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2,061 listings
- Price Drop$25,800great price$3,064 below market
- 50,802 miles
- No accidents, 3 owners, corporate fleet vehicle
- 8 Seats, 21 City / 29 Hwy MPG
- Koons Arlington Toyota (157 mi away)
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Located in Arlington, VA / 157 miles away from Chesapeake, VA
2020 Toyota Highlander LE 3rd row seats: split-bench, Apple CarPlay/Android Auto, Auto High-beam Headlights, Automatic temperature control, Exterior P...
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: 5TDZZRAH6LS508707
Stock: A10685
Certified Pre-Owned: No
Listed since: 04-18-2025 - $25,400great price$3,080 below market
- 74,000 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Fred's Executive Auto (143 mi away)
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Located in Woodbridge, VA / 143 miles away from Chesapeake, VA
LEATHER,3RD-ROW 2 12V DC Power Outlets 2 Seatback Storage Pockets Air Filtration Bucket Folding Captain Front Facing Manual Reclining Fold Forward Sea...
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: 5TDGZRAH1LS010258
Stock: P010258
Certified Pre-Owned: No
Listed since: 12-06-2024 - $25,997great price$3,096 below market
- 73,123 miles
- 2 accidents, 3 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- Fred's Executive Auto (143 mi away)
Close
Located in Woodbridge, VA / 143 miles away from Chesapeake, VA
Your satisfaction is our business! You won't want to miss this excellent value! This SUV is purpose-built for the most treacherous terrain! Top featur...
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: 5TDGZRAH9LS511902
Stock: 511902
Certified Pre-Owned: No
Listed since: 12-17-2024 - Price Drop$24,999great price$2,141 below market
- 104,283 miles
- No accidents, 4 owners, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- DARCARS Honda (154 mi away)
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Located in Bowie, MD / 154 miles away from Chesapeake, VA
2020 Toyota Highlander XLE Magnetic Gray 8-Speed AutomaticAWD, Alloy wheels, Apple CarPlay/Android Auto, Brake assist, Exterior Parking Camera Rear,...
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: 5TDGZRBH2LS009635
Stock: 5P5626A
Certified Pre-Owned: No
Listed since: 03-22-2025 - $24,990good price$2,201 below market
- 83,162 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Jacksonville Kia (149 mi away)
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Located in Jacksonville, NC / 149 miles away from Chesapeake, VA
Priced below KBB Fair Purchase Price! Jacksonville Kia is honored to offer this great-looking 2020 Toyota Highlander Midnight Black Metallic L with th...
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: 5TDZZRAH6LS030546
Stock: 22PC0076
Certified Pre-Owned: No
Listed since: 04-04-2025 - Price Drop$25,000good price$1,379 below market
- 110,012 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Ourisman Hyundai of Bowie (154 mi away)
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Located in Bowie, MD / 154 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: 5TDGZRBH3LS033345
Stock: BH8443
Certified Pre-Owned: No
Listed since: 05-02-2025 - $28,590good price$1,378 below market
- 58,562 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Audi Hunt Valley (190 mi away)
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Located in Cockeysville, MD / 190 miles away from Chesapeake, VA
Sun/Moonroof3rd Row SeatLane Keeping AssistKeyless StartRear Spoiler50 State EmissionsBlack; Softex Seat TrimMagnetic Gray MetallicThis vehi...
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: 5TDGZRAH9LS512905
Stock: LS512905
Certified Pre-Owned: No
Listed since: 05-01-2025 - $33,295good price$850 below market
- 56,711 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- BMW of Rockville (169 mi away)
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Located in Rockville, MD / 169 miles away from Chesapeake, VA
Birds Eye View Camera W/12.3" ScreenSun/MoonroofLeather SeatsNavigation System3rd Row SeatAll Weather Floor Liner & Cargo Tray (Tms)Body Side Mo...
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: 5TDDZRBHXLS032177
Stock: LS032177
Certified Pre-Owned: No
Listed since: 05-21-2025 - $26,500fair price$16 below market
- 64,628 miles
- No accidents, 3 owners, corporate fleet vehicle
- 8 Seats, 21 City / 29 Hwy MPG
- 1 US Motors (187 mi away)
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Located in Edgewood, MD / 187 miles away from Chesapeake, VA
Vehicle Overview: **Vehicles come with complimentary Lifetime Powertrain warranty (with Qualifying purchase) The Eprice does not include state taxes s...
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: 5TDCZRAH1LS031092
Stock: 031092
Certified Pre-Owned: No - Price Drop$34,900fair price$666 above market
- 36,676 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Hall Toyota Virginia Beach (14 mi away)
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Located in Virginia Beach, VA / 14 miles away from Chesapeake, VA
Celestial Silver Metallic 2020 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC AWD, Front dual zone A/C.AWD, Front dual zone A/C, 18" Machi...
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: 5TDHZRBH8LS510985
Stock: 24255528A
Certified Pre-Owned: No
Listed since: 05-06-2025 - $24,995fair price$1,246 below market
- 83,459 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 8 Seats, 21 City / 29 Hwy MPG
- Nation Motors (91 mi away)
Close
Located in Richmond, VA / 91 miles away from Chesapeake, VA
2020 TOYOTA HIGHLANDER LE FRONT WHEEL DRIVE {Sub Title} with powerful 3.5L V6 DOHC -INC DUAL OVERHEAD CAM AND ALUMINUM engine and driven 83459 miles! ...
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: 5TDZZRAH7LS500597
Stock: NM3173
Certified Pre-Owned: No - Price Drop$26,795good price$1,183 below market
- 47,272 miles
- 1 accident, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Koons Woodbridge Ford (145 mi away)
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Located in Woodbridge, VA / 145 miles away from Chesapeake, VA
Priced below KBB Fair Purchase Price! 2020 Toyota Highlander LE Moon DustAWD, 18" Painted Alloy Wheels, ABS brakes, Alloy wheels, Apple CarPlay/Andr...
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: 5TDBZRBH4LS042551
Stock: KFWP200142
Certified Pre-Owned: No
Listed since: 05-05-2025 - New Listing$35,998fair price$302 below market
- 48,187 miles
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax Wilmington (194 mi away)
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Located in Wilmington, NC / 194 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: 5TDFZRAH7LS021583
Stock: 25830592
Certified Pre-Owned: No - New Listing$30,984fair price$275 above market
- 71,281 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Ideal Buick GMC (195 mi away)
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Located in Frederick, MD / 195 miles away from Chesapeake, VA
CARFAX 1-OWNER, CLEAN CARFAX, LOCAL TRADE, AWD. Ideal Hyundai Buick GMC - Proud Member Of The Aschenbach Auto Group - Family Owned - Family Values - N...
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: 5TDHZRBH8LS512980
Stock: H8562541A
Certified Pre-Owned: No
Listed since: 05-23-2025 - 70,144 miles
- No accidents, 2 owners, 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
2020 Toyota Highlander LimitedHighlander Limited, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed Automatic, AWD, Magnetic Gray, Black w/Leather Seat Trim, ...
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: 5TDDZRBH8LS039175
Stock: 52E2030B
Certified Pre-Owned: No
Listed since: 05-07-2025- New Listing
- 60,023 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Gaithersburg (194 mi away)
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Located in Frederick, MD / 194 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: 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: 5TDGZRBH0LS522446
Stock: 26937233
Certified Pre-Owned: No - 79,800 miles
- Frame damage reported, 2 owners, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Fred's Executive Auto (143 mi away)
Close
Located in Woodbridge, VA / 143 miles away from Chesapeake, VA
How about this great vehicle! It offers the latest in technological innovation and style. Top features include power front seats, an automatic dimming...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
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: 5TDGZRAH2LS500160
Stock: 500160
Certified Pre-Owned: No
Listed since: 02-22-2025- Price Drop$23,150great price$3,496 below market
- 69,095 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Koons Annapolis Toyota (156 mi away)
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Located in Annapolis, MD / 156 miles away from Chesapeake, VA
3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes, 6 Speakers, ABS brakes, Air Conditioning, Alloy wheels, AM/FM radio: SiriusXM, Auto...
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: 5TDBZRFH6KS942697
Stock: EE21429A
Certified Pre-Owned: No
Listed since: 05-03-2025 - 82,649 miles
- Frame damage reported, 2 owners, corporate fleet vehicle
- 7 Seats, 21 City / 29 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: 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: 5TDGZRAH5LS502436
Stock: SAI2988
Certified Pre-Owned: No- $25,786great price$4,251 below market
- 73,546 miles
- No accidents, 2 owners, rental vehicle
- 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: 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: 5TDGZRBH2MS072476
Stock: SAI2840
Certified Pre-Owned: No - 44,937 miles
- 2 accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Jerry's Toyota (183 mi away)
Close
Located in Baltimore, MD / 183 miles away from Chesapeake, VA
2020 Toyota Highlander XLE AWD. Only 16,625 miles. Toyota's top selling midsize SUV. Spacious heated leather seating for 7, power glass moonroof, navi...
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: 5TDHZRBH5LS005065
Stock: 251419A
Certified Pre-Owned: No
Listed since: 05-06-2025
Showing 1 - 21 out of 2,061 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 LE 4dr SUV (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $22,742 | $24,619 | $26,427 |
| Clean | $22,153 | $23,974 | $25,726 |
| Average | $21,172 | $22,898 | $24,558 |
| Rough | $19,896 | $21,500 | $23,039 |
The average list price of a used 2020 Toyota Highlander in Chesapeake, Virginia is $28,498. The average mileage on a used Toyota Highlander 2020 for sale in Chesapeake, Virginia is 68,683. Based on the average mileage of 68,683 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 $21,172.
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