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1,730 listings
  • $27,923
    good price
    $1,263 below market
    • 102,726 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 20 City / 27 Hwy MPG
    • Romeo Toyota (99 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Glens Falls, NY / 99 miles away from Springfield, MA

    Romeo Toyota proudly presents this 2021 Toyota Highlander with 18" Machined Alloy Wheels, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc 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: 5TDHZRBH9MS062001
    Stock: TR2548A
    Certified Pre-Owned: No
    Listed since: 06-17-2025

  • $29,995
    good price
    $1,103 below market
    • 78,314 miles
    • No accidents, 2 owners, corporate fleet vehicle
    • 7 Seats, 20 City / 27 Hwy MPG
    • Fazza Motors (51 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Marlborough, MA / 51 miles away from Springfield, MA

    White 2021 Toyota Highlander XLE V6 AWD AWD 8-Speed Automatic 3.5L V6 DOHC 3rd Row Seat, 7 Pass, AWD, Alloy Wheels, Back-up Cam, Blind Spot Monitor, B...

    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: 5TDGZRBH3MS116002
    Stock: 2013M
    Certified Pre-Owned: No
    Listed since: 06-13-2025

  • $41,695
    fair price
    $679 below market
    • 6,687 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 7 Seats, 21 City / 28 Hwy MPG
    • Woburn Toyota (75 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Woburn, MA / 75 miles away from Springfield, MA

    COME VISIT OUR INDOOR CLIMATE CONTROLLED SHOWROOM!, Highlander XLE, 4D Sport Utility, 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp, 8-Speed Au...

    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: 5TDKDRBH0PS026237
    Stock: P17160
    Certified Pre-Owned: Yes
    Listed since: 06-20-2025

  • Price Drop
    $37,787
    fair price
    $359 below market
    • 28,216 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • Kia North Danvers (84 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Danvers, MA / 84 miles away from Springfield, MA

    Experience versatile comfort in this 2022 Toyota Highlander XLE with just 28,216 miles, now available at KIA North Danvers in Danvers, MA. This midsiz...

    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: 5TDGZRBH0NS251410
    Stock: 0702A
    Certified Pre-Owned: No
    Listed since: 06-10-2025

  • $16,499
    good price
    $1,730 below market
    • 132,011 miles
    • No accidents, 3 owners, personal use only
    • 8 Seats, 18 City / 24 Hwy MPG
    • Tim's Truck Capital (94 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Epsom, NH / 94 miles away from Springfield, MA

    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: 5TDJKRFH3GS269004
    Stock: TAZ1454
    Certified Pre-Owned: No
    Listed since: 05-02-2025

  • Price Drop
    $37,995
    fair price
    $53 below market
    • 35,277 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • McGee Toyota of Putnam (36 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Putnam, CT / 36 miles away from Springfield, MA

    McGee Toyota of Putnam is proud to present you with this 2023 Toyota Highlander XLE! ---------- ONE (1) OWNER TRADE-IN, CLEAN CARFAX, AWD, 2.4L I...

    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: 5TDKDRBH6PS042250
    Stock: 25628TA
    Certified Pre-Owned: No
    Listed since: 06-13-2025

  • $10,995
    good price
    $1,030 below market
    • 113,382 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 17 City / 22 Hwy MPG
    • A Better Way Wholesale Autos (51 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Power Driver Seat
    Close

    Located in Naugatuck, CT / 51 miles away from Springfield, MA

    - 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

  • $38,830
    fair price
    $524 below market
    • 39,590 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 21 City / 28 Hwy MPG
    • Nucar Toyota North Attleboro (61 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in North Attleboro, MA / 61 miles away from Springfield, MA

    CARFAX 1-Owner. WAS $41,980. XLE trim, Celestial Silver Metallic exterior and BLACK interior. Third Row Seat, Back-Up Camera, Rear Air, Power Liftgate...

    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: 5TDKDRBH5RS536697
    Stock: A03326
    Certified Pre-Owned: No
    Listed since: 06-09-2025

  • $18,995
    good price
    $1,561 below market
    • 126,409 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 20 City / 26 Hwy MPG
    • Toyota of Colchester (41 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Colchester, CT / 41 miles away from Springfield, MA

    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: 5TDJZRFH9JS863793
    Stock: 20256A
    Certified Pre-Owned: No
    Listed since: 07-19-2025

  • Price Drop
    $37,981
    good price
    $2,369 below market
    • 21,460 miles
    • No accidents, 2 owners, personal use
    • 8 Seats, 21 City / 28 Hwy MPG
    • Key Chevrolet GMC of Newport (85 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Newport, NH / 85 miles away from Springfield, MA

    2023 Toyota Highlander XLE 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp Black AWD, ABS brakes, Active Cruise Control, Alloy wheels, Electronic...

    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: 5TDKDRBH5PS027576
    Stock: E13550A
    Certified Pre-Owned: No
    Listed since: 06-23-2025

  • $41,851
    good price
    $1,625 below market
    • 13,048 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 28 Hwy MPG
    • Ingersoll Auto of Danbury (70 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Danbury, CT / 70 miles away from Springfield, MA

    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

  • New Listing
    $41,995
    fair price
    $52 below market
    • 16,269 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 28 Hwy MPG
    • Lia Toyota of Northampton (14 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Northampton, MA / 14 miles away from Springfield, MA

    Recent Arrival! TOYOTA CERTIFIED / CPO WARRANTY, One Owner - Clean Car Fax, Apple CarPlay, Android Auto, Adaptive Cruise Control, Lane Departure Warni...

    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: 5TDKDRBH0RS568702
    Stock: RS568702R
    Certified Pre-Owned: Yes
    Listed since: 07-25-2025

  • $15,995
    good price
    $1,075 below market
    • 131,332 miles
    • No accidents, 2 owners, personal use only
    • 8 Seats, 18 City / 24 Hwy MPG
    • A Better Way Wholesale Autos (51 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 51 miles away from Springfield, MA

    - **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
    $30,131
    great price
    $1,994 below market
    • 76,079 miles
    • 1 accident, 1 owner, personal use only
    • 8 Seats, 20 City / 27 Hwy MPG
    • Romeo Toyota (99 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Glens Falls, NY / 99 miles away from Springfield, MA

    Romeo Toyota proudly presents this 2022 Toyota Highlander with 2nd Row Bench Seat, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes, ...

    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: 5TDGZRBH6NS593833
    Stock: 29375A
    Certified Pre-Owned: No
    Listed since: 05-30-2025

  • $6,450
    fair price
    $958 below market
    • 144,525 miles
    • 1 accident, 1 owner, personal use only
    • 7 Seats, 16 City / 22 Hwy MPG
    • Choice Motor Car (39 mi away)
    • AWD/4WD
    • Third-row seating
    • Power Driver Seat
    • Tire Pressure Warnin...
    • Auto Climate Control
    Close

    Located in Plainville, CT / 39 miles away from Springfield, MA

    Nice, clean, loaded up Highlander in great condition inside and out. Leather seats, power sliding sunroof, 4wd, power windows locks and seat, nice ne...

    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 (16 City/22 Highway)

    Listing Information:

    VIN: JTEEP21A550080550
    Stock: 080550
    Certified Pre-Owned: No
    Listed since: 09-10-2024

  • New Listing
    $29,998
    fair price
    $874 below market
    • 38,358 miles
    • 1 accident, 2 owners, personal use
    • 8 Seats, 20 City / 27 Hwy MPG
    • Herb Chambers Ford of Westborough (45 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Westborough, MA / 45 miles away from Springfield, MA

    INSPECTION COMPLETED Every Herb Chambers Certified pre-owned vehicle receives a complete multi-point inspection by factory trained technicians who ins...

    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: 5TDBZRBH0MS537962
    Stock: NSW4779B
    Certified Pre-Owned: No
    Listed since: 06-11-2025

  • $21,995
    good price
    $1,565 below market
    • 97,051 miles
    • No accidents, 4 owners, corporate fleet vehicle
    • 8 Seats, 20 City / 26 Hwy MPG
    • A Better Way Wholesale Autos (51 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Naugatuck, CT / 51 miles away from Springfield, MA

    - **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

  • $5,900
    great price
    $1,871 below market
    • 192,000 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 17 City / 23 Hwy MPG
    • Brodster's Roadsters (69 mi away)
    • AWD/4WD
    • Back-up camera
    • Leather Seats
    • Sunroof/Moonroof
    • Third-row seating
    Close

    Located in New Fairfield, CT / 69 miles away from Springfield, MA

    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: 5TDJK3EH0AS026952
    Stock: 026952
    Certified Pre-Owned: No

  • Price Drop
    $42,999
    good price
    $1,793 below market
    • 14,182 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • Toyota of Dartmouth (86 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in North Dartmouth, MA / 86 miles away from Springfield, MA

    Low miles! 8,657 Miles Below Average 2023 Toyota Highlander XSE 12.3-in. Toyota Audio Multimedia with JBL AWD SUV Discover the thrill of driving with ...

    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: 5TDKDRBH2PS019970
    Stock: N75859A
    Certified Pre-Owned: Yes
    Listed since: 07-12-2025

  • Price Drop
    $39,798
    good price
    $2,567 below market
    • 40,740 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • McGee Toyota of Putnam (36 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Putnam, CT / 36 miles away from Springfield, MA

    McGee Toyota of Putnam is proud to present you with this 2023 Toyota Highlander Platinum! ---------- ONE OWNER, CLEAN CARFAX, AWD, 2.4 I-4 TURBO...

    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: 5TDKDRBH5PS031403
    Stock: 25357A
    Certified Pre-Owned: No
    Listed since: 05-17-2025

  • $33,000
    fair price
    $629 below market
    • 36,501 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Automax Pre Owned Marlborough (51 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Marlborough, MA / 51 miles away from Springfield, MA

    Only 36k Miles - AWD XLE Edition - Midnight Black exterior on Beige Leatherette interior with Navigation / GPS / NAV, Sunroof / Moonroof, Heated Seats...

    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: 5TDHZRBH0LS515887
    Stock: 515887
    Certified Pre-Owned: No
    Listed since: 06-20-2025

Showing 22 - 42 out of 1,730 listings

Buying a Toyota Highlander in Springfield Massachusetts

The Toyota Highlander stands out as a versatile option for those living in and around Springfield, MA. Its spacious interior and comfortable seating make it ideal for family outings to the nearby Forest Park or the Dr. Seuss National Memorial Sculpture Garden. The Highlander's smooth, quiet ride enhances the experience of navigating the city’s streets or taking day trips to the scenic Pioneer Valley. With its robust V6 engine, drivers can enjoy a balance of power and efficiency, making it suitable 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.