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2,076 listings
- 38,637 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Danville Toyota (178 mi away)
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Located in Danville, VA / 178 miles away from Chesapeake, VA
Toyota Gold Certified Details: * Roadside Assistance for 7 Year / 100,000 Mile. Standard New-Car Financing Rates Available. Warranty honored at ove...
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: 5TDKDRAH1PS503100
Stock: P6633
Certified Pre-Owned: Yes
Listed since: 05-05-2025- New Listing
- 39,036 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- Battlefield Toyota (155 mi away)
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Located in Culpeper, VA / 155 miles away from Chesapeake, VA
++1-OWNER++ XLE PACKAGE++ LEATHER++ SECOND ROW BENCH SEAT++ AWD++ 2023 Toyota Highlander XLE 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 21/2...
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: 5TDKDRBH9PS013955
Stock: P5503
Certified Pre-Owned: No
Listed since: 05-27-2025 - Price Drop$35,500great price$3,910 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)
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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 - New Listing
- 47,598 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Battlefield Toyota (155 mi away)
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Located in Culpeper, VA / 155 miles away from Chesapeake, VA
ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/C, Heated door mirrors, Heated Front Bucket Seats, He...
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: 5TDKDRAH0PS001291
Stock: P5499
Certified Pre-Owned: No
Listed since: 05-27-2025 - 46,338 miles
- 1 accident, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Haley Certified Preowned (90 mi away)
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Located in Richmond, VA / 90 miles away from Chesapeake, VA
*Vehicle pricing excludes tax, title, tags, $799 processing fee, and $319 fee for theft protection etch.*
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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH7PS023805
Stock: J6687
Certified Pre-Owned: No
Listed since: 05-01-2025- $38,996great price$3,546 below market
- 21,583 miles
- No accidents, 3 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Vineland Hyundai (197 mi away)
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Located in Millville, NJ / 197 miles away from Chesapeake, VA
REMAINDER OF FACTORY WARRANTY, MOONROOF, LOCAL TRADE, CLEAN CAR FAX, BLIND SPOT MONITORING SYSTEM, BACK-UP CAMERA, APPLE CAR PLAY, ANDROID AUTO, ALL 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: 5TDLZRBH4NS240912
Stock: V00915A
Certified Pre-Owned: No
Listed since: 03-29-2025 - Price Drop$32,500great price$3,762 below market
- 66,827 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Hanna Imports (148 mi away)
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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$37,500great price$3,056 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)
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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$40,590great price$3,071 below market
- 26,631 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Carvana - Richmond (100 mi away)
- Home delivery*
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Located in Richmond, VA / 100 miles away from Chesapeake, VA
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: 5TDKDRAH3RS528616
Stock: 2003598548
Certified Pre-Owned: No
Listed since: 04-07-2025 - New ListingNot Priced
- Not provided
- 8 Seats, 21 City / 28 Hwy MPG
- Passport Toyota (150 mi away)
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Located in Suitland, MD / 150 miles away from Chesapeake, VA
Recent Arrival! 2023 Toyota Highlander LE Silver AWD AutomaticAWD.Clean CARFAX.Introducing our PASSPORT ONE PRICE program where qualified pre-own...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBHXPS033941
Stock: B8814
Certified Pre-Owned: No
Listed since: 05-28-2025 - Price Drop$41,590great price$3,350 below market
- 17,947 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Carvana - Richmond (100 mi away)
- Home delivery*
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Located in Richmond, VA / 100 miles away from Chesapeake, VA
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: 5TDKDRBHXRS548585
Stock: 2003525942
Certified Pre-Owned: No
Listed since: 03-26-2025 - $31,000great price$2,792 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)
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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 - Price Drop$41,000great price$3,091 below market
- 21,415 miles
- 1 accident, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Ourisman Toyota of Woodbridge (144 mi away)
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Located in Woodbridge, VA / 144 miles away from Chesapeake, VA
ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/C, Heated door mirrors, Heated Front Bucket Seats, He...
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: 5TDKDRAH3RS541110
Stock: A541110
Certified Pre-Owned: Yes
Listed since: 05-03-2025 - $37,995good price$1,776 below market
- 24,253 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Waldorf Toyota (137 mi away)
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Located in Waldorf, MD / 137 miles away from Chesapeake, VA
**Recent Arrival!** **CLEAN Carfax!** **One Owner Vehicle!** **LOW Miles!** **Priced to Sell!** **2024!** **SmartLED Ambient Lighting!** **Family Fun!...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH2RS529885
Stock: 00081347
Certified Pre-Owned: No
Listed since: 04-19-2025 - $42,525fair price$698 below market
- 16,263 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Capital Subaru of Greenville (104 mi away)
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Located in Winterville, NC / 104 miles away from Chesapeake, VA
Capital Subaru of Greenville is delighted to offer this good-looking 2024 Toyota Highlander Midnight Black Metallic XLE with the following features:...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH2RS538229
Stock: SPK4138A
Certified Pre-Owned: No
Listed since: 04-14-2025 - Price Drop$31,297good price$1,853 below market
- 33,961 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Ourisman Lexus of Rockville (172 mi away)
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Located in Rockville, MD / 172 miles away from Chesapeake, VA
18 ALLOY WHEELS, BLIND SPOT MONITOR W/REAR CROSS TRAFFIC ALERT AND INTUITIVE PARKING ASSIST W/AUTO BRAKING, DYNAMIC RADAR CRUISE CONTROL, PRE-COLLISIO...
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: 5TDBZRBH1NS590350
Stock: TS590350
Certified Pre-Owned: No
Listed since: 04-16-2025 - $33,900good price$1,318 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)
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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 - $32,847fair price$60 below market
- 92,602 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Crossroads Ford of Wake Forest (141 mi away)
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Located in Wake Forest, NC / 141 miles away from Chesapeake, VA
CERTIFIED PRE-OWNED WARRANTY INCLUDED!Clean CARFAX. 2022 Toyota Highlander XLE ...XP PACKAGE! POWER SUNROOF, 8-PASSENGER, PHONE CABLE CHARGE PACKAGE, ...
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: 5TDGZRAH8NS545400
Stock: MC0037A
Certified Pre-Owned: No
Listed since: 04-17-2025 - Price Drop$44,250good price$1,822 below market
- 14,084 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Waldorf Toyota (137 mi away)
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Located in Waldorf, MD / 137 miles away from Chesapeake, VA
**Recent Arrival!** **CLEAN Carfax!** **One Owner Vehicle!** **AWD!** **Local Trade!** **LOW Miles!** **Power Liftgate!** **Perfect Color Combination!...
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: 5TDKDRBH3RS555782
Stock: 0081375A
Certified Pre-Owned: No
Listed since: 05-16-2025 - New Listing$41,550fair price$1,378 below market
- 20,717 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Driveway (2 mi away)
- Home delivery*
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Located in Chesapeake, VA / 2 miles away from Chesapeake, VA
CarFax No Accidents Reported,CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,He...
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: 5TDKDRAH8RS531334
Stock: RS531334P
Certified Pre-Owned: No - Price Drop$29,307good price$1,760 below market
- 25,931 miles
- No accidents, 3 owners, personal use
- 8 Seats, 21 City / 29 Hwy MPG
- Westgate Chrysler Jeep Dodge Ram (152 mi away)
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Located in Raleigh, NC / 152 miles away from Chesapeake, VA
Clean CARFAX. 18" Painted Alloy Wheels, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes, 6 Speakers, ABS brakes, Air Conditioning, 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDCZRAH1NS138968
Stock: 29481P
Certified Pre-Owned: No
Listed since: 01-20-2025
Showing 85 - 105 out of 2,076 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Love the vehicle, Infotainment is unusable
bbells, 04/16/2023
2023 Toyota Highlander LE 4dr SUV (2.4L 4cyl Turbo 8A)
Love the gas mileage, 30+mpg in eco mode. Towing capacity. Comfort. Nice vehicle except the "drive connect" app advertisement makes the entertainment system unusable. It will lock up the system for 1 to 10 minutes so no music, no google maps, no phone, nothing, until it decides to clear itself. Toyota says you can pay $200 a year to remove the advertisement by subscribing to drive … connect. This makes it the definition of ransomware. But there is nothing in the app I need or want. Neither ToyotaUSA, their tech department, or the dealer can fix it. I will either be selling the vehicle or replacing the entertainment system when the free trial of drive connect ends in a couple months. For those of us who use their phone for maps, texts or communication the system makes the vehicle unusable. Update: Can't put in different infotainment system, it is integrated into the vehicle. Toyota gave me a free trial of drive connect. Unfortunately anytime i am in an area without internet the display is locked up asking for a password. Can't enter a password until i get into an internet area, then go s back to asking for a password when i leave it. Worthless and unusable. Toyota wouldn't fix it. After 7 months they bought it back from me. Last Toyota.
Used 2023 Toyota Highlander in Chesapeake, VA Values
Estimated values
2023 Toyota Highlander LE 4dr SUV (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $27,819 | $29,914 | $32,279 |
| Clean | $27,471 | $29,508 | $31,806 |
| Average | $26,890 | $28,831 | $31,019 |
| Rough | $26,135 | $27,951 | $29,996 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $37,316. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 36,668. Based on the average mileage of 36,668 for used 2023 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 2023 in Chesapeake, Virginia to be $26,890.
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