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Used Toyota Highlander for Sale near Windsor, KY

242 results
Windsor, KY
2016 Toyota Highlander Georgetown Auto Sales

2016 Toyota Highlander

Limited AWD

122,567 miles

$18,987

Fair Deal
Georgetown, KY
76 mi away
Year:
2016
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Fuel type:
Gasoline
Transmission:
6-Speed Automatic Overdrive
Mileage:
122,567
Stock number:
G8754
VIN:
5TDDKRFH6GS240092

Sponsored

2019 Toyota Highlander XLE AWD

2019 Toyota Highlander

XLE AWD

100,890 miles

$24,000

Fair Deal
Shepherdsville, KY
75 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
White
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Brown (Saddle Tan)
Transmission:
8-Speed Automatic
Mileage:
100,890
Stock number:
4489A
VIN:
5TDJZRFH6KS592418

Sponsored

2022 Toyota Highlander XLE AWD

2022 Toyota Highlander

XLE AWD

83,223 miles

$27,990

Good Deal
Lexington, KY
67 mi away
Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Gray
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
83,223
Stock number:
10134
VIN:
5TDGZRBH9NS235481

Sponsored

2025 Toyota Highlander LE FWD

2025 Toyota Highlander

LE FWD

34,922 miles

$33,998

Great Deal
Store transfer to Lexington, KY
126 mi away • Price includes $0 shipping Price includes $0 shipping
Year:
2025
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Black
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
34,922
Stock number:
28430909
VIN:
5TDKDRAH8SS551881

2011 Toyota Highlander

2011 Toyota Highlander

165,157 miles

$10,900

Fair Deal
Knoxville, TN
93 mi away
Year:
2011
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Engine:
187 hp 2.7L I4
Exterior color:
White
Fuel type:
Gasoline
Interior color:
Brown (Beige)
Transmission:
6-Speed Automatic
Mileage:
165,157
Stock number:
5160
VIN:
5TDZA3EHXBS010085

2023 Toyota Highlander L FWD

2023 Toyota Highlander

L FWD

42,560 miles

$26,888

Great Deal
Nicholasville, KY
56 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
42,560
Stock number:
P22207
VIN:
5TDKDRAH6PS035591

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2023 Toyota Highlander

L FWD

47,765 miles

$27,777

Great Deal
Nicholasville, KY
56 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
47,765
Stock number:
P22281
VIN:
5TDKDRAH7PS503375

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2018 Toyota Highlander

LE

147,434 miles

$14,720

Good Deal
Knoxville, TN
97 mi away
Year:
2018
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Celestial Silver Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
147,434
Stock number:
633731
VIN:
5TDZARFH5JS036822

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2022 Toyota Highlander

XLE AWD

68,718 miles

$29,945

Great Deal
Lexington, KY
61 mi away
Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Celestial Silver
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
68,718
Stock number:
U247214
VIN:
5TDHZRBH7NS247214

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2021 Toyota Highlander

XLE AWD

82,812 miles

$27,708

Good Deal
Lexington, KY
64 mi away
Year:
2021
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Gray
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
82,812
Stock number:
MS552188
VIN:
5TDGZRBH9MS552188

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2020 Toyota Highlander

XLE AWD

119,871 miles

$22,477

Good Deal
Radcliff, KY
73 mi away
Year:
2020
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
119,871
Stock number:
LS512421
VIN:
5TDGZRBH0LS512421

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2019 Toyota Highlander

XLE AWD

76,662 miles

$24,900

Good Deal
Middlesboro, KY
76 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Predawn Gray Mica
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
76,662
Stock number:
P9048A
VIN:
5TDJZRFH7KS622848

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2019 Toyota Highlander

Limited AWD

92,091 miles

$25,875

Good Deal
Lexington, KY
61 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Predawn Gray Mica
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
92,091
Stock number:
U948303
VIN:
5TDDZRFHXKS948303

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2019 Toyota Highlander

LE Plus FWD

93,800 miles

$20,647

Great Deal
Store transfer to Lexington, KY
782 mi away • Price includes $649 shipping Price includes $649 shipping
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Black
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
93,800
Stock number:
28243721
VIN:
5TDZZRFH7KS322097

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2020 Toyota Highlander

XLE FWD

133,780 miles

$22,955

Fair Deal
Clarksville, IN
93 mi away
Year:
2020
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
133,780
Stock number:
PA10382A
VIN:
5TDGZRAH1LS509948

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2023 Toyota Highlander

L FWD

40,662 miles

$30,998

Good Deal
Store transfer to Lexington, KY
204 mi away • Price includes $0 shipping Price includes $0 shipping
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Silver
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
40,662
Stock number:
28048956
VIN:
5TDKDRAH8PS502624

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2024 Toyota Highlander

LE FWD

52,729 miles

$30,900

Good Deal
Middlesboro, KY
76 mi away
Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Black
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
52,729
Stock number:
P9029
VIN:
5TDKDRAH7RS528182

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2024 Toyota Highlander

XLE FWD

56,329 miles

$31,595

Great Deal
Nicholasville, KY
56 mi away
Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Celestial Silver Metallic
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
56,329
Stock number:
P22208
VIN:
5TDKDRAHXRS533943

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2018 Toyota Highlander

XLE AWD

167,395 miles

$16,000

Good Deal
Lexington, KY
67 mi away
Year:
2018
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Midnight Black Metallic
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
167,395
Stock number:
260628A
VIN:
5TDJZRFH1JS543366

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2016 Toyota Highlander

Limited AWD

182,363 miles

$13,649

Good Deal
Louisville, KY
86 mi away
Year:
2016
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Silver
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
6-Speed Automatic Overdrive
Mileage:
182,363
Stock number:
SI1013C
VIN:
5TDDKRFH8GS237145

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2019 Toyota Highlander

Limited AWD

99,238 miles

$24,495

Good Deal
Lexington, KY
66 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Pearl White
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
99,238
Stock number:
97238
VIN:
5TDDZRFH6KS997238

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2019 Toyota Highlander

XLE AWD

67,307 miles

$25,750

Good Deal
Louisville, KY
83 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Red
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
67,307
Stock number:
9018990
VIN:
5TDJZRFH4KS737536

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2023 Toyota Highlander

LE AWD

69,811 miles

$29,880

Fair Deal
Louisville, KY
82 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Black
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
69,811
Stock number:
CU10931N
VIN:
5TDKDRBHXPS036791

Sponsored

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  5. / Windsor
Overview
Reviews
FAQs

CarGurus recommends the 2022 Toyota Highlander

Picture of Toyota Highlander ## Summary - With 4,445 currently listed for sale on CarGurus and an **average price of $32,524.00**, 32.8% of 2022 Toyota Highlanders for sale on CarGurus are rated as good or great deals. - **Favorably reviewed:** Owners rated the 2022 Toyota Highlander 4.58 / 5 stars. - **82.5% of 2022 Highlander models on CarGurus are accident free**. - The 2022 Toyota Highlander offers a spacious interior with a comfortable ride, solid fuel efficiency, and advanced safety features like Toyota Safety Sense. ## Why it stands out The 2022 Toyota Highlander stands out in the competitive midsize SUV market thanks to its blend of practicality, comfort, and reliability. With a redesign that emphasizes both interior space and a smooth driving experience, this model caters to families and individuals looking for a dependable vehicle. The introduction of hybrid technology in this generation enhances its fuel economy, while the spacious cabin provides ample room for passengers and cargo alike. Additionally, the inclusion of advanced safety features has solidified the Highlander's reputation as a safe and secure option for any driver. ## Other model years to consider - **[2021 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2021-Toyota-Highlander-c30910)** - Average price: $29,272.00 - Good/great deal percentage: 33.6% - User rating: 4.82 / 5 - Total listings: 3,016 - **[2019 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2019-Toyota-Highlander-c27941)** - Average price: $23,159.00 - Good/great deal percentage: 34.8% - User rating: 4.57 / 5 - Total listings: 2,580 - **[2020 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2020-Toyota-Highlander-c29164)** - Average price: $27,061.00 - Good/great deal percentage: 34.4% - User rating: 4.48 / 5 - Total listings: 2,823 These recommendations are based on CarGurus' proprietary market data from February 23, 2026, CarGurus experts' opinions, and generative AI.

4.6 Overall rating

(691 reviews)

Customers say

Overall, the Toyota Highlander has built a strong reputation across its model years for reliability, comfort, and family-friendly features. Drivers appreciate its spacious interiors and smooth rides, often highlighting its impressive safety features as a key asset. Many also enjoy the performance and power of the engines. However, some common criticisms include a lack of advanced infotainment options in older models, tight third-row seating, and varying cargo space depending on configuration. Overall, the Highlander is seen as a dependable choice for families and an excellent value in the SUV market.

AI generated from the text of customer reviews.

What people say

cargo space comfort interior performance safety
Julie W
5.0
Reviewed a 2021 Toyota Highlander on Jul 20, 2024

I loved my Highlander. I give my 2021 Toyota Highlander a 100 out of 10 on its safety. My car was a limited and it had most bells and whistles which I loved but what I loved most was that we all walked away from a collision where we were traveling 40 miles an hour and thanks to the safety design , we’re here.

Melissa C
5.0
Reviewed a 2021 Toyota Highlander on May 05, 2024

Toyota knocked it out of the park again with this 2021 Highlander Platinum. Luxurious quiet ride Lexus feel like. Very happy with this purchase.

Emmanuel S
5.0
Reviewed a 2022 Toyota Highlander on Apr 18, 2024

The car is great with very nice features. It is a good value in terms of price and nothing is missing. It is a good looking car

Anonymous
5.0
Reviewed a 2019 Toyota Highlander on Sep 03, 2024

great combination of reliability, function and features and price. Has more than enough bells and whistles with great driveability and comfort

James S
4.0
Reviewed a 2008 Toyota Highlander on Jul 16, 2024

We own 2 of these. One is the limited and the other is the all wheel drive. Over 150,000 on each and really just general maintenance issues so far with each. The clear coat is peeling and fading on the rear valance of each and the shocks and struts need to be replaced at this age. We have taken our limited everywhere including Texas, Colorado, North Carolina, Maryland, West Virginia, and more. Very good for families or dog owners and flexible with the third row seating. No major issues with either one so far!

Toyota Highlander FAQs

How much does the Toyota Highlander cost in Windsor, KY?

The average Toyota Highlander costs about $26,608.38. The average price has decreased by -7.8% since last year. The 722 for sale near Windsor, KY on CarGurus, range from $4,127 to $56,238 in price.

How many Toyota Highlander vehicles in Windsor, KY have no reported accidents or damage?

497 out of 722 for sale near Windsor, KY have no reported accidents or damage.

What fuel types are available?

Gasoline engines are available.

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