Skip to main content
Skip to Filters
1,092 listings
  • $14,995
    great price
    $3,722 below market
    • 100,300 miles
    • 1 accident, 2 owners, personal use only
    • 8 Seats, 18 City / 24 Hwy MPG
    • A Better Way Wholesale Autos (24 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 24 miles away from Bridgeport, 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

  • $40,833
    good price
    $3,420 below market
    • 5,952 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 28 Hwy MPG
    • Ingersoll Auto of Danbury (21 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Danbury, CT / 21 miles away from Bridgeport, CT

    Priced below KBB Fair Purchase Price! Odometer is 11958 miles below market average! Clean CARFAX. 18' Painted Alloy Wheels, 3rd row seats: split-bench...

    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: 5TDKDRBH3RS532762
    Stock: A532762
    Certified Pre-Owned: No
    Listed since: 06-20-2025

  • $13,995
    great price
    $2,814 below market
    • 99,437 miles
    • 1 accident, 2 owners, personal use only
    • 7 Seats, 17 City / 22 Hwy MPG
    • A Better Way Wholesale Autos (24 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 24 miles away from Bridgeport, CT

    - Experience the perfect blend of power and efficiency with a robust 3.5L V6 engine delivering 270hp. - Luxurious leather interior ensures comfort an...

    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:

    19 Combined MPG (17 City/22 Highway)

    Listing Information:

    VIN: 5TDDK3EH0CS160389
    Stock: 160389N
    Certified Pre-Owned: No

  • $23,195
    great price
    $2,780 below market
    • 70,305 miles
    • 2 accidents, 1 owner, personal use
    • 7 Seats, 20 City / 26 Hwy MPG
    • Autoland USA (23 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Selden, NY / 23 miles away from Bridgeport, CT

    This 2019 Toyota Highlander XLE is a reliable and powerful SUV. With an all-wheel drive system and 3.5 liter 6 cylinder engine, this car has been driv...

    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:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDJZRFH3KS598242
    Stock: 9165F
    Certified Pre-Owned: No
    Listed since: 03-29-2025

  • $11,995
    good price
    $1,642 below market
    • 118,333 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 17 City / 22 Hwy MPG
    • A Better Way Wholesale Autos (24 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 24 miles away from Bridgeport, CT

    - **Proven Reliability:** Award-winning dependability and quality from J.D. Power and Kelley Blue Book. - **Powerful Performance:** Robust 3.5L V6 en...

    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: 5TDBK3EH1CS101004
    Stock: 101004N
    Certified Pre-Owned: No

  • $10,495
    good price
    $1,472 below market
    • 133,554 miles
    • No accidents, 3 owners, personal use only
    • 7 Seats, 17 City / 22 Hwy MPG
    • A Better Way Wholesale Autos (24 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Naugatuck, CT / 24 miles away from Bridgeport, CT

    - Experience the perfect blend of power and efficiency with a robust 3.5L V6 engine delivering 270 horsepower. - Enjoy peace of mind with top accolad...

    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: 5TDBK3EH9CS100411
    Stock: 100411N
    Certified Pre-Owned: No

  • $41,851
    good price
    $1,644 below market
    • 13,048 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 28 Hwy MPG
    • Ingersoll Auto of Danbury (21 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Danbury, CT / 21 miles away from Bridgeport, CT

    Odometer is 9812 miles below market average! CARFAX One-Owner. Clean CARFAX. Back-Up Camera, 18' Painted Alloy Wheels, 3rd row seats: split-bench, Fro...

    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: 5TDKDRBH8RS568057
    Stock: A568057
    Certified Pre-Owned: No
    Listed since: 07-07-2025

  • $10,995
    good price
    $1,031 below market
    • 113,382 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 17 City / 22 Hwy MPG
    • A Better Way Wholesale Autos (24 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Power Driver Seat
    Close

    Located in Naugatuck, CT / 24 miles away from Bridgeport, 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

  • $15,995
    good price
    $1,118 below market
    • 131,332 miles
    • No accidents, 2 owners, personal use only
    • 8 Seats, 18 City / 24 Hwy MPG
    • A Better Way Wholesale Autos (24 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 24 miles away from Bridgeport, CT

    - **Proven Reliability**: Award-winning 2016 Toyota Highlander XLE with a 3.5L V6 engine, recognized by Edmunds, J.D. Power, and Kelley Blue Book for ...

    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: 5TDJKRFH0GS240351
    Stock: 240351N
    Certified Pre-Owned: No

  • Price Drop
    $26,999
    good price
    $1,395 below market
    • 72,196 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 20 City / 27 Hwy MPG
    • Honda of Westport (9 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Westport, CT / 9 miles away from Bridgeport, 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

  • $21,995
    good price
    $1,265 below market
    • 97,051 miles
    • No accidents, 4 owners, corporate fleet vehicle
    • 8 Seats, 20 City / 26 Hwy MPG
    • A Better Way Wholesale Autos (24 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 24 miles away from Bridgeport, CT

    - **Low Mileage & Powerful Performance**: With only 97,051 miles, this 2018 Toyota Highlander SE is equipped with a robust 3.5L V6 engine delivering 2...

    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: 5TDJZRFH1JS822414
    Stock: 822414N
    Certified Pre-Owned: No

  • $21,353
    fair price
    $647 below market
    • 98,403 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 20 City / 26 Hwy MPG
    • Bruce Bennett Nissan of Danbury (22 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Danbury, CT / 22 miles away from Bridgeport, CT

    BLUETOOTH/HANDS FREE/CELL PHONE, BACK UP CAMERA, FORWARD COLLISION WARNING, BLIND SPOT WARNING ALERT, REAR CROSS TRAFFIC ALERT, CLEAN CARFAX/NO ACCIDE...

    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: 5TDJZRFH8JS874302
    Stock: SC115061A
    Certified Pre-Owned: No
    Listed since: 06-02-2025

  • $34,995
    fair price
    $456 above market
    • 41,837 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • Greentree Toyota (21 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Danbury, CT / 21 miles away from Bridgeport, CT

    Certified. 2021 Toyota Highlander XLE AWDAWD.Highlander AWD XLE AWD Silver 3.5L V6 DOHC 8-Speed Automatic 4D Sport Utility Odometer is 12747 miles b...

    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: 5TDGZRBH4MS069241
    Stock: U22549
    Certified Pre-Owned: Yes
    Listed since: 06-12-2025

  • Price Drop
    $34,752
    great price
    $3,225 below market
    • 40,809 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 21 City / 28 Hwy MPG
    • New Country Toyota of Westport (10 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Westport, CT / 10 miles away from Bridgeport, 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: 5TDKDRBH1PS013593
    Stock: PS013593
    Certified Pre-Owned: No

  • $27,980
    good price
    $1,126 below market
    • 70,100 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 20 City / 27 Hwy MPG
    • Performance Motor Cars (16 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Wilton, CT / 16 miles away from Bridgeport, 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

  • $18,500
    fair price
    $415 above market
    • 117,470 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 18 City / 24 Hwy MPG
    • Brandfon Hyundai (15 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in New Haven, CT / 15 miles away from Bridgeport, 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: 5TDJKRFH1GS326400
    Stock: H8498B
    Certified Pre-Owned: No
    Listed since: 07-05-2025

  • $21,995
    fair price
    $779 below market
    • 51,781 miles
    • 1 accident, 2 owners, personal use
    • 8 Seats, 18 City / 24 Hwy MPG
    • A Better Way Wholesale Autos (24 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 24 miles away from Bridgeport, CT

    - Low Mileage: With only 51,781 miles, this 2016 Toyota Highlander XLE is primed for many more adventures. - Luxurious Interior: Enjoy the comfort of...

    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: 5TDJKRFH0GS334522
    Stock: 334522N
    Certified Pre-Owned: No

  • $39,995
    fair price
    $416 below market
    • 41,315 miles
    • 1 accident, 1 owner, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • D'Addario Nissan (8 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Shelton, CT / 8 miles away from Bridgeport, CT

    2022 Toyota Highlander Platinum AWD 8-Speed Automatic 3.5L V6 DOHC AWD. CARFAX One-Owner. 20/27 City/Highway MPG

    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: 5TDFZRBH9NS216781
    Stock: C5106A
    Certified Pre-Owned: No
    Listed since: 04-29-2025

  • $35,495
    fair price
    $1,203 below market
    • 57,100 miles
    • 1 accident, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Greentree Toyota (21 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Danbury, CT / 21 miles away from Bridgeport, CT

    Recent Arrival!Certified. CARFAX One-Owner. 2020 Toyota Highlander Platinum AWDAWD.Highlander AWD Platinum AWD Midnight Black Metallic 3.5L V6 DOHC...

    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: 5TDFZRBHXLS053359
    Stock: U22620
    Certified Pre-Owned: Yes
    Listed since: 07-16-2025

  • New Listing
    $20,998
    fair price
    $304 above market
    • 111,274 miles
    • 1 accident, 2 owners, personal use only
    • 8 Seats, 19 City / 26 Hwy MPG
    • CarMax East Haven (15 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    Close

    Located in East Haven, CT / 15 miles away from Bridgeport, 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:

    22 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 5TDBZRFH4KS967923
    Stock: 26854221
    Certified Pre-Owned: No

  • $31,995
    great price
    $1,824 below market
    • 96,406 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • J&M Automotive (21 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Naugatuck, CT / 21 miles away from Bridgeport, 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: 5TDFZRBH8MS110692
    Stock: 2110692
    Certified Pre-Owned: No

Showing 1 - 21 out of 1,092 listings

Buying a Toyota Highlander in Bridgeport Connecticut

For those exploring Bridgeport, CT, the Toyota Highlander stands out as a practical and versatile choice. Its comfortable and quiet ride makes it well-suited for both daily commutes and weekend excursions to local attractions like Beardsley Zoo or the scenic waterfront. The Highlander’s spacious interior can easily accommodate families heading out for day trips, while its solid V6 engine provides a balance of power and fuel efficiency ideal for navigating city streets and longer drives alike.

Filters
Skip to Results

Applied Filters4Active

Select Buying Experience

Location

Search radius25 miles
Search radius

Make & Model

Year

New / Used

Price & Payments

Price Rating

Body Type

Trim

Mileage

Accidents & History

Engine & Drivetrain

Exterior Color

Interior Color

Total Seating

Edmunds Review

Features

Options & Packages

MPG

Listing Details


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