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2,523 listings
- New Listing$32,491good price$1,200 below market
- 36,660 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Napleton Northlake Kia (109 mi away)
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Located in Palm Beach Gardens, FL / 109 miles away from Naples, FL
2021 Toyota Highlander XLE Beautifully finished in Blizzard Pearl with Black Leather interior. 3.5L V6 DOHC 4D Sport Utility FWD 8-Speed Automatic **O...
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: 5TDGZRAH4MS518855
Stock: KTSI518855
Certified Pre-Owned: No
Listed since: 05-17-2025 - $32,958fair price$1,085 below market
- 44,088 miles
- No accidents, 1 owner, rental vehicle
- 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!! ANDROID AUTO, APPLE CARPLAY, BACK UP CAMERA, HEATED SEATING, LEATHER SEATING, MOON ...
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: 5TDKDRAH3PS009241
Stock: O009241
Certified Pre-Owned: Yes
Listed since: 03-14-2025 - $39,377fair price$337 below market
- 16,968 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Panama City Toyota (366 mi away)
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Located in Panama City, FL / 366 miles away from Naples, FL
CARFAX One-Owner. Certified. Ruby Flare Pearl 2023 Toyota Highlander XLE 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed Automatic FWD To...
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: 5TDKDRAH2PS502540
Stock: 294173A
Certified Pre-Owned: Yes
Listed since: 03-29-2025 - $32,569good price$1,030 below market
- 43,437 miles
- No accidents, 1 owner, rental vehicle
- 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!! ANDROID AUTO, APPLE CARPLAY, BACK UP CAMERA, POWER DRIVER SEAT, POWER SEATING, Allo...
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: 5TDKDRAH9PS509047
Stock: O509047
Certified Pre-Owned: Yes
Listed since: 04-17-2025 - $42,905fair price$310 below market
- 8,193 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Toyota of Hollywood (94 mi away)
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Located in Hollywood, FL / 94 miles away from Naples, FL
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: 5TDKDRAH0PS518798
Stock: R5187980
Certified Pre-Owned: Yes
Listed since: 09-21-2024 - Price Drop$36,778fair price$614 below market
- 43,977 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Volkswagen of Fort Myers (27 mi away)
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Located in Fort Myers, FL / 27 miles away from Naples, FL
ALG Residual Value Awards, Residual Value Awards. Only 43,977 Miles! Boasts 27 Highway MPG and 20 City MPG! This Toyota Highlander boasts a Regular Un...
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: 5TDDZRBH3MS082372
Stock: TMS082372
Certified Pre-Owned: No
Listed since: 04-26-2025 - Price Drop$33,990fair price$799 below market
- 35,618 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Chesapeake, VA / 799 miles away from Naples, FL
CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assi...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH6PS514219
Stock: PS514219P
Certified Pre-Owned: No - Price Drop$31,299good price$1,164 below market
- 59,635 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Mazda of Palm Beach (110 mi away)
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Located in North Palm Beach, FL / 110 miles away from Naples, FL
The Mazda store that gives you MORE!!, Value pricing made us #1, customer service keeps us there!!!, Family Owned and operated since 1975, Discover th...
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: 5TDGZRBH8MS551792
Stock: E14822MC
Certified Pre-Owned: No
Listed since: 03-20-2025 - Price Drop$31,515good price$2,030 below market
- 45,554 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Hoover Chrysler Dodge Jeep Ram of Summerville (482 mi away)
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Located in Summerville, SC / 482 miles away from Naples, FL
2023 Toyota Highlander LE w/Apple CarPlay & Android Auto FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp Wind Chill Pearl P...
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: 5TDKDRAH7PS504946
Stock: 26225A
Certified Pre-Owned: No
Listed since: 04-06-2025 - $39,445good price$1,431 below market
- 20,732 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Toyota of Hollywood (94 mi away)
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Located in Hollywood, FL / 94 miles away from Naples, FL
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: 5TDKDRAH9PS522199
Stock: T2049100
Certified Pre-Owned: Yes
Listed since: 03-15-2025 - $34,855fair price$307 below market
- 35,723 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- AutoNation Toyota Winter Park (169 mi away)
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Located in Winter Park, FL / 169 miles away from Naples, FL
The following items have been reconditioned on this vehicle: new brakes and all new tires! Sun/Moonroof3rd Row SeatLane Keeping AssistKeyless 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/29 Highway)
Listing Information:
VIN: 5TDGZRAH9MS052114
Stock: MS052114
Certified Pre-Owned: Yes
Listed since: 04-21-2025 - New Listing$31,100good price$1,255 below market
- 46,028 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Firkins Chrysler Dodge Jeep Ram (104 mi away)
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Located in Bradenton, FL / 104 miles away from Naples, FL
CARFAX One-Owner. Clean CARFAX. Wind Chill Pearl 2023 Toyota Highlander LE FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp ...
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: 5TDKDRAH1PS503808
Stock: M6380P
Certified Pre-Owned: No
Listed since: 04-11-2025 - $35,350fair price$715 below market
- 21,000 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Summerville Ford (477 mi away)
Close
Located in Summerville, SC / 477 miles away from Naples, FL
2023 Midnight Black Metallic Toyota Highlander L 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed Automatic FWD Priced below KBB Fair Purc...
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: 5TDKDRAH0PS521541
Stock: ZPS521541
Certified Pre-Owned: No
Listed since: 04-09-2025 - $33,007fair price$436 below market
- 36,674 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Toyota of Tampa Bay (138 mi away)
Close
Located in Tampa, FL / 138 miles away from Naples, FL
NATIONWIDE LIFETIME WARRANTY!! FREE HOME DELIVERY UP TO 75 MILES!! *** CLEAN CARFAX ***, *** CLEAN CARFAX, ONE OWNER ***, ANDROID AUTO, APPLE CARPLAY,...
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: 5TDKDRAH4PS510834
Stock: O510834
Certified Pre-Owned: Yes
Listed since: 04-23-2025 - $39,998fair price$492 above market
- 18,892 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from AL to FL*
Close
Located in Hoover, AL / 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: 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: 5TDKDRAH1PS511889
Stock: 27166985
Certified Pre-Owned: No - Price Drop$33,000fair price$948 below market
- 26,042 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Tallahassee Dodge Chrysler Jeep Ram FIAT (336 mi away)
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Located in Tallahassee, FL / 336 miles away from Naples, FL
ONLY 26K MILES MUST SELL THIS WEEK!We've had this Highlander too long and its time to cut it loose. Priced at $33,000, it's Well under market average....
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: 5TDKDRAH8PS500677
Stock: A500677
Certified Pre-Owned: No
Listed since: 09-01-2024 - Price Drop$40,998fair price$2 above market
- 17,671 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from VA to FL*
Close
Located in Harrisonburg, VA / 861 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: 5TDKDRBH7PS527061
Stock: 26947971
Certified Pre-Owned: No - New Listing$33,454good price$1,789 below market
- 61,892 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Peter Boulware Toyota (336 mi away)
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Located in Tallahassee, FL / 336 miles away from Naples, FL
Recent Arrival! Certified. CARFAX One-Owner. Opulent Amber 2021 Toyota Highlander Limited *Boulware Certified Used Vehicle*, Apple Carplay, Android Au...
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: 5TDYZRAHXMS089628
Stock: U606148A
Certified Pre-Owned: Yes
Listed since: 05-17-2025 - $33,300good price$2,080 below market
- 44,553 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Walker-Jones Chrysler Jeep Dodge Ram (348 mi away)
Close
Located in Waycross, GA / 348 miles away from Naples, FL
*Equipment*It's blind spot monitor enhances safety. Good News! This certified CARFAX 1-owner vehicle has only had one owner before you. Protect the ve...
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: 5TDKDRAH2PS505342
Stock: 1901300
Certified Pre-Owned: No
Listed since: 03-05-2025 - Price Drop$32,998good price$1,094 below market
- 52,539 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Ft. Myers (30 mi away)
Close
Located in Fort Myers, FL / 30 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH0MS134431
Stock: 27312892
Certified Pre-Owned: No - $36,998fair price$1,033 below market
- 26,247 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to FL*
Close
Located in San Diego, CA / 2,170 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: 5TDKDRAH2PS502277
Stock: 27002442
Certified Pre-Owned: No
Showing 379 - 399 out of 2,523 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 | $29,700 | $31,981 | $34,268 |
| Clean | $29,068 | $31,284 | $33,504 |
| Average | $28,014 | $30,122 | $32,230 |
| Rough | $26,644 | $28,612 | $30,575 |
The average list price of a used 2021 Toyota Highlander in Naples, Florida is $35,161. The average mileage on a used Toyota Highlander 2021 for sale in Naples, Florida is 35,339. Based on the average mileage of 35,339 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 $28,014.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.