Used 2020 Toyota Highlander for Sale near Winchester, VA
340 results
- 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:
- White
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 81,539
- Stock #:
- KMM17563
- VIN:
- 5TDCZRBH8MS543027
Sponsored by Kargar Motors of Manassas
2021 Toyota Highlander
L AWD
81,539 mi
$24,695
- 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:
- 82,197
- Stock #:
- 234392B
- VIN:
- 5TDGZRBHXMS151717
-$1,751
Sponsored Listing
2021 Toyota Highlander
XLE AWD
82,197 mi
$30,680
$28,929
- 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:
- 47,054
- Stock #:
- G1J0148
- VIN:
- 5TDJZRFH1KS584078
Sponsored Listing
2019 Toyota Highlander
XLE AWD
47,054 mi
$30,650
- 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:
- Silver
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 40,449
- Stock #:
- 28557254
- VIN:
- 5TDLZRBH9MS129416
2021 Toyota Highlander
XSE AWD
40,449 mi
$36,297
- 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
- Transmission:
- Automatic
- Mileage:
- 77,832
- Stock #:
- TGE587101
- VIN:
- 5TDJZRFH7KS587101
2019 Toyota Highlander
XLE AWD
77,832 mi
$26,083
- Year:
- 2021
- 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:
- 8-Speed Automatic
- Mileage:
- 93,337
- Stock #:
- FAD10046
- VIN:
- 5TDGZRAH1MS529442
-$2,500
2021 Toyota Highlander
XLE FWD
93,337 mi
$26,995
$24,495
- 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:
- Gray
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 69,266
- Stock #:
- MX4475
- VIN:
- 5TDBZRFH6KS953103
2019 Toyota Highlander
LE AWD
69,266 mi
$24,374
- 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:
- Blue
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 41,428
- Stock #:
- 59757A
- VIN:
- 5TDHZRBH9MS557363
2021 Toyota Highlander
XLE AWD
41,428 mi
$34,490
- 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:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Saddle Tan)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 87,203
- Stock #:
- KS941260A
- VIN:
- 5TDDZRFH5KS941260
2019 Toyota Highlander
Limited AWD
87,203 mi
$28,203
- 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:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 59,053
- Stock #:
- P4536A
- VIN:
- 5TDJZRFH5KS607054
2019 Toyota Highlander
XLE AWD
59,053 mi
$28,955
- 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:
- Shoreline Mist
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 80,498
- Stock #:
- A13075A
- VIN:
- 5TDBZRFH1KS927279
2019 Toyota Highlander
LE Plus AWD
80,498 mi
$22,074
- 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:
- White (Blizzard Pearl)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 110,856
- Stock #:
- Y6107
- VIN:
- 5TDDZRBH5MS058185
2021 Toyota Highlander
Limited AWD
110,856 mi
$28,576
- 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
$33,987
CarGurus Analysis:
2020 Toyota Highlander
With 3,113 currently listed for sale and an average price of $28,406.00, 34.4% of 2020 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Toyota Highlander 4.6 / 5 stars.
70.7% of 2020 Highlander models on CarGurus are accident-free.
The 2020 Toyota Highlander boasts a redesigned interior focused on passenger comfort, advanced safety features, and a smooth ride, making it an appealing choice for families.
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 52,293
- Stock #:
- 6H3799A
- VIN:
- 5TDHZRBH3MS103948
2021 Toyota Highlander
XLE AWD
52,293 mi
$32,245
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White (Blizzard Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 85,908
- Stock #:
- T136771A
- VIN:
- 5TDYZRAH2MS035725
2021 Toyota Highlander
Limited FWD
85,908 mi
$30,978
- 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:
- 2019
- 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:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 131,131
- Stock #:
- 566997
- VIN:
- 5TDKZRFH0KS566997
2019 Toyota Highlander
SE FWD
131,131 mi
$21,552
- 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:
- Silver
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 8-Speed Automatic
- Mileage:
- 82,723
- Stock #:
- 10349
- VIN:
- 5TDBZRFH7KS932437
2019 Toyota Highlander
LE AWD
82,723 mi
$20,228
- 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:
- Black
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Red
- Transmission:
- Automatic
- Mileage:
- 71,213
- Stock #:
- 121020
- VIN:
- 5TDLZRBHXMS121020
2021 Toyota Highlander
XSE AWD
71,213 mi
$28,844
- 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:
- Almond
- Transmission:
- 8-Speed Automatic
- Mileage:
- 82,429
- Stock #:
- TB076834A
- VIN:
- 5TDJZRFH4KS570644
2019 Toyota Highlander
XLE AWD
82,429 mi
$27,767
- 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:
- Gray
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 54,833
- Stock #:
- KWGTKS571238
- VIN:
- 5TDJZRFH9KS571238
2019 Toyota Highlander
XLE AWD
54,833 mi
$27,995
- 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:
- White (Blizzard Pearl)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 67,487
- Stock #:
- LS035468
- VIN:
- 5TDDZRBH3LS035468
2020 Toyota Highlander
Limited AWD
67,487 mi
$32,990
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 45,528
- Stock #:
- 102617
- VIN:
- 5TDGZRBH8LS513185
Sponsored Listing
2020 Toyota Highlander
XLE AWD
45,528 mi
$30,781
CarGurus Analysis: 2020 Toyota Highlander
overall
Summary
With 3,113 currently listed for sale and an average price of $28,406.00, 34.4% of 2020 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Toyota Highlander 4.6 / 5 stars.
70.7% of 2020 Highlander models on CarGurus are accident-free.
The 2020 Toyota Highlander boasts a redesigned interior focused on passenger comfort, advanced safety features, and a smooth ride, making it an appealing choice for families.
Why it stands out
The 2020 Toyota Highlander distinguishes itself in the crowded midsize SUV segment with its remarkable combination of comfort, spaciousness, and standard advanced safety features. Designed from the ground up, it offers a luxurious feel that rivals some higher-end vehicles, such as Lexus models, making driving it a serene experience. Although some users note concerns about the handling and interior material quality, the vast majority appreciate its smooth ride and extensive technology. The Highlander's advanced infotainment options, including compatibility with Apple CarPlay and Android Auto, coupled with a solid set of safety systems like Toyota Safety Sense 2.0, ensure that it meets the needs of modern families. It's worth mentioning that while the Highlander excels in providing a comfortable passenger experience, the lack of excitement in driving dynamics may not appeal to all buyers.
Other model years to consider
- Average price: $39,151.00
- Good/great deal percentage: 36.1%
- User rating: 5 / 5
- Total listings: 4,033
- 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
This analysis is based on CarGurus' proprietary market data from June 22, 2026, CarGurus experts' opinions, and generative AI.
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4.6 Overall rating
Filter by rating
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.
Anonymous
Reviewed a 2020 Toyota Highlander on Nov 8, 2020
Most comfortable riding vehicle that we have ever purchased. Great features and a great looking vehicle as well.
Kris B
Reviewed a 2020 Toyota Highlander on May 22, 2023
Absolutely love this car. Great comfortable family vehicle with plenty of space, and features
Lee W
Reviewed a 2020 Toyota Highlander on Feb 28, 2020
The ride was smooth, the Highlander is quick and very quiet. I loved many of the features it had, like the posted speed limit on the instrument cluster. What really disappointed me was the passenger seat comfort. The seat bottom only adjusts fron-to-rear, not up or down so I wasn’t as comfortable in it as I was the Hyundai Palisade or the Kia Telluride. It’s still a really good vehicle.
2020 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| Platinum FWD | $46,850 |
| LE FWD | $36,800 |
| LE AWD | $38,400 |
| Limited FWD | $43,650 |
| Platinum AWD | $48,800 |
| Limited AWD | $45,600 |
| XLE FWD | $39,600 |
| XLE AWD | $41,200 |
2020 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2020 Toyota Highlander prices has changed over time.
See more price trends2020 Toyota Highlander Pricing Analysis
Pricing by Popular US Cities
Market Area: Nationwide
Key Insights
- Highest Average Price in Dallas: The average price in Dallas, TX ($28,763) indicates stronger demand relative to inventory, possibly due to regional preferences for larger vehicles.
- Lowest Average Price in New York City: NYC's average price is $28,178, showcasing the potential for better deals in urban markets.
- Price Stability: Cities like Philadelphia (266 listings) and Washington, DC (309 listings) demonstrate average prices close to national trends, reflecting consistent inventory levels.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Dallas, TX | 236 | $28,763 |
| Philadelphia, PA | 266 | $28,742 |
| Washington, DC | 309 | $27,134 |
| Dallas, TX | 236 | $28,763 |
| New York, NY | 313 | $28,178 |
| Los Angeles, CA | 200 | $26,247 |
| Chicago, IL | 242 | $27,493 |
| Houston, TX | 231 | $27,491 |
| Atlanta, GA | 257 | $27,007 |
| Miami, FL | 168 | $26,261 |
Pricing by Trim Packages
Key Insights
- AWD Trims Dominate Market: Trims such as XLE AWD (3,124 listings) lead in market supply, reflecting strong demand for all-weather capability.
- Limited Trims at Premium Pricing: The Limited AWD ($45,600 MSRP) remains among the highest priced trims, about ~10% above average market prices, pointing to consumer preference for luxury features.
- FWD vs AWD Dynamics: The XLE FWD (1,396 listings) offers a lower MSRP ($39,600), catering to budget-conscious buyers while still providing desirable features.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 3124 | $41,200 | AWD | 3.5L 295 hp V6 |
| XLE FWD | 1396 | $39,600 | FWD | 3.5L 295 hp V6 |
| Limited AWD | 1239 | $45,600 | AWD | 3.5L 295 hp V6 |
| LE AWD | 782 | $38,400 | AWD | 3.5L 295 hp V6 |
| LE FWD | 780 | $36,800 | FWD | 3.5L 295 hp V6 |
| Platinum AWD | 559 | $48,800 | AWD | 3.5L 295 hp V6 |
| Limited FWD | 377 | $43,650 | FWD | 3.5L 295 hp V6 |
| Limited Platinum AWD | 309 | $48,800 | AWD | 3.5L 295 hp V6 |
Pricing Analysis by Model Year
Key Insights
- Increase in Newer Models' Average Pricing: The 2026 model is priced at $51,688, indicating strong demand with about a 12.6% markup compared to its original MSRP.
- Significant Depreciation for Older Models: For instance, the 2015 model shows a decline to $17,323, which is ~41.0% below MSRP, making it less appealing as a new buyer option compared to newer models.
- Best Value in the 2022 Model Year: The 2022 Highlander is priced at $34,011, which is about 5.6% depreciation, indicating a minuscule drop in price while still retaining newer features.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 | $45,870 | $51,688 | +12.6% |
| 2025 | $40,320 | $41,521 | +3.0% |
| 2024 | $39,270 | $39,398 | +0.3% |
| 2023 | $36,620 | $36,512 | -0.3% |
| 2022 | $35,855 | $34,011 | -5.6% |
| 2021 | $35,085 | $30,884 | -12.0% |
| 2019 | $31,830 | $24,667 | -22.6% |
| 2018 | $31,230 | $22,588 | -27.7% |
| 2017 | $30,630 | $20,971 | -31.5% |
| 2016 | $30,490 | $19,010 | -37.7% |
| 2015 | $29,765 | $17,323 | -41.0% |
These recommendations are based on CarGurus' proprietary market data from June 25, 2026, CarGurus experts' opinions, and generative AI.
