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2,028 listings
- $27,000great price$4,884 below market
- 84,605 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Beyer Kia Falls Church (153 mi away)
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Located in Falls Church, VA / 153 miles away from Chesapeake, VA
AWD.Red 2021 Toyota Highlander LimitedAWD 8-Speed Automatic 3.5L V6 DOHC Recent Arrival! 20/27 City/Highway MPG
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: 5TDDZRBH1MS526607
Stock: E10748VK
Certified Pre-Owned: No
Listed since: 05-29-2025 - Price Drop$28,400great price$3,102 below market
- 108,320 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Marine Chevrolet (153 mi away)
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Located in Jacksonville, NC / 153 miles away from Chesapeake, VA
This Highlander Platinum is nicely equipped with Highlander Platinum, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed Automatic, AWD, Ruby Flare Pearl, Harves...
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: 5TDFZRBH7MS074235
Stock: P1456
Certified Pre-Owned: No
Listed since: 07-16-2025 - $27,499great price$2,137 below market
- 98,253 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- AutoNation Honda Dulles (166 mi away)
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Located in Sterling, VA / 166 miles away from Chesapeake, VA
The following items have been reconditioned on this vehicle: new brakes! Sun/Moonroof3rd Row SeatLane Keeping AssistKeyless StartRear Spoiler2...
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: 5TDGZRBH6MS096196
Stock: MS096196
Certified Pre-Owned: No
Listed since: 07-16-2025 - $28,995great price$2,701 below market
- 63,236 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Kargar Motors (150 mi away)
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Located in Manassas, VA / 150 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: 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: 5TDLZRAH3MS067884
Stock: KMM13973
Certified Pre-Owned: No - $32,500good price$1,700 below market
- 54,083 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Koons Westminster Toyota (195 mi away)
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Located in Westminster, MD / 195 miles away from Chesapeake, VA
2021 Toyota Highlander XLE **** TOYOTA CERTIFIED **** Balance of Factory Warranty **** Apple Carplay/Android Auto, Bluetooth, Hands-Free, Sunroof, Key...
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: 5TDGZRBH7MS144935
Stock: KTWP220853A
Certified Pre-Owned: Yes
Listed since: 07-24-2025 - $35,700good price$1,097 below market
- 36,416 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Koons Westminster Toyota (195 mi away)
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Located in Westminster, MD / 195 miles away from Chesapeake, VA
2021 Toyota Highlander XSE, Apple Carplay/Android Auto, Bluetooth, Hands-Free, Sunroof, Keyless Entry, Mixed Media Seats, Heated Seats, Toyota Safety ...
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: 5TDJZRBH2MS065209
Stock: KTWS210034
Certified Pre-Owned: No
Listed since: 07-30-2025 - New Listing$30,900fair price$122 below market
- 67,834 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- West Broad Hyundai (91 mi away)
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Located in Richmond, VA / 91 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. 20/27 City/Highway MPG ***ACCIDENT FREE CARFAX***, ***ONE OWNER***, 18' Machined Alloy Wheels, 3.003 Axle Ratio, 3rd r...
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: 5TDGZRBH1MS111848
Stock: 257328A
Certified Pre-Owned: No
Listed since: 07-23-2025 - $32,300good price$1,829 below market
- 72,802 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Len Stoler Lexus (185 mi away)
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Located in Owings Mills, MD / 185 miles away from Chesapeake, VA
Moon Dust 2021 Toyota Highlander Limited AWD 8-Speed Automatic 3.5L V6 DOHCAWD, 12.3" Screen & Birds Eye View, Panoramic View Monitor, Radio: Premium ...
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: 5TDDZRBH4MS133541
Stock: L2661A
Certified Pre-Owned: No
Listed since: 07-19-2025 - $28,995great price$1,922 below market
- 77,712 miles
- 1 accident, 1 owner, corporate fleet vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Imperial Highline (152 mi away)
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Located in Manassas, VA / 152 miles away from Chesapeake, VA
KEY FEATURES AND OPTIONS Comes equipped with: Cockpit Red, Leather Seat Trim. This Toyota Highlander also includes Power Driver's Seat, Clock, Climate...
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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDLZRAH9MS051737
Stock: 51737
Certified Pre-Owned: No
Listed since: 04-29-2025 - $29,590fair price$313 below market
- 75,800 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana - Richmond (95 mi away)
- Home delivery*
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Located in Richmond, VA / 95 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: 5TDGZRBH3MS056951
Stock: 2003940302
Certified Pre-Owned: No
Listed since: 08-01-2025 - $30,777good price$1,640 below market
- 32,532 miles
- No accidents, 2 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- Lease Return Center (134 mi away)
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Located in Triangle, VA / 134 miles away from Chesapeake, VA
--GORGEOUS PEARL WHITE ON BLACK LEATHER--SUPER CLEAN AND CARFAX CERTIFIED!!!--ONLY 32K MILES!!!--FULLY LOADED WITH EVERY OPTIONS!!!--LOOKS AND RUNS AM...
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: 5TDGZRAH4MS520816
Stock: 20816
Certified Pre-Owned: No - $34,498fair price$1,030 below market
- 25,158 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Dulles Kia (174 mi away)
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Located in Leesburg, VA / 174 miles away from Chesapeake, VA
2021 Toyota Highlander XLE Blueprint 3.5L V6 DOHC AWDAWD, 18" Machined Alloy Wheels, 2nd Row Bench Seat, 3rd row seats: split-bench, Apple CarPlay/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: 5TDHZRBH3MS527761
Stock: 24918A
Certified Pre-Owned: No
Listed since: 08-27-2025 - $32,995fair price$563 below market
- 27,855 miles
- No accidents, 2 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- M and B Auto Group (151 mi away)
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Located in Bealeton, VA / 151 miles away from Chesapeake, VA
?? DISCLAIMER ?? Easy Financing available – subject to credit approval. ? 90-Day Limited Warranty included – restrictions apply, ask for details. ?? 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH5MS067967
Stock: mda5342
Certified Pre-Owned: No - $30,995good price$1,142 below market
- 78,352 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Global Auto Outlet (145 mi away)
Close
Located in Temple Hills, MD / 145 miles away from Chesapeake, VA
The 2021 Toyota Highlander XSE with 78,352 miles is a standout midsize SUV that combines sporty appeal with everyday practicality. This XSE trim adds ...
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: 5TDLZRBH8MS102885
Stock: 102885
Certified Pre-Owned: No
Listed since: 05-29-2025 - $31,000fair price$201 above market
- 66,511 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Karen Radley Volkswagen (138 mi away)
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Located in Woodbridge, VA / 138 miles away from Chesapeake, VA
2021 Toyota Highlander XLE 3.5L V6 DOHC 8-Speed Automatic AWD Pearl CARFAX One-Owner.Highlander XLE, 4D Sport Utility, AWD, Pearl, 18" Machined Alloy ...
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: 5TDGZRBH9MS533205
Stock: D8078A
Certified Pre-Owned: No
Listed since: 07-31-2025 - $32,000good price$1,438 below market
- 76,031 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Honda of Owings Mills (182 mi away)
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Located in Owings Mills, MD / 182 miles away from Chesapeake, VA
Magnetic Gray Metallic exterior and GRAPHITE interior. Heated Leather Seats, Third Row Seat, Nav System, Moonroof, BODY SIDE MOLDINGS (TMS), Chrome Wh...
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: 5TDDZRBH6MS075240
Stock: MS075240
Certified Pre-Owned: No
Listed since: 08-11-2025 - Price Drop$28,650fair price$546 below market
- 70,256 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Waldorf Toyota (132 mi away)
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Located in Waldorf, MD / 132 miles away from Chesapeake, VA
**Recent Arrival!** **XLE!** **Price Leader!** **Special Color!** **Premium Alloy Wheels!** **Power Liftgate!** **Toyota Reliability!** **Priced to 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH0MS058688
Stock: 00081635
Certified Pre-Owned: No
Listed since: 08-16-2025 - New Listing$28,950fair price$237 below market
- 47,004 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Westgate Chrysler Jeep Dodge Ram (152 mi away)
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Located in Raleigh, NC / 152 miles away from Chesapeake, VA
With seating for up to eight, advanced safety features, and Toyotas trusted reliability, the Highlander L is built to keep your crew comfortable where...
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: 5TDCZRBH6MS555256
Stock: 32181P
Certified Pre-Owned: No
Listed since: 05-07-2025 - $32,750good price$936 below market
- 65,728 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Global Auto Outlet (145 mi away)
Close
Located in Temple Hills, MD / 145 miles away from Chesapeake, VA
The 2021 Toyota Highlander XSE with 65,728 miles is a dynamic midsize SUV that blends sporty styling with family-friendly versatility. Featuring a bol...
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: 5TDJZRBH3MS142587
Stock: 142587
Certified Pre-Owned: No
Listed since: 05-29-2025 - $38,000fair price$611 below market
- 57,000 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Toyota of Bowie (151 mi away)
Close
Located in Bowie, MD / 151 miles away from Chesapeake, VA
Ruby Flare Pearl exterior and Black interior. Heated Leather Seats, Third Row Seat, Navigation, Moonroof, PLATINUM PACKAGE, Aluminum Wheels, Captains ...
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: 5TDFZRBH2MS099690
Stock: MS099690
Certified Pre-Owned: Yes
Listed since: 08-27-2025 - $34,000good price$1,676 below market
- 25,677 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Hanna Imports (148 mi away)
Close
Located in Raleigh, NC / 148 miles away from Chesapeake, VA
CARFAX One-Owner. Leather Seats, Bluetooth, *Multi Point Inspection*, Highlander XLE, AWD, Apple CarPlay/Android Auto, Exterior Parking Camera Rear, P...
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: 5TDGZRBH1MS094422
Stock: 3021587
Certified Pre-Owned: No
Listed since: 04-27-2025
Showing 1 - 21 out of 2,028 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Couldn’t be happier!
S Curry, 01/02/2021
2021 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 8A)
I’ve been eyeing the Highlander since they redesigned it in 2020. I opted for the Limited AWD trim with the optional 12 inch screen and bench seats. I am completely blown away on how amazing it is to drive the Highlander. Visibility is great but with the bigger screen you also get birds eye view which will definitely help assess your surroundings. The safety features are awesome and the … little things like intuitive climate control are nice. I was worried about access into the third row and comfort but my 12 year old is happy with it. The middle row does slide up giving more leg room to the third row. I came from a minivan so I am used to a lot of cargo room and low entry. If you will be using the third row consistently I recommend getting the cross bars and on roof cargo storage to maximize what you can carry, and if you are transporting smaller kids/adults the step up may be just slightly too high for them but running boards can be installed.
Used 2021 Toyota Highlander in Chesapeake, VA Values
Estimated values
2021 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $31,314 | $33,535 | $35,762 |
| Clean | $30,647 | $32,804 | $34,965 |
| Average | $29,536 | $31,586 | $33,636 |
| Rough | $28,092 | $30,003 | $31,908 |
The average list price of a used 2021 Toyota Highlander in Chesapeake, Virginia is $31,262. The average mileage on a used Toyota Highlander 2021 for sale in Chesapeake, Virginia is 62,436. Based on the average mileage of 62,436 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 $29,536.
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