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Used Toyota Highlander for Sale near Chesterton, IN

641 results
Chesterton, IN
2022 Toyota Highlander XLE AWD Jennings Volkswagen

2022 Toyota Highlander

XLE AWD

31,461 miles

$34,888

Good Deal
Glenview, IL
50 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
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
31,461
Stock number:
P8085VW
VIN:
5TDHZRBH1NS234538

Sponsored

2022 Toyota Highlander XSE AWD

2022 Toyota Highlander

XSE AWD

29,057 miles

$35,333

Good Deal
Skokie, IL
48 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:
Red (Ruby Flare Pearl)
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
29,057
Stock number:
Z2549A
VIN:
5TDJZRBH2NS209438

Sponsored

2024 Toyota Highlander LE AWD

2024 Toyota Highlander

LE AWD

29,202 miles

$33,900

Good Deal
Certified Pre-Owned
Calumet City, IL
28 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:
Magnetic Gray Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
29,202
Stock number:
P7121
VIN:
5TDKDRBH6RS562550

Sponsored

2021 Toyota Highlander XLE AWD

2021 Toyota Highlander

XLE AWD

107,222 miles

$23,995

Good Deal
Palos Hills, IL
40 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:
Blueprint
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Brown (Harvest Beige)
Transmission:
Automatic
Mileage:
107,222
Stock number:
S32519
VIN:
5TDHZRBH1MS537169

2018 Toyota Highlander XLE AWD

2018 Toyota Highlander

XLE AWD

76,904 miles

$23,123

Good Deal
Countryside, IL
44 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

2019 Toyota Highlander LE Plus AWD

2019 Toyota Highlander

LE Plus AWD

64,167 miles

$23,681

Good Deal
Michigan City, IN
9 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
Transmission:
Automatic
Mileage:
64,167
Stock number:
DMK2559B
VIN:
5TDBZRFH5KS721401

Preparing for a close up...

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2019 Toyota Highlander

Limited AWD

88,823 miles

$25,097

Great Deal
Store transfer to Merrillville, IN
260 mi away • Price includes $99 shipping Price includes $99 shipping
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 (Burgundy)
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
CREAM
Transmission:
Automatic
Mileage:
88,823
Stock number:
27645103
VIN:
5TDDZRFH8KS992560

Preparing for a close up...

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2024 Toyota Highlander

LE AWD

37,824 miles

$31,799

Great Deal
Lincolnwood, IL
46 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

Preparing for a close up...

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2016 Toyota Highlander

XLE AWD

116,210 miles

$16,995

Great Deal
Mishawaka, IN
46 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:
Black
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
116,210
Stock number:
262056
VIN:
5TDJKRFH9GS262056

Preparing for a close up...

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2016 Toyota Highlander

LE AWD

130,892 miles

$15,495

Good Deal
Bridgeview, IL
40 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

Preparing for a close up...

Photos coming soon

2021 Toyota Highlander

LE AWD

79,714 miles

$26,897

Fair Deal
Store transfer to Merrillville, IN
1,808 mi away • Price includes $1,899 shipping Price includes $1,899 shipping
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:
Automatic
Mileage:
79,714
Stock number:
28091981
VIN:
5TDBZRBH0MS079856

Preparing for a close up...

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2023 Toyota Highlander

XSE AWD

30,068 miles

$38,922

Fair Deal
Merrillville, IN
20 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:
Magnetic Gray Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
30,068
Stock number:
9520A
VIN:
5TDKDRBHXPS006383

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

Limited AWD

52,024 miles

$33,490

Good Deal
Chicago, IL
42 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:
Black
Transmission:
Automatic
Mileage:
52,024
Stock number:
P16320
VIN:
5TDDZRBH4NS564348

Preparing for a close up...

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2014 Toyota Highlander

Limited AWD

122,494 miles

$19,997

Fair Deal
Store transfer to Merrillville, IN
1,755 mi away • Price includes $1,999 shipping Price includes $1,999 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:
Gray
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
122,494
Stock number:
28107783
VIN:
5TDDKRFH7ES035457

Preparing for a close up...

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2018 Toyota Highlander

Limited AWD

55,896 miles

$27,450

Good Deal
Westmont, IL
50 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:
55,896
Stock number:
D6612AA
VIN:
5TDDZRFH7JS900871

Preparing for a close up...

Photos coming soon

2017 Toyota Highlander

XLE AWD

102,444 miles

$19,995

Good Deal
Chicago, IL
41 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:
Midnight Black Metallic
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
102,444
Stock number:
N23016
VIN:
5TDJZRFHXHS518136

Preparing for a close up...

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2023 Toyota Highlander

XLE FWD

73,150 miles

$28,900

Great Deal
Certified Pre-Owned
Matteson, IL
37 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:
Celestial Silver Metallic
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
73,150
Stock number:
P524681
VIN:
5TDKDRAH9PS524681

Preparing for a close up...

Photos coming soon

2024 Toyota Highlander

XLE AWD

57,315 miles

$32,995

Great Deal
Chicago, IL
41 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
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
57,315
Stock number:
N23329
VIN:
5TDKDRBH6RS558370

Preparing for a close up...

Photos coming soon

2021 Toyota Highlander

Limited AWD

77,332 miles

$28,995

Great Deal
Frankfort, IL
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:
Blueprint
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
77,332
Stock number:
60364S
VIN:
5TDDZRBH2MS120786

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  1. Home
  2. / Used Cars
  3. / Toyota Highlander
  4. / Indiana
  5. / Chesterton
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 Chesterton, IN?

The average Toyota Highlander costs about $27,405.38. The average price has decreased by -6.3% since last year. The 641 for sale near Chesterton, IN on CarGurus, range from $1,500 to $53,998 in price.

How many Toyota Highlander vehicles in Chesterton, IN have no reported accidents or damage?

641 out of 641 for sale near Chesterton, IN have no reported accidents or damage.

What fuel types are available?

Gasoline engines are available.

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