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264 listings
  • New Listing
    Stock photo**
    • 52,117 miles
    • 1 accident, 2 owners, personal use
    • 7 Seats, 35 City / 34 Hwy MPG
    • Toyota of Wallingford (71 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Wallingford, CT / 71 miles away from Pittsfield, MA

    2021 Toyota Highlander Hybrid Platinum Recent Arrival! Certified. 35/34 City/Highway MPGLOCAL TRADE, HEATED LEATHER SEATS, PREMIUM SOUND, LOADED WITH ...

    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:

    35 Combined MPG (35 City/34 Highway)

    Listing Information:

    VIN: 5TDEBRCH5MS022357
    Stock: 250935A
    Certified Pre-Owned: Yes
    Listed since: 07-25-2025

  • $15,900
    fair price
    $462 below market
    • 145,062 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 27 City / 28 Hwy MPG
    • Bloomfield Motors (53 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Bloomfield, CT / 53 miles away from Pittsfield, 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:

    28 Combined MPG (27 City/28 Highway)

    Listing Information:

    VIN: 5TDDCRFH6ES006027
    Stock: 006027
    Certified Pre-Owned: No

    • 60,626 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 35 City / 35 Hwy MPG
    • Herb Chambers Toyota of Auburn (74 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Auburn, MA / 74 miles away from Pittsfield, 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: 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:

    35 Combined MPG (35 City/35 Highway)

    Listing Information:

    VIN: 5TDABRCH4NS542047
    Stock: A285960A
    Certified Pre-Owned: No
    Listed since: 07-11-2025

    • 30,285 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 35 City / 35 Hwy MPG
    • Girard Toyota (96 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in New London, CT / 96 miles away from Pittsfield, MA

    2.5L I4 PDI Hybrid DOHC 16V LEV3-SULEV30, One Owner.Black 2024 Toyota Highlander Hybrid XLE 4D Sport Utility AWD Automatic 2.5L I4 PDI Hybrid DOHC 16V...

    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:

    35 Combined MPG (35 City/35 Highway)

    Listing Information:

    VIN: 5TDKBRCHXRS139779
    Stock: 46883
    Certified Pre-Owned: No
    Listed since: 07-18-2025

  • New Listing
    Photos not available
    • 269,268 miles
    • No accidents, 3 owners, personal use only
    • 7 Seats, 27 City / 25 Hwy MPG
    • Carriage Traders (61 mi away)
    • AWD/4WD
    • Third-row seating
    • Power Driver Seat
    • Trip Computer
    • Rear Bench Seats
    Close

    Located in South Glens Falls, NY / 61 miles away from Pittsfield, MA

    Boasts 27 Highway MPG and 31 City MPG! This Toyota Highlander Hybrid delivers a Gas/Electric V6 3.3L/ engine powering this Variable transmission. Vehi...

    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:

    26 Combined MPG (27 City/25 Highway)

    Listing Information:

    VIN: JTEEW21A860019651
    Stock: T3006A
    Certified Pre-Owned: No
    Listed since: 07-28-2025

  • Stock photo**
    • 21,453 miles
    • 1 accident, 1 owner, personal use only
    • 8 Seats, 35 City / 35 Hwy MPG
    • Lia Toyota of Colonie (38 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Schenectady, NY / 38 miles away from Pittsfield, MA

    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:

    35 Combined MPG (35 City/35 Highway)

    Listing Information:

    VIN: 5TDKBRCH4RS628159
    Stock: RS628159
    Certified Pre-Owned: No
    Listed since: 07-31-2024

  • New Listing
    Stock photo**
    • 32,806 miles
    • 7 Seats, 35 City / 35 Hwy MPG
    • Toyota of Nashua (94 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Nashua, NH / 94 miles away from Pittsfield, MA

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    35 Combined MPG (35 City/35 Highway)

    Listing Information:

    VIN: 5TDGBRCH5MS521569
    Stock: C4122
    Certified Pre-Owned: No
    Listed since: 07-28-2025

  • New Listing
    Stock photo**
    • 100,304 miles
    • 2 accidents, 1 owner, personal use only
    • 7 Seats, 29 City / 27 Hwy MPG
    • Romeo Toyota (62 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Glens Falls, NY / 62 miles away from Pittsfield, MA

    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:

    28 Combined MPG (29 City/27 Highway)

    Listing Information:

    VIN: 5TDDGRFH3KS052964
    Stock: 29526A
    Certified Pre-Owned: No
    Listed since: 07-24-2025

  • $22,987
    great price
    $2,256 below market
    • 140,579 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 29 City / 27 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Van Nuys, CA / 2,484 miles away from Pittsfield, MA

    Rare Find,Green Vehicle,3rd Row Seat,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Leather S...

    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:

    28 Combined MPG (29 City/27 Highway)

    Listing Information:

    VIN: 5TDJGRFH6KS062682
    Stock: KS062682T
    Certified Pre-Owned: No

    • 61,700 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 35 City / 34 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Frisco, TX / 1,428 miles away from Pittsfield, MA

    Rare Find,Green Vehicle,3rd Row Seat,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,Heated Seats,Heated Steering Wheel,K...

    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:

    35 Combined MPG (35 City/34 Highway)

    Listing Information:

    VIN: 5TDEBRCH5NS083984
    Stock: NS083984A
    Certified Pre-Owned: No

    • 97,060 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 7 Seats, 35 City / 35 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Dallas, TX / 1,443 miles away from Pittsfield, MA

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    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:

    35 Combined MPG (35 City/35 Highway)

    Listing Information:

    VIN: 5TDGBRCH5NS560972
    Stock: 2003824701
    Certified Pre-Owned: No
    Listed since: 06-17-2025

  • Price Drop
    $40,749
    great price
    $3,335 below market
    • 50,193 miles
    • No accidents, personal use only
    • 7 Seats, 35 City / 34 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Farmington Hills, MI / 517 miles away from Pittsfield, MA

    Rare Find,Green Vehicle,3rd Row Seat,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,Heated Seats,Heated Steering Wheel,K...

    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:

    35 Combined MPG (35 City/34 Highway)

    Listing Information:

    VIN: 5TDEBRCH1NS085053
    Stock: NS085053P
    Certified Pre-Owned: No

  • New Listing
    $43,998
    great price
    $3,458 below market
    • 9,722 miles
    • 7 Seats, 35 City / 35 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from CA to MA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Costa Mesa, CA / 2,473 miles away from Pittsfield, MA

    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:

    35 Combined MPG (35 City/35 Highway)

    Listing Information:

    VIN: 5TDKBRCH5RS605313
    Stock: 27621824
    Certified Pre-Owned: No

  • Price Drop
    $39,500
    great price
    $3,373 below market
    • 69,863 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 35 City / 34 Hwy MPG
    • Bernardi Toyota (92 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Framingham, MA / 92 miles away from Pittsfield, MA

    2022 Toyota Highlander Hybrid Platinum AWD 2.5L I4 PDI Hybrid DOHC 16V LEV3-SULEV30 186hp 4D Sport Utility eCVT CARFAX One-Owner.WORRY FREE at BERNARD...

    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:

    35 Combined MPG (35 City/34 Highway)

    Listing Information:

    VIN: 5TDEBRCH9NS096897
    Stock: P17400
    Certified Pre-Owned: Yes
    Listed since: 05-10-2025

  • $37,595
    great price
    $2,964 below market
    • 71,001 miles
    • No accidents, 3 owners, personal use only
    • 7 Seats, 35 City / 34 Hwy MPG
    • Lynch Toyota (59 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Manchester, CT / 59 miles away from Pittsfield, MA

    Discover the perfect blend of efficiency, luxury, and reliability with this Certified Pre-Owned 2021 Toyota Highlander Hybrid Platinum. This exception...

    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:

    35 Combined MPG (35 City/34 Highway)

    Listing Information:

    VIN: 5TDEBRCH2MS023353
    Stock: LT9179
    Certified Pre-Owned: Yes
    Listed since: 03-23-2025

  • $41,000
    great price
    $3,152 below market
    • 40,617 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 35 City / 35 Hwy MPG
    • Bernardi Toyota (92 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Framingham, MA / 92 miles away from Pittsfield, MA

    2023 Toyota Highlander Hybrid XLE AWD 2.5L I4 PDI Hybrid DOHC 16V LEV3-SULEV30 4D Sport Utility eCVTOdometer is 8631 miles below market average!WORRY ...

    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:

    35 Combined MPG (35 City/35 Highway)

    Listing Information:

    VIN: 5TDKBRCH9PS580896
    Stock: W0641A
    Certified Pre-Owned: Yes
    Listed since: 06-19-2025

  • $6,495
    great price
    $1,290 below market
    • 269,577 miles
    • 1 accident, 2 owners, personal use only
    • 7 Seats, 27 City / 25 Hwy MPG
    • Mass Motors (78 mi away)
    • AWD/4WD
    • Back-up camera
    • Leather Seats
    • Third-row seating
    • Power Driver Seat
    Close

    Located in Worcester, MA / 78 miles away from Pittsfield, MA

    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:

    26 Combined MPG (27 City/25 Highway)

    Listing Information:

    VIN: JTEEW44A992027189
    Stock: 64322
    Certified Pre-Owned: No
    Listed since: 05-14-2025

  • $38,678
    fair price
    $1,247 below market
    • 45,604 miles
    • No accidents, 1 owner, personal use
    • 8 Seats, 35 City / 34 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Van Nuys, CA / 2,484 miles away from Pittsfield, MA

    Rare Find,Green Vehicle,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Chrome Wheels,Hands-Free Liftgate,Heated S...

    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:

    35 Combined MPG (35 City/34 Highway)

    Listing Information:

    VIN: 5TDDBRCH9MS016721
    Stock: MS016721T
    Certified Pre-Owned: No

  • Price Drop
    $5,995
    good price
    $1,779 below market
    • 211,000 miles
    • 1 accident, 2 owners, personal use only
    • 7 Seats, 27 City / 25 Hwy MPG
    • Carlot Express (91 mi away)
    • AWD/4WD
    • Back-up camera
    • Leather Seats
    • Third-row seating
    • Power Driver Seat
    Close

    Located in Stow, MA / 91 miles away from Pittsfield, MA

    JTEEW44A5820***** 2*** Toyota Highlander Limited Hybrid AWD Clean inside and out. Glossy light blue exterior with grey leather interior. Seats up to 7...

    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:

    26 Combined MPG (27 City/25 Highway)

    Listing Information:

    VIN: JTEEW44A582014194
    Stock: 014194
    Certified Pre-Owned: No
    Listed since: 07-06-2025

    • 57,739 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 36 City / 35 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from TX to MA*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Katy, TX / 1,522 miles away from Pittsfield, MA

    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:

    36 Combined MPG (36 City/35 Highway)

    Listing Information:

    VIN: 5TDFARAH2LS004133
    Stock: 27353562
    Certified Pre-Owned: No

  • Price Drop
    $25,200
    great price
    $1,936 below market
    • 96,569 miles
    • 1 accident, 1 owner, personal use only
    • 7 Seats, 29 City / 27 Hwy MPG
    • New Country Toyota of Clifton Park (37 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Mechanicville, NY / 37 miles away from Pittsfield, MA

    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:

    28 Combined MPG (29 City/27 Highway)

    Listing Information:

    VIN: 5TDDGRFH8JS046995
    Stock: 54571A
    Certified Pre-Owned: No
    Listed since: 07-08-2025

Showing 22 - 42 out of 264 listings
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