Used Toyota Highlander for Sale in Chesapeake, VA
Shop for a versatile Toyota Highlander in the city where Michael Copon was born
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978 listings
- Price Drop$30,999great price$5,214 below market
- 53,756 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Southern Chrysler Dodge Jeep RAM Chesapeake (14 mi away)
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Located in Chesapeake, VA / 14 miles away from Chesapeake, VA
Certified. Celestial Silver Metallic 2023 Toyota Highlander XLE 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed Automatic FWD SUNROOF/MOO...
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: 5TDKDRAH8PS504793
Stock: YP10777
Certified Pre-Owned: No
Listed since: 06-16-2025 - $39,500great price$3,703 below market
- 15,883 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Hall Honda Virginia Beach (11 mi away)
- Five Star Dealer
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Located in Virginia Beach, VA / 11 miles away from Chesapeake, VA
Clean CARFAX. 2024 Toyota Highlander XLE AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp AWD, ABS brakes, Active Cruise Con...
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: 5TDKDRBH7RS569149
Stock: 2252602A
Certified Pre-Owned: No
Listed since: 05-14-2025 - Price Drop$30,398good price$2,194 below market
- 55,253 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- First Team Subaru Norfolk (9 mi away)
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Located in Norfolk, VA / 9 miles away from Chesapeake, VA
Silver 2023 Toyota Highlander L FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hpThe 2023 Toyota Highlander LE is a popular ...
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: 5TDKDRAH5PS502757
Stock: NB1635
Certified Pre-Owned: No
Listed since: 06-23-2025 - $12,990fair price$1,111 below market
- 118,889 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 17 City / 23 Hwy MPG
- The Car Exchange (9 mi away)
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Located in Virginia Beach, VA / 9 miles away from Chesapeake, VA
Come Experience The Car Exchange Difference No haggle pricing No high pressure sales Easy Financing options Great Extended Warranties All cars newly i...
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: 5TDDK3EH7AS030722
Stock: 030722MT
Certified Pre-Owned: No - $14,490fair price$291 below market
- 175,428 miles
- No accidents, 3 owners, personal use
- 8 Seats, 18 City / 24 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,3rd Row Seat,Back-Up Camera,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Leather Seats,Navigation System,Satellite R...
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: 5TDJKRFH5FS142768
Stock: FS142768A
Certified Pre-Owned: No - Price Drop$23,550good price$787 below market
- 114,894 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Driveway (2 mi away)
- Home delivery*
Close
Located in Chesapeake, VA / 2 miles away from Chesapeake, VA
CarFax No Accidents Reported,Rare Find,3rd Row Seat,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Chrome Wheels,Heated Seats,Heated Steerin...
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: 5TDDZRFH5JS888381
Stock: JS888381A
Certified Pre-Owned: No - New Listing$38,700fair price$331 below market
- 29,135 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Hall Honda Virginia Beach (11 mi away)
- Five Star Dealer
Close
Located in Virginia Beach, VA / 11 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. Pearl 2022 Toyota Highlander XSE AWD 8-Speed Automatic 3.5L V6 DOHC AWD.Recent Arrival! Odometer is 18425 miles belo...
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: 5TDLZRBHXNS238260
Stock: 18P6480A
Certified Pre-Owned: No
Listed since: 07-30-2025 - Price Drop$31,963fair price$835 above market
- 58,132 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Southern Nissan Chesapeake (14 mi away)
Close
Located in Chesapeake, VA / 14 miles away from Chesapeake, VA
Discover comfort, capability, and cutting-edge efficiency in this family-first 2023 Toyota Highlander L, VIN 5TDKDRAH3PS504393 a versatile midsize SUV...
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: 5TDKDRAH3PS504393
Stock: MP10656
Certified Pre-Owned: No
Listed since: 06-18-2025 - New Listing$29,550good price$1,348 below market
- 47,873 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- Driveway (2 mi away)
- Home delivery*
Close
Located in Chesapeake, VA / 2 miles away from Chesapeake, VA
CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,3rd Row Seat,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start...
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: 5TDJZRFH0KS622593
Stock: KS622593A
Certified Pre-Owned: No - $31,550fair price$830 below market
- 48,694 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Driveway (2 mi away)
- Home delivery*
Close
Located in Chesapeake, VA / 2 miles away from Chesapeake, VA
CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satellite Radio,T...
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: 5TDKDRAH6PS004857
Stock: PS004857P
Certified Pre-Owned: No - New Listing$43,000fair price$1,637 above market
- 13,719 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- Hall Toyota Virginia Beach (14 mi away)
Close
Located in Virginia Beach, VA / 14 miles away from Chesapeake, VA
Midnight Black Metallic 2023 Toyota Highlander XLE AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp AWD, ABS brakes, Active ...
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: 5TDKDRBH3PS037930
Stock: 24255840A
Certified Pre-Owned: No
Listed since: 07-28-2025 - Price Drop$14,500fair price$562 below market
- 155,619 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Hall Chrysler Dodge Jeep RAM Virginia Beach (11 mi away)
Close
Located in Virginia Beach, VA / 11 miles away from Chesapeake, VA
CARFAX One-Owner. Silver Sky Metallic 2014 Toyota Highlander AWD 6-Speed Automatic Electronic with Overdrive 3.5L V6 DOHC Dual VVT-i 24V 4D Sport Util...
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: 5TDDKRFH4ES033312
Stock: 24255504A
Certified Pre-Owned: No
Listed since: 06-11-2025 - $17,999fair price$194 above market
- 165,038 miles
- No accidents, 3 owners, corporate fleet vehicle
- 8 Seats, 20 City / 26 Hwy MPG
- Paragon Automotive (9 mi away)
Close
Located in Virginia Beach, VA / 9 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 (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH5HS430241
Stock: 1753
Certified Pre-Owned: No - $22,700fair price$201 above market
- 108,379 miles
- No accidents, 3 owners, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Hall Toyota Virginia Beach (14 mi away)
Close
Located in Virginia Beach, VA / 14 miles away from Chesapeake, VA
Blizzard Pearl 2017 Toyota Highlander Limited AWD 8-Speed Automatic Electronic with ECT-i 3.5L V6 AWD, ABS brakes, Active Cruise Control, Alloy wheels...
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: 5TDDZRFH2HS409473
Stock: 2252587G
Certified Pre-Owned: No
Listed since: 07-24-2025 - Price Drop$30,499fair price$224 below market
- 60,966 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Driveway (24 mi away)
- Home delivery*
Close
Located in Hampton, VA / 24 miles away from Chesapeake, VA
CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satellite Radio,Turbo/Supercharged,W...
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: 5TDKDRAHXPS503533
Stock: PS503533E
Certified Pre-Owned: No - Price Drop$34,406fair price$717 above market
- 20,068 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Driveway (24 mi away)
- Home delivery*
Close
Located in Hampton, VA / 24 miles away from Chesapeake, VA
CarFax No Accidents Reported,CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satelli...
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: 5TDKDRAH8PS518757
Stock: PS518757T
Certified Pre-Owned: No - $36,951fair price$818 below market
- 36,432 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Southern Acura Newport News (31 mi away)
Close
Located in Newport News, VA / 31 miles away from Chesapeake, VA
Experience premium comfort, capability, and cutting-edge technology in this 2022 Toyota Highlander XLE AWD, VIN 5TDHZRBH9NS171494—a sophisticated SUV ...
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: 5TDHZRBH9NS171494
Stock: ZP10412
Certified Pre-Owned: No
Listed since: 07-10-2025 - $7,899fair price$515 above market
- 197,210 miles
- No accidents, 3 owners, personal use
- 7 Seats, 17 City / 23 Hwy MPG
- 518 Auto Sales (12 mi away)
Close
Located in Norfolk, VA / 12 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: JTEES41A292127599
Stock: 11797
Certified Pre-Owned: No
Listed since: 07-17-2025 - $23,999fair price$464 above market
- 93,853 miles
- No accidents, 3 owners, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- Paragon Automotive (9 mi away)
Close
Located in Virginia Beach, VA / 9 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/26 Highway)
Listing Information:
VIN: 5TDJZRFH6HS479156
Stock: 1785
Certified Pre-Owned: No - Price Drop$37,800fair price$445 above market
- 36,671 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Hall Toyota Virginia Beach (14 mi away)
Close
Located in Virginia Beach, VA / 14 miles away from Chesapeake, VA
Blueprint 2024 Toyota Highlander LE FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp18" Painted Alloy Wheels, 3.329 Axle R...
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: 5TDKDRAH4RS547255
Stock: 22255037A
Certified Pre-Owned: No
Listed since: 06-09-2025 - New Listing$26,960fair price$178 above market
- 66,022 miles
- No accidents, 3 owners, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Driveway (13 mi away)
- Home delivery*
Close
Located in Norfolk, VA / 13 miles away from Chesapeake, VA
CarFax No Accidents Reported,Rare Find,3rd Row Seat,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping 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 (21 City/27 Highway)
Listing Information:
VIN: 5TDKZRFH2KS316032
Stock: KS316032P
Certified Pre-Owned: No
Showing 1 - 21 out of 978 listings
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.