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1,952 listings
- New Listing
- 115,301 miles
- No accidents, 3 owners, rental vehicle
- 7 Seats, 18 City / 24 Hwy MPG
- Haley Toyota of Richmond (91 mi away)
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Located in Midlothian, VA / 91 miles away from Chesapeake, VA
*Vehicle pricing excludes tax, title, tags, $799 processing fee, and $319 fee for theft protection etch.*
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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: JTEDS41A582020816
Stock: XN316
Certified Pre-Owned: No
Listed since: 05-27-2025 - New Listing$14,816fair price$264 above market
- 122,740 miles
- 2 accidents, 1 owner, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Stevenson-Hendrick Toyota Jacksonville (149 mi away)
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Located in Jacksonville, NC / 149 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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDYK3EHXCS075271
Stock: DS21483A
Certified Pre-Owned: No
Listed since: 03-03-2025 - 151,126 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 17 City / 22 Hwy MPG
- City to City Auto Sales (88 mi away)
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Located in Richmond, VA / 88 miles away from Chesapeake, VA
Toyota toyota touota yes just arrived clean suv all service records ready to go
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:
19 Combined MPG (17 City/22 Highway)
Listing Information:
VIN: 5TDDK3EH1CS112786
Stock: 112786
Certified Pre-Owned: No
Listed since: 04-05-2025- New Listing
- 102,113 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 18 City / 24 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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDDKRFH6ES028726
Stock: 27232645
Certified Pre-Owned: No - 166,788 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Blankenship Auto (75 mi away)
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Located in Accomac, VA / 75 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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDZK3EH9AS018450
Stock: 14162
Certified Pre-Owned: No
Listed since: 11-19-2024- New Listing
- 64,116 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 18 City / 24 Hwy MPG
- CarMax Charlottesville (151 mi away)
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Located in Charlottesville, VA / 151 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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDBKRFH9ES016822
Stock: 26884084
Certified Pre-Owned: No - 136,998 miles
- No accidents, 3 owners, corporate fleet vehicle
- 7 Seats, 17 City / 22 Hwy MPG
- Auto World of Chester (78 mi away)
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Located in Chester, VA / 78 miles away from Chesapeake, VA
AutoWorld of Chester2400 West Hundred RdChester, Va 23831[email protected](8**)7**-4***
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:
19 Combined MPG (17 City/22 Highway)
Listing Information:
VIN: 5TDDK3EH6CS126750
Stock: 126750
Certified Pre-Owned: No
Listed since: 04-28-2025- 95,649 miles
- 1 accident, 2 owners, personal use
- 7 Seats, 17 City / 22 Hwy MPG
- ACT1AUTO.COM (11 mi away)
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Located in Norfolk, VA / 11 miles away from Chesapeake, VA
???? 2012 Toyota Highlander Sport Utility - Adventure Awaits at Act1Auto.com! ?????? Elevate Your Drive with Style and Reliability ??Introducing the 2...
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: Yes
Lemon Status: No
Free History Report: No
Features and Specs:
19 Combined MPG (17 City/22 Highway)
Listing Information:
VIN: 5TDBK3EH3CS131847
Stock: B131847
Certified Pre-Owned: No- New Listing
- 254,007 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- East Carolina Auto Group (115 mi away)
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Located in Wilson, NC / 115 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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDYK3EH3CS056299
Stock: 056299
Certified Pre-Owned: No
Listed since: 03-28-2025 - 166,318 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Nationwide Motors (130 mi away)
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Located in Fredericksburg, VA / 130 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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDZK3EH5CS079488
Stock: 079488
Certified Pre-Owned: No
Listed since: 05-17-2025- New ListingNot Priced
- 149,018 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- RVA Automotive Group (81 mi away)
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Located in Richmond, VA / 81 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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDZK3EH7AS004904
Stock: 004904
Certified Pre-Owned: No
Listed since: 05-22-2025 - 116,769 miles
- 1 accident, 3 owners, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Grace Auto (94 mi away)
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Located in Richmond, VA / 94 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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDYK3EH9CS075780
Stock: P24759
Certified Pre-Owned: No- 112,619 miles
- 1 accident, 2 owners, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Grace Auto (94 mi away)
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Located in Richmond, VA / 94 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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDYK3EH4CS059387
Stock: P25341
Certified Pre-Owned: No- New Listing
- 56,939 miles
- 2 accidents, 2 owners, government vehicle
- 7 Seats, 19 City / 25 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: 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:
21 Combined MPG (19 City/25 Highway)
Listing Information:
VIN: 5TDYKRFHXES025443
Stock: 27080089
Certified Pre-Owned: No - 114,911 miles
- Frame damage reported, 3 owners, corporate fleet vehicle
- 7 Seats, 17 City / 22 Hwy MPG
- Eagle Automotives (154 mi away)
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Located in Arlington, VA / 154 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:
19 Combined MPG (17 City/22 Highway)
Listing Information:
VIN: 5TDDK3EH8CS137197
Stock: 6849
Certified Pre-Owned: No- New Listing
- 106,929 miles
- 7 Seats, 18 City / 24 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Tampa, FL / 707 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 Unavailable.
Features and Specs:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDYK3EH3CS074074
Stock: 2003764692
Certified Pre-Owned: No
Listed since: 05-21-2025 - New Listing$7,998great price$2,142 below market
- 196,196 miles
- No accidents, 3 owners, personal use
- 7 Seats, 18 City / 24 Hwy MPG
- Liberty Motors (6 mi away)
Close
Located in Chesapeake, VA / 6 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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDZK3EH8DS093998
Stock: 093998
Certified Pre-Owned: No
Listed since: 05-27-2025 - $6,599great price$1,966 below market
- 224,102 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Liberty Motors (6 mi away)
Close
Located in Chesapeake, VA / 6 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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDZK3EH3DS140368
Stock: 140368
Certified Pre-Owned: No
Listed since: 04-15-2025 - $5,998great price$1,915 below market
- 174,593 miles
- No accidents, 3 owners, personal use only
- 5 Seats, 20 City / 27 Hwy MPG
- Liberty Motors (6 mi away)
Close
Located in Chesapeake, VA / 6 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:
22 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: JTEDA41A292000706
Stock: 000706
Certified Pre-Owned: No
Listed since: 05-21-2025 - 158,970 miles
- No accidents, 3 owners, personal use only
- 7 Seats, 17 City / 23 Hwy MPG
- Urban Exchange Auto (87 mi away)
Close
Located in Richmond, VA / 87 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:
19 Combined MPG (17 City/23 Highway)
Listing Information:
VIN: 5TDDK3EH9AS037915
Stock: 037915
Certified Pre-Owned: No
Listed since: 05-15-2025- $6,999great price$1,788 below market
- 177,000 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Town Auto (5 mi away)
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Located in Chesapeake, VA / 5 miles away from Chesapeake, VA
2009 Toyota Highlander 177K Miles Limited 4dr SUV 3.5L V6 *1 Owner, No Accidents* TOWN AUTO https://www.townautova.com/ We open monday through saturda...
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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: JTEDS42A792086199
Stock: 086199
Certified Pre-Owned: No
Listed since: 05-13-2025
Showing 127 - 147 out of 1,952 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
The nicest Toyota yet.
bajarainny, 03/04/2011
2011 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 5A)
Having traded in our '04 Camry, this Highlander is our 5th Toyota.
The styling for 2011 is much improved over the '08-'10 version and can actually be called a "looker".
After 2 weeks of owning it, I've had two strangers stop me and ask about it.
Having a great time with the navigation system and bluetooth phone set up and the entertainment system seems to work well (kids and … grandchild).
At first, I was a little daunted by all the electronics and technology, but I'm one of those guys who does read the manuals (no fewer than 6 came with the car) and learning how to use everything is fun.
The best part is, it's a Toyota and everything works as it was designed to.
Used 2008 Toyota Highlander in Chesapeake, VA Values
Estimated values
2008 Toyota Highlander 4dr SUV (3.5L 6cyl 5A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $4,751 | $7,927 | $9,789 |
| Clean | $4,452 | $7,374 | $9,042 |
| Average | $3,954 | $6,453 | $7,797 |
| Rough | $3,307 | $5,255 | $6,179 |
The average list price of a used 2008 Toyota Highlander in Chesapeake, Virginia is $14,917. The average mileage on a used Toyota Highlander 2008 for sale in Chesapeake, Virginia is 141,105. Based on the average mileage of 141,105 for used 2008 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 2008 in Chesapeake, Virginia to be $3,954.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.