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1,165 listings
  • New Listing

    2015 Toyota Highlander
    LE 4dr SUV

    $16,995
    good price
    $608 below market
    • 102,462 miles
    • 8 Seats, 18 City / 24 Hwy MPG
    • J&M Automotive (17 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    Close

    Located in Naugatuck, CT / 17 miles away from Trumbull, CT

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDBKRFH7FS178157
    Stock: 1578157
    Certified Pre-Owned: No

  • New Listing

    2019 Toyota Highlander
    LE 4dr SUV

    $26,998
    fair price
    $613 above market
    • 51,608 miles
    • 8 Seats, 19 City / 26 Hwy MPG
    • CarMax Waterbury (23 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    Close

    Located in Waterbury, CT / 23 miles away from Trumbull, CT

    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:

    22 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 5TDBZRFH2KS938761
    Stock: 26924340
    Certified Pre-Owned: No

  • New Listing

    2022 Toyota Highlander
    LE 4dr SUV

    $32,998
    fair price
    $329 above market
    • 36,625 miles
    • 1 accident, 1 owner, personal use
    • 8 Seats, 20 City / 27 Hwy MPG
    • CarMax Waterbury (23 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Waterbury, CT / 23 miles away from Trumbull, CT

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDBZRBH3NS563229
    Stock: 27320737
    Certified Pre-Owned: No

  • 2021 Toyota Highlander
    LE 4dr SUV

    $29,999
    fair price
    $389 above market
    • 72,196 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 20 City / 27 Hwy MPG
    • Honda of Westport (10 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Westport, CT / 10 miles away from Trumbull, CT

    CARFAX One-Owner.Black 2021 Toyota Highlander LE 4D Sport Utility AWD 8-Speed Automatic 3.5L V6 DOHC 20/27 City/Highway MPG

    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: 5TDBZRBH7MS072063
    Stock: 30983
    Certified Pre-Owned: No
    Listed since: 04-29-2025

  • 5 Offers Nearby

    2025 Toyota Highlander
    • 7 Colors
    • 5 Trims
    • 1 Package
    View Offers 

  • 2016 Toyota Highlander
    XLE 4dr SUV

    $18,995
    fair price
    $270 above market
    • 120,959 miles
    • No accidents, 3 owners, corporate fleet vehicle
    • 8 Seats, 18 City / 24 Hwy MPG
    • J&M Automotive (17 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 17 miles away from Trumbull, CT

    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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDJKRFH3GS234558
    Stock: 1634558
    Certified Pre-Owned: No

  • New Listing

    2016 Toyota Highlander
    XLE 4dr SUV

    $20,998
    • 106,883 miles
    • No accidents, 2 owners, personal use
    • 8 Seats, 18 City / 24 Hwy MPG
    • CarMax East Haven (17 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in East Haven, CT / 17 miles away from Trumbull, CT

    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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDJKRFH2GS246927
    Stock: 27239782
    Certified Pre-Owned: No

  • 2020 Toyota Highlander
    XLE 4dr SUV

    $29,995
    fair price
    $496 above market
    • 70,100 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 20 City / 27 Hwy MPG
    • Performance Motor Cars (12 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Wilton, CT / 12 miles away from Trumbull, CT

    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: 5TDHZRBH4LS512183
    Stock: 512183
    Certified Pre-Owned: No
    Listed since: 02-07-2025

  • New Listing

    2021 Toyota Highlander
    XLE 4dr SUV

    $36,998
    • 32,016 miles
    • No accidents, 2 owners, rental vehicle
    • 7 Seats, 20 City / 27 Hwy MPG
    • CarMax East Haven (17 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in East Haven, CT / 17 miles away from Trumbull, CT

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH9MS060762
    Stock: 27164624
    Certified Pre-Owned: No

  • 5 Offers Nearby

    2025 Toyota Highlander
    • 7 Colors
    • 5 Trims
    • 1 Package
    View Offers 
  • New Listing

    2018 Toyota Highlander
    XLE 4dr SUV

    $27,998
    • 70,871 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • CarMax East Haven (17 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in East Haven, CT / 17 miles away from Trumbull, CT

    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:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDJZRFH5JS845548
    Stock: 27019436
    Certified Pre-Owned: No

  • 2022 Toyota Highlander
    Platinum 4dr SUV

    $45,998
    • 36,736 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • CarMax Waterbury (23 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Waterbury, CT / 23 miles away from Trumbull, CT

    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: 5TDFZRBH0NS216510
    Stock: 27319898
    Certified Pre-Owned: No

  • 2019 Toyota Highlander
    XLE 4dr SUV

    $24,950
    fair price
    $679 above market
    • 103,320 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 20 City / 26 Hwy MPG
    • Affordable Motors (5 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Bridgeport, CT / 5 miles away from Trumbull, CT

    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: 5TDJZRFH1KS612977
    Stock: 612977
    Certified Pre-Owned: No

  • 2020 Toyota Highlander
    LE 4dr SUV

    $24,963
    fair price
    $567 above market
    • 90,491 miles
    • 1 accident, 2 owners, personal use
    • 8 Seats, 20 City / 27 Hwy MPG
    • Ingersoll Auto of Danbury (16 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Danbury, CT / 16 miles away from Trumbull, CT

    Highlander LE, 3.5L V6 DOHC, AWD, 18' Painted Alloy Wheels, Apple CarPlay/Android Auto, Exterior Parking Camera Rear, Front dual zone A/C, Front fog l...

    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: 5TDBZRBH9LS501475
    Stock: P501475
    Certified Pre-Owned: No
    Listed since: 05-14-2025

  • 5 Offers Nearby

    2025 Toyota Highlander
    • 7 Colors
    • 5 Trims
    • 1 Package
    View Offers 
  • Stock photo**

    Certified 2021 Toyota Highlander
    XLE 4dr SUV

    $35,995
    fair price
    $804 above market
    • 37,495 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • Greentree Toyota (16 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Danbury, CT / 16 miles away from Trumbull, CT

    Certified. CARFAX One-Owner. 2021 Toyota Highlander XLE AWDAWD.Highlander AWD XLE AWD Black 3.5L V6 DOHC 8-Speed Automatic 4D Sport Utility Odometer...

    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: 5TDGZRBH2MS147404
    Stock: U22402
    Certified Pre-Owned: Yes
    Listed since: 04-29-2025

  • 2016 Toyota Highlander
    Limited 4dr SUV

    $22,495
    fair price
    $535 above market
    • 89,677 miles
    • 1 accident, 3 owners, personal use
    • 7 Seats, 18 City / 24 Hwy MPG
    • Boulevard Motors (14 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in New Haven, CT / 14 miles away from Trumbull, CT

    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: 5TDDKRFH3GS340568
    Stock: 340568
    Certified Pre-Owned: No

  • New Listing
    Stock photo**

    2023 Toyota Highlander
    XLE 4dr SUV

    $40,944
    fair price
    $135 above market
    • 18,286 miles
    • 7 Seats, 21 City / 28 Hwy MPG
    • Danbury Kia (16 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Danbury, CT / 16 miles away from Trumbull, CT

    CARFAX 1-Owner, LOW MILES - 18,286! XLE trim. EPA 28 MPG Hwy/21 MPG City! Heated Seats, Sunroof, 3rd Row Seat, Power Liftgate, Turbo, Quad Seats, All ...

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH7PS040362
    Stock: K8722
    Certified Pre-Owned: No
    Listed since: 05-29-2025

  • 2021 Toyota Highlander
    XLE 4dr SUV

    $33,998
    • 53,399 miles
    • 1 accident, 1 owner, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • CarMax Waterbury (23 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Waterbury, CT / 23 miles away from Trumbull, CT

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH2MS126603
    Stock: 27449953
    Certified Pre-Owned: No

  • 5 Offers Nearby

    2025 Toyota Highlander
    • 7 Colors
    • 5 Trims
    • 1 Package
    View Offers 

  • 2016 Toyota Highlander
    Limited 4dr SUV

    $24,995
    • 87,442 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 18 City / 24 Hwy MPG
    • J&M Automotive (17 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 17 miles away from Trumbull, CT

    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: 5TDDKRFH4GS313296
    Stock: 1613296
    Certified Pre-Owned: No

  • 2018 Toyota Highlander
    XLE 4dr SUV

    $25,995
    • 80,625 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • J&M Automotive (17 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 17 miles away from Trumbull, CT

    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: 5TDJZRFH1JS893080
    Stock: 1893080
    Certified Pre-Owned: No

  • 2021 Toyota Highlander
    XLE 4dr SUV

    $39,900
    • 51,501 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • Affordable Motors (5 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Bridgeport, CT / 5 miles away from Trumbull, CT

    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: 5TDHZRBH3MS550327
    Stock: 550327
    Certified Pre-Owned: No

  • 2021 Toyota Highlander
    LE 4dr SUV

    $33,000
    • 64,492 miles
    • No accidents, 1 owner, personal use
    • 8 Seats, 20 City / 27 Hwy MPG
    • Affordable Motors (5 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Bridgeport, CT / 5 miles away from Trumbull, CT

    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: 5TDBZRBH0MS128604
    Stock: 128604
    Certified Pre-Owned: No

  • New Listing

    2016 Toyota Highlander
    XLE 4dr SUV

    $24,995
    • 68,402 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 18 City / 24 Hwy MPG
    • J&M Automotive (17 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 17 miles away from Trumbull, CT

    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: 5TDJKRFH7GS264694
    Stock: 1664694
    Certified Pre-Owned: No

Showing 22 - 42 out of 1,165 listings
Highlander Reviews & Specs

Used Toyota Highlander by Year

VehicleDealsStarting PriceTotal Available
2025 Toyota Highlander-$47,9981 listing
2024 Toyota Highlander24 Great Deals$34,998114 listings
2023 Toyota Highlander12 Great Deals$26,137194 listings
2022 Toyota Highlander7 Great Deals$27,528214 listings
2021 Toyota Highlander8 Great Deals$22,590148 listings
2020 Toyota Highlander1 Great Deal$21,99858 listings
2019 Toyota Highlander5 Great Deals$19,888116 listings
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