Used Toyota Highlander for Sale nearChesapeake, VA
730 vehicles found
See the total price upfront.
Only show listings that include dealer fees- 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:
- Gray (Graphite)
- Transmission:
- Automatic
- Mileage:
- 64,980
- Stock #:
- MS056759
- VIN:
- 5TDFZRBH6MS056759
Sponsored by Classic Toyota of Hampton
2021 Toyota Highlander
Platinum AWD
64,980 mi
$35,949
- 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
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 5-Speed Automatic
- Mileage:
- 183,080
- VIN:
- 5TDBK3EH1DS196228
Sponsored Listing
2013 Toyota Highlander
SE AWD
183,080 mi
$8,434
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 22,040
- Stock #:
- PN2986
- VIN:
- 5TDKDRAH9PS034838
Sponsored Listing
2023 Toyota Highlander
XLE FWD
22,040 mi
$40,949
- 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:
- Predawn Gray Mica
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 6-Speed Automatic
- Mileage:
- 134,512
- Stock #:
- GS287740A
- VIN:
- 5TDJKRFH4GS287740
2016 Toyota Highlander
XLE AWD
134,512 mi
$18,616
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 118,156
- Stock #:
- FP3383
- VIN:
- 5TDBZRFH2HS377471
2017 Toyota Highlander
LE Plus AWD
118,156 mi
$18,698
- 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:
- Magnetic Gray Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 36,075
- Stock #:
- 144449
- VIN:
- 5TDHZRBH7MS062675
2021 Toyota Highlander
XLE AWD
36,075 mi
$34,485
- 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:
- Red (Maroon)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 185,741
- Stock #:
- 890053
- VIN:
- 5TDJZRFH5JS890053
2018 Toyota Highlander
SE AWD
185,741 mi
$14,900
- 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:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 89,647
- Stock #:
- 6K252B
- VIN:
- 5TDKZRFH2KS556942
2019 Toyota Highlander
XLE FWD
89,647 mi
$23,689
- 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:
- Silver Sky Metallic
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 87,100
- Stock #:
- TWT75254A
- VIN:
- 5TDDKRFH8GS262952
2016 Toyota Highlander
Limited Platinum AWD
87,100 mi
$25,490
- 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:
- Gray
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 114,583
- Stock #:
- ESRKS996759
- VIN:
- 5TDBZRFH8KS996759
2019 Toyota Highlander
LE AWD
114,583 mi
$16,950
- 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
2021 Toyota Highlander
XLE FWD
93,337 mi
$25,519
- 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:
- Celestial Silver Metallic
- Fuel type:
- Gasoline
- Transmission:
- 6-Speed Automatic
- Mileage:
- 132,782
- Stock #:
- H38384A
- VIN:
- 5TDZARFH1HS025276
2017 Toyota Highlander
LE
132,782 mi
$17,889
- 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:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 31,189
- Stock #:
- T75218A
- VIN:
- 5TDKDRBH9PS045689
2023 Toyota Highlander
XLE AWD
31,189 mi
$38,450
Recommended model year:
2024 Toyota Highlander
Shop 2024 Toyota Highlander »With 3,978 currently listed for sale and an average price of $39,108.00, 34.9% 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.
88.8% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander features a spacious interior, advanced safety technology, and a smooth ride, making it an excellent choice for families.
- 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:
- Pearl
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Red
- Transmission:
- 8-Speed Automatic
- Mileage:
- 42,387
- Stock #:
- 28933
- VIN:
- 5TDKDRAH5PS030396
2023 Toyota Highlander
XSE FWD
42,387 mi
$38,923
- Year:
- 2022
- 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:
- 8-Speed Automatic
- Mileage:
- 88,662
- Stock #:
- WYC-562432
- VIN:
- 5TDDZRBH5NS562432
2022 Toyota Highlander
Limited AWD
88,662 mi
$33,729
- 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:
- 62,296
- Stock #:
- 70003549
- VIN:
- 5TDZARFHXGS018227
2016 Toyota Highlander
LE
62,296 mi
$23,147
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 72,398
- Stock #:
- 91346
- VIN:
- 5TDKDRAH6PS001408
2023 Toyota Highlander
L FWD
72,398 mi
$29,563
- 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
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 102,678
- Stock #:
- CV049068
- VIN:
- 5TDKKRFHXFS049068
2015 Toyota Highlander
XLE
102,678 mi
$17,250
- 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:
- Silver
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 89,585
- Stock #:
- 549650
- VIN:
- 5TDJZRFH6JS549650
2018 Toyota Highlander
XLE AWD
89,585 mi
$23,628
- 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:
- Gray (Graphite)
- Transmission:
- Automatic
- Mileage:
- 64,980
- Stock #:
- MS056759
- VIN:
- 5TDFZRBH6MS056759
2021 Toyota Highlander
Platinum AWD
64,980 mi
$35,949
- 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:
- Black
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 103,675
- Stock #:
- 7545
- VIN:
- 5TDJZRFH2HS422226
2017 Toyota Highlander
XLE AWD
103,675 mi
$22,049
- 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:
- Gray
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 227,121
- VIN:
- 5TDJKRFH6FS165041
2015 Toyota Highlander
XLE
227,121 mi
$9,902
- 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:
- Silver
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 115,838
- Stock #:
- 1983
- VIN:
- 5TDDZRFH8JS852877
Sponsored Listing
2018 Toyota Highlander
Limited Platinum AWD
115,838 mi
$24,998
FAQs
How much does the Toyota Highlander cost in Chesapeake, VA?
How many Toyota Highlander vehicles in Chesapeake, 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.
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
- New Model Premium: The 2026 Toyota Highlander is priced at $52,518, representing a 13.5% increase over its MSRP, indicating strong demand for the latest model.
- Steep Depreciation for Older Models: The 2016 Highlander shows a significant depreciation of -38.5% from its original MSRP, reflecting the typical depreciation curve for vehicles over time.
- Best Value Year: The 2021 model is currently priced at $30,878, which is -12.4% below MSRP, making it an attractive option for budget-conscious buyers.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $46,270 | $52,518 | +13.5% |
| 2025 Toyota Highlander | $40,320 | $41,288 | +2.4% |
| 2024 Toyota Highlander | $39,270 | $39,387 | +0.3% |
| 2023 Toyota Highlander | $36,620 | $36,349 | -0.7% |
| 2022 Toyota Highlander | $35,855 | $33,872 | -5.5% |
| 2021 Toyota Highlander | $35,085 | $30,878 | -12.4% |
| 2020 Toyota Highlander | $34,600 | $28,579 | -17.5% |
| 2019 Toyota Highlander | $31,830 | $24,400 | -23.3% |
| 2018 Toyota Highlander | $31,230 | $22,487 | -28.0% |
| 2017 Toyota Highlander | $30,630 | $20,990 | -31.5% |
| 2016 Toyota Highlander | $30,490 | $18,777 | -38.5% |
Pricing by Popular US Cities
Market Area: Nationwide
Key Insights
- Highest Prices in New York: The New York, NY market has the highest average price at $26,708, likely due to higher demand and lower inventory.
- Lowest Prices in Chicago: Chicago, IL offers the lowest average price at $24,600, indicating a more competitive market with potentially higher inventory levels.
- Price Variation Across Cities: Significant price differences exist, with Los Angeles, CA averaging $25,841, suggesting regional preferences and demand dynamics.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| New York, NY | 648 | $26,708 |
| Los Angeles, CA | 523 | $25,841 |
| Chicago, IL | 350 | $24,600 |
| Dallas, TX | 369 | $26,691 |
| Philadelphia, PA | 272 | $28,176 |
| Houston, TX | 372 | $25,539 |
| Miami, FL | 201 | $29,898 |
| Washington, DC | 467 | $26,938 |
| Atlanta, GA | 306 | $27,223 |
| Boston, MA | 657 | $28,482 |
Pricing by Trim Packages
Key Insights
- XLE AWD Dominates Inventory: The XLE AWD trim leads with 3,171 listings, indicating strong consumer preference for this configuration.
- Premium Pricing for Limited Trim: The Limited AWD trim, priced at $50,725, reflects a significant markup due to its luxury features, appealing to buyers seeking higher-end options.
- Consistent Drivetrain Preference: All trims listed are AWD, suggesting a strong market demand for all-weather capability in the Highlander lineup.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 3,171 | $46,270 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 1,233 | $50,725 | AWD | 2.4L 265 hp I4 |
| XSE AWD | 702 | $48,340 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 566 | $53,925 | AWD | 2.4L 265 hp I4 |
These recommendations are based on CarGurus' proprietary market data from July 9, 2026, CarGurus experts' opinions, and generative AI.
CarGurus recommends the 2024 Toyota Highlander
Summary
With 3,978 currently listed for sale and an average price of $39,108.00, 34.9% 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.
88.8% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander features a spacious interior, advanced safety technology, and a smooth ride, making it an excellent choice for families.
Why it stands out
The 2024 Toyota Highlander continues to build on its reputation as a reliable and family-friendly SUV. With its spacious interior and comfortable seating for up to eight passengers, it caters to families who need room for both kids and cargo. The Highlander is equipped with a suite of advanced safety features, including Toyota Safety Sense, which enhances its appeal to safety-conscious buyers. Additionally, the Highlander's smooth ride and refined handling make it a pleasure to drive, while its strong reliability ratings ensure peace of mind for long-term ownership.
Other model years to consider
- Average price: $36,251.00
- Good/great deal percentage: 35.1%
- User rating: 4.75 / 5
- Total listings: 4,632
- Average price: $16,128.00
- Good/great deal percentage: 34.6%
- User rating: 4.78 / 5
- Total listings: 1,225
- Average price: $33,589.00
- Good/great deal percentage: 35.1%
- User rating: 4.44 / 5
- Total listings: 4,931
These recommendations are based on CarGurus' proprietary market data from July 6, 2026, CarGurus experts' opinions, and generative AI.
Recent expert test drives
2022 Toyota Highlander
- Expert review8/10
- MSRP$35,855-$49,960
- Avg. price$33,175
- User rating4.4444
2020 Toyota Highlander
- Expert review8/10
- MSRP$34,600-$48,800
- Avg. price$28,104
- User rating4.6
2021 Toyota Highlander
- Expert review8/10
- MSRP$35,085-$49,190
- Avg. price$30,319
- User rating4.8636
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