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2,092 listings
- New Listing$34,998fair price$375 above market
- 34,795 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from IL to VA*
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Located in Algonquin, IL / 746 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBHXLS013058
Stock: 27345454
Certified Pre-Owned: No - Price Drop$30,142fair price$229 above market
- 115,520 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Greenville Nissan (104 mi away)
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Located in Greenville, NC / 104 miles away from Chesapeake, VA
11 Speakers, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes, ABS brakes, Air Conditioning, Alloy wheels, AM/FM radio: SiriusXM, App...
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: 5TDYZRAH7NS101042
Stock: U18725
Certified Pre-Owned: No
Listed since: 03-05-2025 - New Listing$27,997fair price$283 below market
- 55,053 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Malloy Toyota (198 mi away)
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Located in Winchester, VA / 198 miles away from Chesapeake, VA
Recent Arrival! **Local Trade ** L ** Dynamic Cruise Control ** Lane Departure Alert ** AWD ** Powered Seat ** 18 in Wheels ** Push Button ** Smart Ke...
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: 5TDCZRBH4LS513411
Stock: MT4072A
Certified Pre-Owned: No
Listed since: 06-01-2025 - New Listing$32,998fair price$31 below market
- 64,620 miles
- No accidents, 3 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- County Ford (183 mi away)
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Located in Graham, NC / 183 miles away from Chesapeake, VA
LOW MILEAGE. ABS BRAKES. ALLOY WHEELS. 8" TOUCHSCREEN. TIRE SPECIFIC MONITORING SYSTEM. BACK UP CAMERA. OUTSIDE TEMP GUAGE. LOCKING GLOVE BOX. BLUETOO...
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: 5TDHZRBH2LS039626
Stock: P7623
Certified Pre-Owned: No
Listed since: 05-28-2025 - $27,500fair price$299 above 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 - New Listing$25,998fair price
- 66,660 miles
- 1 accident, 1 owner, personal use
- 8 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
Located in Killeen, TX / 1,289 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: 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: 5TDCZRAH8LS015083
Stock: 26499072
Certified Pre-Owned: No - Price Drop$29,999fair price$399 above market
- 113,146 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Koons of Woodbridge (142 mi away)
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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: 5TDGZRBH3NS171065
Stock: 37104
Certified Pre-Owned: No - $33,998fair price$153 above market
- 47,190 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CO to VA*
Close
Located in Colorado Springs, CO / 1,556 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDYZRAH7LS005117
Stock: 27247213
Certified Pre-Owned: No - New Listing$35,991fair price$463 above market
- 41,844 miles
- No accidents, 3 owners, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- DARCARS Toyota of Frederick (193 mi away)
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Located in Frederick, MD / 193 miles away from Chesapeake, VA
2020 Toyota Highlander Limited Recent Arrival!Blizzard Pearl AWD, 11 Speakers, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes, ABS ...
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: 5TDDZRBH7LS012856
Stock: P1D1532
Certified Pre-Owned: No
Listed since: 04-17-2025 - New Listing
- 46,739 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NC to VA*
Close
Located in Greensboro, NC / 207 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: 5TDDZRBH9LS033773
Stock: 27059547
Certified Pre-Owned: No - $31,990fair price$378 above market
- 75,666 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Oregon City, OR / 2,453 miles away from Chesapeake, VA
CarFax No Accidents Reported,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,Heated ...
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: 5TDDZRBH1LS030933
Stock: LS030933
Certified Pre-Owned: No - New Listing
- 51,128 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
Close
Located in Roseville, CA / 2,439 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: 5TDGZRBH3LS517693
Stock: 27143227
Certified Pre-Owned: No - $32,998fair price
- 58,169 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
Located in Killeen, TX / 1,289 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDYZRAH7LS020717
Stock: 27039318
Certified Pre-Owned: No - Price Drop$33,200fair price$691 above market
- 62,153 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Jim Coleman Toyota (166 mi away)
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Located in Bethesda, MD / 166 miles away from Chesapeake, VA
1 OWNER, CLEAN CARFAX, LIMITED-AWD, JBL PREMIUM AUDIO, HEATED AND VENTILATED FRONT SEATS, LEATHER SEATS, NAVIGATION, POWER TILT/SLIDE MOONROOF, POWER ...
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: 5TDDZRBH3LS042579
Stock: 93704A
Certified Pre-Owned: No
Listed since: 04-13-2025 - New Listing$34,990fair price$502 above market
- 57,263 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Columbus, OH / 430 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: 5TDDZRBHXLS014584
Stock: 2003699338
Certified Pre-Owned: No
Listed since: 05-11-2025 - New Listing$39,998fair price$405 above market
- 23,477 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Safford Brown CDJR Sterling (170 mi away)
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Located in Sterling, VA / 170 miles away from Chesapeake, VA
Recent Arrival! Celestial Silver 2022 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC AWD.20/27 City/Highway MPG
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: 5TDHZRBH4NS226322
Stock: X872
Certified Pre-Owned: No
Listed since: 06-02-2025 - New Listing$30,998fair price$205 above market
- 69,158 miles
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TN to VA*
Close
Located in Murfreesboro, TN / 573 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH9LS512434
Stock: 26643576
Certified Pre-Owned: No - $25,800fair price$244 above market
- 74,116 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- Volvo Cars Midlothian (91 mi away)
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Located in Midlothian, VA / 91 miles away from Chesapeake, VA
2018 Toyota Highlander XLE At Volvo of Midlothian. Alumina Jade Metallic AWD 8-Speed Automatic Electronic with ECT-i 3.5L V6Clean Carfax, One Owner, L...
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: 5TDJZRFH1JS832389
Stock: VRF160XA
Certified Pre-Owned: No
Listed since: 05-14-2025 - $33,440fair price$3 below market
- 49,080 miles
- 1 accident, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- TAZ Auto Group (185 mi away)
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Located in Sanford, NC / 185 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDYZRAH0LS009719
Stock: J3956
Certified Pre-Owned: No - New Listing$34,500fair price$941 above market
- 60,392 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Mechanicsville Toyota (86 mi away)
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Located in Mechanicsville, VA / 86 miles away from Chesapeake, VA
This 2020 Toyota Highlander in Blizzard Pearl features: Highlander Limited, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed Automatic, AWD, Gray w/Leather Se...
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: 5TDDZRBH0LS029143
Stock: 51758A
Certified Pre-Owned: No
Listed since: 06-01-2025 - New Listing$34,483fair price$495 above market
- 65,052 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- John Hiester Chrysler Dodge Jeep Ram of Sanford (185 mi away)
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Located in Sanford, NC / 185 miles away from Chesapeake, VA
CLEAN CARFAX, ONE OWNER, LOCAL TRADE, BALANCE OF FACTORY WARRANTY, FAST AND EASY FINANCING, THE NEW PRICE OUTLET, 3.003 Axle Ratio, 3rd row seats: spl...
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: 5TDHZRAH4NS127856
Stock: SR3764C
Certified Pre-Owned: No
Listed since: 05-30-2025
Showing 211 - 231 out of 2,092 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 | $27,684 | $30,192 | $32,606 |
| Clean | $26,967 | $29,400 | $31,741 |
| Average | $25,772 | $28,082 | $30,300 |
| Rough | $24,220 | $26,367 | $28,426 |
The average list price of a used 2020 Toyota Highlander in Chesapeake, Virginia is $32,477. The average mileage on a used Toyota Highlander 2020 for sale in Chesapeake, Virginia is 63,416. Based on the average mileage of 63,416 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 $25,772.
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