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Used Toyota Highlander for Sale near Winnetka, IL

352 results
Winnetka, IL
2022 Toyota Highlander XLE AWD McGrath Honda

2022 Toyota Highlander

XLE AWD

45,335 miles

$34,000

Fair Deal
St. Charles, IL
28 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:
Brown (Harvest Beige)
Transmission:
8-Speed Automatic
Mileage:
45,335
Stock number:
DS4488B
VIN:
5TDGZRBH8NS203914

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2021 Toyota Highlander XSE AWD

2021 Toyota Highlander

XSE AWD

68,011 miles

$31,697

Fair Deal
Orland Park, IL
35 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:
Red (Ruby Flare Pearl)
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
68,011
Stock number:
B10546
VIN:
5TDJZRBH2MS143701

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2023 Toyota Highlander L AWD

2023 Toyota Highlander

L AWD

49,461 miles

$34,475

Fair Deal
Certified Pre-Owned
Waukegan, IL
19 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:
Silver
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
49,461
Stock number:
T28830A
VIN:
5TDKDRBH5PS041963

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2011 Toyota Highlander Base

2011 Toyota Highlander

Base

179,986 miles

$7,891

Great Deal
Crystal Lake, IL
29 mi away
Year:
2011
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
187 hp 2.7L I4
Fuel type:
Gasoline
Transmission:
6-Speed Automatic Overdrive
Mileage:
179,986
Stock number:
V55517A
VIN:
5TDZA3EH5BS015212

2018 Toyota Highlander Limited Platinum AWD

2018 Toyota Highlander

Limited Platinum AWD

78,824 miles

$23,997

Great Deal
Orland Park, IL
35 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:
White (Blizzard Pearl)
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
78,824
Stock number:
B10814
VIN:
5TDDZRFH5JS871256

2021 Toyota Highlander XLE AWD

2021 Toyota Highlander

XLE AWD

114,805 miles

$23,916

Good Deal
Racine, WI
43 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:
Midnight Black Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
114,805
Stock number:
7864A
VIN:
5TDGZRBH0MS129757

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2011 Toyota Highlander

Base

132,500 miles

$10,799

Good Deal
Elgin, IL
26 mi away
Year:
2011
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
187 hp 2.7L I4
Exterior color:
Gray
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
5-Speed Automatic
Mileage:
132,500
Stock number:
070624
VIN:
5TDBK3EH8BS070624

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2023 Toyota Highlander

L FWD

56,380 miles

$28,895

Great Deal
Lake Geneva, WI
47 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:
Silver
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
56,380
Stock number:
30P1045
VIN:
5TDKDRAH8PS502767

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2021 Toyota Highlander

LE AWD

78,623 miles

$23,917

Good Deal
Palatine, IL
14 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
Transmission:
Automatic
Mileage:
78,623
Stock number:
903670A
VIN:
5TDBZRBH8MS534453

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2018 Toyota Highlander

XLE AWD

76,904 miles

$22,999

Good Deal
Countryside, IL
23 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:
Predawn Gray Mica
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
8-Speed Automatic
Mileage:
76,904
Stock number:
CS38660A
VIN:
5TDJZRFH1JS554254

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2011 Toyota Highlander

Limited 4WD

119,633 miles

$10,995

Good Deal
Joliet, IL
42 mi away
Year:
2011
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Silver
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
5-Speed Automatic
Mileage:
119,633
VIN:
5TDDK3EH3BS084276

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2014 Toyota Highlander

XLE AWD

142,658 miles

$14,990

Fair Deal
Chicago, IL
11 mi away
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:
Silver Sky Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
142,658
Stock number:
CV7038A
VIN:
5TDJKRFH9ES054742

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2015 Toyota Highlander

LE Plus AWD

117,110 miles

$15,500

Good Deal
McHenry, IL
30 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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2017 Toyota Highlander

XLE AWD

99,721 miles

$19,877

Good Deal
Burns Harbor, IN
48 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:
Gray
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
99,721
Stock number:
34-26144A
VIN:
5TDJZRFH2HS449264

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2024 Toyota Highlander

LE AWD

37,824 miles

$31,199

Great Deal
Lincolnwood, IL
6 mi away
Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
White (Wind Chill Pearl)
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
37,824
Stock number:
P4629
VIN:
5TDKDRBH2RS563341

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2015 Toyota Highlander

LE

105,981 miles

$14,288

Good Deal
Barrington, IL
19 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:
Creme Brulee Mica
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
105,981
Stock number:
260656AA
VIN:
5TDZARFH5FS016450

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2016 Toyota Highlander

LE AWD

130,892 miles

$14,995

Good Deal
Bridgeview, IL
24 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:
Blue
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
130,892
Stock number:
SIY12
VIN:
5TDBKRFH8GS244572

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2009 Toyota Highlander

Limited 4WD

250,102 miles

$5,999

Fair Deal
Dolton, IL
34 mi away
Year:
2009
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Green
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Brown (BEIGE)
Transmission:
5-Speed Automatic Overdrive
Mileage:
250,102
Stock number:
10718
VIN:
JTEES42A492141888

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2022 Toyota Highlander

XLE AWD

62,879 miles

$31,990

Good Deal
Certified Pre-Owned
Kenosha, WI
33 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 Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
62,879
Stock number:
T252830A
VIN:
5TDGZRBHXNS578946

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2025 Toyota Highlander

XLE FWD

15,915 miles

$34,899

Great Deal
Carol Stream, IL
23 mi away
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:
Silver
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
15,915
Stock number:
552182
VIN:
5TDKDRAH9SS552182

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2021 Toyota Highlander

XLE AWD

49,605 miles

$30,196

Good Deal
Saint Charles, IL
31 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:
Moon Dust
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
49,605
Stock number:
F4809
VIN:
5TDHZRBH2MS530439

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2008 Toyota Highlander

Limited 4WD

124,500 miles

$9,995

Fair Deal
Waukegan, IL
19 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:
Red (Burgundy)
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
124,500
Stock number:
054096
VIN:
JTEES42A982054096

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2023 Toyota Highlander

L AWD

46,321 miles

$29,444

Good Deal
Skokie, IL
4 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:
Black
Transmission:
8-Speed Automatic
Mileage:
46,321
Stock number:
Z2509
VIN:
5TDKDRBH9PS039794

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  1. Home
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  5. / Winnetka
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.

Kristy E
5.0
Reviewed a 2010 Toyota Highlander on Jan 25, 2024

Great car that has a reputation for durability. Love the features.

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

Toyota Highlander FAQs

How much does the Toyota Highlander cost in Winnetka, IL?

The average Toyota Highlander costs about $26,920.22. The average price has decreased by -7.8% since last year. The 350 for sale near Winnetka, IL on CarGurus, range from $2,499 to $53,998 in price.

How many Toyota Highlander vehicles in Winnetka, IL have no reported accidents or damage?

350 out of 350 for sale near Winnetka, IL have no reported accidents or damage.

What fuel types are available?

Gasoline engines are available.

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