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New & Used 2026 Toyota Highlander for Sale near Monroe, WI

80 results

Year:
2025
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Midnight Black Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
29,614
Stock #:
SS552008
VIN:
5TDKDRAH4SS552008
Midnight Black Metallic 2025 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic
New arrival
AutoNation Toyota Libertyville

Sponsored by AutoNation Toyota Libertyville

2025 Toyota Highlander

LE FWD

29,614 mi

Libertyville, IL
89 mi away
Good Deal
Manufacturer certified

$36,375

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:
Silver
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
22,891
Stock #:
61966
VIN:
5TDKDRBH1SS589189
Silver 2025 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

Sponsored Listing

2025 Toyota Highlander

XSE AWD

22,891 mi

Des Plaines, IL
98 mi away
Fair Deal

$43,995

Year:
2025
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Black
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
30,427
Stock #:
61924
VIN:
5TDKDRAH1SS555013
Black 2025 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic

Sponsored Listing

2025 Toyota Highlander

LE FWD

30,427 mi

Des Plaines, IL
98 mi away
Fair Deal

$35,898

Year:
2025
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Silver
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
26,764
Stock #:
P132427
VIN:
5TDKDRAH1SS554959
Silver 2025 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic

 

2025 Toyota Highlander

XLE FWD

26,764 mi

Belvidere, IL
46 mi away
Great Deal

$37,748

CarGurus Analysis:

2026 Toyota Highlander

  • With 838 currently listed for sale and an average price of $50,007.00, 38.3% of 2026 Toyota Highlanders for sale on CarGurus are rated as good or great deals.

  • 95.3% of 2026 Highlander models on CarGurus are accident free.

  • The 2026 Toyota Highlander continues to deliver a comfortable and practical driving experience, boasting ample cargo space and advanced safety features that have become hallmarks of this SUV.

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:
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
84 mi away
Good Deal
Manufacturer certified

$41,793

$40,321

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:
Silver
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
20,885
Stock #:
SS588777
VIN:
5TDKDRBH2SS588777
Silver 2025 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

 

2025 Toyota Highlander

XSE AWD

20,885 mi

Libertyville, IL
89 mi away
Good Deal
Manufacturer certified

$43,934

Year:
2025
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Black
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
29,599
Stock #:
61997
VIN:
5TDKDRAH9SS554028
Black 2025 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic

Sponsored Listing

2025 Toyota Highlander

LE FWD

29,599 mi

Des Plaines, IL
98 mi away
Fair Deal

$35,995

Page 1 of 4

CarGurus Analysis: 2026 Toyota Highlander

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Summary

  • With 838 currently listed for sale and an average price of $50,007.00, 38.3% of 2026 Toyota Highlanders for sale on CarGurus are rated as good or great deals.

  • 95.3% of 2026 Highlander models on CarGurus are accident free.

  • The 2026 Toyota Highlander continues to deliver a comfortable and practical driving experience, boasting ample cargo space and advanced safety features that have become hallmarks of this SUV.

Why it stands out

The 2026 Toyota Highlander stands out in the competitive midsize SUV market through its blend of spaciousness, reliability, and a strong safety reputation. It has a solid record of comfort and practicality, with up to 84.3 cubic feet of cargo space available with the seats folded down. While its driving dynamics may not excite buyers, the Highlander's sedan-like ride, quiet interior, and efficient hybrid options have made it a favored choice for families. The introduction of more upscale features over the years, such as enhanced infotainment systems and robust safety protocols via Toyota Safety Sense, ensures that it remains a frontrunner. The Highlander has maintained its affordability and reliability, standing as a wise long-term investment for those in the market for a used SUV.

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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