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2,159 listings
  • $5,998
    great price
    $1,795 below market
    • 174,593 miles
    • No accidents, 3 owners, personal use only
    • 5 Seats, 20 City / 27 Hwy MPG
    • Liberty Motors (6 mi away)
    • Tire Pressure Warnin...
    • Rear Bench Seats
    • Stability Control
    • Aux Audio Inputs
    • Fold Flat Rear Seats
    Close

    Located in Chesapeake, VA / 6 miles away from Chesapeake, VA

    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/27 Highway)

    Listing Information:

    VIN: JTEDA41A292000706
    Stock: 000706
    Certified Pre-Owned: No
    Listed since: 05-21-2025

  • Stock photo**
    • 107,346 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 18 City / 24 Hwy MPG
    • Impex Chevrolet GMC (192 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Reidsville, NC / 192 miles away from Chesapeake, VA

    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: 5TDJKRFH6GS281552
    Stock: 2GT1072A
    Certified Pre-Owned: No
    Listed since: 05-27-2025

    • 128,485 miles
    • Issue reported, 4 owners, corporate fleet vehicle
    • 8 Seats, 18 City / 24 Hwy MPG
    • Can Auto Group (184 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Power Driver Seat
    Close

    Located in Randallstown, MD / 184 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: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDBKRFHXES044452
    Stock: 044452
    Certified Pre-Owned: No

    • 220,000 miles
    • Frame damage reported, 4 owners, corporate fleet vehicle
    • 7 Seats, 18 City / 24 Hwy MPG
    • A1 Classic Motors (164 mi away)
    • Third-row seating
    • Tire Pressure Warnin...
    • Rear Bench Seats
    • Stability Control
    • Aux Audio Inputs
    Close

    Located in Fuquay-varina, NC / 164 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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDZK3EH0AS002931
    Stock: 002931
    Certified Pre-Owned: No
    Listed since: 01-03-2024

  • Stock photo**
    • 174,980 miles
    • 1 accident, 3 owners, personal use only
    • 7 Seats, 17 City / 23 Hwy MPG
    • Urban Exchange Auto (87 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Richmond, VA / 87 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:

    19 Combined MPG (17 City/23 Highway)

    Listing Information:

    VIN: 5TDEK3EH0AS007464
    Stock: 007464
    Certified Pre-Owned: No
    Listed since: 01-04-2024

  • New Listing
    $6,995
    great price
    $1,780 below market
    • 130,700 miles
    • No accidents, 2 owners, personal use only
    • 5 Seats, 17 City / 23 Hwy MPG
    • Ammoury Auto (158 mi away)
    • Power Driver Seat
    • Tire Pressure Warnin...
    • Rear Bench Seats
    • Stability Control
    • Fold Flat Rear Seats
    Close

    Located in Falls Church, VA / 158 miles away from Chesapeake, VA

    Non-smoker owner, Vehicle Runs Well, Smooth ride, very good tires, Regularly maintained, Lots of storage, Arctic cold a/c, No pets, Seats as good as n...

    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: JTEGP21A070130735
    Stock: 2696
    Certified Pre-Owned: No

  • $12,495
    great price
    $2,273 below market
    • 178,642 miles
    • No accidents, 2 owners, personal use only
    • 8 Seats, 21 City / 27 Hwy MPG
    • Car Stop Auto (108 mi away)
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Colonial Beach, VA / 108 miles away from Chesapeake, VA

    2017 TOYOTA HIGHLANDER LE with powerful 3.5L V6 W/D-4S engine and driven only 178642 miles! CAR STOP AUTO OF COLONIAL BEACH CARSTOPVA@GMAIL.COM (804...

    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 (21 City/27 Highway)

    Listing Information:

    VIN: 5TDZZRFH5HS210388
    Stock: CSA2731
    Certified Pre-Owned: No

  • Price Drop
    $17,750
    great price
    $2,512 below market
    • 91,196 miles
    • No accidents, 4 owners, personal use
    • 8 Seats, 18 City / 24 Hwy MPG
    • Car Land Auto Trading (148 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

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

    CLEAN CARFAX ! NO ACCIDENTS ! BEST PRICE IN THE NATION! **EASY FINANCING AVAILABLE !! JUST GO TO OUR WEBSITE @ carlandnc.com CLICK ON THE FINANCE TAB ...

    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: 5TDJKRFH6FS166142
    Stock: 166142
    Certified Pre-Owned: No
    Listed since: 04-11-2025

    • 101,457 miles
    • Frame damage reported, 4 owners, personal use
    • 7 Seats, 18 City / 24 Hwy MPG
    • Kargar Motors (155 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Manassas, VA / 155 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: 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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDJKRFH4GS313883
    Stock: KMM12113
    Certified Pre-Owned: No

  • $13,590
    great price
    $2,196 below market
    • 154,671 miles
    • No accidents, 4 owners, personal use only
    • 8 Seats, 19 City / 25 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Wesley Chapel, FL / 687 miles away from Chesapeake, VA

    CarFax No Accidents Reported,Rare Find,3rd Row Seat,Back-Up Camera,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Leather Seats,Navigation System,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:

    21 Combined MPG (19 City/25 Highway)

    Listing Information:

    VIN: 5TDKKRFH0FS119337
    Stock: M119337A
    Certified Pre-Owned: No

  • New Listing
    $14,900
    great price
    $1,708 below market
    • 168,399 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 19 City / 25 Hwy MPG
    • Carcity (172 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Glen Burnie, MD / 172 miles away from Chesapeake, VA

    MD STATE INSPECTED, CLEAN AUTOCHECK REPORTVisit CARCITY (Glen Burnie) online at carcitymd.com to see more pictures of this vehicle or call us at 4**-7...

    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:

    21 Combined MPG (19 City/25 Highway)

    Listing Information:

    VIN: 5TDYKRFH9FS068883
    Stock: 02568
    Certified Pre-Owned: No
    Listed since: 06-05-2025

  • $12,900
    great price
    $2,083 below market
    • 176,700 miles
    • 2 accidents, 2 owners, personal use only
    • 7 Seats, 18 City / 24 Hwy MPG
    • Front Line Auto (8 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Chesapeake, VA / 8 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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDDKRFH0FS079074
    Stock: 5544
    Certified Pre-Owned: No
    Listed since: 05-26-2025

  • $12,999
    great price
    $1,595 below market
    • 174,690 miles
    • No accidents, 2 owners, personal use only
    • 8 Seats, 18 City / 24 Hwy MPG
    • Select Cars of Thornburg (122 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Fredericksburg, VA / 122 miles away from Chesapeake, VA

    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: 5TDJKRFH6FS106393
    Stock: 106393
    Certified Pre-Owned: No

  • $21,555
    great price
    $3,072 below market
    • 78,126 miles
    • 1 accident, 1 owner, corporate fleet vehicle
    • 8 Seats, 20 City / 26 Hwy MPG
    • Carget Motors (143 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Woodbridge, VA / 143 miles away from Chesapeake, VA

    This 2017 Toyota Highlander XLE | SE is a well-rounded midsize SUV that blends comfort, capability, and reliability with upscale features and a refine...

    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: 5TDJZRFH8HS460270
    Stock: 460270
    Certified Pre-Owned: No
    Listed since: 05-22-2025

  • $19,995
    great price
    $2,411 below market
    • 99,047 miles
    • 1 accident, 2 owners, corporate fleet vehicle
    • 7 Seats, 20 City / 26 Hwy MPG
    • Imperial Highline (157 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

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

    LOADED WITH VALUE! Comes equipped with: Rear Air Conditioning, Sunroof, Bluetooth, Navigation System. This Toyota Highlander also includes Clock, Clim...

    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: 5TDJZRFH7HS434484
    Stock: 34484
    Certified Pre-Owned: No
    Listed since: 10-22-2024

  • $21,000
    good price
    $963 below market
    • 100,274 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Heritage Honda of Parkville (184 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Parkville, MD / 184 miles away from Chesapeake, VA

    Recent Arrival! *AWD*, *POWER DRIVERS SEAT*, *HEATED LEATHER SEATS*, *NAVIGATION SYSTEM*, *POWER SUNROOF*, *POWER LIFTGATE*, *HANDS FREE BLUETOOTH*, *...

    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: 5TDJZRFH3HS384828
    Stock: KU384828
    Certified Pre-Owned: No
    Listed since: 04-18-2025

  • $9,999
    fair price
    $1,470 below market
    • 108,153 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 18 City / 24 Hwy MPG
    • Loudoun Motorcars (165 mi away)
    • Back-up camera
    • Third-row seating
    • Power Driver Seat
    • Tire Pressure Warnin...
    • Trip Computer
    Close

    Located in Chantilly, VA / 165 miles away from Chesapeake, VA

    STOCK#LMC1858 IMMACULATE, LOW MILES BEAUTY, ONE OWNER , NO ACCIDENT, MECHANICALLY PERFECT, TOYOTA HIGHLANDER "SPORT" SUV WITH 3RD ROW SEAT, IS UP 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: JTEDS43A792090882
    Stock: 090882
    Certified Pre-Owned: No
    Listed since: 04-30-2025

  • $14,508
    good price
    $1,761 below market
    • 136,281 miles
    • No accidents, 3 owners, corporate fleet vehicle
    • 8 Seats, 18 City / 24 Hwy MPG
    • Woodbridge Auto Sales (144 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Power Driver Seat
    Close

    Located in Woodbridge, VA / 144 miles away from Chesapeake, VA

    VEHICLE HAS PASSED SAFETY INSPECTION. VEHICLE CHECKED AND SERVICED BY OUR ON SITE MECHANIC WITH A FRESH OIL CHANGE, EXTENDED WARRANTY AND EASY FINANCI...

    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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDBKRFH2FS152436
    Stock: ACH/152436
    Certified Pre-Owned: No
    Listed since: 07-11-2024

  • $8,999
    good price
    $1,757 below market
    • 150,692 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 17 City / 23 Hwy MPG
    • Tru Motors (151 mi away)
    • AWD/4WD
    • Back-up camera
    • Third-row seating
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

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

    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: JTEES43A492127049
    Stock: 127049
    Certified Pre-Owned: No
    Listed since: 04-04-2025

    • 110,300 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 19 City / 25 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Frisco, TX / 1,186 miles away from Chesapeake, VA

    Rare Find,3rd Row Seat,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Chrome Wheels,Heated Seats,Keyless Start,Leather Seats,Navigation Syst...

    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:

    21 Combined MPG (19 City/25 Highway)

    Listing Information:

    VIN: 5TDYKRFH7FS088419
    Stock: FS088419A
    Certified Pre-Owned: No

  • $16,000
    good price
    $1,362 below market
    • 108,267 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 20 City / 25 Hwy MPG
    • Grace Auto (94 mi away)
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Richmond, VA / 94 miles away from Chesapeake, VA

    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/25 Highway)

    Listing Information:

    VIN: 5TDZARFHXFS015942
    Stock: P24996
    Certified Pre-Owned: No

Showing 274 - 294 out of 2,159 listings

Consumer Reviews for the Toyota Highlander

Read recent reviews for the Toyota Highlander
Overall Consumer Rating
4.5 out of 5 stars46 Reviews
Write a vehicle reviewSee all 46 reviews
  • 5 star
    (65%)
  • 4 star
    (28%)
  • 3 star
    (4%)
  • 2 star
    (0%)
  • 1 star
    (2%)
5 out of 5 stars

Nice all around car

bob robinson, 04/08/2016
2012 Toyota Highlander 4dr SUV (2.7L 4cyl 6A)
This is a great car, it gives a nice ride and performance is good also . Need to watch your speed as it goes faster than it feels so I use the cruise control on highways. We climbed Mount Washington in New Hampshire and came down the mountain using hill assist and never had to use the brakes for the whole decline of the mountain. The interior is big and the vehicle is 2 inches wider … than my Toyota Tacoma. With 54,000 miles on the car it only has had regular maintenance and new set of tires. We enjoy the car very much. One thing we don't like is the third row seat can only be used for kids, as we have tryed ourselves to get into them and it was very very difficult.
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Used 2009 Toyota Highlander in Chesapeake, VA Values

Estimated values
2009 Toyota Highlander 4dr SUV (2.7L 4cyl 6A) with no options
ConditionTrade-InPrivate PartyDealer Retail
Outstanding$4,625$5,973$6,786
Clean$4,340$5,566$6,281
Average$3,866$4,888$5,439
Rough$3,249$4,007$4,344

The average list price of a used 2009 Toyota Highlander in Chesapeake, Virginia is $13,612. The average mileage on a used Toyota Highlander 2009 for sale in Chesapeake, Virginia is 136,809. Based on the average mileage of 136,809 for used 2009 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 2009 in Chesapeake, Virginia to be $3,866.

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