Used Toyota Highlander for Sale near Winchester, VA
610 results
- 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:
- Red (Ruby Flare Pearl)
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- Automatic
- Mileage:
- 53,478
- Stock #:
- PS026467
- VIN:
- 5TDKDRAH4PS026467
Sponsored by AutoNation Toyota White Marsh
2023 Toyota Highlander
XLE FWD
53,478 mi
$35,799
- Year:
- 2012
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Tan)
- Transmission:
- 5-Speed Automatic
- Mileage:
- 180,285
- Stock #:
- 6774
- VIN:
- 5TDDK3EHXCS149562
Sponsored Listing
2012 Toyota Highlander
Limited AWD
180,285 mi
$12,076
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 113,656
- Stock #:
- KS993861
- VIN:
- 5TDBZRFH6KS993861
Sponsored Listing
2019 Toyota Highlander
LE AWD
113,656 mi
$21,299
- Year:
- 2012
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Cypress Pearl
- Fuel type:
- Gasoline
- Interior color:
- Brown (Sand Beige)
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 110,880
- Stock #:
- L025872A
- VIN:
- 5TDDK3EH8CS102921
2012 Toyota Highlander
Limited AWD
110,880 mi
$16,794
- Year:
- 2017
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Predawn Gray Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 114,969
- Stock #:
- 25182A
- VIN:
- 5TDJZRFH7HS434484
2017 Toyota Highlander
XLE AWD
114,969 mi
$18,795
- Year:
- 2020
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Red
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 62,461
- Stock #:
- 28077709
- VIN:
- 5TDFZRBH5LS055021
2020 Toyota Highlander
Platinum AWD
62,461 mi
$34,647
- Year:
- 2015
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Ooh La La Rouge Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Beige)
- Transmission:
- 6-Speed Automatic
- Mileage:
- 94,622
- Stock #:
- BM485B
- VIN:
- 5TDJKRFH8FS146510
2015 Toyota Highlander
XLE
94,622 mi
$19,995
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Ooh La La Rouge Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 71,884
- Stock #:
- 61305A
- VIN:
- 5TDJZRFH4JS810032
2018 Toyota Highlander
XLE AWD
71,884 mi
$26,297
- Year:
- 2017
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Gray
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic
- Mileage:
- 91,869
- Stock #:
- 4053
- VIN:
- 5TDJZRFH1HS450163
2017 Toyota Highlander
XLE AWD
91,869 mi
$22,495
- Year:
- 2017
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Silver
- Fuel type:
- Gasoline
- Interior color:
- Brown (Beige)
- Transmission:
- 6-Speed Automatic
- Mileage:
- 121,306
- Stock #:
- 4052
- VIN:
- 5TDBZRFH6HS440166
2017 Toyota Highlander
LE Plus AWD
121,306 mi
$17,995
- Year:
- 2016
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- White (Blizzard Pearl)
- Fuel type:
- Gasoline
- Interior color:
- Almond
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 180,170
- Stock #:
- 28388A
- VIN:
- 5TDJKRFH5GS298925
2016 Toyota Highlander
XLE AWD
180,170 mi
$16,099
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 114,540
- Stock #:
- P18501
- VIN:
- 5TDJZRFH2JS914387
2018 Toyota Highlander
XLE AWD
114,540 mi
$23,599
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Almond
- Transmission:
- 8-Speed Automatic
- Mileage:
- 89,438
- Stock #:
- 19464D
- VIN:
- 5TDJZRFH8JS541274
-$800
2018 Toyota Highlander
XLE AWD
89,438 mi
$25,467
$24,667
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:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Shoreline Blue Pearl
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- Automatic
- Mileage:
- 88,910
- Stock #:
- 266160A
- VIN:
- 5TDJZRFH9JS827859
2018 Toyota Highlander
XLE AWD
88,910 mi
$23,990
- Year:
- 2015
- 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:
- Brown (Beige)
- Transmission:
- 6-Speed Automatic
- Mileage:
- 112,750
- Stock #:
- 4047
- VIN:
- 5TDZKRFH3FS104068
2015 Toyota Highlander
LE Plus
112,750 mi
$17,995
- Year:
- 2017
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Ooh La La Rouge Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 103,301
- Stock #:
- 25959
- VIN:
- 5TDDZRFH2HS455952
2017 Toyota Highlander
Limited AWD
103,301 mi
$22,990
- Year:
- 2016
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Blue
- Fuel type:
- Gasoline
- Interior color:
- Almond
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 164,105
- Stock #:
- 701311AQ
- VIN:
- 5TDJKRFHXGS339789
2016 Toyota Highlander
XLE AWD
164,105 mi
$17,905
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 62,057
- Stock #:
- E818847A
- VIN:
- 5TDBZRFH7KS989009
2019 Toyota Highlander
LE AWD
62,057 mi
$25,485
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Predawn Gray Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 56,380
- Stock #:
- 144427
- VIN:
- 5TDJZRFH0JS546033
2018 Toyota Highlander
XLE AWD
56,380 mi
$28,495
- 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:
- White (Blizzard Pearl)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 25,687
- Stock #:
- 26HT152A
- VIN:
- 5TDDZRFH5KS992516
2019 Toyota Highlander
Limited AWD
25,687 mi
$33,497
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 57,310
- Stock #:
- 28543534
- VIN:
- 5TDJZRBH2MS093852
2021 Toyota Highlander
XSE AWD
57,310 mi
$36,497
- Year:
- 2013
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Nautical Blue Metallic
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 86,362
- Stock #:
- PT14104A
- VIN:
- 5TDBK3EH3DS250662
2013 Toyota Highlander
SE AWD
86,362 mi
$16,800
- 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:
- Blueprint
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 9,560
- Stock #:
- SS588343
- VIN:
- 5TDKDRBH2SS588343
Sponsored Listing
2025 Toyota Highlander
XSE AWD
9,560 mi
$45,799
FAQs
How much does the Toyota Highlander cost in Winchester, VA?
How many Toyota Highlander vehicles in Winchester, VA 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.
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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 | $53,525 |
| XLE AWD | $45,870 |
| XSE AWD | $47,940 |
| Limited AWD | $50,325 |
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$33,228
- User rating4.4444
2020 Toyota Highlander
- Expert review8/10
- MSRP$34,600-$48,800
- Avg. price$28,259
- User rating4.6
2021 Toyota Highlander
- Expert review8/10
- MSRP$35,085-$49,190
- Avg. price$30,331
- User rating4.8636
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