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New & Used 2025 Toyota Highlander for Sale near Madison, WI

125 results

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:
39,385
Stock #:
P21557
VIN:
5TDKDRBH5RS552821
Black 2024 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic
Elgin Toyota

Sponsored by Elgin Toyota

2024 Toyota Highlander

XLE AWD

39,385 mi

Streamwood, IL
94 mi away
Good Deal

$38,558

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:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
39,106
Stock #:
P21705
VIN:
5TDKDRBH4RS536304
Gray 2024 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

Sponsored Listing

2024 Toyota Highlander

XLE AWD

39,106 mi

Streamwood, IL
94 mi away
Fair Deal

$39,658

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
Transmission:
8-Speed Automatic
Mileage:
22,363
Stock #:
3P26072
VIN:
5TDKDRBHXRS575351
Black 2024 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
New arrival

Sponsored Listing

2024 Toyota Highlander

XLE AWD

22,363 mi

Boscobel, WI
66 mi away
Fair Deal

$43,407

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:
Magnetic Gray Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
15,050
Stock #:
C20313
VIN:
5TDKDRBH9SS586279
Magnetic Gray Metallic 2025 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$3,972

 

2025 Toyota Highlander

XSE AWD

15,050 mi

Home delivery from Cedar Rapids, IA
Free home delivery
Good Deal

$49,372

$45,400

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:
26,758
Stock #:
G94171
VIN:
5TDKDRBH0SS582167
Midnight Black Metallic 2025 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$1,392

 

2025 Toyota Highlander

XSE AWD

26,758 mi

West Allis, WI
68 mi away
Great Deal
Manufacturer certified

$41,786

$40,394

CarGurus Analysis:

2025 Toyota Highlander

  • With 1,868 currently listed for sale and an average price of $41,912.00, 36.3% of 2025 Toyota Highlanders for sale on CarGurus are rated as good or great deals.

  • 91.3% of 2025 Highlander models on CarGurus are accident free.

  • The 2025 Toyota Highlander is known for its spacious and comfortable interior, excellent safety features, and reliability, making it a strong contender in the midsize SUV market.

Research summarized using AI

 

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:
Magnetic Gray Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
28,080
Stock #:
G94208
VIN:
5TDKDRBH2SS583725
Magnetic Gray Metallic 2025 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$1,399

 

2025 Toyota Highlander

XSE AWD

28,080 mi

West Allis, WI
68 mi away
Fair Deal
Manufacturer certified

$42,775

$41,376

Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
32,205
Stock #:
P21489
VIN:
5TDKDRBHXRS554788
 2024 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

 

2024 Toyota Highlander

LE AWD

32,205 mi

Streamwood, IL
94 mi away
Good Deal

$33,358

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:
Celestial Silver Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
30,172
Stock #:
G94188
VIN:
5TDKDRBH0SS582573
Celestial Silver Metallic 2025 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$1,472

 

2025 Toyota Highlander

XSE AWD

30,172 mi

West Allis, WI
68 mi away
Good Deal
Manufacturer certified

$41,793

$40,321

Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
54,509
Stock #:
P21654
VIN:
5TDKDRBH3RS571903
 2024 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

Sponsored Listing

2024 Toyota Highlander

XLE AWD

54,509 mi

Streamwood, IL
94 mi away
Good Deal

$36,558

Page 1 of 6

CarGurus Analysis: 2025 Toyota Highlander

Image Not Available

Summary

  • With 1,868 currently listed for sale and an average price of $41,912.00, 36.3% of 2025 Toyota Highlanders for sale on CarGurus are rated as good or great deals.

  • 91.3% of 2025 Highlander models on CarGurus are accident free.

  • The 2025 Toyota Highlander is known for its spacious and comfortable interior, excellent safety features, and reliability, making it a strong contender in the midsize SUV market.

Why it stands out

The 2025 Toyota Highlander continues to uphold the legacy of its predecessors, offering a practical and reliable option for families and individuals alike. This midsize SUV combines car-like handling with the versatility of a family vehicle, thanks to its unibody construction. Reviews continuously highlight its comfortable ride, spacious seating, and user-friendly technology. Although not the most dynamic driving experience, the Highlander's strong reputation for reliability and safety reassures buyers. Furthermore, with options for hybrid models, the Highlander presents a fuel-efficient alternative in the crowded market of midsize SUVs. Owners appreciate its expansive cargo space and the various features that cater to families, maintaining its status as a top choice for those needing utility without sacrificing comfort.

Other model years to consider

  • 2024 Toyota Highlander

    • Average price: $39,151.00
    • Good/great deal percentage: 36.1%
    • User rating: 5 / 5
    • Total listings: 4,033
  • 2023 Toyota Highlander

    • Average price: $36,362.00
    • Good/great deal percentage: 35.1%
    • User rating: 4.75 / 5
    • Total listings: 4,615
  • 2021 Toyota Highlander

    • Average price: $30,529.00
    • Good/great deal percentage: 35.0%
    • User rating: 4.86 / 5
    • Total listings: 3,229

This analysis is based on CarGurus' proprietary market data from June 22, 2026, CarGurus experts' opinions, and generative AI.

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