Used Gray Toyota Highlander for Sale inMilwaukee, WI

Filters (3)

Location:

Only show listings in WI?

Include delivery listings?

134 vehicles found

Shop with transparent pricing.

Only show listings that include dealer fees
Year:
2025
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
14,411
Stock #:
RTK5391
VIN:
5TDKDRBH2SS589721
Gray 2025 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic
Toyota of Fox Lake

Sponsored by Toyota of Fox Lake

2025 Toyota Highlander

XLE AWD

14,411 mi

Fox Lake, IL
47 mi away
Good Deal

$44,344

Year:
2017
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:
Almond
Transmission:
8-Speed Automatic
Mileage:
166,245
Stock #:
46P944A
VIN:
5TDBZRFH5HS365539
Gray 2017 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$500

Sponsored Listing

2017 Toyota Highlander

LE AWD

166,245 mi

Milwaukee, WI
10 mi away
Fair Deal

$15,594

$15,094

Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Gray
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
23,971
Stock #:
RA2663A
VIN:
5TDKDRAH2PS517961
Gray 2023 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic

 

2023 Toyota Highlander

L FWD

23,971 mi

Home delivery from Muscatine, IA
Price includes $390 shipping
Good Deal

$30,385

Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Cockpit Red
Transmission:
8-Speed Automatic
Mileage:
27,679
Stock #:
R89281
VIN:
5TDKDRAH2PS514378
Magnetic Gray Metallic 2023 Toyota Highlander SUV / Crossover Front-Wheel Drive 8-Speed Automatic

 

2023 Toyota Highlander

XSE FWD

27,679 mi

Home delivery from Herculaneum, MO
Price includes $710 shipping
Fair Deal

$39,635

Year:
2014
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Predawn Gray Mica
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
85,852
Stock #:
P26852
VIN:
5TDDKRFH7ES017332
Predawn Gray Mica 2014 Toyota Highlander SUV / Crossover All-Wheel Drive 6-Speed Automatic Overdrive
Price drop

-$1,799

 

2014 Toyota Highlander

Limited Platinum AWD

85,852 mi

Home delivery from Richmond, VA
Price includes $661 shipping
Good Deal

$21,975

$21,475

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:
107,699
Stock #:
R26713
VIN:
5TDDZRFH1KS722912
Predawn Gray Mica 2019 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2019 Toyota Highlander

Limited AWD

107,699 mi

Home delivery from Montpelier, OH
Price includes $388 shipping
Great Deal

$22,810

Year:
2011
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
187 hp 2.7L I4
Exterior color:
Gray
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
5-Speed Automatic Overdrive
Mileage:
108,667
Stock #:
055266
VIN:
5TDBK3EHXBS055266
Gray 2011 Toyota Highlander SUV / Crossover Front-Wheel Drive 5-Speed Automatic Overdrive

 

2011 Toyota Highlander

Base

108,667 mi

Home delivery from Crystal Lake, IL
Price includes $88 shipping
Fair Deal

$13,465

Year:
2015
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Gray
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
6-Speed Automatic
Mileage:
152,615
Stock #:
109100
VIN:
5TDDKRFH6FS109100
Gray 2015 Toyota Highlander SUV / Crossover All-Wheel Drive 6-Speed Automatic

 

2015 Toyota Highlander

Limited AWD

152,615 mi

Home delivery from Fredericksburg, VA
Price includes $960 shipping
Fair Deal

$15,758

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:
MAGNETIC GRAY
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
99,716
Stock #:
6104189
VIN:
5TDBZRFH2JS866457
MAGNETIC GRAY 2018 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic
Price drop

-$500

 

2018 Toyota Highlander

LE AWD

99,716 mi

Home delivery from Jacksonville, FL
Price includes $949 shipping
Good Deal

$20,243

$19,743

Year:
2018
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Predawn Gray Mica
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Ash Gray
Transmission:
8-Speed Automatic
Mileage:
140,159
Stock #:
286049
VIN:
5TDKZRFH1JS286049
Predawn Gray Mica 2018 Toyota Highlander SUV / Crossover Front-Wheel Drive 8-Speed Automatic

 

2018 Toyota Highlander

XLE

140,159 mi

Home delivery from Arlington, TX
Price includes $1,304 shipping
Fair Deal

$19,218

Year:
2008
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Gray
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
5-Speed Automatic
Mileage:
135,449
Stock #:
19856
VIN:
JTEES43A782038655
Gray 2008 Toyota Highlander SUV / Crossover All-Wheel Drive 5-Speed Automatic

 

2008 Toyota Highlander

Sport 4WD

135,449 mi

Milwaukee, WI
11 mi away
Good Deal

$8,639

Year:
2026
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
2
Stock #:
T0F623073
VIN:
5TDKDRBH9TS623073
Gray 2026 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic
New arrival

 

2026 Toyota Highlander

Platinum AWD

Home delivery from Davenport, IA
Price includes $248 shipping

New car

TSRP $56,383

$56,810

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:
Automatic
Mileage:
83,006
Stock #:
C27000A
VIN:
5TDGZRBH0NS592872
Gray 2022 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

 

2022 Toyota Highlander

XLE AWD

83,006 mi

Home delivery from Pontiac, IL
Price includes $399 shipping
Fair Deal

$30,774

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:
Magnetic Gray Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
114,839
Stock #:
14877
VIN:
5TDDZRBH7LS042312
Magnetic Gray Metallic 2020 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$495

 

2020 Toyota Highlander

Limited AWD

114,839 mi

Home delivery from Salem, OH
Price includes $585 shipping
Great Deal

$24,520

$24,025

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:
62,215
Stock #:
CAC11027
VIN:
5TDGZRBH3MS079775
Gray 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2021 Toyota Highlander

XLE AWD

62,215 mi

Home delivery from Syracuse, NY
Price includes $891 shipping
Fair Deal

$30,966

Year:
2025
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
14,411
Stock #:
RTK5391
VIN:
5TDKDRBH2SS589721
Gray 2025 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic
Toyota of Fox Lake

Sponsored by Toyota of Fox Lake

2025 Toyota Highlander

XLE AWD

14,411 mi

Fox Lake, IL
47 mi away
Good Deal

$44,344

Year:
2017
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:
Almond
Transmission:
8-Speed Automatic
Mileage:
166,245
Stock #:
46P944A
VIN:
5TDBZRFH5HS365539
Gray 2017 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$500

Sponsored Listing

2017 Toyota Highlander

LE AWD

166,245 mi

Milwaukee, WI
10 mi away
Fair Deal

$15,594

$15,094

Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Gray
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
23,971
Stock #:
RA2663A
VIN:
5TDKDRAH2PS517961
Gray 2023 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic

 

2023 Toyota Highlander

L FWD

23,971 mi

Home delivery from Muscatine, IA
Price includes $390 shipping
Good Deal

$30,385

Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Cockpit Red
Transmission:
8-Speed Automatic
Mileage:
27,679
Stock #:
R89281
VIN:
5TDKDRAH2PS514378
Magnetic Gray Metallic 2023 Toyota Highlander SUV / Crossover Front-Wheel Drive 8-Speed Automatic

 

2023 Toyota Highlander

XSE FWD

27,679 mi

Home delivery from Herculaneum, MO
Price includes $710 shipping
Fair Deal

$39,635

Year:
2014
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Predawn Gray Mica
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
85,852
Stock #:
P26852
VIN:
5TDDKRFH7ES017332
Predawn Gray Mica 2014 Toyota Highlander SUV / Crossover All-Wheel Drive 6-Speed Automatic Overdrive
Price drop

-$1,799

 

2014 Toyota Highlander

Limited Platinum AWD

85,852 mi

Home delivery from Richmond, VA
Price includes $661 shipping
Good Deal

$21,975

$21,475

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:
107,699
Stock #:
R26713
VIN:
5TDDZRFH1KS722912
Predawn Gray Mica 2019 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2019 Toyota Highlander

Limited AWD

107,699 mi

Home delivery from Montpelier, OH
Price includes $388 shipping
Great Deal

$22,810

Year:
2011
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
187 hp 2.7L I4
Exterior color:
Gray
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
5-Speed Automatic Overdrive
Mileage:
108,667
Stock #:
055266
VIN:
5TDBK3EHXBS055266
Gray 2011 Toyota Highlander SUV / Crossover Front-Wheel Drive 5-Speed Automatic Overdrive

 

2011 Toyota Highlander

Base

108,667 mi

Home delivery from Crystal Lake, IL
Price includes $88 shipping
Fair Deal

$13,465

Year:
2015
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Gray
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
6-Speed Automatic
Mileage:
152,615
Stock #:
109100
VIN:
5TDDKRFH6FS109100
Gray 2015 Toyota Highlander SUV / Crossover All-Wheel Drive 6-Speed Automatic

 

2015 Toyota Highlander

Limited AWD

152,615 mi

Home delivery from Fredericksburg, VA
Price includes $960 shipping
Fair Deal

$15,758

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:
MAGNETIC GRAY
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
99,716
Stock #:
6104189
VIN:
5TDBZRFH2JS866457
MAGNETIC GRAY 2018 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic
Price drop

-$500

 

2018 Toyota Highlander

LE AWD

99,716 mi

Home delivery from Jacksonville, FL
Price includes $949 shipping
Good Deal

$20,243

$19,743

Year:
2018
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Predawn Gray Mica
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Ash Gray
Transmission:
8-Speed Automatic
Mileage:
140,159
Stock #:
286049
VIN:
5TDKZRFH1JS286049
Predawn Gray Mica 2018 Toyota Highlander SUV / Crossover Front-Wheel Drive 8-Speed Automatic

 

2018 Toyota Highlander

XLE

140,159 mi

Home delivery from Arlington, TX
Price includes $1,304 shipping
Fair Deal

$19,218

Year:
2008
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Gray
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
5-Speed Automatic
Mileage:
135,449
Stock #:
19856
VIN:
JTEES43A782038655
Gray 2008 Toyota Highlander SUV / Crossover All-Wheel Drive 5-Speed Automatic

 

2008 Toyota Highlander

Sport 4WD

135,449 mi

Milwaukee, WI
11 mi away
Good Deal

$8,639

Year:
2026
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
2
Stock #:
T0F623073
VIN:
5TDKDRBH9TS623073
Gray 2026 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic
New arrival

 

2026 Toyota Highlander

Platinum AWD

Home delivery from Davenport, IA
Price includes $248 shipping

New car

TSRP $56,383

$56,810

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:
Automatic
Mileage:
83,006
Stock #:
C27000A
VIN:
5TDGZRBH0NS592872
Gray 2022 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

 

2022 Toyota Highlander

XLE AWD

83,006 mi

Home delivery from Pontiac, IL
Price includes $399 shipping
Fair Deal

$30,774

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:
Magnetic Gray Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
114,839
Stock #:
14877
VIN:
5TDDZRBH7LS042312
Magnetic Gray Metallic 2020 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$495

 

2020 Toyota Highlander

Limited AWD

114,839 mi

Home delivery from Salem, OH
Price includes $585 shipping
Great Deal

$24,520

$24,025

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:
62,215
Stock #:
CAC11027
VIN:
5TDGZRBH3MS079775
Gray 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2021 Toyota Highlander

XLE AWD

62,215 mi

Home delivery from Syracuse, NY
Price includes $891 shipping
Fair Deal

$30,966

A better way to discover your best deal

Let us help you find a car you’ll love.