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1,877 listings
- New Listing$28,998fair price$50 above market
- 40,782 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NJ to VA*
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Located in Sicklersville, NJ / 218 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: 5TDCZRBH8LS518837
Stock: 26684360
Certified Pre-Owned: No - $24,500good price$1,678 below market
- 50,862 miles
- No accidents, 3 owners, personal use
- 8 Seats, 19 City / 26 Hwy MPG
- Toyota of Bowie (156 mi away)
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Located in Bowie, MD / 156 miles away from Chesapeake, VA
Blizzard Pearl exterior and Ash interior. Third Row Seat, iPod/MP3 Input, Back-Up Camera, Rear Air, Aluminum Wheels, ALL-WEATHER FLOOR LINER PACKAGE, ...
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: 5TDBZRFH8JS801046
Stock: JS801046
Certified Pre-Owned: No
Listed since: 05-16-2025 - $33,995fair price$479 below market
- 83,801 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Waldorf Toyota (137 mi away)
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Located in Waldorf, MD / 137 miles away from Chesapeake, VA
**Recent Arrival!** **Local Trade!** **AWD!** **XSE!** **Special Color!** **Premium Audio Package!** **JBL Speakers!** **Black Emblem Overlays!** **Pr...
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: 5TDJZRBH3NS167720
Stock: 0N38148A
Certified Pre-Owned: No
Listed since: 05-24-2025 - $27,500fair price$417 below market
- 100,514 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Trax Auto II (191 mi away)
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Located in Broadway, VA / 191 miles away from Chesapeake, VA
Just in!1-Owner Toyota Highlander XLE Loaded, Stylish & Ready for the Road!Looking for a reliable, family-friendly SUV that blends comfort, performanc...
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: 5TDHZRBH0LS004101
Stock: 004101
Certified Pre-Owned: No
Listed since: 05-09-2025 - Price Drop$34,766fair price$434 below market
- 51,669 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Ourisman Toyota of Richmond (96 mi away)
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Located in Richmond, VA / 96 miles away from Chesapeake, VA
CLEAN CARFAX, DYNAMIC RADAR CRUISE CONTROL, PRE-COLLISION SYSTEM, LANE DEPARTURE ALERT, REAR CROSS TRAFFIC ALERT, BLIND SPOT MONITOR, PARKING SONAR, B...
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: 5TDDZRBH5LS013701
Stock: A013701
Certified Pre-Owned: Yes
Listed since: 04-23-2025 - Price Drop$32,995fair price$237 below market
- 65,451 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Waldorf Toyota (137 mi away)
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Located in Waldorf, MD / 137 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: 5TDGZRBH1NS226239
Stock: 00081348
Certified Pre-Owned: No
Listed since: 06-02-2025 - New Listing$38,528fair price$113 below market
- 35,830 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Passport Toyota (150 mi away)
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Located in Suitland, MD / 150 miles away from Chesapeake, VA
Recent Arrival! Certified. 2022 Toyota Highlander XLE Ruby Flare Pearl AWD AutomaticToyota Gold Certified, Sunroof/Moonroof, Heated Seats, Blind Spo...
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: 5TDGZRBHXNS244285
Stock: P8807
Certified Pre-Owned: Yes
Listed since: 05-22-2025 - $36,000fair price$928 below market
- 48,581 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Warrenton Toyota (162 mi away)
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Located in Warrenton, VA / 162 miles away from Chesapeake, VA
Discover the perfect blend of luxury, performance, and practicality with this 2020 Toyota Highlander Platinum. With only 48,581 miles, this well-maint...
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: 5TDFZRBH4LS031292
Stock: W250284A
Certified Pre-Owned: No
Listed since: 05-02-2025 - $25,980good price$1,029 below market
- 82,114 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Impex Chevrolet GMC (192 mi away)
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Located in Reidsville, NC / 192 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: 5TDYZRFH5JS273475
Stock: G00378B
Certified Pre-Owned: No
Listed since: 05-23-2025 - Price Drop$19,499fair price$969 below market
- 97,554 miles
- 1 accident, 1 owner, corporate fleet vehicle
- 8 Seats, 19 City / 26 Hwy MPG
- Supreme Motors (133 mi away)
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Located in Stafford, VA / 133 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:
22 Combined MPG (19 City/26 Highway)
Listing Information:
VIN: 5TDBZRFH4JS914394
Stock: JS914394
Certified Pre-Owned: No - $22,500fair price$836 above market
- 116,559 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 26 Hwy MPG
- LA Auto Star (14 mi away)
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Located in Virginia Beach, VA / 14 miles away from Chesapeake, VA
ONE OWNER and packed with premium features! Leather seats, sunroof, heated seats, navigation, blind spot monitor, and more!Spacious, reliable, and sty...
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: 5TDJZRFH8JS485403
Stock: 7305
Certified Pre-Owned: No - New Listing$41,988fair price$505 below market
- 23,905 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Johnson Lexus of Raleigh (144 mi away)
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Located in Raleigh, NC / 144 miles away from Chesapeake, VA
RECENT TRADE, INFO COMING SOON!!This vehicle is located at Johnson Lexus of Raleigh.Here at Johnson Lexus we price our cars online aggressively to...
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: 5TDLZRBH0NS203534
Stock: P12104A
Certified Pre-Owned: No
Listed since: 05-29-2025 - $34,430fair price$341 below market
- 58,611 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Waldorf Chevrolet (137 mi away)
Close
Located in Waldorf, MD / 137 miles away from Chesapeake, VA
****NAVIGATION, ***AUTOMATIC, **BACKUP CAMERA, **SUNROOF, **LEATHER, **USB PORTS, ***BLUE TOOTH CAPABLE, ***ALLOY WHEELS, ***APPLE CAR PLAY, ***7 PASS...
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: 5TDHZRBH8NS164262
Stock: FFF0491A
Certified Pre-Owned: No
Listed since: 05-07-2025 - $31,998fair price$109 above market
- 53,052 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from FL to VA*
Close
Located in Ocola, FL / 629 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: 5TDGZRBH2LS043252
Stock: 27423946
Certified Pre-Owned: No - New Listing$37,500fair price$222 below market
- 25,107 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Koons Tysons Chrysler Dodge Jeep Ram (161 mi away)
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Located in Vienna, VA / 161 miles away from Chesapeake, VA
*** 2022 TOYOTA HIGHLANDER XLE AWD *** GREAT COLOR COMBINATION *** LOADED W/ TOYOTA SAFETY SENSE 2.5 + *** LANE TRACING ASSIST *** BLIND SPOT MONITOR ...
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: 5TDGZRBH4NS238062
Stock: J16078
Certified Pre-Owned: No
Listed since: 05-29-2025 - $20,783fair price$206 above market
- 121,134 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Wholesale Direct Auto (194 mi away)
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Located in Wilmington, NC / 194 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: 5TDKZRFH5JS535503
Stock: 12914
Certified Pre-Owned: No
Listed since: 04-28-2025 - $35,611fair price$360 above market
- 20,369 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Medlin Buick GMC (119 mi away)
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Located in Wilson, NC / 119 miles away from Chesapeake, VA
Highlander LE, 4D Sport Utility, 3rd Row, Roof Rails, 3.5L V6 DOHC, 8-Speed Automatic, AWD, Cloth. CARFAX One-Owner.Recent Arrival! Odometer is 18799 ...
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: 5TDBZRBH8NS207701
Stock: 16665A
Certified Pre-Owned: No
Listed since: 05-12-2025 - $38,690fair price$875 above market
- 19,411 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- Driveway (151 mi away)
- Home delivery*
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Located in Springfield, VA / 151 miles away from Chesapeake, VA
CarFax No Accidents Reported,CarFax 1-Owner,Low Mileage,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,...
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: 5TDGZRAH9NS130540
Stock: 24803P
Certified Pre-Owned: No - $24,945fair price$1,066 below market
- 99,791 miles
- No accidents, 3 owners, corporate fleet vehicle
- 8 Seats, 21 City / 29 Hwy MPG
- Arlington Motors of Woodbridge (142 mi away)
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Located in Woodbridge, VA / 142 miles away from Chesapeake, VA
**(Facebook) All Prices indicate estimated entry for down payment** Visit Arlington Motors online at www.arlingtonmotorsva.com ...
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: 5TDZZRAH8LS500236
Stock: M9900
Certified Pre-Owned: No - $36,597good price$1,451 below market
- 34,953 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Vineland Hyundai (197 mi away)
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Located in Millville, NJ / 197 miles away from Chesapeake, VA
ONE OWNER, MOONROOF, LOCAL TRADE, BLIND SPOT MONITORING SYSTEM, BACK-UP CAMERA, APPLE CAR PLAY, ANDROID AUTO, ALL WHEEL DRIVE, 3RD ROW SEAT, BLUETOOTH...
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: 5TDGZRBH1NS580780
Stock: V01137A
Certified Pre-Owned: No
Listed since: 05-07-2025 - New Listing$29,989fair price$1,111 below market
- 50,427 miles
- No accidents, 1 owner, personal use
- 8 Seats, 21 City / 29 Hwy MPG
- Leith Toyota (142 mi away)
Close
Located in Raleigh, NC / 142 miles away from Chesapeake, VA
CARFAX One-Owner. Blueprint 2022 Toyota Highlander L FWD 8-Speed Automatic 3.5L V6 DOHC Clean Carfax 1 Owner/No Accident Vehicle, LOCAL TRADE IN, BACK...
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: 5TDCZRAHXNS110120
Stock: T110120P
Certified Pre-Owned: Yes
Listed since: 05-29-2025
Showing 169 - 189 out of 1,877 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 L 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $23,780 | $26,289 | $28,706 |
| Clean | $23,164 | $25,600 | $27,944 |
| Average | $22,138 | $24,452 | $26,675 |
| Rough | $20,804 | $22,959 | $25,026 |
The average list price of a used 2020 Toyota Highlander in Chesapeake, Virginia is $31,323. The average mileage on a used Toyota Highlander 2020 for sale in Chesapeake, Virginia is 60,975. Based on the average mileage of 60,975 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 $22,138.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.