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2,487 listings
- Price Drop$30,398good price$2,336 below market
- 61,777 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Enterprise Car Sales South Miami (94 mi away)
- Home delivery*
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Located in Miami, FL / 94 miles away from Naples, FL
Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...
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: 5TDGZRAH5MS051137
Stock: 7VGLJY
Certified Pre-Owned: No
Listed since: 03-06-2025 - $31,281good price$2,221 below market
- 37,457 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Arlington Toyota Jacksonville (286 mi away)
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Located in Jacksonville, FL / 286 miles away from Naples, FL
Odometer is 5729 miles below market average!CERTIFIED BY CARFAX - ONE OWNER, REMAINDER OF FACTORY WARRANTY STILL APPLIES, BACKUP CAMERA, BLUETOOTH HAN...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH4PS027778
Stock: 58059A
Certified Pre-Owned: No
Listed since: 04-07-2025 - $26,800good price$1,981 below market
- 80,907 miles
- No accidents, 2 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- Napleton's Volkswagen Of Sanford (179 mi away)
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Located in Sanford, FL / 179 miles away from Naples, FL
2021 Toyota Highlander XLE Certified by Carfax - No Accidents, Backup Camera, Bluetooth Hands Free Calling, MP3/USB/IPOD Compatible, Alloy Wheels, Hig...
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: 5TDGZRAH1MS521938
Stock: POE0723A
Certified Pre-Owned: No
Listed since: 04-22-2025 - $43,998good price$1,191 below market
- 10,694 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to FL*
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Located in Spokane Valley, WA / 2,428 miles away from Naples, FL
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH1PS511020
Stock: 26757757
Certified Pre-Owned: No - $41,998good price$1,731 below market
- 19,708 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from LA to FL*
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Located in Kenner, LA / 583 miles away from Naples, FL
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH3PS029862
Stock: 26951338
Certified Pre-Owned: No - $27,147good price$1,876 below market
- 80,030 miles
- No accidents, 2 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- Driveway (137 mi away)
- Home delivery*
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Located in Tampa, FL / 137 miles away from Naples, FL
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Remote Start,Satell...
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: 5TDGZRAH2MS516733
Stock: MS516733T
Certified Pre-Owned: No - $40,881fair price$490 below market
- 13,474 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Arlington Toyota Jacksonville (286 mi away)
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Located in Jacksonville, FL / 286 miles away from Naples, FL
Odometer is 25046 miles below market average!REMAINDER OF FACTORY WARRANTY STILL APPLIES, BACKUP CAMERA, BLUETOOTH HANDS FREE, BLIND SPOT MONITORING, ...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH6PS003871
Stock: AX20408
Certified Pre-Owned: Yes
Listed since: 04-05-2025 - $35,999fair price$176 below market
- 53,853 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
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Located in Raleigh, NC / 691 miles away from Naples, FL
Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH1PS003695
Stock: 7VDN1H
Certified Pre-Owned: No
Listed since: 04-16-2025 - $27,788good price$1,310 below market
- 42,898 miles
- No accidents, 2 owners, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Bomnin Chevrolet West Kendall (91 mi away)
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Located in Miami, FL / 91 miles away from Naples, FL
Priced below KBB Fair Purchase Price! Odometer is 12057 miles below market average! 2021 Toyota Highlander L in Blizzard Pearl vehicle highlights incl...
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: 5TDCZRBH4MS062630
Stock: L149379A
Certified Pre-Owned: No
Listed since: 03-21-2025 - $42,977good price$2,030 below market
- 17,321 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Troy, MI / 1,135 miles away from Naples, FL
Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Remote St...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH4PS525977
Stock: PS525977C
Certified Pre-Owned: No - $32,538good price$1,770 below market
- 40,109 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Toyota of Tampa Bay (138 mi away)
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Located in Tampa, FL / 138 miles away from Naples, FL
NATIONWIDE LIFETIME WARRANTY!! FREE HOME DELIVERY UP TO 75 MILES!! Magnetic Gray Metallic Highlander L FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged ...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH9PS522638
Stock: 522638
Certified Pre-Owned: Yes
Listed since: 04-19-2025 - $35,191great price
- 27,216 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Houston, TX / 885 miles away from Naples, FL
3rd Row Seat,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satellite Radio,Turbo/Supercharged,WiFi Hotspot,Pow...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH9PS009860
Stock: PS009860A
Certified Pre-Owned: No - New Listing$40,593good price$834 below market
- 18,993 miles
- No accidents, 1 owner, personal use
- 7 Seats, 22 City / 29 Hwy MPG
- Courtesy Hyundai Tampa (134 mi away)
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Located in Tampa, FL / 134 miles away from Naples, FL
RECALL NOTICE: Some vehicles offered for sale may be subject to unrepaired manufacturer safety recalls. To determine the recall status of a vehicle, v...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH3PS026668
Stock: CTH251092A
Certified Pre-Owned: No
Listed since: 04-26-2025 - $42,998fair price$653 above market
- 7,525 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to FL*
Close
Located in Vancouver, WA / 2,613 miles away from Naples, FL
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH0PS045497
Stock: 27075438
Certified Pre-Owned: No - Price Drop$35,998fair price$1,395 below market
- 7,970 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to FL*
Close
Located in Spokane Valley, WA / 2,428 miles away from Naples, FL
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH9PS019173
Stock: 26694186
Certified Pre-Owned: No - $26,991good price$1,922 below market
- 91,316 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Seminole Chevrolet (182 mi away)
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Located in Sanford, FL / 182 miles away from Naples, FL
ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/C, Heated door mirrors, Illuminated entry, Low tire p...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH4PS043382
Stock: SR240678A
Certified Pre-Owned: No
Listed since: 04-16-2025 - $31,998fair price$1,432 below market
- 37,670 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to FL*
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Located in Fairfield, CA / 2,480 miles away from Naples, FL
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH8PS517138
Stock: 27382553
Certified Pre-Owned: No - $30,777good price$1,493 below market
- 49,269 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Ed Morse Honda (108 mi away)
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Located in Riviera Beach, FL / 108 miles away from Naples, FL
Priced below KBB Fair Purchase Price! 2021 Toyota Highlander XLE White Carfax Accident Free, Leather, Local Trade, AndroidTM Auto/Apple Carplay, Colli...
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: 5TDGZRAH8MS534007
Stock: SB060007A
Certified Pre-Owned: No
Listed since: 05-01-2025 - $46,998fair price$1,553 below market
- 16,142 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CO to FL*
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Located in Littleton, CO / 1,630 miles away from Naples, FL
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH7PS516643
Stock: 26604206
Certified Pre-Owned: No - $34,998fair price$118 above market
- 16,226 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to FL*
Close
Located in Lynnwood, WA / 2,648 miles away from Naples, FL
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH9PS518833
Stock: 27194328
Certified Pre-Owned: No - $39,999good price$2,461 below market
- 62,041 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- I-95 Toyota of Brunswick (350 mi away)
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Located in Brunswick, GA / 350 miles away from Naples, FL
As part of the I-95 Toyota family, you'll benefit from courtesy lifetime oil changes and car washes, ensuring your Toyota stays in top condition for ...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAHXPS022391
Stock: EP5971
Certified Pre-Owned: No
Listed since: 01-21-2025
Showing 316 - 336 out of 2,487 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Love the vehicle, Infotainment is unusable
bbells, 04/16/2023
2023 Toyota Highlander LE 4dr SUV (2.4L 4cyl Turbo 8A)
Love the gas mileage, 30+mpg in eco mode. Towing capacity. Comfort. Nice vehicle except the "drive connect" app advertisement makes the entertainment system unusable. It will lock up the system for 1 to 10 minutes so no music, no google maps, no phone, nothing, until it decides to clear itself. Toyota says you can pay $200 a year to remove the advertisement by subscribing to drive … connect. This makes it the definition of ransomware. But there is nothing in the app I need or want. Neither ToyotaUSA, their tech department, or the dealer can fix it. I will either be selling the vehicle or replacing the entertainment system when the free trial of drive connect ends in a couple months. For those of us who use their phone for maps, texts or communication the system makes the vehicle unusable. Update: Can't put in different infotainment system, it is integrated into the vehicle. Toyota gave me a free trial of drive connect. Unfortunately anytime i am in an area without internet the display is locked up asking for a password. Can't enter a password until i get into an internet area, then go s back to asking for a password when i leave it. Worthless and unusable. Toyota wouldn't fix it. After 7 months they bought it back from me. Last Toyota.
Used 2021 Toyota Highlander in Naples, FL Values
Estimated values
2021 Toyota Highlander XLE 4dr SUV (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $29,543 | $31,802 | $34,067 |
| Clean | $28,914 | $31,109 | $33,307 |
| Average | $27,866 | $29,954 | $32,041 |
| Rough | $26,503 | $28,452 | $30,396 |
The average list price of a used 2021 Toyota Highlander in Naples, Florida is $35,636. The average mileage on a used Toyota Highlander 2021 for sale in Naples, Florida is 37,743. Based on the average mileage of 37,743 for used 2021 Toyota Highlander for sale in Naples, FL 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 Naples, Florida to be $27,866.
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