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Used 2020 Toyota Highlander for Sale near Madison, WI

253 results
Madison, WI
2019 Toyota Highlander XLE AWD Dart Motors LLC

2019 Toyota Highlander

XLE AWD

94,064 miles

$24,999

Fair Deal
Mchenry, IL
78 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:
8-Speed Automatic
Mileage:
94,064
Stock number:
1837
VIN:
5TDJZRFH8KS567830

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2019 Toyota Highlander LE AWD

2019 Toyota Highlander

LE AWD

68,590 miles

$23,300

Fair Deal
Milwaukee, WI
74 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:
Predawn Gray Mica
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
68,590
Stock number:
250475B
VIN:
5TDBZRFH4KS730297

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2019 Toyota Highlander LE FWD

2019 Toyota Highlander

LE FWD

84,678 miles

$20,994

Fair Deal
Mount Pleasant, WI
77 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 (Blizzard Pearl)
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
84,678
Stock number:
69584A
VIN:
5TDZZRFH3KS298820

Sponsored

2021 Toyota Highlander LE AWD

2021 Toyota Highlander

LE AWD

35,500 miles

$28,989

Great Deal
Dubuque, IA
78 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:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
35,500
Stock number:
P25384
VIN:
5TDBZRBH7MS149322

2019 Toyota Highlander SE AWD

2019 Toyota Highlander

SE AWD

112,597 miles

$21,995

Good Deal
Rockford, IL
58 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:
Blue
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
112,597
Stock number:
12425
VIN:
5TDJZRFHXKS939426

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2021 Toyota Highlander

XLE AWD

49,605 miles

$30,990

Fair Deal
Saint Charles, IL
97 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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2019 Toyota Highlander

XLE AWD

88,483 miles

$24,112

Good Deal
Dubuque, IA
78 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:
Celestial Silver Metallic
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
Automatic
Mileage:
88,483
Stock number:
26023B
VIN:
5TDJZRFH2KS584283

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2020 Toyota Highlander

XLE AWD

113,662 miles

$23,998

Good Deal
Portage, WI
35 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
Transmission:
8-Speed Automatic
Mileage:
113,662
Stock number:
F2983A
VIN:
5TDGZRBH6LS023215

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2021 Toyota Highlander

Platinum AWD

30,927 miles

$38,998

Fair Deal
Sheboygan, WI
93 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:
Glazed Caramel
Transmission:
8-Speed Automatic
Mileage:
30,927
Stock number:
D414583C
VIN:
5TDFZRBH8MS156815

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2019 Toyota Highlander

SE AWD

49,175 miles

$27,423

Good Deal
Barrington, IL
91 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:
Midnight Black Metallic
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
49,175
Stock number:
650090B
VIN:
5TDJZRFH2KS577351

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2021 Toyota Highlander

XSE AWD

44,978 miles

$35,560

Fair Deal
Appleton, WI
97 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)
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Dual Clutch
Mileage:
44,978
Stock number:
TH26219A
VIN:
5TDJZRBH6MS078075

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2021 Toyota Highlander

Limited AWD

71,820 miles

$29,990

Good Deal
Streamwood, IL
94 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
Interior color:
Gray
Transmission:
Automatic
Mileage:
71,820
Stock number:
P20969
VIN:
5TDDZRBH8MS530184

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2019 Toyota Highlander

XLE AWD

76,977 miles

$24,802

Fair Deal
Libertyville, IL
93 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:
Predawn Gray Mica
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
8-Speed Automatic
Mileage:
76,977
Stock number:
XBP8010
VIN:
5TDJZRFH7KS562795

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2021 Toyota Highlander

XLE AWD

77,648 miles

$28,492

Fair Deal
Fox Lake, IL
77 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:
Silver
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
77,648
Stock number:
P2746
VIN:
5TDHZRBHXMS122898

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  1. Home
  2. / Used Cars
  3. / Toyota Highlander
  4. / 2020
  5. / Wisconsin
  6. / Madison
Overview
Reviews
FAQs

CarGurus Analysis: 2020 Toyota Highlander

Picture of 2020 Toyota Highlander

Summary

  • With 3,672 currently listed for sale on CarGurus and an average price of $28,162.50, 36.7% of 2020 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
  • Favorably reviewed: Owners rated the 2020 Toyota Highlander 4.5 / 5 stars and CarGurus experts gave it an 7.7 / 10.
  • 73.2% of 2020 Highlander models on CarGurus are accident free.
  • The 2020 Toyota Highlander excelled in providing a spacious and tranquil ride, featuring a premium-like interior that offered comfort comparable to luxury brands, while incorporating standard advanced safety features.

Why it stands out

The 2020 Toyota Highlander distinguished itself in the midsize three-row SUV segment with its exceptional passenger comfort and tranquil ride quality. Its redesigned interior offered a luxurious feel akin to that of higher-end Lexus models, making it a standout choice for families seeking both space and serenity during their journeys. While it may not have boasted the most exciting styling or handling, the Highlander excelled in providing a quiet, effortless driving experience, supported by standard advanced safety features that enhanced its appeal.

Other model years to consider

  • 2022 Toyota Highlander: This year offers $33,925.22 average price, 34% good/great deals, 4.6/5 user rating, 8.2/10 expert rating, 6,414 listings.
  • 2021 Toyota Highlander: This year offers $30,564.27 average price, 35% good/great deals, 4.8/5 user rating, 7.5/10 expert rating, 4,592 listings.
  • 2023 Toyota Highlander: This year offers $35,595.40 average price, 34% good/great deals, 4.4/5 user rating, 6,158 listings.

This analysis is based on CarGurus' proprietary market data from December 3, 2025, CarGurus experts' opinions, and generative AI.

4.5 Overall rating

(33 reviews)
Karen D
4.0
Reviewed a 2020 Toyota Highlander on Mar 11, 2024

The 2020 Toyota Highlander XLE drives great!! Very smooth ride and great acceleration. I loved how it could turn tight corners, like when pulling out onto a 4-lane road. A lot of great features. The sound system was ok, but realized it wasnt that great after comparing it to the 2021 Limited with JBL speakers. Wish it had the nicer sound system. There were two things I was very disappointed in. The seats seemed rather shallow, compared to the seats in my 2012 Limited Highlander. My friend and I both felt like we were sliding off the edge of the front seats. Does Toyota think that Americans are getting smaller? The other thing was that the visors were not long enough to come all the way out to the edge of the windshield. There was at least a two inch gap between the outside edge of the visor and the outside edge of the windshield!! What the heck were they thinking! Driving toward the sun in the late afternoon was terrible because the sun was in my eyes and there was nothing I could do about it. Again, my 2012 Highlander has this one beat because the visor is plenty long enough. What a stupid place to try to save a buck! Those two things have me looking at other vehicles because I dont want to settle for something that is uncomfortable, and when you pay 40K for a vehicle, it better be good in every aspect!

Anonymous
5.0
Reviewed a 2020 Toyota Highlander on Nov 07, 2020

Most comfortable riding vehicle that we have ever purchased. Great features and a great looking vehicle as well.

Kris B
5.0
Reviewed a 2020 Toyota Highlander on May 22, 2023

Absolutely love this car. Great comfortable family vehicle with plenty of space, and features

Lee W
4.0
Reviewed a 2020 Toyota Highlander on Feb 27, 2020

The ride was smooth, the Highlander is quick and very quiet. I loved many of the features it had, like the posted speed limit on the instrument cluster. What really disappointed me was the passenger seat comfort. The seat bottom only adjusts fron-to-rear, not up or down so I wasn’t as comfortable in it as I was the Hyundai Palisade or the Kia Telluride. It’s still a really good vehicle.

Becky S
5.0
Reviewed a 2020 Toyota Highlander on Nov 22, 2022

Just picked one up Saturday! Absolutely love it, love the features, everything about it. Love the 3 row seats for all the grandkids. Had a Lexus RX350, feel there very similar just a little more room in the Highlander. Levy’s very smooth driving though.

2020 Toyota Highlander FAQs

How much does the 2020 Toyota Highlander cost in Madison, WI?

The average 2020 Toyota Highlander costs about $28,086.09. The average price has decreased by -7.1% since last year. The 187 for sale near Madison, WI on CarGurus, range from $17,750 to $42,998 in price.

Is the 2020 Toyota Highlander a good car?

CarGurus experts gave the 2020 Toyota Highlander an overall rating of 7.7/10 and 2020 Toyota Highlander owners have rated the vehicle a 4.5/5 stars on average. If a vehicle has both strong expert and owner reviews, you can feel confident in its quality. If either expert reviews, owner reviews, or both are spotty, you might want to do some research to figure out where the car falls short.

How many 2020 Toyota Highlander vehicles in Madison, WI have no reported accidents or damage?

187 out of 187 for sale near Madison, WI have no reported accidents or damage.

Is the 2020 Toyota Highlander safe?

CarGurus experts gave the 2020 Toyota Highlander a safety rating of 9/10.

What is the fuel economy of the 2020 Toyota Highlander?

Depending on the engine and options, the 2020 Toyota Highlander gets between 22 and 23 MPG (or MPGe).

What fuel types are available?

Gasoline engines are available.

  • 2023 Toyota Highlander in Madison WI

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