New & Used 2026 Toyota Highlander for Sale near Windermere, FL
60 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:
- Silver
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 26,655
- Stock #:
- 73725
- VIN:
- 5TDKDRAH1SS553312
Sponsored Listing
2025 Toyota Highlander
LE FWD
26,655 mi
Orlando, FL
15 mi away
Fair Deal
$34,798
- 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:
- Blue
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 6,305
- Stock #:
- F21190B
- VIN:
- 5TDKDRAH1SS554038
Sponsored Listing
2025 Toyota Highlander
XLE FWD
6,305 mi
Orlando, FL
9 mi away
Fair Deal
$44,353
- 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:
- 25,174
- Stock #:
- 73724
- VIN:
- 5TDKDRAH6SS551460
Sponsored Listing
2025 Toyota Highlander
LE FWD
25,174 mi
Orlando, FL
15 mi away
Fair Deal
$34,898
- 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
- Transmission:
- Automatic
- Mileage:
- 33,095
- Stock #:
- 74072
- VIN:
- 5TDKDRBH8SS579484
2025 Toyota Highlander
XSE AWD
33,095 mi
Orlando, FL
15 mi away
Fair Deal
$41,198
- 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:
- 8-Speed Automatic
- Mileage:
- 28,588
- Stock #:
- 16672551
- VIN:
- 5TDKDRAH5SS554639
2025 Toyota Highlander
LE FWD
28,588 mi
15 mi away
Good Deal
$34,598
- 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:
- 26,326
- Stock #:
- 73733
- VIN:
- 5TDKDRAHXSS552160
2025 Toyota Highlander
LE FWD
26,326 mi
Orlando, FL
15 mi away
Fair Deal
$34,798
- 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:
- 8-Speed Automatic
- Mileage:
- 28,202
- Stock #:
- 16671874
- VIN:
- 5TDKDRAHXSS554622
2025 Toyota Highlander
LE FWD
28,202 mi
15 mi away
Fair Deal
$34,598
- 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:
- Cement
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 11,369
- Stock #:
- PM589245
- VIN:
- 5TDKDRBH7SS589245
2025 Toyota Highlander
XSE AWD
11,369 mi
Home delivery from Pleasantville, NJ
Price includes $1,796 shipping
Fair Deal
$46,686
- 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:
- 29,823
- Stock #:
- SS576585P
- VIN:
- 5TDKDRBHXSS576585
2025 Toyota Highlander
XSE AWD
29,823 mi
Sanford, FL
25 mi away
Fair Deal
$42,394
- 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:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 25,794
- Stock #:
- S551779
- VIN:
- 5TDKDRAH6SS551779
2025 Toyota Highlander
XLE FWD
25,794 mi
Orlando, FL
10 mi away
Fair Deal
$42,707
- 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 $1,800 shipping
Fair Deal
$43,454
- 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:
- 32,528
- Stock #:
- 28734437
- VIN:
- 5TDKDRAHXSS553891
2025 Toyota Highlander
LE FWD
32,528 mi
Store transfer to Orlando, FL
Price includes $1,999 shipping
Fair Deal
$34,997
- 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:
- 28,619
- Stock #:
- SS552017
- VIN:
- 5TDKDRAH5SS552017
Price drop
-$900
2025 Toyota Highlander
LE FWD
28,619 mi
Home delivery from Palmetto Bay, FL
Free home delivery
Great Deal
$33,098
$32,198
CarGurus Analysis:
2026 Toyota Highlander
- With 929 currently listed for sale and an average price of $50,200.00, 37.0% of 2026 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
- 94.5% of 2026 Highlander models on CarGurus are accident free.
- 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
- Transmission:
- Automatic
- Mileage:
- 17,690
- Stock #:
- 73851
- VIN:
- 5TDKDRBH6SS588703
2025 Toyota Highlander
XSE AWD
17,690 mi
Orlando, FL
15 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:
- 23,689
- Stock #:
- 73601
- VIN:
- 5TDKDRAH7SS554741
2025 Toyota Highlander
LE FWD
23,689 mi
Orlando, FL
15 mi away
Good Deal
$35,098
- 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:
- Blue
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 6,305
- Stock #:
- F21190B
- VIN:
- 5TDKDRAH1SS554038
2025 Toyota Highlander
XLE FWD
6,305 mi
Orlando, FL
9 mi away
Fair Deal
$44,353
- 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:
- 26,655
- Stock #:
- 73725
- VIN:
- 5TDKDRAH1SS553312
2025 Toyota Highlander
LE FWD
26,655 mi
Orlando, FL
15 mi away
Fair Deal
$34,798
- 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:
- 26,147
- Stock #:
- 73723
- VIN:
- 5TDKDRAH6SS550664
2025 Toyota Highlander
LE FWD
26,147 mi
Orlando, FL
15 mi away
Fair Deal
$34,798
- 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 $741 shipping
Fair Deal
$46,535
- 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:
- 25,174
- Stock #:
- 73724
- VIN:
- 5TDKDRAH6SS551460
2025 Toyota Highlander
LE FWD
25,174 mi
Orlando, FL
15 mi away
Fair Deal
$34,898
- 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:
- Gray
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 22,913
- Stock #:
- 73645
- VIN:
- 5TDKDRAH7SS551368
2025 Toyota Highlander
LE FWD
22,913 mi
Orlando, FL
15 mi away
Fair Deal
$35,335
- 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:
- 13,401
- Stock #:
- TS595290
- VIN:
- 5TDKDRBH7TS595290
2026 Toyota Highlander
Limited AWD
13,401 mi
Orlando, FL
19 mi away
Fair Deal
$50,417
- 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:
- 23,689
- Stock #:
- 73601
- VIN:
- 5TDKDRAH7SS554741
Sponsored Listing
2025 Toyota Highlander
LE FWD
23,689 mi
Orlando, FL
15 mi away
Good Deal
$35,098
CarGurus Analysis: 2026 Toyota Highlander
Summary
- With 929 currently listed for sale and an average price of $50,200.00, 37.0% of 2026 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
- 94.5% of 2026 Highlander models on CarGurus are accident free.
Why it stands out
The 2026 Toyota Highlander continues to be a top choice in the crossover segment, thanks to its blend of spaciousness, comfort, and reliability. Having pioneered the midsize crossover market, the Highlander offers a smooth, car-like driving experience aided by its unibody construction, which enhances fuel efficiency and handling compared to traditional body-on-frame SUVs. This model year, with an average price of $50,200, features a thoughtful design that emphasizes interior versatility, making it an ideal family vehicle. While its performance may not excite driving enthusiasts, the Highlander's ample cargo space, advanced safety features, and reputation for reliability make it appealing to practical buyers. The 2026 model also benefits from a high accident-free percentage, reinforcing its standing as a reliable and safe option for families.
Other model years to consider
- Average price: $39,141.00
- Good/great deal percentage: 36.5%
- User rating: 5 / 5
- Total listings: 4,139
- Average price: $36,279.00
- Good/great deal percentage: 35.1%
- User rating: 4.75 / 5
- Total listings: 4,691
- Average price: $16,094.00
- Good/great deal percentage: 34.3%
- User rating: 4.78 / 5
- Total listings: 1,198
This analysis is based on CarGurus' proprietary market data from June 29, 2026, CarGurus experts' opinions, and generative AI.
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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
$50,131
0.7%
2026 Toyota Highlander
Index Price
$29,183
0.3%
All used vehicles
2026 Toyota Highlander Pricing Analysis
Pricing by Popular US Cities
Market Area: Nationwide
Key Insights
- Highest Prices in Houston: The market in Houston, TX ($54,991) exhibits the highest average price, potentially influenced by demand factors unique to the area.
- Lowest Prices in Dallas: Conversely, Dallas, TX ($46,991) offers the lowest average pricing among the listed cities, suggesting it may be more competitive or have different inventory dynamics.
- Moderate Inventory Across Cities: Most cities show a moderate number of listings, with Philadelphia (52 listings) and Dallas (52 listings) maintaining solid inventory levels, contributing to price stability.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Houston, TX | 78 | $54,991 |
| Philadelphia, PA | 52 | $53,923 |
| New York, NY | 49 | $53,887 |
| Boston, MA | 82 | $53,987 |
| Los Angeles, CA | 75 | $51,025 |
| Miami, FL | 29 | $50,591 |
| Atlanta, GA | 53 | $51,265 |
| Chicago, IL | 43 | $49,880 |
| Washington, DC | 40 | $49,900 |
| Dallas, TX | 52 | $46,991 |
Pricing by Trim Packages
Key Insights
- XLE AWD is Most Abundant: The XLE AWD trim leads inventory with 3,124 listings, reflecting strong demand for this variant.
- Price Range Among Trims: The trims exhibit a range of prices, with the Limited AWD ($50,325 MSRP) being the highest, indicating the premium features it offers compared to lower-end trims like XLE AWD ($45,870 MSRP).
- AWD Appeal: The high inventory of AWD trims underscores a strong market preference for enhanced traction and performance.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 3,124 | $45,870 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 1,239 | $50,325 | AWD | 2.4L 265 hp I4 |
| XSE AWD | 728 | $47,940 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 559 | $53,525 | AWD | 2.4L 265 hp I4 |
Pricing Analysis by Model Year
Key Insights
- Minimal Depreciation in New Models: The 2025 Highlander currently averages $41,521, roughly 0.5% higher than MSRP, reflecting high demand for new vehicles.
- Steep Declines for Older Models: Notably, the 2015 Highlander shows significant depreciation, with its average price at $17,323, down ~41% from its original MSRP.
- Value Retention for Recent Years: The 2021 Highlander holds relatively well at -12%, indicating it may be a good value option for shoppers looking for a balance of price and modern features.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2025 Toyota Highlander | $40,320 | $41,521 | +3.0% |
| 2024 Toyota Highlander | $39,270 | $39,398 | +0.3% |
| 2023 Toyota Highlander | $36,620 | $36,512 | -0.3% |
| 2022 Toyota Highlander | $35,855 | $34,011 | -5.1% |
| 2021 Toyota Highlander | $35,085 | $30,884 | -12.0% |
| 2020 Toyota Highlander | $34,600 | $28,914 | -16.5% |
| 2019 Toyota Highlander | $31,830 | $24,667 | -22.7% |
| 2018 Toyota Highlander | $31,230 | $22,588 | -27.8% |
| 2017 Toyota Highlander | $30,630 | $20,971 | -31.5% |
| 2016 Toyota Highlander | $30,490 | $19,010 | -37.6% |
| 2015 Toyota Highlander | $29,765 | $17,323 | -41.7% |
These recommendations are based on CarGurus' proprietary market data from June 25, 2026, CarGurus experts' opinions, and generative AI.
FAQs
How much does the 2026 Toyota Highlander cost in Windermere, FL?
The average 2026 Toyota Highlander costs about $50,130.79. The average price has decreased by -1.2% since last year. The 37 for sale near Windermere, FL on CarGurus, range from $32,198 to $51,998 in price.
How many 2026 Toyota Highlander vehicles in Windermere, FL have no reported accidents or damage?
35 out of 37 for sale near Windermere, FL 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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