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230 listings
  • Price Drop
    $28,719
    great price
    $3,021 below market
    • 33,172 miles
    • No accidents, 2 owners, personal use only
    • 8 Seats, 21 City / 29 Hwy MPG
    • Coggin DeLand Honda (26 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Orange City, FL / 26 miles away from Winter Park, FL

    2022 Toyota Highlander LE 8-Speed Automatic Midnight**3RD-ROW SEATS**, **REARVIEW CAMERA**, **KEYLESS ENTRY**, **APPLE CARPLAY**, **ANDROID AUTO**, *...

    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/29 Highway)

    Listing Information:

    VIN: 5TDZZRAHXNS134542
    Stock: CDH251118A
    Certified Pre-Owned: No
    Listed since: 05-30-2025

  • Price Drop
    $31,000
    great price
    $2,619 below market
    • 47,290 miles
    • No accidents, 2 owners, rental vehicle
    • 7 Seats, 21 City / 29 Hwy MPG
    • Napleton's Volkswagen Of Sanford (11 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Sanford, FL / 11 miles away from Winter Park, FL

    2022 Toyota Highlander XLE Highlander XLE, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed Automatic, FWD, Midnight Black Metallic, Black w/Leather Seat Trim,...

    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/29 Highway)

    Listing Information:

    VIN: 5TDHZRAH2NS545297
    Stock: TORL5297
    Certified Pre-Owned: No
    Listed since: 03-24-2025

  • $30,698
    good price
    $1,330 below market
    • 22,027 miles
    • No accidents, 1 owner, personal use
    • 8 Seats, 21 City / 29 Hwy MPG
    • AutoNation Toyota Winter Park (3 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Winter Park, FL / 3 miles away from Winter Park, FL

    3rd Row SeatLane Keeping AssistKeyless StartRear Spoiler50 State EmissionsBlack; Fabric Seat TrimL Grade PackageMidnight Black MetallicThis ...

    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/29 Highway)

    Listing Information:

    VIN: 5TDCZRAH4NS558448
    Stock: NS558448
    Certified Pre-Owned: Yes
    Listed since: 05-14-2025

  • Price Drop
    $32,999
    great price
    $3,396 below market
    • 72,096 miles
    • 1 accident, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Starling Ford (31 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Titusville, FL / 31 miles away from Winter Park, FL

    Wind Chill Pearl 2022 Toyota Highlander Limited AWD 8-Speed Automatic 3.5L V6 DOHC AWD, Carpet Floor Mats, Envelope Cargo Net (TMS), First Aid Kit (TM...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDDZRBHXNS215890
    Stock: 215890T
    Certified Pre-Owned: No
    Listed since: 04-05-2025

  • $29,995
    good price
    $2,002 below market
    • 55,813 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 29 Hwy MPG
    • Driveway (14 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Sanford, FL / 14 miles away from Winter Park, FL

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

    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/29 Highway)

    Listing Information:

    VIN: 5TDGZRAHXNS142034
    Stock: NS142034
    Certified Pre-Owned: No

  • New Listing
    $28,599
    good price
    $2,502 below market
    • 49,678 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 29 Hwy MPG
    • AutoNation Toyota Winter Park (3 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Winter Park, FL / 3 miles away from Winter Park, FL

    3rd Row SeatLane Keeping AssistKeyless StartRear Spoiler50 State EmissionsGraphite; Fabric Seat TrimMidnight Black MetallicThis vehicle inclu...

    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/29 Highway)

    Listing Information:

    VIN: 5TDZZRAH5NS124291
    Stock: NS124291
    Certified Pre-Owned: Yes
    Listed since: 06-14-2025

  • $37,998
    fair price
    $798 above market
    • 18,674 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 29 Hwy MPG
    • CarMax Orlando (9 mi away)
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Orlando, FL / 9 miles away from Winter Park, FL

    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/29 Highway)

    Listing Information:

    VIN: 5TDHZRAH2NS132991
    Stock: 27307816
    Certified Pre-Owned: No

  • $32,998
    fair price
    $304 below market
    • 49,385 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 21 City / 29 Hwy MPG
    • CarMax Daytona (44 mi away)
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Daytona Beach, FL / 44 miles away from Winter Park, FL

    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/29 Highway)

    Listing Information:

    VIN: 5TDGZRAHXNS560710
    Stock: 27481215
    Certified Pre-Owned: No

  • New Listing
    • 24,672 miles
    • No accidents, 2 owners, rental vehicle
    • 8 Seats, 21 City / 29 Hwy MPG
    • CarMax Sanford (14 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Sanford, FL / 14 miles away from Winter Park, FL

    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: 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/29 Highway)

    Listing Information:

    VIN: 5TDCZRAH3NS137126
    Stock: 27522243
    Certified Pre-Owned: No

  • New Listing
    $33,949
    fair price
    $826 above market
    • 58,460 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 29 Hwy MPG
    • AutoNation Chevrolet West Colonial (5 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Orlando, FL / 5 miles away from Winter Park, FL

    Sun/Moonroof3rd Row SeatLane Keeping AssistKeyless StartRear Spoiler50 State EmissionsBlack; Softex Seat TrimOpulent AmberThis vehicle inclu...

    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/29 Highway)

    Listing Information:

    VIN: 5TDGZRAH0NS118115
    Stock: NS118115
    Certified Pre-Owned: No
    Listed since: 06-16-2025

  • Price Drop
    • 48,732 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 29 Hwy MPG
    • Phillips Toyota (32 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Leesburg, FL / 32 miles away from Winter Park, FL

    One Owner, Nonsmoker, Local Trade, Leather Seats, Sunroof, Navigation, 3rd Row Seating, Backup Camera, Keyless Entry, *Carfax Accident Free*, Adaptive...

    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/29 Highway)

    Listing Information:

    VIN: 5TDGZRAH0NS547951
    Stock: 251031A
    Certified Pre-Owned: No
    Listed since: 05-10-2025

  • $39,990
    fair price
    $525 below market
    • 45,551 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • F2 Motor Sales (13 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Orlando, FL / 13 miles away from Winter Park, FL

    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: 5TDFZRBH8NS190478
    Stock: new-190478
    Certified Pre-Owned: No

  • New Listing
    Stock photo**
    • 57,295 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 21 City / 29 Hwy MPG
    • Phillips Toyota (32 mi away)
    • Home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Leesburg, FL / 32 miles away from Winter Park, FL

    Recent Arrival! One Owner, Nonsmoker, Local Trade, Leather Seats, Sunroof, Navigation, 3rd Row Seating, Backup Camera, Keyless Entry, *Carfax Accident...

    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/29 Highway)

    Listing Information:

    VIN: 5TDFZRAH7NS127924
    Stock: 251219A
    Certified Pre-Owned: No
    Listed since: 06-16-2025

    • 97,769 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 21 City / 29 Hwy MPG
    • MagiCar Group (6 mi away)
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Orlando, FL / 6 miles away from Winter Park, FL

    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/29 Highway)

    Listing Information:

    VIN: 5TDGZRAH3NS125849
    Stock: 158
    Certified Pre-Owned: No

    • 71,654 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 21 City / 29 Hwy MPG
    • Parks Toyota of DeLand (28 mi away)
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Deland, FL / 28 miles away from Winter Park, FL

    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/29 Highway)

    Listing Information:

    VIN: 5TDGZRAHXNS104268
    Stock: SS553761A
    Certified Pre-Owned: No

    • 56,112 miles
    • Water damage reported, 1 owner, personal use only
    • 8 Seats, 21 City / 29 Hwy MPG
    • Auto Exchange of Central Florida (21 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Kissimmee, FL / 21 miles away from Winter Park, FL

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Issue reported

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    24 Combined MPG (21 City/29 Highway)

    Listing Information:

    VIN: 5TDCZRAH4NS110856
    Stock: 110856
    Certified Pre-Owned: No

    • 51,344 miles
    • 1 accident, 1 owner, personal use only
    • 7 Seats, 21 City / 29 Hwy MPG
    • Parks Toyota of DeLand (28 mi away)
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Deland, FL / 28 miles away from Winter Park, FL

    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:

    24 Combined MPG (21 City/29 Highway)

    Listing Information:

    VIN: 5TDGZRAH4NS111989
    Stock: PM111989
    Certified Pre-Owned: No

  • New Listing
    • 28,865 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 21 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from TX to FL*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Houston, TX / 857 miles away from Winter Park, FL

    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/29 Highway)

    Listing Information:

    VIN: 5TDLZRAH7NS131300
    Stock: 27354638
    Certified Pre-Owned: No

  • $37,000
    great price
    $3,652 below market
    • 26,793 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Troy, MI / 970 miles away from Winter Park, FL

    Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Remote St...

    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: 5TDLZRBH6NS235775
    Stock: NS235775C
    Certified Pre-Owned: No

  • Price Drop
    $36,998
    good price
    $2,279 below market
    • 23,362 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from Naples, FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Naples, FL / 171 miles away from Winter Park, FL

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBHXNS213876
    Stock: 27159513
    Certified Pre-Owned: No

  • Price Drop
    $30,998
    great price
    $3,127 below market
    • 73,613 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from NC to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Pineville, NC / 450 miles away from Winter Park, FL

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH1NS561453
    Stock: 27208080
    Certified Pre-Owned: No

Showing 1 - 21 out of 230 listings
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