New & Used 2026 Toyota Highlander for Sale nearMilwaukee, WI
43 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- 11,902
- Stock #:
- T16905A
- VIN:
- 5TDKDRBH3TS596114
New arrival
Sponsored by Toyota of Brookfield
2026 Toyota Highlander
XLE AWD
11,902 mi
Brookfield, WI
13 mi away
Good Deal
$46,736
- 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:
- Celestial Silver Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 34,749
- Stock #:
- 43P2016
- VIN:
- 5TDKDRAH8SS552187
Sponsored Listing
2025 Toyota Highlander
LE FWD
34,749 mi
Greenfield, WI
8 mi away
Fair Deal
$35,436
- 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:
- 8-Speed Automatic
- Mileage:
- 31,961
- Stock #:
- 44P2421
- VIN:
- 5TDKDRAH8SS553016
Sponsored Listing
2025 Toyota Highlander
LE FWD
31,961 mi
Oak Creek, WI
8 mi away
Fair Deal
$35,833
- 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:
- 32,163
- Stock #:
- G94195
- VIN:
- 5TDKDRBH5SS583475
2025 Toyota Highlander
XSE AWD
32,163 mi
West Allis, WI
8 mi away
Good Deal
$38,899
- 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
2025 Toyota Highlander
XSE AWD
26,758 mi
West Allis, WI
8 mi away
Good Deal
$40,394
- 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:
- 34,261
- Stock #:
- G94265
- VIN:
- 5TDKDRBH0SS583688
2025 Toyota Highlander
XSE AWD
34,261 mi
West Allis, WI
8 mi away
Good Deal
$39,390
- 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:
- 8-Speed Automatic
- Mileage:
- 24,968
- Stock #:
- 44151
- VIN:
- 5TDKDRAH9SS551968
2025 Toyota Highlander
LE FWD
24,968 mi
Home delivery from Lubbock, TX
Price includes $3,018 shipping
Fair Deal
$36,529
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 31,732
- Stock #:
- 28957156
- VIN:
- 5TDKDRBH1SS585790
2025 Toyota Highlander
XSE AWD
31,732 mi
Store transfer to Milwaukee, WI
Price includes $499 shipping
Fair Deal
$43,497
- 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:
- 27,451
- Stock #:
- G94209
- VIN:
- 5TDKDRBH1SS579925
Price drop
-$1,396
2025 Toyota Highlander
XSE AWD
27,451 mi
West Allis, WI
8 mi away
Good Deal
$41,387
$40,390
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 32,374
- Stock #:
- 13GB0124P
- VIN:
- 5TDKDRBH2SS583448
2025 Toyota Highlander
XSE AWD
32,374 mi
Home delivery from Burnsville, MN
Price includes $438 shipping
Fair Deal
$41,786
- 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:
- 28,703
- Stock #:
- G94196
- VIN:
- 5TDKDRBH8SS575984
2025 Toyota Highlander
XSE AWD
28,703 mi
West Allis, WI
8 mi away
Good Deal
$40,332
- 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:
- 29,167
- Stock #:
- G94199
- VIN:
- 5TDKDRBH4SS582124
2025 Toyota Highlander
XSE AWD
29,167 mi
West Allis, WI
8 mi away
Good Deal
$40,354
- 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:
- Gray
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 32,533
- Stock #:
- 28734437
- VIN:
- 5TDKDRAHXSS553891
2025 Toyota Highlander
LE FWD
32,533 mi
Store transfer to Milwaukee, WI
Price includes $1,999 shipping
Fair Deal
$34,997
CarGurus Analysis:
2026 Toyota Highlander
With 822 currently listed for sale and an average price of $49,988.00, 40.1% of 2026 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
94.0% of 2026 Highlander models on CarGurus are accident free.
The 2026 Toyota Highlander continues to impress with its spacious interior, excellent safety ratings, and the availability of hybrid models, making it a practical choice for families.
- 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:
- 31,255
- Stock #:
- G94212
- VIN:
- 5TDKDRBHXSS582094
2025 Toyota Highlander
XSE AWD
31,255 mi
West Allis, WI
8 mi away
Fair Deal
$40,179
- 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
2025 Toyota Highlander
XSE AWD
28,080 mi
West Allis, WI
8 mi away
Fair Deal
$41,376
- 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:
- 34,559
- Stock #:
- G94267
- VIN:
- 5TDKDRBH2SS579397
2025 Toyota Highlander
XSE AWD
34,559 mi
West Allis, WI
8 mi away
Fair Deal
$40,349
- 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:
- 11,902
- Stock #:
- T16905A
- VIN:
- 5TDKDRBH3TS596114
New arrival
2026 Toyota Highlander
XLE AWD
11,902 mi
Brookfield, WI
13 mi away
Good Deal
$46,736
- 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
2025 Toyota Highlander
XSE AWD
30,172 mi
West Allis, WI
8 mi away
Good Deal
$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:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 27,825
- Stock #:
- S576363
- VIN:
- 5TDKDRBH3SS576363
2025 Toyota Highlander
XSE AWD
27,825 mi
Home delivery from Defiance, OH
Price includes $436 shipping
Fair Deal
$41,627
- 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:
- 8-Speed Automatic
- Mileage:
- 31,961
- Stock #:
- 44P2421
- VIN:
- 5TDKDRAH8SS553016
2025 Toyota Highlander
LE FWD
31,961 mi
Oak Creek, WI
8 mi away
Fair Deal
$35,833
- 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:
- Heavy Metal
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 48,883
- Stock #:
- AH552334
- VIN:
- 5TDKDRAH6SS552334
2025 Toyota Highlander
XLE FWD
48,883 mi
Home delivery from Nashville, TN
Price includes $476 shipping
Fair Deal
$38,990
- 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:
- 10,042
- Stock #:
- 1TT89976
- VIN:
- 5TDKDRBH2SS589976
2025 Toyota Highlander
XSE AWD
10,042 mi
Home delivery from Greensboro, NC
Price includes $906 shipping
Fair Deal
$46,500
- 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:
- Celestial Silver Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 34,749
- Stock #:
- 43P2016
- VIN:
- 5TDKDRAH8SS552187
2025 Toyota Highlander
LE FWD
34,749 mi
Greenfield, WI
8 mi away
Fair Deal
$35,436
CarGurus Analysis: 2026 Toyota Highlander
Summary
With 822 currently listed for sale and an average price of $49,988.00, 40.1% of 2026 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
94.0% of 2026 Highlander models on CarGurus are accident free.
The 2026 Toyota Highlander continues to impress with its spacious interior, excellent safety ratings, and the availability of hybrid models, making it a practical choice for families.
Why it stands out
The 2026 Toyota Highlander stands out in the crowded midsize SUV market due to its blend of reliability, spaciousness, and safety features. With a history of strong performance since its debut, the Highlander has evolved to meet the needs of modern families, offering a comfortable ride and ample cargo space. The latest model maintains its reputation for safety, boasting a high accident-free percentage of 94.0%. Additionally, the Highlander is available in hybrid variants, providing excellent fuel efficiency without sacrificing power. While it may not be the most exciting vehicle to drive, its soft suspension and quiet cabin make it a favorite among those prioritizing comfort and practicality. The Highlander's consistent updates and improvements, such as enhanced technology and safety features, ensure it remains a top contender in its class.
Other model years to consider
- Average price: $39,166.00
- Good/great deal percentage: 38.0%
- User rating: 5 / 5
- Total listings: 3,845
- Average price: $36,159.00
- Good/great deal percentage: 37.2%
- User rating: 4.75 / 5
- Total listings: 4,496
- Average price: $30,445.00
- Good/great deal percentage: 36.1%
- User rating: 4.86 / 5
- Total listings: 3,248
This analysis is based on CarGurus' proprietary market data from July 13, 2026, CarGurus experts' opinions, and generative AI.
2026 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| Platinum AWD | $53,925 |
| XLE AWD | $46,270 |
| XSE AWD | $48,340 |
| Limited AWD | $50,725 |
2026 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2026 Toyota Highlander prices has changed over time.
See more price trendsAVG Price
$50,021
0.7%
2026 Toyota Highlander
Index Price
$29,141
0.5%
All used vehicles
2026 Toyota Highlander Pricing Analysis: Milwaukee, WI Market Report
Pricing by Nearby Locations
Market Area: Milwaukee, WI
Key Insights
- Highest Prices in Kenosha: The average price in Kenosha, WI ($43,899) is the highest among nearby cities, indicating strong demand or limited supply.
- Uniform Pricing Across Cities: Cities like Janesville, Palatine, Rockford, Chicago, and Aurora all share the same average price of $43,899, suggesting a regional pricing consistency.
- Limited Inventory: The total listings across these cities are relatively low, with Kenosha having the highest at 45 listings, which may contribute to the elevated pricing.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Kenosha, WI | 45 | $43,899 |
| Janesville, WI | 30 | $43,899 |
| Palatine, IL | 35 | $43,899 |
| Rockford, IL | 26 | $43,899 |
| Chicago, IL | 34 | $43,899 |
| Aurora, IL | 35 | $43,899 |
Pricing by Trim Packages
Key Insights
- XLE AWD is the Most Common Trim: With 187 listings, the XLE AWD trim is the most prevalent, indicating strong consumer preference for this configuration.
- Premium Pricing for Limited AWD: The Limited AWD trim, priced at $50,725 MSRP, reflects a significant premium over the base trims, likely due to its extensive feature set.
- Feature-Rich Offerings: All trims include desirable features such as Backup Camera, Sunroof/Moonroof, and Adaptive Cruise Control, appealing to a wide range of buyers.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 187 | $46,270 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 87 | $50,725 | AWD | 2.4L 265 hp I4 |
| XSE AWD | 45 | $48,340 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 39 | $53,925 | AWD | 2.4L 265 hp I4 |
Pricing Analysis by Model Year
Key Insights
- Newer Models Retain Value: The 2025 Highlander is currently priced at $38,382, which is about -3.3% below MSRP, indicating strong demand for newer vehicles.
- Significant Depreciation for Older Models: The 2019 Highlander shows a steep decline, with an average price of $22,160, reflecting a -30.2% depreciation from its original MSRP.
- Best Value in Recent Years: The 2022 Highlander is priced at $33,870, which is -5.5% below MSRP, making it a compelling option for buyers seeking a balance of price and features.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2025 Toyota Highlander | $40,320 | $38,382 | -3.3% |
| 2024 Toyota Highlander | $39,270 | $39,194 | -0.2% |
| 2023 Toyota Highlander | $36,620 | $36,268 | -1.0% |
| 2022 Toyota Highlander | $35,855 | $33,870 | -5.5% |
| 2021 Toyota Highlander | $35,085 | $32,941 | -6.1% |
| 2020 Toyota Highlander | $34,600 | $30,971 | -10.5% |
| 2019 Toyota Highlander | $31,830 | $22,160 | -30.2% |
| 2018 Toyota Highlander | $31,230 | $20,749 | -33.6% |
| 2017 Toyota Highlander | $30,630 | $18,497 | -39.8% |
| 2016 Toyota Highlander | $30,490 | $13,714 | -55.1% |
| 2015 Toyota Highlander | $29,765 | $17,944 | -39.7% |
These recommendations are based on CarGurus' proprietary market data from July 9, 2026, CarGurus experts' opinions, and generative AI.
FAQs
How much does the 2026 Toyota Highlander cost in Milwaukee, WI?
The average 2026 Toyota Highlander costs about $50,021.44. The average price has decreased by -1.4% since last year. The 30 for sale near Milwaukee, WI on CarGurus, range from $32,998 to $52,237 in price.
How many 2026 Toyota Highlander vehicles in Milwaukee, WI have no reported accidents or damage?
30 out of 30 for sale near Milwaukee, WI have no reported accidents or damage.
What is the fuel economy of the 2026 Toyota Highlander?
Depending on the engine and options, the 2026 Toyota Highlander gets between 24 and 24 MPG (or EV battery range).
What fuel types are available?
Gasoline engines are available.
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