Skip to main content
Skip to Filters
2,136 listings
    • 88,380 miles
    • 1 accident, 2 owners, corporate fleet vehicle
    • 8 Seats, 20 City / 26 Hwy MPG
    • Koons of Woodbridge (142 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Woodbridge, VA / 142 miles away from Chesapeake, VA

    Visit Koons Automotive of Woodbridge online at www.koonsofwoodbridge.com to see more pictures of this vehicle or call us at 571-285-3277 today to sch...

    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:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDJZRFH3KS614357
    Stock: 34267A
    Certified Pre-Owned: No

    • 54,161 miles
    • Frame damage reported, 2 owners, corporate fleet vehicle
    • 8 Seats, 20 City / 27 Hwy MPG
    • Kargar Motors (156 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Manassas, VA / 156 miles away from Chesapeake, VA

    BUYING A CAR HAS NEVER BEEN THIS EASY.We specialize in 100% GUARANTEED APPROVAL. BAD CREDIT, NO CREDIT, BANKRUPTCY, REPO, FORECLOSURE...NO PROBLEM. NO...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Issue reported

    Salvage Vehicle: No

    Frame Damage: Yes

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDBZRBH0MS099993
    Stock: KMM12668
    Certified Pre-Owned: No

    • 156,270 miles
    • Frame damage reported, 2 owners, rental vehicle
    • 8 Seats, 19 City / 26 Hwy MPG
    • Kargar Motors (156 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    Close

    Located in Manassas, VA / 156 miles away from Chesapeake, VA

    BUYING A CAR HAS NEVER BEEN THIS EASY.We specialize in 100% GUARANTEED APPROVAL. BAD CREDIT, NO CREDIT, BANKRUPTCY, REPO, FORECLOSURE...NO PROBLEM. NO...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Issue reported

    Salvage Vehicle: No

    Frame Damage: Yes

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    22 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 5TDBZRFH0KS947698
    Stock: KMM12617
    Certified Pre-Owned: No

  • New Listing
    • 60,602 miles
    • 1 accident, 3 owners, personal use only
    • 7 Seats, 21 City / 27 Hwy MPG
    • CarMax Jacksonville NC (149 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Jacksonville, NC / 149 miles away from Chesapeake, VA

    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:

    23 Combined MPG (21 City/27 Highway)

    Listing Information:

    VIN: 5TDKZRFH0KS569687
    Stock: 26982790
    Certified Pre-Owned: No

  • Price Drop
    $35,500
    great price
    $3,768 below market
    • 23,477 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • Safford Brown Manassas Hyundai (156 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Manassas, VA / 156 miles away from Chesapeake, VA

    Celestial Silver Metallic 2022 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC Third Row Seating, Blind Spot Monitoring, Navigation System, A...

    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: 5TDHZRBH4NS226322
    Stock: H046813A
    Certified Pre-Owned: No
    Listed since: 03-24-2025

  • Price Drop
    • 43,983 miles
    • 2 accidents, 2 owners, personal use
    • 8 Seats, 20 City / 27 Hwy MPG
    • Auction Direct USA (151 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Raleigh, NC / 151 miles away from Chesapeake, VA

    CARFAX One-Owner. Auction Direct is proud to present you with another True Market Priced Pre-Owned Vehicle. This 2021 Toyota Highlander XLE is loaded ...

    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: 5TDGZRBH8MS548634
    Stock: AD01052
    Certified Pre-Owned: No
    Listed since: 05-09-2025

    • 51,451 miles
    • 2 accidents, 1 owner, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • M and B Auto Group (156 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Bealeton, VA / 156 miles away from Chesapeake, VA

    **ONE OWNER** 2021 TOYOTA HIGHLANDER AWD with powerful 3.5L V6 DOHC -INC 24-VALVE D-4S INJECTION engine and driven 51451 miles!CARFAX CERTIFIED**FINA...

    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: Yes

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH3MS548508
    Stock: mda5050
    Certified Pre-Owned: No

  • New Listing
    • 60,336 miles
    • 1 accident, 1 owner, personal use
    • 7 Seats, 20 City / 26 Hwy MPG
    • CarMax Ellicott City (179 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Ellicott City, MD / 179 miles away from Chesapeake, VA

    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 (20 City/26 Highway)

    Listing Information:

    VIN: 5TDDZRFH2KS722210
    Stock: 27096769
    Certified Pre-Owned: No

    • 65,521 miles
    • 1 accident, 1 owner, corporate fleet vehicle
    • 7 Seats, 20 City / 27 Hwy MPG
    • Koons of Woodbridge (142 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Woodbridge, VA / 142 miles away from Chesapeake, VA

    Visit Koons Automotive of Woodbridge online at www.koonsofwoodbridge.com to see more pictures of this vehicle or call us at 571-285-3277 today to sch...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDLZRBHXMS056802
    Stock: 36908
    Certified Pre-Owned: No

    • 83,863 miles
    • Frame damage reported, 1 owner, corporate fleet vehicle
    • 8 Seats, 20 City / 27 Hwy MPG
    • CarHub (138 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Stafford, VA / 138 miles away from Chesapeake, VA

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Issue reported

    Salvage Vehicle: No

    Frame Damage: Yes

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH9MS107983
    Stock: 107983
    Certified Pre-Owned: No

  • Price Drop
    $37,500
    great price
    $3,167 below market
    • 17,502 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Ourisman Chevrolet of Rockville (168 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Rockville, MD / 168 miles away from Chesapeake, VA

    CARFAX One-Owner. This 2022 Midnight Black Toyota Highlander XSE AWD is well equipped and includes these features and benefits:.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: 5TDLZRBH5NS222239
    Stock: B5052
    Certified Pre-Owned: No
    Listed since: 04-01-2025

  • Price Drop
    Stock photo**
    • 82,203 miles
    • Frame damage reported, 1 owner, personal use only
    • 8 Seats, 21 City / 29 Hwy MPG
    • Xride Cars (148 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Raleigh, NC / 148 miles away from Chesapeake, VA

    We are excited to offer this 2021 Toyota Highlander L Sport Utility 4D, now available at Xride Cars, located at 1733 Capital Blvd, Raleigh, NC 27604. ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Issue reported

    Salvage Vehicle: No

    Frame Damage: Yes

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    24 Combined MPG (21 City/29 Highway)

    Listing Information:

    VIN: 5TDCZRAH1MS041672
    Stock: 041672
    Certified Pre-Owned: No

  • Price Drop
    $32,500
    great price
    $3,679 below market
    • 66,827 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 7 Seats, 20 City / 27 Hwy MPG
    • Hanna Imports (148 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Raleigh, NC / 148 miles away from Chesapeake, VA

    *Carfax Accident Free*, *Multi Point Inspection*, AWD, 3rd row seats: split-bench, Alloy wheels, Apple CarPlay/Android Auto, Automatic temperature con...

    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: 5TDGZRBH0NS577868
    Stock: 3021149
    Certified Pre-Owned: No
    Listed since: 03-04-2025

  • Price Drop
    $32,900
    great price
    $2,406 below market
    • 64,314 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • DARCARS Toyota of Baltimore (177 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Baltimore, MD / 177 miles away from Chesapeake, VA

    2022 Toyota Highlander XSE CARFAX One-Owner. Clean CARFAX.Highlander XSE, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed Automatic, AWD, Blueprint, Black w...

    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: 5TDLZRBH7NS241004
    Stock: 52E2027A
    Certified Pre-Owned: No
    Listed since: 04-15-2025

  • Price Drop
    $17,000
    great price
    $2,286 below market
    • 121,541 miles
    • No accidents, 4 owners, corporate fleet vehicle
    • 8 Seats, 19 City / 26 Hwy MPG
    • Jerry's Ford of Leesburg (179 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    Close

    Located in Leesburg, VA / 179 miles away from Chesapeake, VA

    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 (19 City/26 Highway)

    Listing Information:

    VIN: 5TDBZRFH9JS902631
    Stock: L7559PA
    Certified Pre-Owned: No
    Listed since: 05-17-2025

  • New Listing
    • 92,032 miles
    • 8 Seats, 20 City / 27 Hwy MPG
    • Kargar Motors (156 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Manassas, VA / 156 miles away from Chesapeake, VA

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH6MS059455
    Stock: KMM8582
    Certified Pre-Owned: No

  • Stock photo**
    • 40,593 miles
    • 1 accident, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Toyota of Bowie (156 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Bowie, MD / 156 miles away from Chesapeake, VA

    Celestial Silver Metallic exterior and BLACK interior. Heated Seats, Moonroof, Third Row Seat, All Wheel Drive, Power Liftgate, Aluminum Wheels, BODY ...

    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: 5TDGZRBH9MS119289
    Stock: MS119289
    Certified Pre-Owned: No
    Listed since: 05-23-2025

  • New Listing
    Stock photo**
    • 75,253 miles
    • 8 Seats, 20 City / 27 Hwy MPG
    • Battlefield Toyota (155 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Culpeper, VA / 155 miles away from Chesapeake, VA

    AWD.2021 Toyota Highlander Limited 3.5L V6 DOHC 20/27 City/Highway MPG

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDDZRBH5MS526657
    Stock: T18858A
    Certified Pre-Owned: No
    Listed since: 05-30-2025

  • Stock photo**
    • 142,385 miles
    • 4 accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Mr. Car of Glen Burnie (169 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Glen Burnie, MD / 169 miles away from Chesapeake, VA

    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: 5TDJZRFH4KS596970
    Stock: CC596970M
    Certified Pre-Owned: No
    Listed since: 03-25-2025

  • $22,998
    great price
    $3,205 below market
    • 102,690 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from FL to VA*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Davie, FL / 772 miles away from Chesapeake, VA

    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:

    24 Combined MPG (21 City/29 Highway)

    Listing Information:

    VIN: 5TDGZRAH3LS002856
    Stock: 27310366
    Certified Pre-Owned: No

  • $31,000
    great price
    $2,875 below market
    • 74,234 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 20 City / 27 Hwy MPG
    • Koons Arlington Toyota (157 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Arlington, VA / 157 miles away from Chesapeake, VA

    2022 Toyota Highlander XLE 2nd Row Bench Seat, Automatic temperature control, Heated front seats, Power Liftgate, Power moonroof, Radio: Premium Audio...

    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: 5TDHZRBH5NS580883
    Stock: A10686
    Certified Pre-Owned: No
    Listed since: 03-27-2025

Showing 127 - 147 out of 2,136 listings

Consumer Reviews for the Toyota Highlander

Read recent reviews for the Toyota Highlander
Overall Consumer Rating
3.9 out of 5 stars89 Reviews
Write a vehicle reviewSee all 89 reviews
  • 5 star
    (53%)
  • 4 star
    (15%)
  • 3 star
    (11%)
  • 2 star
    (8%)
  • 1 star
    (13%)
4 out of 5 stars

"Some Adjustment Needed"

Bill, 01/11/2020
2020 Toyota Highlander Limited 4dr SUV (3.5L 6cyl 8A)
Test drove the 2020 Limited. V-6 engine was responsive and ride was very quiet. Very good standard technology and driving safety packages. Interior had quality materials and good fit and finish. Second row captains chair seats are comfortable with plenty of room behind first row, third row seats useless except for small children which you would want in second row. Big disappointment … was drivers seat height adjustment; you better be 5'4" or above to have clear visibility over steering wheel and dash. Also, passenger seat has NO height adjustment; passengers 6'3" or above will be at or close to the ceiling. Except for the lack of adequate front seat height adjustments, I loved the car.
Report abuse

Used 2019 Toyota Highlander in Chesapeake, VA Values

Estimated values
2019 Toyota Highlander XLE 4dr SUV AWD (3.5L 6cyl 8A) with no options
ConditionTrade-InPrivate PartyDealer Retail
Outstanding$24,744$27,448$29,853
Clean$23,990$26,605$28,927
Average$22,733$25,198$27,384
Rough$21,100$23,370$25,379

The average list price of a used 2019 Toyota Highlander in Chesapeake, Virginia is $30,254. The average mileage on a used Toyota Highlander 2019 for sale in Chesapeake, Virginia is 74,648. Based on the average mileage of 74,648 for used 2019 Toyota Highlander for sale in Chesapeake, VA and using an average vehicle condition rating, which means the vehicle may have a few mechanical and/or cosmetic problems and may require a considerable amount of reconditioning, we appraise the average trade-in value of a used Toyota Highlander 2019 in Chesapeake, Virginia to be $22,733.

Filters
Skip to Results

Applied Filters4Active

Select Buying Experience

Location

Search radius200 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.