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1,084 listings
  • Price Drop
    $31,990
    great price
    $4,036 below market
    • 53,756 miles
    • No accidents, 1 owner, rental vehicle
    • 8 Seats, 22 City / 29 Hwy MPG
    • Southern Chrysler Dodge Jeep RAM Chesapeake (32 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Chesapeake, VA / 32 miles away from Williamsburg, VA

    Certified. Celestial Silver Metallic 2023 Toyota Highlander XLE 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed Automatic FWD SUNROOF/MOO...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH8PS504793
    Stock: YP10777
    Certified Pre-Owned: No
    Listed since: 06-16-2025

  • Price Drop
    $39,500
    great price
    $3,164 below market
    • 15,883 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • Hall Honda Virginia Beach (45 mi away)
    • Five Star Dealer
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Virginia Beach, VA / 45 miles away from Williamsburg, VA

    Clean CARFAX. 2024 Toyota Highlander XLE AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp AWD, ABS brakes, Active Cruise Con...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH7RS569149
    Stock: 2252602A
    Certified Pre-Owned: No
    Listed since: 05-14-2025

  • $29,500
    great price
    $3,647 below market
    • 45,722 miles
    • No accidents, 1 owner, rental vehicle
    • 8 Seats, 22 City / 29 Hwy MPG
    • Haley Certified Preowned (49 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Richmond, VA / 49 miles away from Williamsburg, VA

    *Vehicle pricing excludes tax, title, tags, $799 processing fee, and $319 fee for theft protection etch.*

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH0PS010542
    Stock: J6882
    Certified Pre-Owned: No
    Listed since: 05-22-2025

  • $12,990
    fair price
    $1,443 below market
    • 118,879 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 17 City / 23 Hwy MPG
    • The Car Exchange (47 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Virginia Beach, VA / 47 miles away from Williamsburg, VA

    Come Experience The Car Exchange Difference No haggle pricing No high pressure sales Easy Financing options Great Extended Warranties All cars newly i...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    19 Combined MPG (17 City/23 Highway)

    Listing Information:

    VIN: 5TDDK3EH7AS030722
    Stock: 030722MT
    Certified Pre-Owned: No

  • New Listing
    $14,500
    fair price
    $431 below market
    • 155,619 miles
    • 1 accident, 1 owner, personal use only
    • 7 Seats, 18 City / 24 Hwy MPG
    • Hall Chrysler Dodge Jeep RAM Virginia Beach (45 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Virginia Beach, VA / 45 miles away from Williamsburg, VA

    JUST ARRIVED. PENDING INSPECTION. CARFAX One-Owner. Silver Sky Metallic 2014 Toyota Highlander AWD 6-Speed Automatic Electronic with Overdrive 3.5L V6...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDDKRFH4ES033312
    Stock: 24255504A
    Certified Pre-Owned: No
    Listed since: 06-11-2025

  • $9,995
    fair price
    $788 below market
    • 162,886 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 20 City / 25 Hwy MPG
    • Streamline Auto Outlet (41 mi away)
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    • USB Inputs
    • Trip Computer
    Close

    Located in Norfolk, VA / 41 miles away from Williamsburg, VA

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    22 Combined MPG (20 City/25 Highway)

    Listing Information:

    VIN: 5TDZA3EH8DS043847
    Stock: P3136
    Certified Pre-Owned: No
    Listed since: 07-16-2025

  • Price Drop
    $14,000
    good price
    $827 below market
    • 175,413 miles
    • No accidents, 3 owners, personal use
    • 8 Seats, 18 City / 24 Hwy MPG
    • Driveway (45 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Chesapeake, VA / 45 miles away from Williamsburg, VA

    CarFax No Accidents Reported,3rd Row Seat,Back-Up Camera,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Leather Seats,Navigation System,Satellite R...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDJKRFH5FS142768
    Stock: FS142768A
    Certified Pre-Owned: No

  • Price Drop
    $15,300
    fair price
    $211 below market
    • 112,720 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 17 City / 22 Hwy MPG
    • Hall Toyota Virginia Beach (47 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Virginia Beach, VA / 47 miles away from Williamsburg, VA

    Cypress Pearl 2013 Toyota Highlander Limited AWD 5-Speed Automatic with Overdrive 3.5L V6 DOHC Dual VVT-i 24V AWD.AWD, 2.928 Axle Ratio, 3rd row sea...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    19 Combined MPG (17 City/22 Highway)

    Listing Information:

    VIN: 5TDDK3EH0DS220611
    Stock: 24255652B
    Certified Pre-Owned: No
    Listed since: 07-07-2025

  • Price Drop
    $30,800
    good price
    $2,181 below market
    • 55,253 miles
    • No accidents, 1 owner, rental vehicle
    • 8 Seats, 22 City / 29 Hwy MPG
    • First Team Subaru Norfolk (41 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Norfolk, VA / 41 miles away from Williamsburg, VA

    Silver 2023 Toyota Highlander L FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hpThe 2023 Toyota Highlander LE is a popular ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH5PS502757
    Stock: NB1635
    Certified Pre-Owned: No
    Listed since: 06-23-2025

  • $38,500
    fair price
    $535 above market
    • 36,671 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 22 City / 29 Hwy MPG
    • Hall Toyota Virginia Beach (47 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Virginia Beach, VA / 47 miles away from Williamsburg, VA

    Blueprint 2024 Toyota Highlander LE FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp18" Painted Alloy Wheels, 3.329 Axle R...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH4RS547255
    Stock: 22255037A
    Certified Pre-Owned: No
    Listed since: 06-09-2025

  • Price Drop
    $22,095
    good price
    $556 below market
    • 107,418 miles
    • No accidents, 3 owners, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Mechanicsville DriveTime (43 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Henrico, VA / 43 miles away from Williamsburg, VA

    Shop at DriveTime: Get started on your personalized car-buying journey today. With no credit impact, you can get approved for your real, personalized ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDDZRFH7HS461651
    Stock: 1630093240
    Certified Pre-Owned: No
    Listed since: 06-05-2025

  • $24,295
    good price
    $1,465 below market
    • 101,757 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Arch Road DriveTime (50 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Richmond, VA / 50 miles away from Williamsburg, VA

    Shop at DriveTime: Get started on your personalized car-buying journey today. With no credit impact, you can get approved for your real, personalized ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDJZRFH3KS714281
    Stock: 1630095197
    Certified Pre-Owned: No
    Listed since: 07-14-2025

  • $6,999
    fair price
    $131 below market
    • 197,210 miles
    • No accidents, 3 owners, personal use
    • 7 Seats, 17 City / 23 Hwy MPG
    • 518 Auto Sales (36 mi away)
    • AWD/4WD
    • Third-row seating
    • Tire Pressure Warnin...
    • Rear Bench Seats
    • Stability Control
    Close

    Located in Norfolk, VA / 36 miles away from Williamsburg, VA

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    19 Combined MPG (17 City/23 Highway)

    Listing Information:

    VIN: JTEES41A292127599
    Stock: 11797
    Certified Pre-Owned: No
    Listed since: 07-17-2025

  • Price Drop
    $25,295
    good price
    $836 below market
    • 95,346 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 20 City / 26 Hwy MPG
    • Arch Road DriveTime (50 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Richmond, VA / 50 miles away from Williamsburg, VA

    Shop at DriveTime: Get started on your personalized car-buying journey today. With no credit impact, you can get approved for your real, personalized ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDJZRFH4KS563659
    Stock: 1630093782
    Certified Pre-Owned: No
    Listed since: 07-02-2025

  • Price Drop
    $33,400
    good price
    $1,586 below market
    • 51,298 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 22 City / 29 Hwy MPG
    • Haley Certified Preowned (49 mi away)
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Richmond, VA / 49 miles away from Williamsburg, VA

    *Vehicle pricing excludes tax, title, tags, $799 processing fee, and $319 fee for theft protection etch.*

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH2PS009067
    Stock: J6830
    Certified Pre-Owned: No
    Listed since: 05-13-2025

  • Price Drop
    $36,834
    good price
    $818 below market
    • 36,432 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Southern Acura Newport News (15 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Newport News, VA / 15 miles away from Williamsburg, VA

    Priced below KBB Fair Purchase Price! Clean CARFAX.Sunroof/Moonroof, ALLOY WHEELS, APPLE ANDROID CARPLAY, BACKUP CAMERA, KEYLESS ENTRY, LEATHER SEAT...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDHZRBH9NS171494
    Stock: ZP10412
    Certified Pre-Owned: No
    Listed since: 07-10-2025

  • Price Drop
    $31,990
    fair price
    $746 below market
    • 48,694 miles
    • No accidents, 1 owner, rental vehicle
    • 8 Seats, 22 City / 29 Hwy MPG
    • Driveway (45 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Chesapeake, VA / 45 miles away from Williamsburg, VA

    CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satellite Radio,T...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH6PS004857
    Stock: PS004857P
    Certified Pre-Owned: No

  • $37,000
    good price
    $701 below market
    • 45,667 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 22 City / 29 Hwy MPG
    • Haley Certified Preowned (49 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Richmond, VA / 49 miles away from Williamsburg, VA

    *Vehicle pricing excludes tax, title, tags, $799 processing fee, and $319 fee for theft protection etch.*

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH7PS018380
    Stock: J6820
    Certified Pre-Owned: No
    Listed since: 05-08-2025

  • $34,899
    fair price
    $1,108 above market
    • 20,068 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 22 City / 29 Hwy MPG
    • Driveway (23 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Hampton, VA / 23 miles away from Williamsburg, VA

    CarFax No Accidents Reported,CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satelli...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH8PS518757
    Stock: PS518757T
    Certified Pre-Owned: No

  • $17,999
    fair price
    $383 above market
    • 165,038 miles
    • No accidents, 3 owners, corporate fleet vehicle
    • 8 Seats, 20 City / 26 Hwy MPG
    • Paragon Automotive (42 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Virginia Beach, VA / 42 miles away from Williamsburg, VA

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDJZRFH5HS430241
    Stock: 1753
    Certified Pre-Owned: No

  • New Listing
    $22,700
    fair price
    $284 above market
    • 108,394 miles
    • No accidents, 3 owners, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Hall Toyota Virginia Beach (47 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Virginia Beach, VA / 47 miles away from Williamsburg, VA

    Blizzard Pearl 2017 Toyota Highlander Limited AWD 8-Speed Automatic Electronic with ECT-i 3.5L V6 AWD, ABS brakes, Active Cruise Control, Alloy wheels...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDDZRFH2HS409473
    Stock: 2252587G
    Certified Pre-Owned: No
    Listed since: 07-24-2025

Showing 1 - 21 out of 1,084 listings

Buying a Toyota Highlander in Williamsburg Virginia

For those exploring the charming streets and historic landmarks of Williamsburg, VA, the Toyota Highlander stands out as a practical choice. With its comfortable and quiet ride, it ensures a pleasant journey as families make their way to attractions like Colonial Williamsburg or the vibrant Busch Gardens. The vehicle's well-designed cabin offers excellent visibility, which is particularly beneficial when navigating the town's busy roads or scenic routes. Plus, the powerful V6 engine provides a good balance of performance and fuel efficiency, making it suitable for both daily commutes and weekend getaways.

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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.