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79 listings
  • $33,496
    good price
    $1,641 below market
    • 58,141 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 35 City / 35 Hwy MPG
    • New Country Lexus of Latham (34 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Latham, NY / 34 miles away from Pittsfield, MA

    **HYBRID** **3RD ROW** **PREMIUM AUDIO** **HEATED SEATS** **MOONROOF** **CARFAX One-Owner** **Clean CARFAX** Magnetic Gray Metallic 2021 Toyota Highla...

    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: 5TDHBRCH2MS535806
    Stock: TX25776A
    Certified Pre-Owned: No
    Listed since: 07-21-2025

    • 110,602 miles
    • No accidents, 1 owner, personal use only
    • 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

    Recent Arrival! Toyota of Nashua is proud to present this Toyota Silver Certified... Moon Dust Gray 2021 Toyota Highlander Hybrid XLE AWD 2.5L I4 PDI ...

    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: 5TDGBRCH9MS051482
    Stock: C4067C
    Certified Pre-Owned: Yes
    Listed since: 07-18-2025

  • $35,990
    fair price
    $26 above market
    • 47,796 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 35 City / 35 Hwy MPG
    • Driveway (33 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Latham, NY / 33 miles away from Pittsfield, MA

    CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,Green Vehicle,3rd Row Seat,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,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:

    35 Combined MPG (35 City/35 Highway)

    Listing Information:

    VIN: 5TDGBRCH8MS528418
    Stock: MS528418A
    Certified Pre-Owned: No

  • $39,800
    fair price
    $183 below market
    • 32,806 miles
    • No accidents, 1 owner, personal use only
    • 8 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

    Recent Arrival! Toyota of Nashua is proud to present this Toyota Gold Certified... Midnight Black Metallic 2021 Toyota Highlander Hybrid XLE AWD 2.5L ...

    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: 5TDGBRCH5MS521569
    Stock: C4122
    Certified Pre-Owned: Yes
    Listed since: 07-28-2025

  • $37,849
    fair price
    $155 below market
    • 52,996 miles
    • No accidents, 1 owner, personal use
    • 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

    Recent Arrival! Toyota of Nashua is proud to present this Toyota Gold Certified... Blizzard Pearl White 2021 Toyota Highlander Hybrid XLE AWD 2.5L I4 ...

    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: 5TDGBRCH9MS521851
    Stock: C4134
    Certified Pre-Owned: Yes
    Listed since: 08-08-2025

  • New Listing
    Stock photo**
    $29,271
    good price
    $977 below market
    • 98,056 miles
    • 7 Seats, 35 City / 35 Hwy MPG
    • McGee Mazda of Claremont (77 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Claremont, NH / 77 miles away from Pittsfield, MA

    Recent Arrival!2.5L I4 PDI Hybrid DOHC 16V LEV3-SULEV30 186hp.*Why Buy at McGee Mazda Claremont*-- Complete buy online experience through McGee ...

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    35 Combined MPG (35 City/35 Highway)

    Listing Information:

    VIN: 5TDGBRCH6MS524299
    Stock: 25278A
    Certified Pre-Owned: No
    Listed since: 09-02-2025

    • 52,218 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 Certified. 35/34 City/Highway MPGLOCAL TRADE, HEATED LEATHER SEATS, PREMIUM SOUND, LOADED WITH LUXURY, TOYOTA 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:

    35 Combined MPG (35 City/34 Highway)

    Listing Information:

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

  • Stock photo**
    • 58,429 miles
    • 2 accidents, 2 owners, personal use
    • 7 Seats, 35 City / 34 Hwy MPG
    • Lia Toyota of Wilbraham (45 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Wilbraham, MA / 45 miles away from Pittsfield, MA

    Recent Arrival! Moon Dust 2021 Toyota Highlander Hybrid Limited 2.5L I4 PDI Hybrid DOHC 16V LEV3-SULEV30 186hp eCVT AWDService Records Available *, Ba...

    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: 5TDXBRCHXMS027367
    Stock: MS027367T
    Certified Pre-Owned: No
    Listed since: 08-21-2025

  • Price Drop
    $37,788
    great price
    $2,623 below market
    • 28,247 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 35 City / 35 Hwy MPG
    • Curry Toyota (86 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Cortlandt Manor, NY / 86 miles away from Pittsfield, MA

    Celestial Silver Metallic 2021 Toyota Highlander Hybrid XLE AWD eCVT 2.5L I4 PDI Hybrid DOHC 16V LEV3-SULEV30 186hp 2.5L I4 PDI Hybrid DOHC 16V LEV...

    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: 5TDGBRCH4MS065712
    Stock: 8562T
    Certified Pre-Owned: Yes
    Listed since: 08-19-2025

  • $30,998
    great price
    $1,867 below market
    • 98,402 miles
    • No accidents, 3 owners, rental vehicle
    • 8 Seats, 35 City / 34 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from OK to MA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Norman, OK / 1,390 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: 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/34 Highway)

    Listing Information:

    VIN: 5TDDBRCH5MS525396
    Stock: 27204896
    Certified Pre-Owned: No

  • $33,590
    fair price
    $806 below market
    • 90,849 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 35 City / 34 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Cincinnati, OH / 632 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: 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: 5TDXBRCH8MS521727
    Stock: 2003826951
    Certified Pre-Owned: No
    Listed since: 07-12-2025

  • $28,779
    fair price
    $621 below market
    • 111,670 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 7 Seats, 35 City / 35 Hwy MPG
    • Blasius North (45 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Torrington, CT / 45 miles away from Pittsfield, MA

    2021 Toyota Highlander Hybrid 4D Sport Utility Celestial Silver Metallic XLE ONE OWNER, 2.5L I4 PDI Hybrid DOHC 16V LEV3-SULEV30 186hp, 3rd row seats:...

    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: 5TDGBRCH6MS535917
    Stock: N5196
    Certified Pre-Owned: No
    Listed since: 08-06-2025

  • $32,590
    good price
    $1,534 below market
    • 88,392 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 36 City / 35 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Phoenix, AZ / 2,180 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: 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: 5TDFARAH8MS005546
    Stock: 2003862136
    Certified Pre-Owned: No
    Listed since: 07-19-2025

  • Price Drop
    $38,998
    good price
    $1,335 below market
    • 22,556 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 35 City / 35 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Fresno, CA / 2,474 miles away from Pittsfield, MA

    Low Mileage,Rare Find,Green Vehicle,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lan...

    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: 5TDHBRCHXMS049826
    Stock: MS049826PK
    Certified Pre-Owned: No

  • $26,900
    good price
    $1,601 below market
    • 124,105 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 35 City / 35 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Sterling Heights, MI / 496 miles away from Pittsfield, MA

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

    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: 5TDGBRCH3MS049680
    Stock: MS049680A
    Certified Pre-Owned: No

  • New Listing
    $39,990
    fair price
    $299 below market
    • 22,899 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 Richmond, VA / 404 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: 5TDGBRCH8MS535546
    Stock: 2004005805
    Certified Pre-Owned: No
    Listed since: 08-29-2025

  • Price Drop
    $32,590
    fair price
    $593 below market
    • 75,243 miles
    • No accidents, 3 owners, personal use only
    • 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 Chicago, IL / 772 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: 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: 5TDGBRCH4MS515777
    Stock: 2003843173
    Certified Pre-Owned: No
    Listed since: 07-04-2025

  • $33,647
    good price
    $1,446 below market
    • 71,780 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 35 City / 35 Hwy MPG
    • Imperial Toyota (92 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

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

    Sunroof / Moonroof, Blind Spot Monitor, Lane Keeping Assistance, Apple CarPlay / Android Auto, Collision Avoidance Assistance, Power Seats, Heated Sea...

    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: 5TDGBRCH7MS519385
    Stock: TM25-1011A
    Certified Pre-Owned: Yes
    Listed since: 07-26-2025

  • $31,500
    fair price
    $495 above market
    • 89,762 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 35 City / 35 Hwy MPG
    • New Country Toyota of Clifton Park (38 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

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

    * CLEAN CARFAX ONE-OWNER * MOONROOF * REARVIEW CAMERA * APPLE CARPLAY * ANDROID AUTO * AM/FM RADIO * AIR CONDITIONING * AUTOMATIC TEMPERATURE CONTROL ...

    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: 5TDGBRCH7MS057345
    Stock: 54278A
    Certified Pre-Owned: No
    Listed since: 08-11-2025

  • New Listing
    $29,990
    good price
    $1,359 below market
    • 88,812 miles
    • No accidents, 1 owner, personal use only
    • 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 Chicago, IL / 772 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: 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: 5TDGBRCH0MS515078
    Stock: 2003820506
    Certified Pre-Owned: No
    Listed since: 06-12-2025

  • $27,325
    good price
    $1,093 below market
    • 116,877 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 35 City / 35 Hwy MPG
    • Superior Motors (86 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Milford, CT / 86 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:

    35 Combined MPG (35 City/35 Highway)

    Listing Information:

    VIN: 5TDGBRCH3MS038288
    Stock: 038288
    Certified Pre-Owned: No
    Listed since: 08-06-2025

Showing 1 - 21 out of 79 listings
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