Used 2025 Toyota Highlander for Sale nearMilwaukee, WI

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76 vehicles found

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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:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
38,313
Stock #:
PRS2939
VIN:
5TDKDRBHXSS588364
Midnight Black Metallic 2025 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Toyota of Brookfield

Sponsored by Toyota of Brookfield

2025 Toyota Highlander

XSE AWD

38,313 mi

Brookfield, WI
13 mi away
Fair Deal
Manufacturer certified

$41,735

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:
Blueprint
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
19,220
Stock #:
P3906
VIN:
5TDKDRBH6TS595930
Blueprint 2026 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

Sponsored Listing

2026 Toyota Highlander

Platinum AWD

19,220 mi

Kenosha, WI
33 mi away
Fair Deal
Manufacturer certified

$53,979

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

 

2026 Toyota Highlander

Platinum AWD

Home delivery from Davenport, IA
Price includes $248 shipping

New car

TSRP $56,383

$56,810

Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
22,171
Stock #:
P5466
VIN:
5TDKDRBH8RS534409
Midnight Black Metallic 2024 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$1,000

 

2024 Toyota Highlander

LE AWD

22,171 mi

Home delivery from Monroe, WI
Price includes $93 shipping
Great Deal

$33,506

$32,506

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:
Pearl
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Mileage:
3
Stock #:
261087T
VIN:
5TDKDRBH7TS620897
Pearl 2026 Toyota Highlander SUV / Crossover All-Wheel Drive

 

2026 Toyota Highlander

XSE AWD

Milwaukee, WI
7 mi away

New car

TSRP $53,258

$54,256

Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Black
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
31,605
Stock #:
29128147
VIN:
5TDKDRBH2RS547138
Black 2024 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

 

2024 Toyota Highlander

XLE AWD

31,605 mi

Store transfer to Milwaukee, WI
Price includes $1,199 shipping
Good Deal

$38,197

CarGurus Analysis:

2025 Toyota Highlander

  • With 53 currently listed for sale and an average price of $44,593, 64.2% of 2025 Toyota Highlander listings on CarGurus are rated as good or great deals.

  • 100.0% of 2025 Toyota Highlander listings on CarGurus are accident free.

Research summarized using AI

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:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Glazed Caramel
Transmission:
8-Speed Automatic
Mileage:
5
Stock #:
TA6572
VIN:
5TDKDRBH4TS621943
Midnight Black Metallic 2026 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2026 Toyota Highlander

Platinum AWD

Home delivery from Ottawa, IL
Price includes $125 shipping

New car

TSRP $57,616

$58,154

Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Black
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
31,077
Stock #:
70285203
VIN:
5TDKDRAH7RS532457
Black 2024 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic

 

2024 Toyota Highlander

XLE FWD

31,077 mi

Store transfer to Milwaukee, WI
Price includes $899 shipping
Fair Deal

$38,897

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:
Pearl
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
3
Stock #:
TN43A461
VIN:
5TDKDRBH3TS623473
Pearl 2026 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
New arrival

 

2026 Toyota Highlander

Platinum AWD

Home delivery from Whitestown, IN
Price includes $280 shipping

New car

TSRP $55,995

$56,535

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:
Blueprint
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
19,220
Stock #:
P3906
VIN:
5TDKDRBH6TS595930
Blueprint 2026 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2026 Toyota Highlander

Platinum AWD

19,220 mi

Kenosha, WI
33 mi away
Fair Deal
Manufacturer certified

$53,979

Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
White (Wind Chill Pearl)
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
32,439
Stock #:
9827
VIN:
5TDKDRBH3RS548914
White (Wind Chill Pearl) 2024 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
New arrival

 

2024 Toyota Highlander

XLE AWD

32,439 mi

Home delivery from Hinsdale, IL
Price includes $128 shipping
Fair Deal

$40,538

Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
45,163
Stock #:
6043A
VIN:
5TDKDRBH0RS537062
Magnetic Gray Metallic 2024 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2024 Toyota Highlander

LE AWD

45,163 mi

Home delivery from Albuquerque, NM
Price includes $1,708 shipping
Fair Deal

$34,556

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:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
38,313
Stock #:
PRS2939
VIN:
5TDKDRBHXSS588364
Midnight Black Metallic 2025 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Toyota of Brookfield

Sponsored by Toyota of Brookfield

2025 Toyota Highlander

XSE AWD

38,313 mi

Brookfield, WI
13 mi away
Fair Deal
Manufacturer certified

$41,735

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:
Blueprint
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
19,220
Stock #:
P3906
VIN:
5TDKDRBH6TS595930
Blueprint 2026 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

Sponsored Listing

2026 Toyota Highlander

Platinum AWD

19,220 mi

Kenosha, WI
33 mi away
Fair Deal
Manufacturer certified

$53,979

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

 

2026 Toyota Highlander

Platinum AWD

Home delivery from Davenport, IA
Price includes $248 shipping

New car

TSRP $56,383

$56,810

Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
22,171
Stock #:
P5466
VIN:
5TDKDRBH8RS534409
Midnight Black Metallic 2024 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$1,000

 

2024 Toyota Highlander

LE AWD

22,171 mi

Home delivery from Monroe, WI
Price includes $93 shipping
Great Deal

$33,506

$32,506

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:
Pearl
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Mileage:
3
Stock #:
261087T
VIN:
5TDKDRBH7TS620897
Pearl 2026 Toyota Highlander SUV / Crossover All-Wheel Drive

 

2026 Toyota Highlander

XSE AWD

Milwaukee, WI
7 mi away

New car

TSRP $53,258

$54,256

Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Black
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
31,605
Stock #:
29128147
VIN:
5TDKDRBH2RS547138
Black 2024 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

 

2024 Toyota Highlander

XLE AWD

31,605 mi

Store transfer to Milwaukee, WI
Price includes $1,199 shipping
Good Deal

$38,197

CarGurus Analysis:

2025 Toyota Highlander

  • With 53 currently listed for sale and an average price of $44,593, 64.2% of 2025 Toyota Highlander listings on CarGurus are rated as good or great deals.

  • 100.0% of 2025 Toyota Highlander listings on CarGurus are accident free.

Research summarized using AI

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:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Glazed Caramel
Transmission:
8-Speed Automatic
Mileage:
5
Stock #:
TA6572
VIN:
5TDKDRBH4TS621943
Midnight Black Metallic 2026 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2026 Toyota Highlander

Platinum AWD

Home delivery from Ottawa, IL
Price includes $125 shipping

New car

TSRP $57,616

$58,154

Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Black
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
31,077
Stock #:
70285203
VIN:
5TDKDRAH7RS532457
Black 2024 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic

 

2024 Toyota Highlander

XLE FWD

31,077 mi

Store transfer to Milwaukee, WI
Price includes $899 shipping
Fair Deal

$38,897

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:
Pearl
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
3
Stock #:
TN43A461
VIN:
5TDKDRBH3TS623473
Pearl 2026 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
New arrival

 

2026 Toyota Highlander

Platinum AWD

Home delivery from Whitestown, IN
Price includes $280 shipping

New car

TSRP $55,995

$56,535

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:
Blueprint
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
19,220
Stock #:
P3906
VIN:
5TDKDRBH6TS595930
Blueprint 2026 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2026 Toyota Highlander

Platinum AWD

19,220 mi

Kenosha, WI
33 mi away
Fair Deal
Manufacturer certified

$53,979

Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
White (Wind Chill Pearl)
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
32,439
Stock #:
9827
VIN:
5TDKDRBH3RS548914
White (Wind Chill Pearl) 2024 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
New arrival

 

2024 Toyota Highlander

XLE AWD

32,439 mi

Home delivery from Hinsdale, IL
Price includes $128 shipping
Fair Deal

$40,538

Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
45,163
Stock #:
6043A
VIN:
5TDKDRBH0RS537062
Magnetic Gray Metallic 2024 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2024 Toyota Highlander

LE AWD

45,163 mi

Home delivery from Albuquerque, NM
Price includes $1,708 shipping
Fair Deal

$34,556

CarGurus Analysis: 2025 Toyota Highlander

Image Not Available

Summary

  • With 53 currently listed for sale and an average price of $44,593, 64.2% of 2025 Toyota Highlander listings on CarGurus are rated as good or great deals.

  • 100.0% of 2025 Toyota Highlander listings on CarGurus are accident free.

Why it stands out

The 2025 Toyota Highlander stands out as a practical, comfort-focused midsize SUV rather than a flashy one. In the current generation, Toyota has kept the formula centered on comfort and everyday usefulness, with a reinforced body, upscale styling, and a cabin that emphasizes versatility. It also offers both gas and hybrid powertrains, and the hybrid is notable for returning 35 mpg combined, which is much more than most other midsize SUVs.

What makes the Highlander appealing is how much it can do without feeling complicated. It offers up to 84.3 cubic feet of cargo space with the seats folded down, and every Highlander comes with an 8-inch touchscreen, USB inputs, Apple CarPlay, Android Auto, and Amazon Alexa. Toyota Safety Sense is standard as well, and the SUV has earned strong safety recognition throughout this generation. The tradeoff is that the Highlander still isn’t especially exciting to drive, and Toyota’s tech can be a hassle to use, but buyers who value reliability, safety, economy, and a smooth ride will find a lot to like.

Other model years to consider

  • 2024 Toyota Highlander
    • Average price: $37,040
    • Good/great deal percentage: 68.2%
    • User rating: 5 / 5
    • Total listings: 132
  • 2021 Toyota Highlander
    • Average price: $29,302
    • Good/great deal percentage: 51.3%
    • User rating: 4.9 / 5
    • Total listings: 236
  • 2023 Toyota Highlander
    • Average price: $35,329
    • Good/great deal percentage: 63.6%
    • User rating: 4.8 / 5
    • Total listings: 209

Similar models to consider

  • 2025 Honda Pilot
    • Average price: $42,407
    • Good/great deal percentage: 79.9%
    • User rating: 4.9 / 5
    • Total listings: 144
  • 2025 Ford Explorer
    • Average price: $39,982
    • Good/great deal percentage: 44.2%
    • User rating: 5 / 5
    • Total listings: 414
  • 2025 Chevrolet Traverse
    • Average price: $39,748
    • Good/great deal percentage: 112.6%
    • User rating: 5 / 5
    • Total listings: 222

This analysis is based on CarGurus' proprietary market data from November 2, 2026, CarGurus experts' opinions, and generative AI.

*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.

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