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874 listings
  • Price Drop
    • 94,496 miles
    • 1 accident, 1 owner, personal use only
    • 8 Seats, 18 City / 24 Hwy MPG
    • CarMax Winchester (4 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Power Driver Seat
    Close

    Located in Winchester, VA / 4 miles away from Winchester, VA

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    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: 5TDBKRFH6FS140645
    Stock: 27573245
    Certified Pre-Owned: No

  • $38,990
    good price
    $4,417 below market
    • 29,262 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 22 City / 29 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Tampa, FL / 815 miles away from Winchester, VA

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    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: 5TDKDRAHXRS534705
    Stock: 2003798232
    Certified Pre-Owned: No
    Listed since: 07-16-2025

  • Price Drop
    $32,990
    great price
    $5,031 below market
    • 39,311 miles
    • No accidents, 1 owner, rental vehicle
    • 8 Seats, 21 City / 28 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Atlanta, GA / 511 miles away from Winchester, VA

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    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: Yes

    Features and Specs:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBHXPS040808
    Stock: 2003876411
    Certified Pre-Owned: No
    Listed since: 07-10-2025

  • $33,590
    great price
    $4,476 below market
    • 39,011 miles
    • No accidents, 1 owner, rental vehicle
    • 8 Seats, 21 City / 28 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Tampa, FL / 815 miles away from Winchester, VA

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH6PS032883
    Stock: 2003864526
    Certified Pre-Owned: No
    Listed since: 07-10-2025

  • $33,499
    great price
    $6,901 below market
    • 24,020 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 28 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Farmington Hills, MI / 355 miles away from Winchester, VA

    3rd Row Seat,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satellite Radio,Turbo/Supercharged,WiFi Hotspot,Pow...

    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: 5TDKDRBH0PS505502
    Stock: PS505502P
    Certified Pre-Owned: No

  • $35,590
    great price
    $7,634 below market
    • 30,149 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 22 City / 29 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Chicago, IL / 571 miles away from Winchester, VA

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    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: 5TDKDRAH1RS528906
    Stock: 2003602037
    Certified Pre-Owned: No
    Listed since: 03-31-2025

  • New Listing
    $35,990
    great price
    $7,462 below market
    • 33,541 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 7 Seats, 21 City / 28 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Atlanta, GA / 511 miles away from Winchester, VA

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH0PS035262
    Stock: 2004001196
    Certified Pre-Owned: No
    Listed since: 08-25-2025

  • $39,998
    great price
    $3,601 below market
    • 14,259 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from OR to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Beaverton, OR / 2,290 miles away from Winchester, VA

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    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: Yes

    Features and Specs:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH2RS539914
    Stock: 27272092
    Certified Pre-Owned: No

  • Price Drop
    $33,310
    great price
    $5,254 below market
    • 51,415 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Wesley Chapel, FL / 796 miles away from Winchester, VA

    CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free L...

    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: 5TDFZRBH0MS145680
    Stock: M145680P
    Certified Pre-Owned: No

  • New Listing
    $34,998
    great price
    $4,017 below market
    • 28,384 miles
    • 8 Seats, 21 City / 28 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from WA to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Spokane Valley, WA / 2,025 miles away from Winchester, VA

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH2RS545924
    Stock: 27470795
    Certified Pre-Owned: No

  • Price Drop
    $41,590
    great price
    $4,217 below market
    • 37,174 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Oklahoma City, OK / 1,092 miles away from Winchester, VA

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    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: 5TDFZRBH4NS235643
    Stock: 2003949332
    Certified Pre-Owned: No
    Listed since: 08-09-2025

  • New Listing
    • 50,563 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 7 Seats, 22 City / 29 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Houston, TX / 1,183 miles away from Winchester, VA

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    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: 5TDKDRAH0PS500429
    Stock: 2003659661
    Certified Pre-Owned: No
    Listed since: 04-29-2025

  • Price Drop
    $27,499
    great price
    $2,960 below market
    • 98,253 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 20 City / 27 Hwy MPG
    • AutoNation Honda Dulles (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Sterling, VA / 41 miles away from Winchester, VA

    The following items have been reconditioned on this vehicle: new brakes! Sun/Moonroof3rd Row SeatLane Keeping AssistKeyless StartRear Spoiler2...

    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: 5TDGZRBH6MS096196
    Stock: MS096196
    Certified Pre-Owned: No
    Listed since: 07-16-2025

  • $41,998
    good price
    $2,867 below market
    • 6,585 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from OR to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Salem, OR / 2,303 miles away from Winchester, VA

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    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: 5TDKDRBH6RS556151
    Stock: 27100036
    Certified Pre-Owned: No

  • Price Drop
    $31,590
    great price
    $2,370 below market
    • 89,234 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Indianapolis, IN / 429 miles away from Winchester, VA

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    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: 5TDFZRBH9MS096947
    Stock: 2003844166
    Certified Pre-Owned: No
    Listed since: 07-08-2025

  • New Listing
    $30,998
    great price
    $6,051 below market
    • 29,525 miles
    • 8 Seats, 22 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from FL to VA*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Clermont, FL / 763 miles away from Winchester, VA

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH0PS500415
    Stock: 27688494
    Certified Pre-Owned: No

  • New Listing
    $19,997
    great price
    $2,297 below market
    • 92,819 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 21 City / 27 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in New Port Richey, FL / 802 miles away from Winchester, VA

    CarFax No Accidents Reported,3rd Row Seat,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Leat...

    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 (21 City/27 Highway)

    Listing Information:

    VIN: 5TDKZRFH5HS218296
    Stock: HS218296A
    Certified Pre-Owned: No

  • New Listing
    • 119,452 miles
    • No accidents, 3 owners, corporate fleet vehicle
    • 8 Seats, 19 City / 25 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Grapevine, TX / 1,138 miles away from Winchester, VA

    CarFax No Accidents Reported,Rare Find,3rd Row Seat,Back-Up Camera,Bluetooth,Brake Assist,V6 Cylinder Engine,Power Door Locks,Brake Assist,Front Wheel...

    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:

    21 Combined MPG (19 City/25 Highway)

    Listing Information:

    VIN: 5TDZKRFH0FS105002
    Stock: FS105002AA
    Certified Pre-Owned: No

  • New Listing
    $40,590
    great price
    $5,633 below market
    • 30,235 miles
    • 1 accident, 1 owner, rental vehicle
    • 7 Seats, 21 City / 28 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Los Angeles, CA / 2,234 miles away from Winchester, VA

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH6RS529550
    Stock: 2003684681
    Certified Pre-Owned: No
    Listed since: 04-28-2025

  • $35,888
    good price
    $2,963 below market
    • 11,569 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 22 City / 29 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Eatontown, NJ / 231 miles away from Winchester, VA

    CarFax No Accidents Reported,CarFax 1-Owner,Low Mileage,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated 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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH8PS005413
    Stock: PS005413P
    Certified Pre-Owned: No

  • Price Drop
    $28,990
    good price
    $1,007 below market
    • 64,834 miles
    • No accidents, 2 owners, rental vehicle
    • 8 Seats, 20 City / 27 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Richmond, VA / 111 miles away from Winchester, VA

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDBZRBH5NS566794
    Stock: 2003873766
    Certified Pre-Owned: No
    Listed since: 07-10-2025

Showing 1 - 21 out of 874 listings

Buying a Toyota Highlander in Winchester Virginia

For those exploring the scenic beauty of Winchester, VA, the Toyota Highlander stands out as a practical choice. The vehicle's comfortable and quiet ride makes it well-suited for long drives through the picturesque countryside and winding roads. With its spacious interior, you can easily accommodate family and friends for outings to local attractions such as the historic Old Town or the nearby Shenandoah National Park. The Highlander's powerful V6 engine provides ample performance while maintaining good fuel economy, making it an efficient option for both daily commutes and weekend adventures.

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