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2,165 listings
- Price Drop$23,291great price$4,023 below market
- 83,162 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Jacksonville Kia (150 mi away)
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Located in Jacksonville, NC / 150 miles away from Chesapeake, VA
Jacksonville Kia is very proud to offer this handsome 2020 Toyota Highlander Midnight Black Metallic L with the following features:CARFAX One-Owner....
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 - $25,400great price$3,180 below market
- 74,000 miles
- No accidents, 2 owners, corporate fleet 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 - Price Drop$24,966great price$2,655 below market
- 92,800 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Carget Motors (143 mi away)
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Located in Woodbridge, VA / 143 miles away from Chesapeake, VA
The 2020 Toyota Highlander XLE is a refined and versatile midsize SUV that seamlessly blends comfort, technology, and practicality. With its sleek, 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: 5TDHZRBH0LS038653
Stock: 038653
Certified Pre-Owned: No
Listed since: 06-06-2025 - $24,049great price$2,521 below market
- 104,283 miles
- No accidents, 4 owners, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- DARCARS Honda (153 mi away)
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Located in Bowie, MD / 153 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 - $25,997great price$3,190 below market
- 73,123 miles
- 2 accidents, 3 owners, corporate fleet 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
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: 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: 5TDGZRAH9LS511902
Stock: 511902
Certified Pre-Owned: No
Listed since: 12-17-2024 - Price Drop$28,999great price$2,871 below market
- 57,968 miles
- No accidents, 1 owner, 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 XLE CARFAX One-Owner.Highlander XLE, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed Automatic, AWD, Ruby Flare Pearl, Black w/SofTex...
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: 5TDHZRBH7LS049858
Stock: 52E8523A
Certified Pre-Owned: No
Listed since: 06-07-2025 - Price Drop$27,998good price$1,055 below market
- 73,385 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Cox Chrysler Dodge Jeep Ram (184 mi away)
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Located in Burlington, NC / 184 miles away from Chesapeake, VA
Summary- EXTENDED WARRANTY / MAINTENANCE PROTECTION AVAILABLE ... - SUNROOF / MOONROOF ... - Good CARFAX...- TOWING / TRAILER HITCH ...<...
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: 5TDGZRAH2LS508369
Stock: P08369
Certified Pre-Owned: No
Listed since: 06-06-2025 - New Listing$33,998good price$1,430 below market
- 50,154 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Fayetteville (191 mi away)
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Located in Fayetteville, NC / 191 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: 5TDDZRBH8LS056056
Stock: 27472348
Certified Pre-Owned: No - Price Drop$28,987good price$689 below market
- 71,281 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Ideal Buick GMC (194 mi away)
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Located in Frederick, MD / 194 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 - $30,756good price$821 below market
- 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 - $27,997fair price$183 below market
- 80,523 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Ourisman Lexus of Rockville (171 mi away)
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Located in Rockville, MD / 171 miles away from Chesapeake, VA
ONE OWNER, APPLE CAR PLAY/ANDROID AUTO, HEATED SEATS, MOONROOF, 18 ALLOY WHEELS, BLIND SPOT MONITOR, BLUE TOOTH, BACK UP CAMERA, AWD, 4-Wheel Disc Bra...
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: 5TDGZRBH0LS500737
Stock: TS500737
Certified Pre-Owned: No
Listed since: 06-18-2025 - New Listing$23,999fair price$99 below market
- 131,150 miles
- 2 accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Paragon Automotive (8 mi away)
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Located in Virginia Beach, VA / 8 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 - New Listing$29,870good price$712 below market
- 62,110 miles
- No accidents, 2 owners, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- DARCARS Toyota of Silver Spring (165 mi away)
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Located in Silver Spring, MD / 165 miles away from Chesapeake, VA
2020 Toyota Highlander XLE Recent Arrival!Amber AWD. AWD 3.5L V6 DOHC 8-Speed Automatic Odometer is 13399 miles below market average! 20/27 City/Hig...
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: 5TDGZRBH7LS021022
Stock: P1A1418
Certified Pre-Owned: No
Listed since: 06-23-2025 - $24,995fair price$905 below market
- 83,459 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 8 Seats, 21 City / 29 Hwy MPG
- Nation Motors (91 mi away)
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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 - $27,500good price$683 below market
- 73,462 miles
- 1 accident, 2 owners, personal use only
- 7 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
Recent Arrival! Priced below KBB Fair Purchase Price! 2020 Toyota Highlander XLE SilverAWD, 18" Machined Alloy Wheels, Alloy wheels, Apple CarPlay/A...
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: 5TDGZRBH0LS508322
Stock: KWFP0220
Certified Pre-Owned: No
Listed since: 06-15-2025 - Price Drop$27,400fair price$47 below market
- 113,536 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- i.g. Burton Toyota of Dover (174 mi away)
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Located in Dover, DE / 174 miles away from Chesapeake, VA
TOYOTA CERTIFIED, ONE OWNER, CLEAN CARFAX, CAR PLAY, SUNROOF, HEATED LEATHER SEATS, POWER LIFTGATE, BLIND SPOT MONITORS, BACKUP CAMERA, AWD!! 2020 T...
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: 5TDGZRBH1LS508166
Stock: TP25131
Certified Pre-Owned: Yes
Listed since: 06-16-2025 - $26,500fair price$294 above market
- 64,628 miles
- No accidents, 3 owners, corporate fleet vehicle
- 8 Seats, 21 City / 29 Hwy MPG
- 1 US Motors (186 mi away)
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Located in Edgewood, MD / 186 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 - New Listing
- 12,741 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Brandywine (138 mi away)
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Located in Brandywine, MD / 138 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: 5TDFZRBH8LS050444
Stock: 27301866
Certified Pre-Owned: No - New Listing
- 20,737 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Carvana - Richmond (99 mi away)
- Home delivery*
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Located in Richmond, VA / 99 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: 5TDBZRBH9LS511682
Stock: 2003805146
Certified Pre-Owned: No
Listed since: 06-12-2025 - $31,999fair price$267 above market
- 53,182 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Herb Gordon Subaru (166 mi away)
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Located in Silver Spring, MD / 166 miles away from Chesapeake, VA
JUST ARRIVED. PENDING INSPECTION. 2020 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC AWD.Recent Arrival! 20/27 City/Highway MPG*Your additi...
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: 5TDHZRBHXLS522474
Stock: S51480A
Certified Pre-Owned: No
Listed since: 06-21-2025 - New Listing
- 48,613 miles
- No accidents, 2 owners, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Carvana - Richmond (99 mi away)
- Home delivery*
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Located in Richmond, VA / 99 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: 5TDBZRBH3LS005037
Stock: 2003824309
Certified Pre-Owned: No
Listed since: 06-25-2025
Showing 1 - 21 out of 2,165 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 | $20,955 | $23,557 | $26,062 |
| Clean | $20,412 | $22,939 | $25,370 |
| Average | $19,508 | $21,910 | $24,218 |
| Rough | $18,333 | $20,573 | $22,721 |
The average list price of a used 2020 Toyota Highlander in Chesapeake, Virginia is $28,604. The average mileage on a used Toyota Highlander 2020 for sale in Chesapeake, Virginia is 71,164. Based on the average mileage of 71,164 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 $19,508.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.