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2,027 listings
- $20,800great price$3,366 below market
- 84,615 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 19 City / 25 Hwy MPG
- Len Stoler Chrysler Dodge Jeep Ram (199 mi away)
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Located in Westminster, MD / 199 miles away from Chesapeake, VA
2016 Toyota Highlander Limited Gold 6-Speed Automatic Electronic with Overdrive FWD 3.5L V6 DOHC Dual VVT-i 24VCARFAX One-Owner. Clean CARFAX. Odomete...
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:
21 Combined MPG (19 City/25 Highway)
Listing Information:
VIN: 5TDYKRFH9GS128856
Stock: BJ1612
Certified Pre-Owned: No
Listed since: 05-29-2025 - New Listing$15,600great price$2,722 below market
- 129,285 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 18 City / 24 Hwy MPG
- Carget Motors (143 mi away)
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Located in Woodbridge, VA / 143 miles away from Chesapeake, VA
This 2016 Toyota Highlander LE is a well-equipped midsize SUV that offers the perfect balance of space, comfort, and reliability for families and acti...
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: 5TDJKRFH9GS314088
Stock: 314088
Certified Pre-Owned: No
Listed since: 07-31-2025 - Price Drop$20,230great price$1,692 below market
- 101,983 miles
- 1 accident, 2 owners, personal use
- 7 Seats, 18 City / 24 Hwy MPG
- Koons Annapolis Toyota (156 mi away)
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Located in Annapolis, MD / 156 miles away from Chesapeake, VA
ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/C, Heated door mirrors, Heated front seats, Heated re...
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: 5TDDKRFHXGS340423
Stock: KAT250044B
Certified Pre-Owned: No
Listed since: 07-04-2025 - Price Drop$18,445good price$1,044 below market
- 120,508 miles
- No accidents, 2 owners, personal use
- 7 Seats, 19 City / 25 Hwy MPG
- Parkway of Wilmington Used Cars (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:
21 Combined MPG (19 City/25 Highway)
Listing Information:
VIN: 5TDYKRFH7GS136194
Stock: 25H0836A
Certified Pre-Owned: No
Listed since: 05-14-2025 - New Listing$20,605good price$1,030 below market
- 83,134 miles
- No accidents, 3 owners, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Koons Annapolis Toyota (156 mi away)
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Located in Annapolis, MD / 156 miles away from Chesapeake, VA
**LEATHER SEATING**, **NAVIGATION**, **POWER MOONROOF**, **AWD**, **POWER LIFTGATE**, **BLUETOOTH**, **BACK-UP CAMERA**, **3RD ROW SEATING**, 3rd row ...
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: 5TDJKRFH7GS251198
Stock: KAT250377AA
Certified Pre-Owned: No
Listed since: 07-31-2025 - New Listing$19,928fair price$530 below market
- 101,599 miles
- No accidents, 2 owners, personal use
- 8 Seats, 18 City / 24 Hwy MPG
- AutoNation Toyota Leesburg (179 mi away)
- Five Star Dealer
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Located in Leesburg, VA / 179 miles away from Chesapeake, VA
Sun/MoonroofLeather SeatsNavigation System3rd Row SeatSpecial ColorCarpet Floor Mats & Carpet Cargo MatKeyless StartRear Spoiler50 State Emiss...
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: 5TDJKRFH5GS240488
Stock: GS240488
Certified Pre-Owned: No
Listed since: 08-02-2025 - Price Drop$23,990fair price$456 above market
- 86,067 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Carvana - Richmond (100 mi away)
- Home delivery*
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Located in Richmond, VA / 100 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: 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: 5TDDKRFH0GS258247
Stock: 2003832190
Certified Pre-Owned: No
Listed since: 06-21-2025 - New Listing$23,891good price$1,664 below market
- 65,648 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- i.g. Burton Buick GMC of Glen Burnie (171 mi away)
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Located in Glen Burnie, MD / 171 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: 5TDDKRFH6GS265333
Stock: G251445A
Certified Pre-Owned: No
Listed since: 07-29-2025 - $17,995fair price$232 above market
- 112,750 miles
- No accidents, 3 owners, personal use
- 8 Seats, 18 City / 24 Hwy MPG
- DMV Auto (138 mi away)
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Located in Stafford, VA / 138 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: 5TDBKRFH7GS247169
Stock: DMV1468
Certified Pre-Owned: No - $19,000good price$844 below market
- 101,700 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 18 City / 24 Hwy MPG
- Ourisman Hyundai of Bowie (154 mi away)
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Located in Bowie, MD / 154 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: 5TDJKRFH0GS243461
Stock: 238872A
Certified Pre-Owned: No
Listed since: 07-23-2025 - Price Drop$19,555fair price$281 below market
- 99,772 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 18 City / 24 Hwy MPG
- Carget Motors (143 mi away)
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Located in Woodbridge, VA / 143 miles away from Chesapeake, VA
This 2016 Toyota Highlander XLE V6 is a well-equipped midsize SUV that offers the perfect balance of space, comfort, and reliability for families and ...
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: 5TDJKRFH7GS289918
Stock: 289918
Certified Pre-Owned: No
Listed since: 05-23-2025 - $23,988fair price$651 below market
- 67,998 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Fitzgerald Gaithersburg Hyundai (176 mi away)
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Located in Gaithersburg, MD / 176 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: 5TDDKRFH9GS313973
Stock: H069664A
Certified Pre-Owned: No
Listed since: 07-15-2025 - New Listing$19,999fair price$92 above market
- 107,812 miles
- No accidents, 3 owners, personal use
- 7 Seats, 18 City / 24 Hwy MPG
- AutoNation Honda Dulles (171 mi away)
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Located in Sterling, VA / 171 miles away from Chesapeake, VA
Sun/MoonroofLeather SeatsNavigation System3rd Row Seat2Nd Row Captain ChairsCarpet Floor Mats & Cargo LinerKeyless StartRear Spoiler50 State E...
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: 5TDJKRFH2GS304146
Stock: GS304146
Certified Pre-Owned: No
Listed since: 07-31-2025 - $18,358fair price$266 above market
- 121,068 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 18 City / 24 Hwy MPG
- AutoNation Toyota Leesburg (179 mi away)
- Five Star Dealer
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Located in Leesburg, VA / 179 miles away from Chesapeake, VA
Sun/MoonroofLeather SeatsNavigation System3rd Row SeatKeyless StartRear Spoiler50 State EmissionsAsh; Leather Seat MaterialPredawn Gray Mica...
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: 5TDJKRFH5GS321135
Stock: GS321135
Certified Pre-Owned: No
Listed since: 07-08-2025 - $19,510fair price$46 below market
- 106,047 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Genesis of Annapolis (156 mi away)
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Located in Annapolis, MD / 156 miles away from Chesapeake, VA
This Highlander was owned by one person only, then traded into Genesis of Annapolis for a new car. It was driven about 12,000 miles each year and very...
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: 5TDJKRFH5GS326108
Stock: G599B
Certified Pre-Owned: No
Listed since: 07-26-2025 - $21,700good price$2,175 below market
- 87,954 miles
- No accidents, 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: 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: 5TDJKRFH3GS231613
Stock: P25134
Certified Pre-Owned: No - $15,450fair price$510 above market
- 168,853 miles
- 1 accident, 2 owners, personal use only
- 8 Seats, 18 City / 24 Hwy MPG
- Prime Motors (154 mi away)
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Located in Arlington, VA / 154 miles away from Chesapeake, VA
ASK ABOUT OUR MD INSPECTION PROGRAMVideo walk-around, virtual test drives, E-purchase, shipping , financing and we accept all trades. Call/Text 703-67...
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: 5TDJKRFH3GS294887
Stock: 294887
Certified Pre-Owned: No - Price Drop
- Not provided
- No accidents, 2 owners, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Fitzgerald Toyota Gaithersburg (176 mi away)
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Located in Gaithersburg, MD / 176 miles away from Chesapeake, VA
Introducing the 2016 Toyota Highlander! It just arrived on our lot this past week! Toyota prioritized practicality, efficiency, and style by including...
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: 5TDDKRFH2GS264308
Stock: EB61729B
Certified Pre-Owned: No
Listed since: 06-28-2025 - 131,002 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 18 City / 24 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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDJKRFH7GS307205
Stock: 2GT94428A
Certified Pre-Owned: No
Listed since: 03-29-2025- 121,951 miles
- No accidents, 4 owners, personal use
- 8 Seats, 19 City / 25 Hwy MPG
- NextGear Motors (147 mi away)
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Located in Raleigh, NC / 147 miles away from Chesapeake, VA
Visit NextGear Motors online at WWW.NEXTGEARMOTORS.COM to see more pictures of this vehicle and a free Auto-check report. Easy Financing available! Ap...
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:
21 Combined MPG (19 City/25 Highway)
Listing Information:
VIN: 5TDZKRFH3GS177071
Stock: 16075A049
Certified Pre-Owned: No
Listed since: 06-04-2025- 55,093 miles
- No accidents, 2 owners, corporate fleet vehicle
- 7 Seats, 18 City / 24 Hwy MPG
- Paragon Automotive (9 mi away)
Close
Located in Virginia Beach, VA / 9 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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDDKRFH4GS332933
Stock: 1771
Certified Pre-Owned: No
Showing 1 - 21 out of 2,027 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Lexus in Toyota Clothing (with sportier handling)
Thomas from Westchester Cty, NY, 07/31/2016
2016 Toyota Highlander Limited Platinum 4dr SUV AWD (3.5L 6cyl 6A)
Pros: Rock solid look, feel and handling. Calm-instilling, smooth, quiet ride. Sensible, simple, intuitive controls. Luxury car look, feel and performance at a below-luxury price and with lower cost regular fuel! Safe, effective all wheel drive and active safety systems. Cons: Smaller than ideal cargo space. Very tight third row -- for young children or emergency, short trips only. … Lane departure sensor is a little too sensitive. Navigation slightly less intuitive and useful than other controls and systems in this vehicle and than navigation systems in other vehicles and after-market or cell phone based systems. Overall: An easy 5 out of 5 stars! This vehicle should be on anyone's list for a mid-size SUV with a third row seat. There is a wide variety of option levels with corresponding wide variety in cost so it can fit into many budgets whether you choose the top end to compete with luxury vehicles as we ultimately did or a "lower" level which can compete with almost any but the smallest, compact SUVs on price (which we also considered).
Used 2016 Toyota Highlander in Chesapeake, VA Values
Estimated values
2016 Toyota Highlander Limited 4dr SUV (3.5L 6cyl 6A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $17,067 | $20,277 | $22,552 |
| Clean | $16,331 | $19,375 | $21,518 |
| Average | $15,105 | $17,872 | $19,795 |
| Rough | $13,512 | $15,918 | $17,555 |
The average list price of a used 2016 Toyota Highlander in Chesapeake, Virginia is $20,128. The average mileage on a used Toyota Highlander 2016 for sale in Chesapeake, Virginia is 97,849. Based on the average mileage of 97,849 for used 2016 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 2016 in Chesapeake, Virginia to be $15,105.
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