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Used 2019 Toyota Highlander for Sale near Madison, WI

198 results
Madison, WI
2019 Toyota Highlander Limited AWD AutoNation Toyota Libertyville

2019 Toyota Highlander

Limited AWD

82,429 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:
82,429
Stock number:
KS707496
VIN:
5TDDZRFH4KS707496

Sponsored

2019 Toyota Highlander XLE AWD

2019 Toyota Highlander

XLE AWD

76,016 miles

$23,925

Good Deal
East Dundee, IL
89 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:
Black
Transmission:
8-Speed Automatic
Mileage:
76,016
Stock number:
K8540
VIN:
5TDJZRFH6KS984668

Sponsored

2019 Toyota Highlander

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

Sponsored

2020 Toyota Highlander XLE AWD

2020 Toyota Highlander

XLE AWD

70,930 miles

$28,990

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

2019 Toyota Highlander SE AWD

2019 Toyota Highlander

SE AWD

112,597 miles

$21,495

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

2019 Toyota Highlander

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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2019 Toyota Highlander

Limited FWD

75,759 miles

$26,797

Fair Deal
Store transfer to Madison, WI
1,591 mi away • Price includes $1,799 shipping Price includes $1,799 shipping
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:
Brown (TAN)
Transmission:
Automatic
Mileage:
75,759
Stock number:
27885082
VIN:
5TDYZRFH2KS301542

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2018 Toyota Highlander

SE AWD

153,134 miles

$17,490

Fair Deal
Mequon, WI
71 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:
Black
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
153,134
Stock number:
260262B
VIN:
5TDJZRFH8JS857693

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2020 Toyota Highlander

L AWD

73,261 miles

$23,995

Good 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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2018 Toyota Highlander

Limited AWD

123,014 miles

$20,911

Good Deal
Madison, WI
5 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:
Silver
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
123,014
Stock number:
G4957
VIN:
5TDDZRFH8JS898693

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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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2019 Toyota Highlander

Limited AWD

59,217 miles

$29,900

Fair Deal
Fond Du Lac, WI
67 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:
Brown (Saddle Tan)
Transmission:
8-Speed Automatic
Mileage:
59,217
Stock number:
C320137T
VIN:
5TDDZRFH5KS937273

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2019 Toyota Highlander

Limited AWD

82,429 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:
82,429
Stock number:
KS707496
VIN:
5TDDZRFH4KS707496

Preparing for a close up...

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2019 Toyota Highlander

SE AWD

101,154 miles

$23,322

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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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

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2019 Toyota Highlander

SE AWD

66,734 miles

$24,849

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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2018 Toyota Highlander

Limited AWD

151,211 miles

$19,998

Fair Deal
Crystal Lake, IL
80 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:
Alumina Jade Metallic
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
La00 Almond
Transmission:
8-Speed Automatic
Mileage:
151,211
Stock number:
40459A
VIN:
5TDDZRFH3JS494104

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2019 Toyota Highlander

Limited AWD

105,055 miles

$23,799

Good Deal
Waukegan, 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:
White
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
105,055
Stock number:
T28829A
VIN:
5TDDZRFH5KS921574

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2019 Toyota Highlander

XLE AWD

87,662 miles

$24,388

Fair Deal
Oshkosh, WI
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:
8-Speed Automatic
Mileage:
87,662
Stock number:
1260
VIN:
5TDJZRFH6KS623280

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2019 Toyota Highlander

XLE AWD

78,415 miles

$25,997

Fair Deal
Watertown, WI
36 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:
Toasted Walnut Pearl
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Almond
Transmission:
8-Speed Automatic
Mileage:
78,415
Stock number:
N26029A
VIN:
5TDJZRFH0KS566767

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2020 Toyota Highlander

Limited AWD

156,234 miles

$21,998

Fair Deal
Middleton, WI
7 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:
Silver
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Dual Clutch
Mileage:
156,234
Stock number:
260013B
VIN:
5TDDZRBH7LS005969

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2019 Toyota Highlander

SE AWD

66,610 miles

$26,349

Fair Deal
Arlington Heights, IL
99 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:
White (Blizzard Pearl)
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black w/Silver Stitching
Transmission:
Automatic
Mileage:
66,610
Stock number:
3914A
VIN:
5TDJZRFH3KS569971

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  1. Home
  2. / Used Cars
  3. / Toyota Highlander
  4. / 2019
  5. / Wisconsin
  6. / Madison
Overview
Reviews
FAQs

CarGurus Analysis: 2019 Toyota Highlander

Picture of 2019 Toyota Highlander

Summary

  • With 3,041 currently listed for sale on CarGurus and an average price of $23,940.50, 35.6% of 2019 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
  • Favorably reviewed: Owners rated the 2019 Toyota Highlander 4.6 / 5 stars.
  • 66.3% of 2019 Highlander models on CarGurus are accident free.
  • The 2019 Toyota Highlander featured a stylish design, offered spacious seating for up to eight, and included advanced safety technology, making it a reliable choice for families.

Why it stands out

The 2019 Toyota Highlander distinguished itself in the midsize SUV segment with its combination of stylish design and family-friendly features, offering an eight-passenger seating option for larger families. It provided a suite of advanced safety technologies, including adaptive cruise control and automatic emergency braking, making it a standout choice for safety-conscious buyers. Additionally, its reliable performance, bolstered by a powerful V6 engine and competitive fuel efficiency, ensured that it maintained strong resale value in the market.

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.
  • 2016 Toyota Highlander: This year offers $18,438.19 average price, 39% good/great deals, 4.6/5 user rating, 1,955 listings.

This analysis is based on CarGurus' proprietary market data from December 16, 2025, CarGurus experts' opinions, and generative AI.

4.6 Overall rating

(83 reviews)
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

Jordan A
5.0
Reviewed a 2019 Toyota Highlander on Feb 07, 2024

Great value! I absolutely love the heated seats and back up camera.

Suzanne M
5.0
Reviewed a 2019 Toyota Highlander on Oct 11, 2024

It’s roomy, has all the bells and whistles. Nice smooth ride. Takes a little time to manipulate all the “bells and whistles”. Also aesthetically good .

Candice O
4.0
Reviewed a 2019 Toyota Highlander on Jul 22, 2024

Drives very nicely, compared to new ford explorer which drove terrible and had constant bells. Front seats are terrible compared to 2004 Highlander. Headrests are so forward I had to be unsafe and turn them around so I did not constantly have a headache while driving. Will have to buy cushions to correct this. No knee room in passenger seat as dash board very low. Has decent size cup holders in front compared to small ones in new Highlander. Back seat is larger and more comfortable for kids than old Highlander, stealing from the 3rd row. Storage is about the same.

Anonymous
5.0
Reviewed a 2019 Toyota Highlander on Jan 16, 2022

Our family absolutely LOVES this vehicle. Glad that we bought it. No regrets.

2019 Toyota Highlander FAQs

How much does the 2019 Toyota Highlander cost in Madison, WI?

The average 2019 Toyota Highlander costs about $23,321.21. The average price has decreased by -8.1% since last year. The 157 for sale near Madison, WI on CarGurus, range from $14,976 to $41,998 in price.

How many 2019 Toyota Highlander vehicles in Madison, WI have no reported accidents or damage?

148 out of 157 for sale near Madison, WI have no reported accidents or damage.

What is the fuel economy of the 2019 Toyota Highlander?

Depending on the engine and options, the 2019 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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