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$349,900 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 3,034 Sq. Ft.
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5392 Chandler Drive, Winter Haven, FLVideo Tour of 5392 Chandler Drive, Winter Haven, FL.
PEACEFUL WATERFRONT Living! Many Beautiful Features & Oversized Living Areas Great for Entertaining! 3.2 Miles to Legoland! Formal Living & Dining Rooms, Family Room, and BONUS Room Upstairs (great for crafts, reading, or toys). Primary Suite offers sitting area & plenty of closet space. So much Extra Space that you could have a roommate helping pay the mortgage. Beautiful Kitchen Featuring Extra Space with Cooking Island & LARGE WALK-IN PANTRY! Eat-in Space OVERLOOKING THE WATER! Enjoy Living in the Waterski Capital of the World Featuring the Chain of Lakes! All sizes are approximate. You will love this home!!

Full Property Details for 5392 Chandler Dr

General

  • Price: $349,900
  • HOA FEE: $42/month
  • HOA FEE FREQ.: Annually
  • Taxes: $6,137 (2025)
  • Status: Pending
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: L4955399
  • Updated: 3/24/2026
  • Added to Site: 229 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 3
  • Interior Features: Ceiling Fan(s), Eating Space In Kitchen, Walk-In Closet(s)
  • Appliances: Dishwasher, Electric Water Heater, Microwave, Range, Refrigerator
  • Flooring: Carpet, Porcelain Tile, Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Inside

Exterior

  • Exterior Features: Sliding Doors
  • Deck/Patio: Front Porch
  • Porch/Patio/Deck: Front Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 33884 - Winter Haven / Cypress Gardens
  • County: Polk
  • Development Name: 33884 - Winter Haven / Cypress Gardens
  • Subdivision: BENTLEY PLACE
  • Driving Directions: Hwy 27 to W. on Cypress Gardens Blvd./540 to N. on Cypress Gardens Rd. to W. on Harbor Isle Blvd. to South or Left on Chandler Dr. to the address which is on the Southwest side of Road or Left side.
  • Direction Faces: Northeast

Community

  • Community Name: 33884 - Winter Haven / Cypress Gardens
  • Association: Yes
  • Assoc. Name: Garrison Property Services
  • Pet Restrictions: PLEASE REVIEW HOMEOWNERS RULES & REGULATIONS FOR DETAILS, REGARDING PETS.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Electricity Available

Structural Information

  • Architectural Info: Contemporary
  • Architectural Style: Contemporary
  • Exterior Const.: Block, Stucco, Wood Frame
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 3,034
  • Sq. Ft. Source: Public Records
  • Year Built: 2006

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.16
  • Lot Size (Sq. Ft.): 7,070
  • Lot Size: 7070
  • Street/Road Desc.: Paved

Water Features

  • Water View: Yes

Financial Considerations

  • Association Fee: $500
  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $6,137.25
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: BENTLEY PLACE PB 130 PGS 26-27 LOT 15
  • Flood Zone Info: X
  • APN: 262901663574000150
  • Property ID: 262901663574000150

Listed by Keller Williams Realty Smart

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Listing agent

— 5392 Chandler Dr —

  • Keller Williams Realty Smart

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5392 Chandler Dr

School District:Polk County School District
NameGradesDistance
Garden Grove Elementary School
4599 Cypress Gardens Road, Winter Haven, FL 33884
PK-50.6 mi
Denison Middle School
400 Avenue A Southeast, Winter Haven, FL 33880
6-84.4 mi
Winter Haven Senior High School
600 6th Street Southeast, Winter Haven, FL 33880
9-124 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5392 Chandler Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/25/2025
Price Reduced
$349,900
-12.5%
MLS
9/08/2025
Price Reduced
$399,900
-5.88%
MLS
8/24/2025
Listed
$424,900
77.12%
MLS
2/16/2021
Sold
$239,900
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5392 Chandler Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,137
—
$328,232
-6%
2024
$6,151
7%
$348,121
5%
2023
$5,724
36%
$330,918
56%
2021
$4,204
-17%
$212,641
-20%
2022
$5,049
20%
$265,355
37%
2021
$4,204
38%
$194,134
13%
2017
$3,037
—
$172,205
10%
2017
$3,037
-19%
$156,550
-15%
2019
$3,738
29%
$184,032
25%
2016
$2,907
1%
$147,569
7%
2015
$2,888
14%
$137,658
10%
2014
$2,541
8%
$125,144
10%
2013
$2,342
—
$113,767
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 5392 Chandler Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Keller Williams Realty Smart

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5392 Chandler Drive, Winter Haven, FL 33884 (MLS# L4955399) is a Single Family property with 4 bedrooms and 3 full bathrooms. 5392 Chandler Drive is currently listed for $349,900 and was received on August 24, 2025. Want to learn more about 5392 Chandler Drive? Do you have questions about finding other Single Family real estate for sale in Winter Haven? You can browse all Winter Haven real estate or contact a Coldwell Banker agent to request more information.

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