Used Toyota Highlander for Sale near Windermere, FL
215 results
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Predawn Gray Mica
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 94,500
- Stock #:
- JS546537
- VIN:
- 5TDKZRFH0JS546537
Sponsored by Audi South Orlando
2018 Toyota Highlander
XLE
94,500 mi
$22,983
- Year:
- 2017
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Shoreline Blue Pearl
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 91,064
- Stock #:
- HS224658
- VIN:
- 5TDKZRFHXHS224658
Sponsored Listing
2017 Toyota Highlander
XLE
91,064 mi
$20,396
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Moon Dust
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 50,006
- Stock #:
- PS035468
- VIN:
- 5TDKDRAH7PS035468
Sponsored Listing
2023 Toyota Highlander
XLE FWD
50,006 mi
$35,645
- Year:
- 2017
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 86,736
- Stock #:
- I254817A
- VIN:
- 5TDYZRFH0HS210469
2017 Toyota Highlander
Limited
86,736 mi
$23,035
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 112,013
- Stock #:
- 26735A
- VIN:
- 5TDZZRAH5NS094466
-$510
2022 Toyota Highlander
LE FWD
112,013 mi
$22,273
$21,763
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 41,324
- Stock #:
- 1120263215
- VIN:
- 5TDCZRAHXNS540018
2022 Toyota Highlander
L FWD
41,324 mi
$29,195
- Year:
- 2023
- 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:
- 40,650
- Stock #:
- W187709A
- VIN:
- 5TDKDRBH9PS006990
2023 Toyota Highlander
Limited AWD
40,650 mi
$35,576
- Year:
- 2020
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 72,029
- Stock #:
- LS026072
- VIN:
- 5TDGZRAH1LS026072
2020 Toyota Highlander
XLE FWD
72,029 mi
$26,765
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Celestial Silver Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 8-Speed Automatic
- Mileage:
- 95,191
- Stock #:
- 429987A
- VIN:
- 5TDZZRAH1NS541701
2022 Toyota Highlander
LE FWD
95,191 mi
$25,642
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Predawn Gray Mica
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 72,336
- Stock #:
- KS348592
- VIN:
- 5TDZZRFH4KS348592
2019 Toyota Highlander
LE FWD
72,336 mi
$20,794
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Predawn Gray Mica
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 6-Speed Automatic
- Mileage:
- 59,272
- Stock #:
- ST058799
- VIN:
- 5TDZARFH1KS058799
-$490
2019 Toyota Highlander
LE FWD
59,272 mi
$24,067
$23,577
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Black
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 181,998
- Stock #:
- 574009
- VIN:
- 5TDJZRFH9KS574009
-$2,000
2019 Toyota Highlander
SE AWD
181,998 mi
$17,987
$15,987
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Predawn Gray Mica
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 94,500
- Stock #:
- JS546537
- VIN:
- 5TDKZRFH0JS546537
2018 Toyota Highlander
XLE
94,500 mi
$22,983
Recommended model year:
2024 Toyota Highlander
Shop 2024 Toyota Highlander »With 4,033 currently listed for sale and an average price of $39,151.00, 36.1% of 2024 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2024 Toyota Highlander 5 / 5 stars.
88.4% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander boasts an upgraded powertrain with improved fuel efficiency and a spacious interior that remains comfortable for family journeys.
- Year:
- 2014
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- White
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 106,361
- Stock #:
- ES004313
- VIN:
- 5TDYKRFH2ES004313
2014 Toyota Highlander
Limited
106,361 mi
$18,196
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Silver
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 52,394
- Stock #:
- 28430371
- VIN:
- 5TDKZRFH8KS332154
2019 Toyota Highlander
XLE FWD
52,394 mi
$28,097
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Moon Dust
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 23,968
- Stock #:
- PS522568
- VIN:
- 5TDKDRAH3PS522568
2023 Toyota Highlander
Limited FWD
23,968 mi
$38,107
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 59,600
- Stock #:
- NS555461
- VIN:
- 5TDGZRAH1NS555461
2022 Toyota Highlander
XLE FWD
59,600 mi
$30,922
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Gray
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 67,543
- Stock #:
- 125
- VIN:
- 5TDKDRAH3PS007604
2023 Toyota Highlander
XLE FWD
67,543 mi
$29,590
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Pearl
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 49,401
- Stock #:
- 139042
- VIN:
- 5TDLZRAH7NS139042
2022 Toyota Highlander
XSE FWD
49,401 mi
$36,507
- Year:
- 2016
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Silver
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 113,891
- Stock #:
- GS121005
- VIN:
- 5TDYKRFH2GS121005
2016 Toyota Highlander
Limited
113,891 mi
$18,245
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 73,895
- Stock #:
- S086453
- VIN:
- 5TDZZRAH2MS086453
-$500
2021 Toyota Highlander
LE FWD
73,895 mi
$22,048
$21,548
- Year:
- 2017
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 92,926
- Stock #:
- P230863
- VIN:
- 5TDYZRFH5HS230863
2017 Toyota Highlander
Limited
92,926 mi
$21,791
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Black
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 181,998
- Stock #:
- 574009
- VIN:
- 5TDJZRFH9KS574009
-$2,000
Sponsored Listing
2019 Toyota Highlander
SE AWD
181,998 mi
$17,987
$15,987
FAQs
How much does the Toyota Highlander cost in Windermere, FL?
How many Toyota Highlander vehicles in Windermere, FL have no reported accidents or damage?
What fuel types are available?
4.7 Overall rating
Customers say
Overall, the Toyota Highlander has built a strong reputation across its model years for reliability, comfort, and family-friendly features. Drivers appreciate its spacious interiors and smooth rides, often highlighting its impressive safety features as a key asset. Many also enjoy the performance and power of the engines. However, some common criticisms include a lack of advanced infotainment options in older models, tight third-row seating, and varying cargo space depending on configuration. Overall, the Highlander is seen as a dependable choice for families and an excellent value in the SUV market.
AI generated from the text of customer reviews.
Filter by year
Filter by rating
What people say
Anonymous
Reviewed a 2024 Toyota XLE AWD on Dec 10, 2025
The 2024 Toyota Highlander XLE offers insane cabin room, comfort and luxury feel. The chassis makes an absolute smooth, dream and comfortable ride. Cabin rear chairs makes four adults feel like your in a Sequoia with room. Absolute beautiful and enjoyable ride and purchase
Julie W
Reviewed a 2021 Toyota Highlander on Jul 20, 2024
I loved my Highlander. I give my 2021 Toyota Highlander a 100 out of 10 on its safety. My car was a limited and it had most bells and whistles which I loved but what I loved most was that we all walked away from a collision where we were traveling 40 miles an hour and thanks to the safety design , we’re here.
Luong S
Reviewed a 2012 Toyota Base on Apr 26, 2026
This car's features are very good and have great value the only missing is it has only one key.
Sarah T
Reviewed a 2020 Toyota Highlander on Dec 7, 2025
It’s well-equipped, comfortable, and family-friendly SUV with strong safety tech, a smooth ride, and premium touches (thanks to the platinum trim) like a panoramic moonroof, leather seating, and 12” touchscreen. Its V6 offers solid power and decent fuel efficiency for a 3-row SUV, and overall it feels modern, quiet, and refined. It’s a great value if you want a reliable, upscale daily driver! The main thing it’s missing is more usable third-row and cargo space. The 3rd row is tight for adults and cargo behind it is limited. Otherwise, it’s a strong all-around pick and fits exactly what I was looking for. I would compare this to the Kia Telluride, Hyundai Palisade, Honda Pilot, and the Ford Explorer.
Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| Platinum AWD | $53,925 |
| XLE AWD | $46,270 |
| XSE AWD | $48,340 |
| Limited AWD | $50,725 |
Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of Toyota Highlander prices has changed over time.
See more price trendsToyota Highlander Pricing Analysis
Pricing Analysis by Model Year
Key Insights
- Strong Demand for Newer Models: The 2026 Toyota Highlander is priced at $51,688, marking about +12.3% above MSRP, indicating robust demand for the latest model.
- Accelerated Depreciation in Older Models: The 2016 Highlander shows a steep depreciation of −37.8% compared to MSRP, reflecting the diminishing value of older models.
- Best Value Years: The 2024 Highlander has a current average price of $39,398, only +0.3% above its MSRP, making it a strong candidate for value shopping.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $45,870 | $51,688 | +12.3% |
| 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 | -16.4% |
| 2019 Toyota Highlander | $31,830 | $24,667 | -22.6% |
| 2018 Toyota Highlander | $31,230 | $22,588 | -27.8% |
| 2017 Toyota Highlander | $30,630 | $20,971 | -31.6% |
| 2016 Toyota Highlander | $30,490 | $19,010 | -37.8% |
Pricing by Popular US Cities
Market Area: Nationwide
Key Insights
- Highest Prices in Major Urban Areas: Philadelphia, PA has the highest average price at $29,531, likely due to higher demand in dense urban areas.
- Best Value in Los Angeles: Los Angeles, CA offers a competitive average price of $26,139, showing lower pricing relative to some metropolitan areas.
- Strong Market Inventory: Cities like New York, NY and Boston, MA have significant listings (697 and 636 respectively), highlighting strong market activity and availability.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| New York, NY | 697 | $27,151 |
| Los Angeles, CA | 519 | $26,139 |
| Chicago, IL | 372 | $25,366 |
| Dallas, TX | 362 | $27,380 |
| Philadelphia, PA | 291 | $29,531 |
| Houston, TX | 374 | $25,720 |
| Miami, FL | 218 | $29,343 |
| Washington, DC | 465 | $26,757 |
| Atlanta, GA | 337 | $27,145 |
| Boston, MA | 636 | $28,250 |
Pricing by Trim Packages
Key Insights
- XLE AWD is the Most Popular Trim: With 3,124 listings, the XLE AWD represents the most common choice among consumers, indicating strong demand for this configuration.
- Price Range Among Trims: The Limited AWD trim, priced at $50,325, is the highest MSRP option and reflects a substantial increase in features and luxury compared to the base trim.
- AWD Preference: All available trims are AWD, aligning with consumer preferences for handling in various weather conditions.
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 |
These recommendations are based on CarGurus' proprietary market data from June 25, 2026, CarGurus experts' opinions, and generative AI.
CarGurus recommends the 2024 Toyota Highlander
Summary
With 4,033 currently listed for sale and an average price of $39,151.00, 36.1% of 2024 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2024 Toyota Highlander 5 / 5 stars.
88.4% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander boasts an upgraded powertrain with improved fuel efficiency and a spacious interior that remains comfortable for family journeys.
Why it stands out
The 2024 Toyota Highlander continues to uphold the reputation established by its predecessors, combining reliability with family-friendly features. Its spacious cabin provides ample comfort and versatility, making it suitable for various needs, from daily commutes to long road trips. One notable feature is the hybrid variant, offering excellent fuel efficiency without compromising on power, making it an appealing choice for eco-conscious buyers. Additionally, the Highlander’s strong safety ratings, bolstered by Toyota Safety Sense technology, ensure that families can travel with confidence.
Other model years to consider
- Average price: $36,362.00
- Good/great deal percentage: 35.1%
- User rating: 4.75 / 5
- Total listings: 4,615
- Average price: $30,529.00
- Good/great deal percentage: 35.0%
- User rating: 4.86 / 5
- Total listings: 3,229
- Average price: $18,740.00
- Good/great deal percentage: 33.6%
- User rating: 4.93 / 5
- Total listings: 1,846
These recommendations are based on CarGurus' proprietary market data from June 22, 2026, CarGurus experts' opinions, and generative AI.
Recent expert test drives
2022 Toyota Highlander
- Expert review8/10
- MSRP$35,855-$49,960
- Avg. price$33,363
- User rating4.4444
2020 Toyota Highlander
- Expert review8/10
- MSRP$34,600-$48,800
- Avg. price$28,191
- User rating4.6
2021 Toyota Highlander
- Expert review8/10
- MSRP$35,085-$49,190
- Avg. price$30,271
- User rating4.8636
Relevant articles
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.
The Best Used SUVs Under $10,000 in 2026
Can you get a great SUV for less than $10,000? Heck, yes! Our guide runs through the top 10, with options including family favorites and some upscale options.
Toyota Highlander Buying Guide: Cost, Reliability, and the Best Years to Buy
Discover the ultimate buying guide for purchasing a used Toyota Highlander, covering every generation since 2001. Whether you're a first-time buyer or a Toyota loyalist, this comprehensive overview will help you research your next pre-owned Toyota Highlander.
