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Used Toyota Highlander for Sale near Windsor, WI

267 results
Windsor, WI
2021 Toyota Highlander XSE AWD Dart Motors LLC

2021 Toyota Highlander

XSE AWD

65,566 miles

$30,999

Fair Deal
Mchenry, IL
83 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:
Blue
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
65,566
Stock number:
1681
VIN:
5TDJZRBH2MS123108

Sponsored

2015 Toyota Highlander XLE

2015 Toyota Highlander

XLE

170,044 miles

$14,489

Fair Deal
Johnson Creek, WI
29 mi away
Year:
2015
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Silver
Fuel type:
Gasoline
Transmission:
6-Speed Automatic Overdrive
Mileage:
170,044
Stock number:
9539A
VIN:
5TDJKRFH9FS187387

Sponsored

2022 Toyota Highlander Platinum AWD

2022 Toyota Highlander

Platinum AWD

59,854 miles

$38,251

Fair Deal
Oak Creek, WI
73 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:
White
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
59,854
Stock number:
44P2089
VIN:
5TDFZRBH2NS166239

Sponsored

2017 Toyota Highlander XLE AWD

2017 Toyota Highlander

XLE AWD

82,346 miles

$22,677

Fair Deal
Antioch, IL
80 mi away
Year:
2017
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
White (Blizzard Pearl)
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Almond
Transmission:
8-Speed Automatic
Mileage:
82,346
Stock number:
21033N
VIN:
5TDJZRFH4HS513336

2022 Toyota Highlander XSE AWD

2022 Toyota Highlander

XSE AWD

29,748 miles

$38,714

Fair Deal
Kenosha, WI
83 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:
Midnight Black Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Cockpit Red
Transmission:
Automatic
Mileage:
29,748
Stock number:
KB3240
VIN:
5TDJZRBH1NS179154

2020 Toyota Highlander XLE AWD

2020 Toyota Highlander

XLE AWD

70,930 miles

$28,990

Fair Deal
Mukwonago, WI
56 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:
Midnight Black Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
70,930
Stock number:
JP1453A
VIN:
5TDHZRBH5LS506862

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2015 Toyota Highlander

LE Plus AWD

127,156 miles

$14,598

Great Deal
Sheboygan, WI
88 mi away
Year:
2015
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Nautical Blue Metallic
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
6-Speed Automatic Overdrive
Mileage:
127,156
Stock number:
U194340T
VIN:
5TDBKRFH6FS200911

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2018 Toyota Highlander

Limited AWD

123,014 miles

$20,911

Good Deal
Madison, WI
13 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:
Silver
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
123,014
Stock number:
G4957
VIN:
5TDDZRFH8JS898693

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2022 Toyota Highlander

XLE AWD

41,030 miles

$34,600

Good Deal
Hortonville, WI
86 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:
Midnight Black Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
41,030
Stock number:
12A2119
VIN:
5TDGZRBHXNS584147

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2008 Toyota Highlander

Sport 4WD

169,760 miles

$7,999

Fair Deal
Waukegan, IL
95 mi away
Year:
2008
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Black
Fuel type:
Gasoline
Interior color:
Brown (Tan)
Transmission:
5-Speed Automatic
Mileage:
169,760
Stock number:
37230S
VIN:
JTEES43A982093785

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2014 Toyota Highlander

Limited AWD

108,671 miles

$19,297

Fair Deal
Store transfer to Madison, WI
1,222 mi away • Price includes $1,299 shipping Price includes $1,299 shipping
Year:
2014
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Red (Burgundy)
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
108,671
Stock number:
27869257
VIN:
5TDDKRFHXES047117

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2013 Toyota Highlander

Limited FWD

77,724 miles

$16,995

Fair Deal
Dixon, IL
93 mi away
Year:
2013
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Magnetic Gray Metallic
Fuel type:
Gasoline
Interior color:
Brown (Sand Beige)
Transmission:
5-Speed Automatic Overdrive
Mileage:
77,724
Stock number:
FTT072B
VIN:
5TDYK3EH4DS142089

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2023 Toyota Highlander

XLE FWD

70,771 miles

$28,994

Good Deal
Elkhorn, WI
53 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:
White
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
70,771
Stock number:
06P2408
VIN:
5TDKDRAH5PS010889

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2015 Toyota Highlander

LE Plus AWD

117,110 miles

$15,500

Good Deal
McHenry, IL
81 mi away
Year:
2015
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Black
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
117,110
Stock number:
1219
VIN:
5TDBKRFH2FS089189

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2012 Toyota Highlander

Limited AWD

244,400 miles

$7,518

Good Deal
Dubuque, IA
87 mi away
Year:
2012
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:
5-Speed Automatic Overdrive
Mileage:
244,400
Stock number:
26H274AA
VIN:
5TDDK3EH5CS123371

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2018 Toyota Highlander

Limited Platinum AWD

92,854 miles

$25,995

Fair Deal
Germantown, WI
59 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:
Black
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black (Charcoal)
Transmission:
8-Speed Automatic
Mileage:
92,854
Stock number:
8-26
VIN:
5TDDZRFH6JS887904

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2020 Toyota Highlander

L AWD

73,261 miles

$23,995

Good Deal
Milwaukee, WI
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:
Black
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
73,261
Stock number:
052225
VIN:
5TDCZRBH2LS052225

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2023 Toyota Highlander

XLE AWD

67,779 miles

$32,998

Good Deal
Certified Pre-Owned
Madison, WI
13 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:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
67,779
Stock number:
PTS016194
VIN:
5TDKDRBH2PS016194

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2022 Toyota Highlander

XLE AWD

57,614 miles

$31,990

Good Deal
Middleton, WI
11 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:
Magnetic Gray Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
57,614
Stock number:
50953
VIN:
5TDGZRBHXNS165635

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2012 Toyota Highlander

SE AWD

184,151 miles

$10,500

Fair Deal
Certified Pre-Owned
Madison, WI
13 mi away
Year:
2012
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Black
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
184,151
Stock number:
TS083448A
VIN:
5TDBK3EH9CS169535

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2019 Toyota Highlander

XLE FWD

89,007 miles

$21,995

Good Deal
Milwaukee, WI
74 mi away
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:
White
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
89,007
VIN:
5TDKZRFH6KS556507

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2019 Toyota Highlander

XLE AWD

91,877 miles

$22,998

Good Deal
Waukesha, WI
59 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:
Black
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
91,877
Stock number:
V26180A
VIN:
5TDJZRFH9KS704855

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2020 Toyota Highlander

XLE AWD

70,930 miles

$28,990

Fair Deal
Mukwonago, WI
56 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:
Midnight Black Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
70,930
Stock number:
JP1453A
VIN:
5TDHZRBH5LS506862

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  1. Home
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  4. / Wisconsin
  5. / Windsor
Overview
Reviews
FAQs

CarGurus recommends the 2022 Toyota Highlander

Picture of Toyota Highlander

Summary

  • With 6,308 currently listed for sale on CarGurus and an average price of $33,572.40, 35.5% of 2022 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
  • Favorably reviewed: Owners rated the 2022 Toyota Highlander 4.6 / 5 stars and CarGurus experts gave it an 8.2 / 10.
  • 83.7% of 2022 Highlander models on CarGurus are accident free.
  • The 2022 Toyota Highlander featured an impressive 84.3 cubic feet of cargo space with seats folded down, making it highly versatile for families and adventures.

Why it stands out

The 2022 Toyota Highlander stands out in the family SUV segment due to its spacious three-row seating, making it ideal for families needing ample room for passengers and cargo. It features a robust V6 engine that delivers reliable performance, coupled with standard safety technologies that enhance peace of mind on the road. With a variety of trims available, the Highlander caters to diverse preferences and budgets while maintaining Toyota's reputation for reliability and efficiency.

Other model years to consider

For buyers considering the Toyota Highlander, model years 2015 and 2021 stand out as attractive options. The 2015 Highlander combines a competitive average price with an impressive user rating of 4.8/5 and a high percentage of good deals, making it a strong value proposition for those seeking reliability and satisfaction. Similarly, the 2021 model offers modern features at a reasonable price point while maintaining high user satisfaction ratings, positioning it well in today’s marketplace.

Other noteworthy alternatives include the 2019 Highlander, which offers solid user feedback and value for money, as well as the 2016 version, which has an appealing price point along with high user ratings. These models collectively provide diverse options that cater to different budgets while ensuring consistent quality and satisfaction among users.

Model years to approach with caution

The Toyota Highlander model years 2014, 2018, and 2011 should be approached with caution due to several financial and quality considerations. Despite decent user ratings, a significant percentage of these models are categorized as not providing good or great deals, indicating potential overpricing in the market. Furthermore, as newer models become available, availability constraints for earlier years may limit options for buyers seeking a balance between quality and price.

These recommendations are based on CarGurus' proprietary market data from December 17, 2025, 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, WI?

The average Toyota Highlander costs about $26,851.62. The average price has decreased by -7.6% since last year. The 549 for sale near Windsor, WI on CarGurus, range from $3,094 to $47,998 in price.

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

549 out of 549 for sale near Windsor, WI have no reported accidents or damage.

What fuel types are available?

Gasoline engines are available.

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