Skip to FiltersReport abuse
2,076 listings
- Not Priced
- 106,205 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Mr. Car of Glen Burnie (169 mi away)
Close
Located in Glen Burnie, MD / 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: 5TDGZRBH8LS012491
Stock: CC012491B
Certified Pre-Owned: No
Listed since: 03-21-2025 - New Listing$22,797great price$2,467 below market
- 102,299 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Auto Park Honda (159 mi away)
Close
Located in Cary, NC / 159 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 (21 City/27 Highway)
Listing Information:
VIN: 5TDKZRFH5KS552013
Stock: CH109322B
Certified Pre-Owned: No
Listed since: 04-13-2025 - Price Drop$24,950great price$2,934 below market
- 55,311 miles
- No accidents, 2 owners, rental vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Safford Brown Mazda Fairfax (158 mi away)
Close
Located in Fairfax, VA / 158 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRFH5KS735296
Stock: 103252A
Certified Pre-Owned: No
Listed since: 05-17-2025 - $26,900great price$2,339 below market
- 72,924 miles
- No accidents, 3 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- DARCARS Toyota of Baltimore (177 mi away)
Close
Located in Baltimore, MD / 177 miles away from Chesapeake, VA
2021 Toyota Highlander XLE Recent Arrival! Clean CARFAX.Highlander XLE, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed Automatic, FWD, Magnetic Gray, Graph...
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: 5TDGZRAH1MS067951
Stock: 52E2032A
Certified Pre-Owned: No
Listed since: 04-30-2025 - $30,495great price$2,404 below market
- 76,757 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Waldorf Toyota (137 mi away)
Close
Located in Waldorf, MD / 137 miles away from Chesapeake, VA
**Recent Arrival!** **Local Trade!** **V6!** **AWD!** **Priced to Sell!** **Premium Audio!** **Black Emblems!** **Family Fun!** **Ask For a Video Walk...
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: 5TDHZRBH7MS148584
Stock: 0N38039A
Certified Pre-Owned: Yes
Listed since: 05-02-2025 - $24,750great price$1,581 below market
- 99,693 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Koons Easton Toyota (139 mi away)
Close
Located in Easton, MD / 139 miles away from Chesapeake, VA
2021 Toyota Highlander LE 2021 Toyota Highlander LE in Blizzard Pearl, Please call 410-822-8000 with any equipment or availability questions!, Schedul...
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: 5TDBZRBH5MS089928
Stock: KET250059A
Certified Pre-Owned: No
Listed since: 05-05-2025 - $25,267great price$2,410 below market
- 75,085 miles
- No accidents, 2 owners, personal use
- 8 Seats, 20 City / 26 Hwy MPG
- Lexus of Towson (186 mi away)
Close
Located in Towson, MD / 186 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: 5TDJZRFH4KS579487
Stock: T2762AAA
Certified Pre-Owned: No
Listed since: 05-12-2025 - Price Drop$29,695good price$842 below market
- 56,897 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 26 Hwy MPG
- Bill Page Toyota (157 mi away)
Close
Located in Falls Church, VA / 157 miles away from Chesapeake, VA
Certified. New Price! 2019 Toyota Highlander XLE Blizzard Pearl AWD 8-Speed Automatic Electronic with ECT-i 3.5L V6Toyota Safety Sense P (TSS-P): Incl...
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: 5TDJZRFH1KS584419
Stock: P8477
Certified Pre-Owned: Yes
Listed since: 04-18-2025 - $34,000fair price$259 below market
- 34,771 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Ourisman Honda of Tysons Corner (161 mi away)
Close
Located in Vienna, VA / 161 miles away from Chesapeake, VA
ONE OWNER, CLEAN CARFAX, FACTORY WARRENTY, BACKUP CAMERA / REAR VIEW CAMERA / REVERSE CAMERA, ADAPTIVE CRUISE CONTROL / ACC / DYNAMIC RADAR 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH5MS548283
Stock: A548283
Certified Pre-Owned: No
Listed since: 04-14-2025 - Price Drop$31,390great price$2,117 below market
- 52,897 miles
- 2 accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Westgate Chrysler Jeep Dodge Ram (152 mi away)
Close
Located in Raleigh, NC / 152 miles away from Chesapeake, VA
CARFAX One-Owner. AWD, 3rd row seats: split-bench, Apple CarPlay/Android Auto, Power Liftgate, Power moonroof, Steering wheel mounted audio controls, ...
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: 5TDGZRBH7MS075616
Stock: 28479P
Certified Pre-Owned: No
Listed since: 12-10-2024 - Price Drop$25,575good price$1,696 below market
- 81,559 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- BMW of Catonsville (179 mi away)
- Five Star Dealer
Close
Located in Baltimore, MD / 179 miles away from Chesapeake, VA
AWD.Recent Arrival! CARFAX One-Owner. Clean CARFAX.*Your additional costs are sales tax, tag and title fees for the state in which the vehicle will be...
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: 5TDDZRFHXKS944641
Stock: 4P2659
Certified Pre-Owned: No
Listed since: 05-21-2025 - Price Drop$24,051fair price$387 below market
- 99,412 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Len Stoler Chevrolet (199 mi away)
Close
Located in Westminster, MD / 199 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: 5TDJZRFH8KS614113
Stock: BV1345
Certified Pre-Owned: No
Listed since: 04-21-2025 - Price Drop$22,000fair price$524 below market
- 121,621 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- Koons Tysons Chevy GMC (161 mi away)
Close
Located in Vienna, VA / 161 miles away from Chesapeake, VA
AWD, ABS brakes, Active Cruise Control, Electronic Stability Control, Front dual zone A/C, Heated door mirrors, Heated Front Bucket Seats, Heated fron...
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: 5TDJZRFH5KS589820
Stock: 0250875B
Certified Pre-Owned: No
Listed since: 05-22-2025 - Price Drop$33,895fair price$423 above market
- 39,094 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Trust Auto (193 mi away)
Close
Located in Sykesville, MD / 193 miles away from Chesapeake, VA
You can find this Loaded 2021 Toyota Highlander XLE 7-Passenger SUV FWD (Front Wheel Drive) and many others like it at Trust Auto. This Toyota include...
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: 5TDGZRAHXMS044670
Stock: 044670
Certified Pre-Owned: No
Listed since: 04-22-2025 - $19,998good price$832 below market
- 141,865 miles
- No accidents, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 26 Hwy MPG
- CarHub (138 mi away)
Close
Located in Stafford, VA / 138 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: 5TDJZRFHXKS600505
Stock: 600505
Certified Pre-Owned: No - $27,500good price$1,530 below market
- 87,698 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Ourisman Honda of Laurel (166 mi away)
Close
Located in Laurel, MD / 166 miles away from Chesapeake, VA
CARFAX One-Owner. This 2021 Ruby Flare Pearl Toyota Highlander XLE AWD is well equipped and includes these features and benefits:. 8-Speed Automatic...
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: 5TDHZRBHXMS124487
Stock: MH10430
Certified Pre-Owned: No
Listed since: 05-13-2025 - $30,055good price$1,772 below market
- 99,625 miles
- No accidents, 2 owners, 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: 5TDJZRBH3MS097084
Stock: 36516
Certified Pre-Owned: No - $38,598fair price$1,037 above market
- 57,162 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Crossroads INFINITI of Raleigh (143 mi away)
Close
Located in Raleigh, NC / 143 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. 2021 Toyota HighlanderClean Carfax, One Owner, 20" Painted Alloy Wheels, Apple CarPlay/Android Auto, Auto High-beam 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDFZRAH2MS064374
Stock: PU4374
Certified Pre-Owned: No
Listed since: 04-22-2025 - New Listing$25,000fair price$709 below market
- 60,330 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 19 City / 26 Hwy MPG
- Koons Ford Baltimore (181 mi away)
Close
Located in Baltimore, MD / 181 miles away from Chesapeake, VA
The 2019 Toyota Highlander LE blends practicality, comfort, and trusted reliability in a versatile midsize SUV. Powered by a 3.5L V6 engine paired wit...
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 (19 City/26 Highway)
Listing Information:
VIN: 5TDBZRFH2KS997731
Stock: KS997731
Certified Pre-Owned: No
Listed since: 05-26-2025 - New Listing$26,998fair price$45 below market
- 51,604 miles
- No accidents, 2 owners, corporate fleet vehicle
- 8 Seats, 19 City / 26 Hwy MPG
- CarMax Newport News (34 mi away)
Close
Located in Newport News, VA / 34 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: 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: 5TDBZRFH5KS702816
Stock: 27140904
Certified Pre-Owned: No - New Listing$34,500good price$1,157 below market
- 65,464 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Safford Brown Manassas Hyundai (156 mi away)
Close
Located in Manassas, VA / 156 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. Midnight Black 2021 Toyota Highlander XSE AWD 8-Speed Automatic 3.5L V6 DOHC Leather Seats, Sunroof/Moonroof, Third Ro...
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: 5TDJZRBH3MS142587
Stock: X047846A
Certified Pre-Owned: No
Listed since: 04-12-2025
Showing 22 - 42 out of 2,076 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 XLE 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $24,982 | $27,207 | $29,349 |
| Clean | $24,335 | $26,494 | $28,570 |
| Average | $23,257 | $25,305 | $27,273 |
| Rough | $21,856 | $23,761 | $25,586 |
The average list price of a used 2020 Toyota Highlander in Chesapeake, Virginia is $27,921. The average mileage on a used Toyota Highlander 2020 for sale in Chesapeake, Virginia is 78,013. Based on the average mileage of 78,013 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 $23,257.
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.