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2,076 listings
- Price Drop
- 93,581 miles
- No accidents, 3 owners, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Capital Subaru of Greenville (104 mi away)
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Located in Winterville, NC / 104 miles away from Chesapeake, VA
Recent Arrival! Capital Subaru of Greenville is very proud to offer this handsome 2021 Toyota Highlander Celestial Silver Metallic XLE with the follow...
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: 5TDGZRBH1MS087339
Stock: SAT4160A
Certified Pre-Owned: No
Listed since: 05-20-2025 - New Listing
- 103,681 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Capital Blvd DriveTime (145 mi away)
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Located in Raleigh, NC / 145 miles away from Chesapeake, VA
Shop at DriveTime: Get started on your personalized car-buying journey today. With no credit impact, you can get approved for your real, personalized ...
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: 5TDDZRFH1KS930630
Stock: 1190215865
Certified Pre-Owned: No
Listed since: 05-22-2025 - $15,444great price$4,811 below market
- 94,336 miles
- 4 accidents, 3 owners, personal use only
- 8 Seats, 19 City / 26 Hwy MPG
- Auto Buying Service (158 mi away)
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Located in Fairfax, VA / 158 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:
22 Combined MPG (19 City/26 Highway)
Listing Information:
VIN: 5TDBZRFH7JS803371
Stock: ABS4408
Certified Pre-Owned: No
Listed since: 05-24-2022 - 49,623 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- CarMax Laurel (169 mi away)
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Located in Laurel, MD / 169 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH5KS626574
Stock: 27283729
Certified Pre-Owned: No- Price Drop
- 72,678 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Crossroads Ford of Dunn-Benson (166 mi away)
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Located in Dunn, NC / 166 miles away from Chesapeake, VA
1 Owner, AWD, 3rd row seats: split-bench, 6 Speakers, AM/FM radio: SiriusXM, Apple CarPlay/Android Auto, Automatic temperature control, Exterior Parki...
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: 5TDLZRBHXMS082686
Stock: U649A
Certified Pre-Owned: No
Listed since: 05-10-2025 - 54,775 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Harrisonburg (187 mi away)
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Located in Harrisonburg, VA / 187 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: 5TDLZRBH7MS064212
Stock: 26948363
Certified Pre-Owned: No- New Listing$32,900fair price$152 above market
- 57,927 miles
- 8 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
2021 Toyota Highlander XLE Recent Arrival! CARFAX One-Owner.Highlander XLE, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed Automatic, AWD, Blueprint.Blue...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH3MS538596
Stock: 52E2039A
Certified Pre-Owned: No
Listed since: 05-28-2025 - New Listing
- 44,101 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Charles Boyd Chevrolet GMC (126 mi away)
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Located in Henderson, NC / 126 miles away from Chesapeake, VA
Thank You for shopping at Charles Boyd Chevrolet Cadillac GMC! AWD. White 2021 Toyota Highlander XLE Odometer is 12551 miles below market average! AWD...
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: 5TDGZRBH7MS133501
Stock: 117-25B
Certified Pre-Owned: No
Listed since: 03-27-2025 - 103,073 miles
- 1 accident, 2 owners, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Sir Walter Chevrolet (151 mi away)
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Located in Raleigh, NC / 151 miles away from Chesapeake, VA
**2021 Toyota Highlander LE** For Sale at **Sir Walter Chevrolet** âś… 8-Speed Automatic Transmission âś… 3.5L V6 Engine âś… Toyota Safety Sense 2.5...
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: 5TDZZRAH2MS518636
Stock: 255102B
Certified Pre-Owned: No
Listed since: 04-24-2025- New Listing
- 31,007 miles
- 8 Seats, 20 City / 26 Hwy MPG
- CarMax Virginia Beach (10 mi away)
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Located in Virginia Beach, VA / 10 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH8KS625855
Stock: 27431194
Certified Pre-Owned: No - New Listing
- 88,424 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- CMA's Colonial Chevrolet (78 mi away)
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Located in Chester, VA / 78 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: 5TDZZRFH6KS334225
Stock: C6610C
Certified Pre-Owned: No
Listed since: 05-28-2025 - $22,420great price$3,872 below market
- 112,092 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Bayside Toyota (128 mi away)
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Located in Prince Frederick, MD / 128 miles away from Chesapeake, VA
3 Great Owners, Clean Carfax with 24 Service History records...This 2020 Toyota Highlander XLE AWD has 112,000 miles of stories under its belt and it'...
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: 5TDHZRBH2LS508245
Stock: LS508245A
Certified Pre-Owned: No
Listed since: 02-18-2025 - Not Priced
- 75,800 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Royal Auto Club (169 mi away)
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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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH2MS516196
Stock: SAI2966
Certified Pre-Owned: No - Not Priced
- 88,744 miles
- No accidents, 3 owners, corporate fleet vehicle
- 8 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: 5TDZZRFH5KS304763
Stock: SAI2967
Certified Pre-Owned: No - New Listing
- 73,025 miles
- 1 accident, 3 owners, personal use
- 8 Seats, 20 City / 26 Hwy MPG
- CarMax Virginia Beach (10 mi away)
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Located in Virginia Beach, VA / 10 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDDZRFH0KS724795
Stock: 27080424
Certified Pre-Owned: No - Price Drop$35,500great price$3,910 below market
- 23,477 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Safford Brown Manassas Hyundai (156 mi away)
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Located in Manassas, VA / 156 miles away from Chesapeake, VA
Celestial Silver Metallic 2022 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC Third Row Seating, Blind Spot Monitoring, Navigation System, A...
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: H046813A
Certified Pre-Owned: No
Listed since: 03-24-2025 - Price Drop
- 85,585 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- Reynolds Subaru (147 mi away)
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Located in Orange, VA / 147 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH9KS588489
Stock: 38903P
Certified Pre-Owned: No
Listed since: 05-24-2025 - 88,380 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 26 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: 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 (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH3KS614357
Stock: 34267A
Certified Pre-Owned: No- 54,161 miles
- Frame damage reported, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Kargar Motors (156 mi away)
Close
Located in Manassas, VA / 156 miles away from Chesapeake, VA
BUYING A CAR HAS NEVER BEEN THIS EASY.We specialize in 100% GUARANTEED APPROVAL. BAD CREDIT, NO CREDIT, BANKRUPTCY, REPO, FORECLOSURE...NO PROBLEM. NO...
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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRBH0MS099993
Stock: KMM12668
Certified Pre-Owned: No- New Listing
- 92,182 miles
- 7 Seats, 20 City / 26 Hwy MPG
- Glen Burnie DriveTime (169 mi away)
Close
Located in Glen Burnie, MD / 169 miles away from Chesapeake, VA
Shop at DriveTime: Get started on your personalized car-buying journey today. With no credit impact, you can get approved for your real, personalized ...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH3KS590898
Stock: 1630092693
Certified Pre-Owned: No
Listed since: 05-22-2025 - 156,270 miles
- Frame damage reported, 2 owners, rental vehicle
- 8 Seats, 19 City / 26 Hwy MPG
- Kargar Motors (156 mi away)
Close
Located in Manassas, VA / 156 miles away from Chesapeake, VA
BUYING A CAR HAS NEVER BEEN THIS EASY.We specialize in 100% GUARANTEED APPROVAL. BAD CREDIT, NO CREDIT, BANKRUPTCY, REPO, FORECLOSURE...NO PROBLEM. NO...
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:
22 Combined MPG (19 City/26 Highway)
Listing Information:
VIN: 5TDBZRFH0KS947698
Stock: KMM12617
Certified Pre-Owned: No
Showing 106 - 126 out of 2,076 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 2021 Toyota Highlander in Chesapeake, VA Values
Estimated values
2021 Toyota Highlander XLE 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $25,083 | $26,872 | $28,666 |
| Clean | $24,549 | $26,286 | $28,027 |
| Average | $23,659 | $25,310 | $26,961 |
| Rough | $22,502 | $24,041 | $25,577 |
The average list price of a used 2021 Toyota Highlander in Chesapeake, Virginia is $28,984. The average mileage on a used Toyota Highlander 2021 for sale in Chesapeake, Virginia is 78,234. Based on the average mileage of 78,234 for used 2021 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 2021 in Chesapeake, Virginia to be $23,659.
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