Used Toyota Highlander for Sale nearWinchester, OR
18 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:
- Midnight Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black Softexfab
- Transmission:
- 8-Speed Automatic
- Mileage:
- 3
- Stock #:
- 614826
- VIN:
- 5TDKDRBH9TS614826
2026 Toyota Highlander
XLE AWD
Home delivery from Marina Del Rey, CA
Price includes $1,214 shipping
New car
TSRP $48,778
$50,114
- 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:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 2
- Stock #:
- 36476
- VIN:
- 5TDKDRBH4TS614698
2026 Toyota Highlander
Platinum AWD
Grants Pass, OR
59 mi away
New car
TSRP $56,423
$55,673
- 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:
- Blue
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 8
- Stock #:
- TC260678
- VIN:
- 5TDKDRBH0TS613838
2026 Toyota Highlander
Platinum AWD
Corvallis, OR
89 mi away
New car
TSRP $57,277
$57,437
- 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:
- 01l5
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 8
- Stock #:
- 60614
- VIN:
- 5TDKDRBH5TS614077
2026 Toyota Highlander
Platinum AWD
Albany, OR
94 mi away
New car
TSRP $57,492
$57,692
- 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 1
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Mileage:
- 0
- Stock #:
- T57545
- VIN:
- 5TDKDRBH5TS617660
2026 Toyota Highlander
Platinum AWD
Eugene, OR
56 mi away
New car
TSRP $57,597
$57,847
- 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:
- 2
- Stock #:
- 36599
- VIN:
- 5TDKDRBH3TS617074
2026 Toyota Highlander
Platinum AWD
Grants Pass, OR
59 mi away
New car
TSRP $57,597
$56,847
- 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:
- Gray (Graphite Leather Trim)
- Transmission:
- 8-Speed Dual Clutch
- Mileage:
- 0
- Stock #:
- 5TDKDRBH3TS37A725
- VIN:
- 5TDKDRBH3TS37A725
![Wind Chill Pearl [Extra_Cost_Color] 2026 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Dual Clutch](https://cdn.dlron.us/inventoryphotos/15361/5tdkdrbh3ts37a725/sp/2.png?io=true&width=640&height=480&fit=bounds&format=jpg&auto=webp)
2026 Toyota Highlander
Platinum AWD
Home delivery from Warrenton, OR
Price includes $597 shipping
New car
TSRP $57,492
$58,339
- 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
- Mileage:
- 0
- VIN:
- 5TDKDRBH0TS38A466
New arrival
2026 Toyota Highlander
Platinum AWD
Eugene, OR
56 mi away
New car
TSRP $56,899
$57,422
- 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:
- Glazed Caramel Leather Trim
- Transmission:
- 8-Speed Dual Clutch
- Mileage:
- 0
- Stock #:
- 5TDKDRBH9TS38B048
- VIN:
- 5TDKDRBH9TS38B048
![Wind Chill Pearl [Extra_Cost_Color] 2026 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Dual Clutch](https://cdn.dlron.us/inventoryphotos/15361/5tdkdrbh9ts38b048/sp/2.png?io=true&width=640&height=480&fit=bounds&format=jpg&auto=webp)
New arrival
2026 Toyota Highlander
Platinum AWD
Home delivery from Warrenton, OR
Price includes $597 shipping
New car
TSRP $57,492
$58,339
- 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:
- 0
- Stock #:
- TS617895
- VIN:
- 5TDKDRBHXTS617895
Photos coming soon
New arrival
2026 Toyota Highlander
Limited AWD
Springfield, OR
55 mi away
New car
TSRP $54,772
$53,022
- 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:
- 0
- Stock #:
- TS617357
- VIN:
- 5TDKDRBH4TS617357
Photos coming soon
2026 Toyota Highlander
XSE AWD
Springfield, OR
55 mi away
New car
TSRP $51,063
$51,063
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 1
- Stock #:
- T26555
- VIN:
- 5TDKDRBH1TS617834
Photos coming soon
New arrival
2026 Toyota Highlander
Platinum AWD
South Beach, OR
98 mi away
New car
TSRP $57,597
$57,532
- 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:
- 25
- Stock #:
- T26566
- VIN:
- 5TDKDRBH2TS613761
Photos coming soon
2026 Toyota Highlander
Platinum AWD
South Beach, OR
98 mi away
New car
TSRP $55,908
$55,643
- 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:
- 4
- Stock #:
- TS614162
- VIN:
- 5TDKDRBH7TS614162
Photos coming soon
2026 Toyota Highlander
XSE AWD
Springfield, OR
55 mi away
New car
TSRP $50,798
$50,798
- 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:
- 0
- Stock #:
- TS618255
- VIN:
- 5TDKDRBH1TS618255
Photos coming soon
New arrival
2026 Toyota Highlander
Platinum AWD
Medford, OR
69 mi away
New car
TSRP $57,017
$56,267
- 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
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 3
- Stock #:
- T26597
- VIN:
- 5TDKDRBH7TS615392
Photos coming soon
2026 Toyota Highlander
Platinum AWD
Roseburg, OR
4 mi away
New car
TSRP $57,719
No Price Listed
- 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:
- 3
- Stock #:
- T26647
- VIN:
- 5TDKDRBH2TS617762
Photos coming soon
2026 Toyota Highlander
Limited AWD
Roseburg, OR
4 mi away
New car
TSRP $54,882
No Price Listed
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 0
- Stock #:
- TS616885
- VIN:
- 5TDKDRBH2TS616885
Photos coming soon
New arrival
2026 Toyota Highlander
Platinum AWD
Medford, OR
69 mi away
New car
TSRP $57,597
$56,847
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
$28,998
0.5%
All used vehicles
2027 Toyota Highlander Pricing Analysis
Pricing Analysis by Model Year
Key Insights
- New Model Premium: The 2026 Highlander is priced at $51,380, reflecting a 10.4% increase 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 $23,997, which is -24.5% compared to its original MSRP.
- Best Value in Recent Models: The 2022 Highlander is priced at $33,135, representing a -7.5% depreciation, making it a competitive option for buyers seeking value.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $46,270 | $51,380 | +10.4% |
| 2025 Toyota Highlander | $40,320 | $41,965 | +4.1% |
| 2024 Toyota Highlander | $39,270 | $39,271 | +0.0% |
| 2023 Toyota Highlander | $36,620 | $35,398 | -3.3% |
| 2022 Toyota Highlander | $35,855 | $33,135 | -7.5% |
| 2021 Toyota Highlander | $35,085 | $30,496 | -13.1% |
| 2020 Toyota Highlander | $34,600 | $28,171 | -18.7% |
| 2019 Toyota Highlander | $31,830 | $23,997 | -24.5% |
| 2018 Toyota Highlander | $31,230 | $21,925 | -29.8% |
| 2017 Toyota Highlander | $30,630 | $20,641 | -32.5% |
| 2016 Toyota Highlander | $30,490 | $18,568 | -39.1% |
| 2015 Toyota Highlander | $29,765 | $16,968 | -42.9% |
These recommendations are based on CarGurus' proprietary market data from September 3, 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.
Relevant articles
CarGurus Editorial Team
The Best Three-Row SUVs of 2026
There’s no escaping it: SUVs are everywhere. Minivans offer the space for the most passengers and gear, but big, three-row SUVs deliver on both while offering some level of performance, on and off the paved roads.
Jeremy Korzeniewski
2026 Toyota Highlander Pricing, Specs, and Release Date
Now in its final year as a gas-powered model, the three-row 2026 Toyota Highlander crossover SUV is essentially a carryover with standard all-wheel drive and a turbocharged engine.
CarGurus Editorial Team
Best Cars for New Parents
Discover the best family cars for first-time parents in 2025, accounting for door access, car seat compatibility, and other real-world considerations new parents will want to keep in mind.
2027 Toyota Highlander in Eugene OR2027 Toyota Highlander in Grants Pass OR2027 Toyota Highlander in Corvallis OR2027 Toyota Highlander in Klamath Falls OR2027 Toyota Highlander in Bend OR2027 Toyota Highlander in Salem OR2027 Toyota Highlander in Portland OR2027 Toyota Highlander in Eureka CA2027 Toyota Highlander in Redding CA
Toyota Highlander in Winchester ORToyota Sedans for Sale in Winchester ORToyota SUVs & Crossovers for Sale in Winchester OROld Toyota Pickups for Sale in Winchester ORUsed Toyota Electric Cars for SaleReliable Cars For Sale in Winchester ORToyota Trucks for Sale in Winchester ORBest 3-Row SUVs For Sale in Winchester OR
All Used CarsManual Transmission CarsLuxury CarsCars with Red InteriorCheap Manual CarsHybrid CarsSports CarsElectric SUVsCheap TrucksSmall CarsThird Row SUVsThree Quarter Ton TrucksLifted TrucksManual Transmission TrucksDiesel TrucksHybrid SUVsDually TrucksOne Ton TrucksCheap SUVsLifted Ford Trucks4x4 TrucksWork TrucksAWD SUVsFord TrucksChevrolet TrucksToyota TrucksTrucks Under $10,000Cars Under $15,000Sports Cars Under $20,000Trucks Under $20,000Used Sedans for Sale with Low Mileage in WinchesterUsed SUVs / Crossovers for Sale with Low Mileage in WinchesterUsed Hatchbacks for Sale with Low Mileage in WinchesterUsed Convertibles for Sale with Low Mileage in WinchesterUsed Vans for Sale with Low Mileage in WinchesterUsed Minivans for Sale with Low Mileage in WinchesterUsed Pickup Trucks for Sale with Low Mileage in WinchesterUsed Coupes for Sale with Low Mileage in WinchesterUsed Wagons for Sale with Low Mileage in Winchester
