Used 2020 Toyota Highlander for Sale near Wisconsin

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220 vehicles found

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Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Engine:
295 hp 3.5L V6
Exterior color:
Shoreline Blue Pearl
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
8-Speed Automatic
Mileage:
144,484
Stock #:
29892A
VIN:
5TDJZRFH1KS921056
Shoreline Blue Pearl 2019 Toyota Highlander SUV / Crossover  8-Speed Automatic
Lexus of Brookfield

Sponsored by Lexus of Brookfield

2019 Toyota Highlander

144,484 mi

Brookfield, WI
12 mi away
Fair Deal

$21,012

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:
2020
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
75,871
Stock #:
S003826
VIN:
5TDGZRAHXLS003826
 2020 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic

 

2020 Toyota Highlander

XLE FWD

75,871 mi

Home delivery from Houston, TX
Price includes $1,521 shipping
Fair Deal

$28,041

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:
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:
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:

2020 Toyota Highlander

4.6

  • With 3,176 currently listed for sale and an average price of $27,993.00, 33.6% of 2020 Toyota Highlanders for sale on CarGurus are rated as good or great deals.

  • Favorably reviewed: Owners rated the 2020 Toyota Highlander 4.6 / 5 stars and CarGurus experts gave it a 7.67 / 10.

  • 72.0% of 2020 Highlander models on CarGurus are accident free.

Research summarized using AI

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:
2021
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:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
49,961
Stock #:
7131
VIN:
5TDHZRBH4MS107054
Silver 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2021 Toyota Highlander

XLE AWD

49,961 mi

Home delivery from Jacksonville, FL
Price includes $1,408 shipping
Good Deal

$32,300

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:
Brown (Saddle Tan)
Transmission:
8-Speed Automatic
Mileage:
77,361
Stock #:
14955X
VIN:
5TDDZRFH1KS710890
Black 2019 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2019 Toyota Highlander

Limited AWD

77,361 mi

Home delivery from Lehi, UT
Price includes $1,244 shipping
Fair Deal

$30,239

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:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Cockpit Red
Transmission:
Automatic
Mileage:
111,027
Stock #:
089952
VIN:
5TDLZRAH5MS089952
Midnight Black Metallic 2021 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic

 

2021 Toyota Highlander

XSE FWD

111,027 mi

Home delivery from Carrollton, TX
Price includes $1,275 shipping
Fair Deal

$27,719

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:
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:
8-Speed Automatic
Mileage:
127,000
Stock #:
2864
VIN:
5TDJZRFH4KS932665
Black 2019 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2019 Toyota Highlander

XLE AWD

127,000 mi

Home delivery from Chesapeake, VA
Price includes $907 shipping
Good Deal

$21,776

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:
Celestial Silver Metallic
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
8-Speed Automatic
Mileage:
76,576
Stock #:
946327
VIN:
5TDBZRFH4KS946327
Celestial Silver Metallic 2019 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2019 Toyota Highlander

LE Plus AWD

76,576 mi

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

$23,687

CarGurus Analysis: 2020 Toyota Highlander

7.7
of 10
overall
Look and feel7/10
Technology7/10
Performance6/10
Safety9/10
Form & function9/10
Cost effectiveness8/10
Image Not Available

Summary

  • With 3,176 currently listed for sale and an average price of $27,993.00, 33.6% of 2020 Toyota Highlanders for sale on CarGurus are rated as good or great deals.

  • Favorably reviewed: Owners rated the 2020 Toyota Highlander 4.6 / 5 stars and CarGurus experts gave it a 7.67 / 10.

  • 72.0% of 2020 Highlander models on CarGurus are accident free.

Why it stands out

The 2020 Toyota Highlander stands out by putting comfort ahead of flash. It was redesigned for 2020, and the result is a midsize three-row SUV that emphasizes silent operation, a soft ride, and a cosseting interior. The Highlander is described as the most comfortable midsize SUV, and its upper trims are said to feel and drive just like a Lexus, without the upcharge. That makes it appealing to buyers who want a family SUV that feels calm and upscale rather than exciting.

It also brings standard advanced safety features and a spacious cabin, two qualities that matter a lot in this segment. At the same time, the Highlander is not trying to win over drivers who value sharp responses or standout styling. Its handling is described as poor, and its styling as uninspired, so its strengths are clearly in comfort, space, and an easygoing character rather than driving enjoyment or visual drama.

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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