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1,122 listings
  • New Listing

    2017 Toyota Highlander
    XLE 4dr SUV

    $18,995
    great price
    $3,630 below market
    • 97,221 miles
    • 1 accident, 2 owners, personal use only
    • 7 Seats, 21 City / 27 Hwy MPG
    • A Better Way Wholesale Autos (20 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Naugatuck, CT / 20 miles away from Trumbull, CT

    - **Mileage**: Only 97,221 miles, offering a wealth of adventures ahead. - **Luxury Interior**: Gray leather-trimmed seats with dual-zone automatic c...

    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 (21 City/27 Highway)

    Listing Information:

    VIN: 5TDKZRFH3HS214845
    Stock: 214845N
    Certified Pre-Owned: No

  • 2019 Toyota Highlander
    XLE 4dr SUV

    $21,795
    great price
    $3,103 below market
    • 101,600 miles
    • No accidents, 1 owner, taxi vehicle
    • 8 Seats, 20 City / 26 Hwy MPG
    • A Better Way Wholesale Autos (20 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 20 miles away from Trumbull, CT

    - Sleek black exterior with luxurious black leather interior - Powerful 3.5L V6 engine with 295hp and 263ft. lbs. torque - Advanced safety features:...

    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: 5TDJZRFH3KS585278
    Stock: 585278NL
    Certified Pre-Owned: No

  • Price Drop

    2019 Toyota Highlander
    XLE 4dr SUV

    $22,995
    great price
    $1,952 below market
    • 101,020 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 7 Seats, 20 City / 26 Hwy MPG
    • A Better Way Wholesale Autos (20 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 20 miles away from Trumbull, CT

    - Experience luxury and comfort with the 2019 Toyota Highlander SE's plush leather interior and advanced infotainment system. - Feel the power of the...

    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: 5TDJZRFH6KS602669
    Stock: 602669N
    Certified Pre-Owned: No

  • Price Drop

    2015 Toyota Highlander
    XLE 4dr SUV

    $17,495
    great price
    $2,222 below market
    • 94,280 miles
    • 1 accident, 1 owner, personal use only
    • 8 Seats, 18 City / 24 Hwy MPG
    • A Better Way Wholesale Autos (20 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 20 miles away from Trumbull, CT

    - **Mileage:** Well-maintained with 94,280 miles, offering reliability and longevity. - **Luxury Interior:** Other leather interior for a comfortable...

    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: 5TDJKRFH2FS114250
    Stock: 114250N
    Certified Pre-Owned: No

  • 5 Offers Nearby

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

  • 2008 Toyota Highlander
    Limited 4dr SUV

    $10,995
    good price
    $1,633 below market
    • 90,842 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 17 City / 23 Hwy MPG
    • A Better Way Wholesale Autos (20 mi away)
    • AWD/4WD
    • Back-up camera
    • Leather Seats
    • Third-row seating
    • Power Driver Seat
    Close

    Located in Naugatuck, CT / 20 miles away from Trumbull, CT

    - Impressive 270hp V6 engine with smooth 5-Speed Automatic transmission, perfect for power and efficiency. - Luxurious leather interior with award-wi...

    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: JTEES42A682045078
    Stock: 45078N
    Certified Pre-Owned: No

  • Certified 2024 Toyota Highlander
    XLE 4dr SUV

    $43,395
    fair price
    $54 below market
    • 21,147 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 28 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. 2024 Toyota Highlander XLE AWDAWD, ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front ...

    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: 5TDKDRBH0RS548210
    Stock: U22380A
    Certified Pre-Owned: Yes
    Listed since: 04-24-2025

  • 2015 Toyota Highlander
    XLE 4dr SUV

    $16,995
    good price
    $1,149 below market
    • 100,300 miles
    • 1 accident, 2 owners, personal use only
    • 8 Seats, 18 City / 24 Hwy MPG
    • A Better Way Wholesale Autos (20 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 20 miles away from Trumbull, CT

    - Experience luxury with a sophisticated black exterior and plush gray leather interior. - Powered by a robust 3.5L V6 engine delivering 270hp with a...

    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: 5TDJKRFH4FS161358
    Stock: 161358N
    Certified Pre-Owned: No

  • 2012 Toyota Highlander
    SE 4dr SUV

    $12,999
    good price
    $908 below market
    • 116,742 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 17 City / 22 Hwy MPG
    • Honda of Westport (10 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Westport, CT / 10 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:

    19 Combined MPG (17 City/22 Highway)

    Listing Information:

    VIN: 5TDBK3EH2CS159543
    Stock: 30837
    Certified Pre-Owned: No
    Listed since: 03-21-2025

  • 5 Offers Nearby

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

    2011 Toyota Highlander
    Base 4dr SUV

    $12,995
    fair price
    $449 above market
    • 113,382 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 17 City / 22 Hwy MPG
    • A Better Way Wholesale Autos (20 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Power Driver Seat
    Close

    Located in Naugatuck, CT / 20 miles away from Trumbull, CT

    - Reliable and powerful 3.5L V6 engine with 270 horsepower - Spacious interior with second-row rear vents and privacy glass - Award-winning family v...

    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: 5TDBK3EH8BS062068
    Stock: 62068N
    Certified Pre-Owned: No

  • 2023 Toyota Highlander
    LE 4dr SUV

    $33,998
    fair price
    $508 below market
    • 30,123 miles
    • 1 accident, 2 owners, personal use only
    • 8 Seats, 21 City / 28 Hwy MPG
    • CarMax East Haven (17 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    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: 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/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH5PS031370
    Stock: 26324009
    Certified Pre-Owned: No

  • 2013 Toyota Highlander
    Base 4dr SUV

    $14,677
    fair price
    $168 above market
    • 120,724 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 17 City / 22 Hwy MPG
    • Wallingford Auto Park (25 mi away)
    • AWD/4WD
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Wallingford, CT / 25 miles away from Trumbull, CT

    Advertised price does not include state or local taxes, registration costs, or dealer conveyance fee of $799 (which is subject to negotiation) not inc...

    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: 5TDBK3EH7DS250972
    Stock: 19149
    Certified Pre-Owned: No
    Listed since: 04-11-2025

  • 2022 Toyota Highlander
    XLE 4dr SUV

    $36,999
    good price
    $1,222 below market
    • 38,580 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 20 City / 27 Hwy MPG
    • Enterprise Car Sales Milford (7 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Milford, CT / 7 miles away from Trumbull, CT

    Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...

    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: 5TDGZRBH2NS244300
    Stock: 7V5BDW
    Certified Pre-Owned: No
    Listed since: 04-07-2025

  • 5 Offers Nearby

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

  • 2021 Toyota Highlander
    XLE 4dr SUV

    $34,000
    fair price
    $437 below market
    • 34,760 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • Brandfon Hyundai (17 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

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

    CLEAN CARFAX!, ALL WHEEL DRIVE!, ONE OWNER!, MARKET BASED PRICE DEALER!. 20/27 City/Highway MPG 20/27 City/Highway MPG Awards: * ALG Residual Value Aw...

    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: 5TDGZRBH0MS157025
    Stock: H8498A
    Certified Pre-Owned: No
    Listed since: 03-29-2025

  • New Listing

    2022 Toyota Highlander
    LE 4dr SUV

    $32,998
    fair price
    $271 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

  • 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

  • Price Drop

    2024 Toyota Highlander
    Limited 4dr SUV

    $46,000
    good price
    $3,029 below market
    • 6,267 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • New Country Toyota of Westport (11 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Westport, CT / 11 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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBHXRS553320
    Stock: RS553320
    Certified Pre-Owned: No

  • 5 Offers Nearby

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

  • 2020 Toyota Highlander
    XLE 4dr SUV

    $29,995
    fair price
    $417 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

  • 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

  • 2007 Toyota Highlander
    Base 4dr SUV

    $6,895
    good price
    $911 below market
    • 147,806 miles
    • No accidents, 2 owners, personal use only
    • 5 Seats, 19 City / 25 Hwy MPG
    • Boulevard Motors (14 mi away)
    • Tire Pressure Warnin...
    • Rear Bench Seats
    • Stability Control
    • Fold Flat Rear Seats
    • 2500lb Towing Capaci...
    Close

    Located in New Haven, CT / 14 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 (19 City/25 Highway)

    Listing Information:

    VIN: JTEGD21A470166291
    Stock: 166291
    Certified Pre-Owned: No

  • New Listing
    Stock photo**

    Certified 2021 Toyota Highlander
    XLE 4dr SUV

    $35,995
    fair price
    $790 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

  • New Listing

    2015 Toyota Highlander
    XLE 4dr SUV

    $24,998
    • 66,520 miles
    • 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 Unavailable.

    Features and Specs:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDJKRFH9FS149593
    Stock: 27320428
    Certified Pre-Owned: No

Showing 1 - 21 out of 1,122 listings
Highlander Reviews & Specs

Used Toyota Highlander by Year

VehicleDealsStarting PriceTotal Available
2025 Toyota Highlander-$47,9981 listing
2024 Toyota Highlander15 Great Deals$34,998107 listings
2023 Toyota Highlander12 Great Deals$26,137185 listings
2022 Toyota Highlander8 Great Deals$27,528210 listings
2021 Toyota Highlander9 Great Deals$22,590140 listings
2020 Toyota Highlander1 Great Deal$21,99857 listings
2019 Toyota Highlander7 Great Deals$15,950112 listings
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