Skip to FiltersReport abuse
2,231 listings
- New Listing$34,590fair price$157 above market
- 57,263 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Cleveland, OH / 440 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: 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: 5TDDZRBHXLS014584
Stock: 2003699338
Certified Pre-Owned: No
Listed since: 05-11-2025 - 61,137 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Auction Direct USA (151 mi away)
Close
Located in Raleigh, NC / 151 miles away from Chesapeake, VA
The 2022 Toyota Highlander Limited is like your go-anywhere luxury chariotleather-trimmed comfort, a moonroof, and room for the whole crew (plus cargo...
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: 5TDYZRAH5NS103064
Stock: AD01118
Certified Pre-Owned: No
Listed since: 06-05-2025- 96,512 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- John Hiester Chrysler Jeep Dodge Ram (171 mi away)
Close
Located in Lillington, NC / 171 miles away from Chesapeake, VA
ONE OWNER ACCIDENT FREE CARFAX, AWD, FAST AND EASY FINANCING, THE NEW PRICE OUTLET, AWD, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Br...
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: 5TDHZRBH8NS180221
Stock: P10077
Certified Pre-Owned: No
Listed since: 05-28-2025- 137,559 miles
- 2 accidents, 2 owners, personal use
- 8 Seats, 20 City / 26 Hwy MPG
- Paragon Automotive (8 mi away)
Close
Located in Virginia Beach, 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDDZRFH5JS801532
Stock: 1745
Certified Pre-Owned: No- 81,139 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Oklahoma City, OK / 1,189 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: 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: 5TDGZRBH3LS020322
Stock: 2003761905
Certified Pre-Owned: No
Listed since: 05-24-2025- 113,146 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Koons of Woodbridge (142 mi away)
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: 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: 5TDGZRBH3NS171065
Stock: 37104
Certified Pre-Owned: No- 83,437 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Morehead Motor Company (142 mi away)
Close
Located in Morehead City, NC / 142 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDYZRAH8LS019057
Stock: 5377
Certified Pre-Owned: No
Listed since: 03-22-2025- 76,488 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Salem, OR / 2,474 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Remote Start,Satell...
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: 5TDGZRBH6LS521253
Stock: LS521253
Certified Pre-Owned: No- New Listing
- 58,036 miles
- Frame damage reported, 3 owners, corporate fleet vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Kargar Motors (155 mi away)
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: 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH9NS539721
Stock: KMM13306
Certified Pre-Owned: No - Not Priced
- 72,500 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Royal Auto Club (169 mi away)
Close
Located in Sterling, VA / 169 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH5NS250693
Stock: SAI2965
Certified Pre-Owned: No - 31,749 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Jerry's Toyota (183 mi away)
Close
Located in Baltimore, MD / 183 miles away from Chesapeake, VA
2022 Toyota Highlander XLE AWD. Only 31,749 miles. Toyota's best selling midsize SUV. Spacious interior and cargo area with heated leather seating 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH4NS221505
Stock: 242511A
Certified Pre-Owned: No
Listed since: 06-02-2025- New Listing
- 77,844 miles
- No accidents, 2 owners, personal use
- 8 Seats, 20 City / 26 Hwy MPG
- Battlefield Toyota (155 mi away)
Close
Located in Culpeper, VA / 155 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: 5TDJZRFH3JS534393
Stock: P5515
Certified Pre-Owned: No
Listed since: 06-10-2025 - New Listing
- 66,702 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Terry Subaru (172 mi away)
Close
Located in Lynchburg, VA / 172 miles away from Chesapeake, VA
This 2022 Toyota Highlander XLE in Gray features: Recent Arrival! 3.5L V6 DOHC AWD Stock numbers starting with VA are located at Terry Auto Outlet at ...
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: 5TDGZRBH9NS167943
Stock: P12503
Certified Pre-Owned: No
Listed since: 06-09-2025 - Price Drop$33,900great price$5,131 below market
- 40,946 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Passport Toyota (149 mi away)
Close
Located in Suitland, MD / 149 miles away from Chesapeake, VA
Certified. 2023 Toyota Highlander LE Magnetic Gray Metallic AWD AutomaticToyota Gold Certified, New Tires, Blind Spot Monitor, Backup Camera, Blueto...
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: 5TDKDRBH7PS017874
Stock: B8784
Certified Pre-Owned: Yes
Listed since: 05-09-2025 - $12,495great price$2,738 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)
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
- 93,493 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Glen Burnie DriveTime (169 mi away)
Close
Located in Glen Burnie, MD / 169 miles away from Chesapeake, VA
Shop at DriveTime: Get started on your personalized car-buying journey today. With no credit impact, you can get approved for your real, personalized ...
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: 5TDBZRFH4JS822668
Stock: 1630091678
Certified Pre-Owned: No
Listed since: 05-20-2025 - New ListingNot Priced
- 71,439 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Haley Certified Preowned (90 mi away)
Close
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: 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/29 Highway)
Listing Information:
VIN: 5TDGZRAH4NS547497
Stock: J5342
Certified Pre-Owned: No
Listed since: 06-07-2025 - New Listing
- 41,293 miles
- 8 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
Close
Located in Canoga Park, CA / 2,371 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 Unavailable.
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDCZRAH0LS506344
Stock: 27452789
Certified Pre-Owned: No - New Listing
- 39,279 miles
- 1 accident, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
Close
Located in Stockton, CA / 2,450 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH1LS502742
Stock: 27433568
Certified Pre-Owned: No - Price Drop$30,000great price$3,878 below market
- 44,779 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Koons Arlington Toyota (157 mi away)
Close
Located in Arlington, VA / 157 miles away from Chesapeake, VA
2023 Toyota Highlander LE 3rd row seats: split-bench, ABS brakes, Active Cruise Control, Alloy wheels, Brake assist, Electronic Stability Control, Fro...
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: 5TDKDRAH1PS505218
Stock: R10799
Certified Pre-Owned: No
Listed since: 05-09-2025 - 113,857 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Arlington Motors (156 mi away)
Close
Located in Falls Church, VA / 156 miles away from Chesapeake, VA
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: 5TDGZRBH8LS503711
Stock: W9896
Certified Pre-Owned: No
Showing 316 - 336 out of 2,231 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
"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.
Used 2020 Toyota Highlander in Chesapeake, VA Values
Estimated values
2020 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $27,515 | $29,694 | $31,793 |
| Clean | $26,803 | $28,916 | $30,950 |
| Average | $25,615 | $27,619 | $29,544 |
| Rough | $24,072 | $25,933 | $27,717 |
The average list price of a used 2020 Toyota Highlander in Chesapeake, Virginia is $30,768. The average mileage on a used Toyota Highlander 2020 for sale in Chesapeake, Virginia is 77,964. Based on the average mileage of 77,964 for used 2020 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 2020 in Chesapeake, Virginia to be $25,615.
Filters
Skip to ResultsApplied Filters4Active
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
* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.