Used 2021 Toyota Highlander for Sale near Wisconsin

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193 vehicles found

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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
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
88,662
Stock #:
WYC-562432
VIN:
5TDDZRBH5NS562432
Red 2022 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Your Choice Autos - Waukegan

Sponsored by Your Choice Autos - Waukegan

2022 Toyota Highlander

Limited AWD

88,662 mi

Waukegan, IL
48 mi away
Fair Deal

$32,999

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:
Black
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
71,808
Stock #:
144083
VIN:
5TDLZRBH6MS144083
Black 2021 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

 

2021 Toyota Highlander

XSE AWD

71,808 mi

Home delivery from Fort Dodge, IA
Price includes $400 shipping
Good Deal

$32,395

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:
Pearl
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
59,309
Stock #:
PER1050
VIN:
5TDJZRBH8NS208648
Pearl 2022 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$1,235

 

2022 Toyota Highlander

XSE AWD

59,309 mi

Brookfield, WI
13 mi away
Good Deal

$35,652

$34,417

Year:
2021
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
68,646
Stock #:
26019A
VIN:
5TDYZRAH3MS519080
Magnetic Gray Metallic 2021 Toyota Highlander SUV / Crossover Front-Wheel Drive 8-Speed Automatic

 

2021 Toyota Highlander

Limited FWD

68,646 mi

Home delivery from Okatie, SC
Price includes $1,668 shipping
Good Deal

$31,637

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:
Celestial Silver Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
89,930
Stock #:
29142
VIN:
5TDCZRBHXMS530280
Celestial Silver Metallic 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2021 Toyota Highlander

L AWD

89,930 mi

Home delivery from Cambridge, OH
Price includes $580 shipping
Great Deal

$23,158

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:
91,466
Stock #:
NP12576
VIN:
5TDFZRBH1MS057446
Moon Dust 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2021 Toyota Highlander

Platinum AWD

91,466 mi

Home delivery from Indianapolis, IN
Price includes $350 shipping
Good Deal

$30,750

Year:
2021
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:
Black
Transmission:
Automatic
Mileage:
67,857
Stock #:
70092858
VIN:
5TDYZRAH7MS066999
Gray 2021 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic

 

2021 Toyota Highlander

Limited FWD

67,857 mi

Store transfer to Milwaukee, WI
Price includes $1,399 shipping
Great Deal

$31,397

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:
Black
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
125,240
Stock #:
T173231
VIN:
5TDHZRBH9NS173231
Black 2022 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

 

2022 Toyota Highlander

XLE AWD

125,240 mi

Home delivery from Fort Wayne, IN
Price includes $194 shipping
Great Deal

$24,639

Year:
2021
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
Transmission:
8-Speed Automatic
Mileage:
77,829
Stock #:
068055
VIN:
5TDJZRBH5MS068055
 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
New arrival

 

2021 Toyota Highlander

XSE AWD

77,829 mi

Home delivery from Astoria, NY
Price includes $921 shipping
Great Deal

$27,920

CarGurus Analysis:

2021 Toyota Highlander

4.9

  • With 3,213 currently listed for sale and an average price of $30,037.00, 34.1% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.

  • Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.86 / 5 stars and CarGurus experts gave it a 7.5 / 10.

  • 77.3% of 2021 Highlander models on CarGurus are accident free.

Research summarized using AI

Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Blue
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
85,430
Stock #:
2026-187
VIN:
5TDJZRAH0NS112451
Blue 2022 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic
Price drop

-$1,000

 

2022 Toyota Highlander

XSE FWD

85,430 mi

Home delivery from Albuquerque, NM
Price includes $1,704 shipping
Great Deal

$29,699

$28,699

Year:
2021
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:
Red
Transmission:
Automatic
Mileage:
49,457
Stock #:
45850
VIN:
5TDLZRAH8MS045850
White 2021 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic

 

2021 Toyota Highlander

XSE FWD

49,457 mi

Home delivery from Gallatin, TN
Price includes $465 shipping
Good Deal

$32,954

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:
8-Speed Automatic
Mileage:
48,063
Stock #:
14798
VIN:
5TDGZRBH0NS257899
Gray 2022 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2022 Toyota Highlander

XLE AWD

48,063 mi

Home delivery from Philadelphia, PA
Price includes $868 shipping
Great Deal

$33,582

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:
White
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
119,942
Stock #:
11453
VIN:
5TDGZRAHXLS503453
White 2020 Toyota Highlander SUV / Crossover Front-Wheel Drive 8-Speed Automatic

 

2020 Toyota Highlander

XLE FWD

119,942 mi

Home delivery from Springfield, MO
Price includes $495 shipping
Fair Deal

$23,817

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:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
88,342
Stock #:
562987
VIN:
5TDBZRBH7NS562987
Midnight Black Metallic 2022 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$510

 

2022 Toyota Highlander

LE AWD

88,342 mi

Home delivery from Lilburn, GA
Price includes $999 shipping
Great Deal

$26,197

$25,687

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:
Black
Transmission:
8-Speed Automatic
Mileage:
65,932
Stock #:
L9697
VIN:
5TDCZRBHXMS059747
Gray 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2021 Toyota Highlander

L AWD

65,932 mi

Home delivery from Maplewood, MN
Price includes $288 shipping
Fair Deal

$28,258

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:
Automatic
Mileage:
33,857
Stock #:
70172257
VIN:
5TDZZRAH6LS504737
Gray 2020 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic

 

2020 Toyota Highlander

LE FWD

33,857 mi

Store transfer to Milwaukee, WI
Price includes $1,499 shipping
Fair Deal

$31,497

CarGurus Analysis: 2021 Toyota Highlander

7.5
of 10
overall
Look and feel8/10
Technology7/10
Performance6/10
Safety10/10
Form & function7/10
Cost effectiveness7/10
Image Not Available

Summary

  • With 3,213 currently listed for sale and an average price of $30,037.00, 34.1% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.

  • Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.86 / 5 stars and CarGurus experts gave it a 7.5 / 10.

  • 77.3% of 2021 Highlander models on CarGurus are accident free.

Why it stands out

The 2021 Toyota Highlander stands out as a familiar three-row family SUV that leans heavily on comfort and safety. It already sits near the top of the sales charts for its segment, and the Highlander name carries strong recognition as it enters its 20th year of production. For 2021, Toyota adds additional safety-feature technology as standard equipment, reinforcing the Highlander’s appeal to buyers who want a practical family vehicle with a reassuring feature set.

Behind that straightforward mission, the Highlander’s strengths are easy to understand: it offers a great ride quality, a comfortable cabin, and plenty of space. Those qualities make it especially appealing for families who value everyday usability over flash. At the same time, it is not the most exciting choice in the class. Its styling is uninspired, the base engine is underwhelming, and its technology is described as outdated, so shoppers looking for the latest performance or infotainment polish may find it less compelling than its core virtues suggest.

Owner feedback generally reinforces that picture. Drivers commonly praise the 2021 Toyota Highlander for its comfort, reliability, smooth ride, high-quality interior, spaciousness, and safety features. Some, however, have been disappointed by fuel economy and by limited configurability for certain settings, including the third-row seating and lane assist functions.

Other model years to consider

  • 2024 Toyota Highlander

    • Average price: $39,321.00
    • Good/great deal percentage: 34.6%
    • User rating: 5 / 5
    • Total listings: 3,433
  • 2023 Toyota Highlander

    • Average price: $35,671.00
    • Good/great deal percentage: 35.0%
    • User rating: 4.75 / 5
    • Total listings: 4,094
  • 2022 Toyota Highlander

    • Average price: $33,097.00
    • Good/great deal percentage: 35.1%
    • User rating: 4.5 / 5
    • Total listings: 4,514

This analysis is based on CarGurus' proprietary market data from August 10, 2026, CarGurus experts' opinions, and generative AI.

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