Skip to main content
Skip to Filters
101 listings
  • $42,388
    fair price
    $531 above market
    • 24,168 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 21 City / 28 Hwy MPG
    • Prestige Toyota (18 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Kingston, NY / 18 miles away from Poughkeepsie, NY

    Certified. 2023 Toyota Highlander AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hpRecent Arrival! 21/28 City/Highway MPGToyo...

    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: 5TDKDRBH5PS016075
    Stock: PS016075
    Certified Pre-Owned: Yes
    Listed since: 07-23-2025

  • Price Drop
    $37,299
    fair price
    $1,118 above market
    • 33,665 miles
    • 1 accident, 1 owner, personal use only
    • 8 Seats, 21 City / 28 Hwy MPG
    • Mercedes-Benz of Wappingers Falls (9 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Wappingers Falls, NY / 9 miles away from Poughkeepsie, NY

    CARFAX One-Owner. Magnetic Gray Metallic 2023 Toyota Highlander XLE 4D Sport Utility AWD 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 21/28 Ci...

    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: 5TDKDRBH0PS000964
    Stock: U4522T
    Certified Pre-Owned: No
    Listed since: 09-03-2025

  • $37,500
    fair price
    $1,080 above market
    • 35,632 miles
    • No accidents, 1 owner, personal use
    • 8 Seats, 21 City / 28 Hwy MPG
    • Romeo Kia of Kingston (20 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Lake Katrine, NY / 20 miles away from Poughkeepsie, NY

    Romeo Kia proudly presents this 2023 Toyota Highlander with 18 Painted Alloy Wheels, 3.329 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes...

    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: 5TDKDRBH1PS003596
    Stock: 25881SA
    Certified Pre-Owned: No
    Listed since: 08-28-2025

  • $36,888
    fair price
    $696 above market
    • 58,776 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • Prestige Toyota (18 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Kingston, NY / 18 miles away from Poughkeepsie, NY

    Certified. Celestial Silver 2023 Toyota Highlander XLE AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hpRecent Arrival! 21/28...

    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: 5TDKDRBHXPS500453
    Stock: PS50045A
    Certified Pre-Owned: Yes
    Listed since: 07-30-2025

  • Price Drop
    $33,590
    great price
    $10,129 below market
    • 33,541 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 7 Seats, 21 City / 28 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Atlanta, GA / 792 miles away from Poughkeepsie, NY

    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: Yes

    Features and Specs:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH0PS035262
    Stock: 2004001196
    Certified Pre-Owned: No
    Listed since: 08-25-2025

    • 37,729 miles
    • No accidents, 3 owners, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Dallas, TX / 1,394 miles away from Poughkeepsie, NY

    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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH3PS015815
    Stock: 2003974371
    Certified Pre-Owned: No
    Listed since: 08-18-2025

  • New Listing
    Stock photo**
    $35,995
    great price
    $7,747 below market
    • 42,842 miles
    • No accidents, 1 owner, personal use
    • 8 Seats, 21 City / 28 Hwy MPG
    • Toyota of Manhattan (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in New York, NY / 65 miles away from Poughkeepsie, NY

    Buy any preowned vehicle from our large inventory here at Toyota of Manhattan drive worry free. All of our hand selected vehicles are put through a ri...

    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: 5TDKDRBH8PS034215
    Stock: T18963
    Certified Pre-Owned: No
    Listed since: 09-25-2025

  • Price Drop
    $37,495
    good price
    $5,383 below market
    • 13,707 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 28 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Washington, MI / 473 miles away from Poughkeepsie, NY

    CarFax No Accidents Reported,Low Mileage,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,...

    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: 5TDKDRBH5PS506113
    Stock: PPS506113S
    Certified Pre-Owned: No

  • Price Drop
    $33,372
    great price
    $7,061 below market
    • 30,645 miles
    • 1 accident, 2 owners, personal use only
    • 7 Seats, 22 City / 29 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Tampa, FL / 1,058 miles away from Poughkeepsie, NY

    3rd Row Seat,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satellite Radio,Turbo/Supercharged,WiFi Hotspot,3rd...

    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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH1PS042819
    Stock: PS042819P
    Certified Pre-Owned: No

  • New Listing
    $29,999
    good price
    $1,295 below market
    • 50,683 miles
    • No accidents, 1 owner, rental vehicle
    • 8 Seats, 22 City / 29 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Columbia, SC / 659 miles away from Poughkeepsie, NY

    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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH1PS035000
    Stock: 7W2B76
    Certified Pre-Owned: No
    Listed since: 08-14-2025

  • New Listing
    $41,999
    great price
    $3,766 below market
    • 15,213 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 21 City / 28 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in North Brunswick, NJ / 92 miles away from Poughkeepsie, NY

    CarFax 1-Owner,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,Heated Seats,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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH5PS514938
    Stock: BTP11853
    Certified Pre-Owned: No

  • New Listing
    • 19,690 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 8 Seats, 21 City / 28 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Dallas, TX / 1,394 miles away from Poughkeepsie, NY

    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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBHXPS522940
    Stock: 2003772375
    Certified Pre-Owned: No
    Listed since: 06-06-2025

  • $35,723
    great price
    $2,991 below market
    • 29,619 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 28 Hwy MPG
    • BMW of Freeport (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Freeport, NY / 74 miles away from Poughkeepsie, NY

    Heated Seats, Sunroof, 3rd Row Seat, Power Liftgate, Turbo Charged, All Wheel Drive, Alloy Wheels, RADIO: 12.3 TOYOTA AUDIO MULTIMEDIA. BLACK ALL-WEA...

    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: Yes

    Features and Specs:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH4PS022837
    Stock: PS022837T
    Certified Pre-Owned: No
    Listed since: 07-23-2025

  • New Listing
    $39,590
    good price
    $2,445 below market
    • 31,291 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 21 City / 28 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Atlanta, GA / 792 miles away from Poughkeepsie, NY

    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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH2PS029267
    Stock: 2003903936
    Certified Pre-Owned: No
    Listed since: 08-02-2025

  • Price Drop
    $33,900
    good price
    $1,312 below market
    • 50,786 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 22 City / 29 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Jacksonville, FL / 893 miles away from Poughkeepsie, NY

    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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH9PS020972
    Stock: 7WXY9D
    Certified Pre-Owned: No
    Listed since: 08-19-2025

  • $36,595
    good price
    $1,231 below market
    • 35,033 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 28 Hwy MPG
    • Lia Toyota of Rockland (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Blauvelt, NY / 43 miles away from Poughkeepsie, NY

    CARFAX One-Owner. Clean CARFAX. Magnetic Gray Metallic 2023 Toyota Highlander L AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 2...

    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: 5TDKDRBH6PS524023
    Stock: PS524023T
    Certified Pre-Owned: No
    Listed since: 08-20-2025

  • New Listing
    $34,990
    fair price
    $1,279 below market
    • 39,699 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 7 Seats, 22 City / 29 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Indianapolis, IN / 654 miles away from Poughkeepsie, NY

    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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH6PS038166
    Stock: 2003993885
    Certified Pre-Owned: No
    Listed since: 08-22-2025

  • Price Drop
    $32,990
    good price
    $1,284 below market
    • 66,324 miles
    • No accidents, 2 owners, rental vehicle
    • 7 Seats, 21 City / 28 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Nashville, TN / 789 miles away from Poughkeepsie, NY

    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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH9PS007699
    Stock: 2003986149
    Certified Pre-Owned: No
    Listed since: 08-20-2025

  • $33,398
    fair price
    $1,125 below market
    • 58,096 miles
    • 1 accident, 1 owner, rental vehicle
    • 7 Seats, 22 City / 29 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Morrow, GA / 800 miles away from Poughkeepsie, NY

    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: No

    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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH3PS022281
    Stock: 7W2C1V
    Certified Pre-Owned: No
    Listed since: 07-17-2025

  • New Listing
    • 11,913 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 28 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Dallas, TX / 1,394 miles away from Poughkeepsie, NY

    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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH4PS022854
    Stock: 2003928674
    Certified Pre-Owned: No
    Listed since: 08-13-2025

  • $39,827
    fair price
    $364 above market
    • 15,903 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 21 City / 28 Hwy MPG
    • BMW of the Hudson Valley (5 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Poughkeepsie, NY / 5 miles away from Poughkeepsie, NY

    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: 5TDKDRBH6PS527276
    Stock: B17124
    Certified Pre-Owned: No
    Listed since: 07-29-2025

Showing 1 - 21 out of 101 listings
Filters
Skip to Results

Applied Filters3Active

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.