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1,971 listings
- $26,778great price$3,487 below market
- 93,137 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Passport Toyota (145 mi away)
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Located in Suitland, MD / 145 miles away from Chesapeake, VA
Recent Arrival! Certified. 2020 Toyota Highlander Limited Blueprint AWD AutomaticToyota Silver Certified, Navigation System, Sunroof/Moonroof, Heate...
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: 5TDDZRBH9LS020120
Stock: T208187A
Certified Pre-Owned: Yes
Listed since: 08-20-2025 - $21,999great price$2,062 below market
- 135,164 miles
- 1 accident, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Supreme Motors (127 mi away)
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Located in Stafford, VA / 127 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH2LS002068
Stock: LS002068
Certified Pre-Owned: No - Price Drop$26,476good price$842 below market
- 97,617 miles
- No accidents, 3 owners, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Land Rover Bethesda (162 mi away)
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Located in North Bethesda, MD / 162 miles away from Chesapeake, VA
Sun/Moonroof3rd Row SeatLane Keeping AssistKeyless StartRear Spoiler50 State EmissionsBlack; Softex Seat TrimMidnight Black MetallicThis veh...
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: 5TDGZRBH2LS013166
Stock: LS013166
Certified Pre-Owned: No
Listed since: 08-11-2025 - Price Drop$29,500good price$876 below market
- 62,749 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Mercedes-Benz of Catonsville (174 mi away)
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Located in Baltimore, MD / 174 miles away from Chesapeake, VA
Recent Arrival! Priced below KBB Fair Purchase Price! Odometer is 5484 miles below market average! 2020 Toyota Highlander XLE, 4D Sport Utility, 3.5L ...
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: 5TDHZRBH6LS044246
Stock: KMBP200048
Certified Pre-Owned: No
Listed since: 07-30-2025 - $34,300fair price$755 below market
- 53,379 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Len Stoler Lexus (185 mi away)
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Located in Owings Mills, MD / 185 miles away from Chesapeake, VA
CARFAX One-Owner.Midnight Black Metallic 2020 Toyota Highlander Platinum AWD 8-Speed Automatic 3.5L V6 DOHCAWD, Electronic Rear-View Mirror, High Grad...
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: 5TDFZRBH7LS030850
Stock: L2551A
Certified Pre-Owned: No
Listed since: 08-23-2025 - $26,999good price$710 below market
- 83,501 miles
- No accidents, 3 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Complete Auto Center (146 mi away)
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Located in Raleigh, NC / 146 miles away from Chesapeake, VA
Finance Available, High Quality Pre-Owned Vehicles,5 years Maintenance Plan, Non-smoker owner, Vehicle Runs Well, Smooth ride, All records in possessi...
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: 5TDGZRAH0LS022045
Stock: 022045-13
Certified Pre-Owned: No - $25,999good price$1,773 below market
- 77,509 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Royal Auto Club (164 mi away)
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Located in Sterling, VA / 164 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: 5TDGZRAH6LS514255
Stock: SAI3192
Certified Pre-Owned: No - $26,750good price$1,560 below market
- 58,884 miles
- 1 accident, 2 owners, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Koons Tysons Toyota (157 mi away)
- Five Star Dealer
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Located in Vienna, VA / 157 miles away from Chesapeake, VA
RECALL NOTICE: Some vehicles offered for sale may be subject to unrepaired manufacturer safety recalls. To determine the recall status of a vehicle, v...
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: 5TDZZRAHXLS001504
Stock: KTT250979A
Certified Pre-Owned: Yes
Listed since: 08-21-2025 - $29,500fair price$63 below market
- 78,003 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Toyota of Bowie (151 mi away)
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Located in Bowie, MD / 151 miles away from Chesapeake, VA
Opulent Amber exterior and BLACK interior. Heated Seats, Third Row Seat, Nav System, Moonroof, All Wheel Drive, Power Liftgate, Aluminum Wheels, RADIO...
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: 5TDHZRBH0LS024378
Stock: LS024378
Certified Pre-Owned: No
Listed since: 08-18-2025 - $28,994good price$891 below market
- 75,345 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Bill Page Toyota (151 mi away)
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Located in Falls Church, VA / 151 miles away from Chesapeake, VA
2020 Toyota Highlander XLE Blizzard Pearl AWD 8-Speed Automatic 3.5L V6 DOHCToyota Safety Sense 2.0: Pre-Collision System w/Pedestrian Detection, Full...
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: 5TDHZRBH5LS038745
Stock: P8666
Certified Pre-Owned: No
Listed since: 08-21-2025 - Price Drop$24,255fair price$268 below market
- 125,418 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Bleecker Chrysler Dodge Jeep Ram (167 mi away)
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Located in Dunn, NC / 167 miles away from Chesapeake, VA
Midnight Black Metallic exterior and BLACK interior. Sunroof, 3rd Row Seat, Heated Seats, Onboard Communications System, iPod/MP3 Input, Satellite Rad...
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: 5TDGZRAH4LS503075
Stock: P13747A
Certified Pre-Owned: No
Listed since: 08-22-2025 - $31,977fair price$64 below market
- 56,651 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Jerry's Toyota (178 mi away)
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Located in Baltimore, MD / 178 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: 5TDHZRBHXLS018975
Stock: 252175A
Certified Pre-Owned: No
Listed since: 08-11-2025 - Price Drop$34,534fair price$373 above market
- 50,669 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Passport Toyota (145 mi away)
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Located in Suitland, MD / 145 miles away from Chesapeake, VA
Recent Arrival! 2020 Toyota Highlander Limited Ruby Flare Pearl AWD AutomaticNavigation System, Sunroof/Moonroof, Heated Seats, Leather Seats, Blind...
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: 5TDDZRBH6LS013285
Stock: T013285P
Certified Pre-Owned: No
Listed since: 08-19-2025 - $23,999fair price$342 above market
- 131,150 miles
- 2 accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Paragon Automotive (7 mi away)
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Located in Virginia Beach, VA / 7 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH2LS501664
Stock: 1761
Certified Pre-Owned: No 
Photos not available$27,170fair price$624 above market- 56,725 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Medlin Buick GMC (120 mi away)
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Located in Wilson, NC / 120 miles away from Chesapeake, VA
Highlander LE, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed Automatic, FWD, Cloth. CARFAX One-Owner.Recent Arrival! Odometer is 13324 miles below market av...
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: 5TDZZRAH3LS030987
Stock: 50054A
Certified Pre-Owned: No
Listed since: 08-22-2025- New Listing$28,990fair price$666 above market
- 88,355 miles
- 8 Seats, 20 City / 27 Hwy MPG
- Carvana - Richmond (95 mi away)
- Home delivery*
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Located in Richmond, VA / 95 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 Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH7LS513733
Stock: 2003980275
Certified Pre-Owned: No
Listed since: 08-27-2025 - $31,000fair price$758 above market
- 68,533 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Toyota of Bowie (151 mi away)
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Located in Bowie, MD / 151 miles away from Chesapeake, VA
Celestial Silver Metallic exterior and BLACK interior. Heated Seats, Third Row Seat, Nav System, Moonroof, All Wheel Drive, Power Liftgate, Aluminum 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: 5TDHZRBH3LS517794
Stock: LS517794
Certified Pre-Owned: No
Listed since: 08-11-2025 - 155,261 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Safford Mazda of Fredericksburg (121 mi away)
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Located in Fredericksburg, VA / 121 miles away from Chesapeake, VA
2020 Toyota Highlander Limited AWD Magnetic GraySpacious, powerful, and packed with premium features, this Highlander Limited is perfect for famili...
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: 5TDDZRBH9LS042201
Stock: P176A
Certified Pre-Owned: No
Listed since: 08-03-2025- 61,168 miles
- No accidents, 4 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana - Richmond (95 mi away)
- Home delivery*
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Located in Richmond, VA / 95 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: 5TDGZRBH5LS018345
Stock: 2003815482
Certified Pre-Owned: No
Listed since: 06-25-2025- 91,298 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Koons Automotive of Fredericksburg South (122 mi away)
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Located in Fredericksburg, VA / 122 miles away from Chesapeake, VA
Introducing the Moondust 2020 Toyota Highlander - a versatile chariot ready to take you on all your adventures! This ravishing ride radiates elegance ...
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: Yes
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDDZRBH1LS006843
Stock: 37765
Certified Pre-Owned: No- New Listing$28,988fair price$247 above market
- 90,289 miles
- 7 Seats, 20 City / 27 Hwy MPG
- Fitzgerald Hyundai (162 mi away)
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Located in Rockville, MD / 162 miles away from Chesapeake, VA
Recent Arrival! CARFAX One-Owner. Clean CARFAX.Certified. 20/27 City/Highway MPGCertification Program Details: FitzWay Value: FitzWay Comprehensi...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDDZRBH5LS004450
Stock: S295769A
Certified Pre-Owned: No
Listed since: 08-29-2025
Showing 1 - 21 out of 1,971 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 | $27,074 | $29,334 | $31,510 |
| Clean | $26,373 | $28,565 | $30,674 |
| Average | $25,205 | $27,284 | $29,281 |
| Rough | $23,686 | $25,618 | $27,471 |
The average list price of a used 2020 Toyota Highlander in Chesapeake, Virginia is $28,367. The average mileage on a used Toyota Highlander 2020 for sale in Chesapeake, Virginia is 85,276. Based on the average mileage of 85,276 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 $25,205.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.