 06-20-2025 - $26,987fair price$134 above market
- 47,957 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Dan Cummins Chevrolet Buick of Paris (15 mi away)
Close
Located in Paris, KY / 15 miles away from Winchester, KY
Discover the 2017 Toyota Highlander XLE: A Toasted Walnut Pearl Adventure Awaits with a 3.5L V6 Engine and 8-Speed Automatic TransmissionStep 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH6HS462664
Stock: 122154A
Certified Pre-Owned: No
Listed since: 03-04-2025 - Price Drop$43,680fair price$875 above market
- 14,158 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- Columbia Hyundai (88 mi away)
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Located in Cincinnati, OH / 88 miles away from Winchester, KY
AWD, ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/C, Heated door mirrors, Heated Front Bucket Seat...
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: 5TDKDRBH8RS567023
Stock: 5706151
Certified Pre-Owned: No
Listed since: 06-30-2025 - $9,995fair price$509 above market
- 167,310 miles
- No accidents, 4 owners, personal use only
- 7 Seats, 17 City / 22 Hwy MPG
- Cincinnati Used Auto Sales (75 mi away)
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Located in Cincinnati, OH / 75 miles away from Winchester, KY
The 2011 Toyota Highlander SE is a reliable and versatile SUV designed to meet the needs of drivers seeking comfort, performance, and functionality. E...
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: 5TDBK3EHXBS061259
Stock: 1759
Certified Pre-Owned: No - $34,987good price$1,154 below market
- 51,888 miles
- 1 accident, 1 owner, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Dan Cummins Chevrolet Buick of Paris (15 mi away)
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, replaced engine air filter, replaced wiper blades, and v...
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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH1NS596756
Stock: 63817
Certified Pre-Owned: No
Listed since: 05-29-2025 - $29,987fair price$21 below market
- 54,171 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Dan Cummins Chrysler Dodge Jeep Ram of Paris (16 mi away)
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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRBH3NS242467
Stock: 18067
Certified Pre-Owned: No
Listed since: 07-10-2025
Showing 43 - 63 out of 1,375 listings
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