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Used 2020 Toyota Highlander for Sale near Madison, WI

229 results
Madison, WI
2021 Toyota Highlander XSE AWD Elgin Toyota

2021 Toyota Highlander

XSE AWD

59,443 miles

$31,990

Fair 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:
Black
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
59,443
Stock number:
P21155
VIN:
5TDJZRBH5MS062742

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2019 Toyota Highlander Limited AWD

2019 Toyota Highlander

Limited AWD

82,431 miles

$25,495

Great Deal
Certified Pre-Owned
Libertyville, IL
92 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:
Ooh La La Rouge Mica
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Almond
Transmission:
Automatic
Mileage:
82,431
Stock number:
KS707496
VIN:
5TDDZRFH4KS707496

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2019 Toyota Highlander XLE AWD

2019 Toyota Highlander

XLE AWD

92,303 miles

$21,222

Great Deal
Huntley, IL
81 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
Transmission:
8-Speed Automatic
Mileage:
92,303
Stock number:
V2557A
VIN:
5TDJZRFH9KS578609

Sponsored

2019 Toyota Highlander

2019 Toyota Highlander

136,422 miles

$19,990

Good Deal
Brookfield, WI
63 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Engine:
295 hp 3.5L V6
Exterior color:
Black
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
136,422
Stock number:
B586B
VIN:
5TDDZRFH1KS983070

2019 Toyota Highlander XLE AWD

2019 Toyota Highlander

XLE AWD

91,877 miles

$22,998

Good Deal
Waukesha, WI
61 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:
Automatic
Mileage:
91,877
Stock number:
V26180A
VIN:
5TDJZRFH9KS704855

2019 Toyota Highlander SE AWD

2019 Toyota Highlander

SE AWD

101,154 miles

$23,069

Good Deal
Dubuque, IA
77 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:
Red
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
101,154
Stock number:
Q52045C
VIN:
5TDJZRFH1KS931568

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2021 Toyota Highlander

LE AWD

104,956 miles

$22,490

Good Deal
Middleton, WI
7 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:
Black
Transmission:
8-Speed Automatic
Mileage:
104,956
Stock number:
50895
VIN:
5TDBZRBH2MS527238

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2021 Toyota Highlander

XLE AWD

65,180 miles

$29,990

Fair Deal
Madison, WI
2 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:
Black
Transmission:
8-Speed Automatic
Mileage:
65,180
Stock number:
39868
VIN:
5TDGZRBHXMS557450

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2020 Toyota Highlander

XLE AWD

70,930 miles

$28,790

Fair Deal
Mukwonago, WI
56 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:
Midnight Black Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
70,930
Stock number:
JP1453A
VIN:
5TDHZRBH5LS506862

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2019 Toyota Highlander

XLE AWD

157,580 miles

$17,999

Fair Deal
Cary, IL
82 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:
157,580
Stock number:
617807
VIN:
5TDJZRFH1KS617807

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2019 Toyota Highlander

42,916 miles

$29,300

Fair Deal
Kenosha, WI
81 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Engine:
295 hp 3.5L V6
Exterior color:
White
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
42,916
Stock number:
P4710
VIN:
5TDJZRFH7KS998773

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2020 Toyota Highlander

L AWD

73,261 miles

$23,995

Fair Deal
Milwaukee, WI
75 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
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
73,261
Stock number:
052225
VIN:
5TDCZRBH2LS052225

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2019 Toyota Highlander

XLE FWD

89,007 miles

$21,995

Good Deal
Milwaukee, WI
75 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
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
89,007
VIN:
5TDKZRFH6KS556507

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2021 Toyota Highlander

Limited AWD

64,847 miles

$31,991

Fair Deal
Viroqua, WI
83 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
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
64,847
Stock number:
F25388A
VIN:
5TDDZRBH4MS531316

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2021 Toyota Highlander

XSE AWD

70,497 miles

$29,999

Good Deal
Lake Villa, IL
81 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:
Magnetic Gray Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
70,497
Stock number:
LV565
VIN:
5TDLZRBH2MS147269

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2019 Toyota Highlander

SE AWD

66,734 miles

$24,848

Great Deal
Fox Lake, IL
77 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:
Silver
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
66,734
Stock number:
P2742
VIN:
5TDJZRFHXKS570034

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2021 Toyota Highlander

XLE AWD

77,469 miles

$28,062

Good Deal
West Bend, WI
64 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:
White (Blizzard Pearl)
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
77,469
Stock number:
TPMD6698
VIN:
5TDGZRBH5MS060161

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2019 Toyota Highlander

Limited AWD

82,431 miles

$25,495

Great Deal
Certified Pre-Owned
Libertyville, IL
92 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:
Ooh La La Rouge Mica
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Almond
Transmission:
Automatic
Mileage:
82,431
Stock number:
KS707496
VIN:
5TDDZRFH4KS707496

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2021 Toyota Highlander

XLE FWD

89,250 miles

$25,455

Good Deal
Arlington Heights, IL
99 mi away
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:
Celestial Silver Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
Automatic
Mileage:
89,250
Stock number:
4171
VIN:
5TDGZRAH2MS534598

Sponsored

  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 3,587 currently listed for sale on CarGurus and an average price of $27,857.10, 35.7% 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% of 2020 Highlander models on CarGurus are accident free.
  • The 2020 Toyota Highlander excelled in passenger comfort with its tranquil interior, soft ride, and advanced safety features, making it a top choice in the midsize SUV segment.

Why it stands out

The 2020 Toyota Highlander distinguished itself with a premium feel that rivaled luxury vehicles like Lexus, especially in its upper trims. It provided a remarkably quiet and smooth ride, enhancing passenger comfort across all three rows. Additionally, the Highlander came equipped with standard advanced safety features, making it a practical choice for families seeking both space and peace of mind.

Other model years to consider

  • 2022 Toyota Highlander: This year offers $33,572.41 average price, 36% good/great deals, 4.6/5 user rating, 8.2/10 expert rating, 6,308 listings.
  • 2021 Toyota Highlander: This year offers $30,215.79 average price, 36% good/great deals, 4.8/5 user rating, 7.5/10 expert rating, 4,417 listings.
  • 2023 Toyota Highlander: This year offers $35,244.49 average price, 35% good/great deals, 4.4/5 user rating, 6,084 listings.

This analysis is based on CarGurus' proprietary market data from December 16, 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 $27,221.50. The average price has decreased by -7.9% since last year. The 170 for sale near Madison, WI on CarGurus, range from $14,776 to $43,998 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?

170 out of 170 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 EV battery range).

What fuel types are available?

Gasoline engines are available.

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