Used Toyota Highlander for Sale nearMilton, WI
47 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 8,056
- Stock #:
- TS601793
- VIN:
- 5TDKDRBHXTS601793
Sponsored by Off Lease Cars
2026 Toyota Highlander
XLE AWD
8,056 mi
Crystal Lake, IL
49 mi away
Great Deal
$44,254
- 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:
- 13,892
- Stock #:
- T0061
- VIN:
- 5TDKDRBH0TS604413
New arrival
Sponsored Listing
2026 Toyota Highlander
XLE AWD
13,892 mi
Lincolnwood, IL
80 mi away
Fair Deal
$48,741
- 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
Price drop
-$1,723
Sponsored Listing
2026 Toyota Highlander
XLE AWD
11,902 mi
Brookfield, WI
44 mi away
Good Deal
$48,516
$46,793
- 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
Price drop
-$1,723
2026 Toyota Highlander
XLE AWD
11,902 mi
Brookfield, WI
44 mi away
Good Deal
$48,516
$46,793
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 8,056
- Stock #:
- TS601793
- VIN:
- 5TDKDRBHXTS601793
2026 Toyota Highlander
XLE AWD
8,056 mi
Crystal Lake, IL
49 mi away
Great Deal
$44,254
- 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:
- Red (Ruby Flare Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Glazed Caramel
- Transmission:
- 8-Speed Automatic
- Mileage:
- 15,195
- Stock #:
- R5346
- VIN:
- 5TDKDRBH2TS598808
2026 Toyota Highlander
Platinum AWD
15,195 mi
Naperville, IL
79 mi away
Good Deal
$52,313
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 6,436
- Stock #:
- 70134644
- VIN:
- 5TDKDRBH9TS600473
2026 Toyota Highlander
XLE AWD
6,436 mi
Store transfer to Madison, WI
Price includes $549 shipping
Fair Deal
$49,547
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 242
- Stock #:
- 10C0006P
- VIN:
- 5TDKDRBH0TS605299
New arrival
2026 Toyota Highlander
XSE AWD
242 mi
Home delivery from Baxter, MN
Price includes $360 shipping
Fair Deal
$52,708
- 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:
- 13,892
- Stock #:
- T0061
- VIN:
- 5TDKDRBH0TS604413
New arrival
2026 Toyota Highlander
XLE AWD
13,892 mi
Lincolnwood, IL
80 mi away
Fair Deal
$48,741
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 843
- Stock #:
- 29080586
- VIN:
- 5TDKDRBHXTS606248
2026 Toyota Highlander
Platinum AWD
843 mi
Store transfer to Madison, WI
Price includes $699 shipping
Fair Deal
$55,697
- 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:
- Red
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 3,340
- Stock #:
- 70134094
- VIN:
- 5TDKDRBH4TS598924
New arrival
2026 Toyota Highlander
XSE AWD
3,340 mi
Store transfer to Madison, WI
Price includes $599 shipping
Fair Deal
$51,597
- 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:
- Heavy Metal
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 3
- Stock #:
- 26TT180
- VIN:
- 5TDKDRBH6TS612189
2026 Toyota Highlander
XLE AWD
Home delivery from Kokomo, IN
Price includes $328 shipping
New car
TSRP $49,953
$50,526
- 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:
- White
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Lb20/Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 22
- Stock #:
- TS613724
- VIN:
- 5TDKDRBH7TS613724
2026 Toyota Highlander
Limited AWD
West Allis, WI
47 mi away
New car
TSRP $54,033
$54,033
- 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:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Mileage:
- 0
- VIN:
- 5TDKDRBH9TS30J503
2026 Toyota Highlander
Limited AWD
Milwaukee, WI
51 mi away
New car
TSRP $54,787
$55,785
- 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
- Mileage:
- 0
- VIN:
- 5TDKDRBH2TS31A015
2026 Toyota Highlander
Platinum AWD
Elmhurst, IL
78 mi away
New car
TSRP $55,908
$56,906
- 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
- Mileage:
- 0
- VIN:
- 5TDKDRBH0TS31A790
2026 Toyota Highlander
XLE AWD
Milwaukee, WI
51 mi away
New car
TSRP $50,446
$51,444
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Unknown
- Mileage:
- 3
- Stock #:
- CT6148
- VIN:
- 5TDKDRBH5TS613561
2026 Toyota Highlander
Platinum AWD
Clinton, IA
95 mi away
New car
TSRP $55,508
$55,688
- Year:
- 2026
- 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
- Transmission:
- Automatic
- Mileage:
- 0
- Stock #:
- K6447
- VIN:
- 5TDKDRBH6TS615240
New arrival
2026 Toyota Highlander
Platinum AWD
Fox Lake, IL
47 mi away
New car
TSRP $57,352
$58,133
- 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:
- Wind Chill Pearl [Extra_Cost_Color]
- Fuel type:
- Gasoline
- Interior color:
- Black Leather & Dinamica® Trim
- Transmission:
- 8-Speed Dual Clutch
- Mileage:
- 0
- VIN:
- 5TDKDRBHXTS35A214
![Wind Chill Pearl [Extra_Cost_Color] 2026 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Dual Clutch](https://static.cargurus.com/images/forsale/2026/07/18/00/32/2026_toyota_highlander-pic-8346619801160609299-1024x768.jpeg?io=true&width=640&height=480&fit=bounds&format=jpg&auto=webp)
New arrival
2026 Toyota Highlander
Platinum AWD
Crystal Lake, IL
50 mi away
New car
TSRP $57,672
$58,050
- 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:
- Heavy Metal
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 4
- Stock #:
- N260717
- VIN:
- 5TDKDRBH8TS613179
2026 Toyota Highlander
Platinum AWD
Hodgkins, IL
89 mi away
New car
$55,591
- 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:
- Glazed Caramel
- Transmission:
- 8-Speed Automatic
- Mileage:
- 5
- Stock #:
- 6915078
- VIN:
- 5TDKDRBH1TS615078
New arrival
2026 Toyota Highlander
Platinum AWD
Chicago, IL
84 mi away
New car
TSRP $57,727
$58,104
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 2
- Stock #:
- 260043
- VIN:
- 5TDKDRBH4TS614118
2026 Toyota Highlander
Platinum AWD
Lincolnwood, IL
80 mi away
New car
TSRP $56,010
$56,756
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 0
- Stock #:
- T29346
- VIN:
- 5TDKDRBH6TS30J006
2026 Toyota Highlander
XLE AWD
Waukegan, IL
61 mi away
New car
TSRP $49,013
$49,391
- 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:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Mileage:
- 0
- VIN:
- 5TDKDRBH0TS34A856
New arrival
2026 Toyota Highlander
Platinum AWD
Milwaukee, WI
51 mi away
New car
TSRP $57,142
$58,140
2027 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2027 Toyota Highlander prices has changed over time.
See more price trendsAVG Price
Not Available
2027 Toyota Highlander
Index Price
$29,086
0.4%
All used vehicles
2027 Toyota Highlander Pricing Analysis
Pricing Analysis by Model Year
Key Insights
- Newer Models Retain Value: The 2026 Highlander is priced at $51,568, reflecting a 11.4% premium over its original MSRP, indicating strong demand for the latest model.
- Significant Depreciation for Older Models: The 2019 Highlander shows a steep decline, priced at $24,096, which is -24.5% compared to its original MSRP, highlighting the rapid depreciation typical of older vehicles.
- Best Value in Recent Years: The 2022 Highlander is priced at $33,596, representing a -6.9% depreciation, making it a compelling option for buyers seeking a balance between price and modern features.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $46,270 | $51,568 | +11.4% |
| 2025 Toyota Highlander | $40,320 | $41,401 | +2.7% |
| 2024 Toyota Highlander | $39,270 | $39,300 | +0.1% |
| 2023 Toyota Highlander | $36,620 | $35,869 | -2.0% |
| 2022 Toyota Highlander | $35,855 | $33,596 | -6.9% |
| 2021 Toyota Highlander | $35,085 | $30,458 | -13.2% |
| 2020 Toyota Highlander | $34,600 | $28,397 | -17.9% |
| 2019 Toyota Highlander | $31,830 | $24,096 | -24.5% |
| 2018 Toyota Highlander | $31,230 | $22,318 | -28.5% |
| 2017 Toyota Highlander | $30,630 | $20,938 | -31.6% |
| 2016 Toyota Highlander | $30,490 | $18,699 | -38.7% |
| 2015 Toyota Highlander | $29,765 | $17,096 | -42.8% |
These recommendations are based on CarGurus' proprietary market data from July 30, 2026, CarGurus experts' opinions, and generative AI.
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