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$325,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 3,010 Sq. Ft.
  • Updated 2 days ago
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Welcome to 5445 Chandler in Winter Haven-a great opportunity for buyers looking to add their own personal touch! This home offers generous square footage and plenty of living space, giving you room to spread out, entertain, or reimagine the layout to fit your needs. The property has already seen some key updates, including a brand-new roof and fresh interior paint, providing a solid foundation for future improvements. Inside, you'll find a functional layout with large living areas and ample space, making it ideal for those seeking both comfort and potential. While the home could use some additional updates and TLC, it presents an excellent chance for homeowners or investors to build equity and truly make it their own. Conveniently located near shopping, dining, and Winter Haven's beautiful lakes, this property offers both space and opportunity. If you're looking for a home with room to grow and the ability to add value, this is one you won't want to miss!

Full Property Details for 5445 Chandler Dr

General

  • Price: $325,000
  • HOA FEE: $48/month
  • HOA FEE FREQ.: Annually
  • Taxes: $5,826 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: S5146003
  • Updated: 3/17/2026
  • Added to Site: 3 day(s) ago

Rental Information

  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 7
  • Interior Features: Eating Space In Kitchen, High Ceilings, Thermostat, Walk-In Closet(s)
  • Appliances: Built-In Oven, Cooktop, Microwave
  • Furnishings: Unfurnished
  • Flooring: Carpet, Ceramic Tile, Laminate

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Inside

Exterior

  • Exterior Features: Sidewalk, Sliding Doors

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: Take Hwy 27 to Cypress Gardens Blvd./SR 540 and head west. Continue to Cypress Gardens Rd. and turn right (north). From there, turn left onto Harbor Isle Blvd., then make a left onto Chandler Dr. Follow Chandler Dr. to the property—5445 Chandler will be on the left (southwest side of the road).
  • Direction Faces: Southwest

Community

  • Community Name: 33884 - Winter Haven / Cypress Gardens
  • Association: Yes
  • Assoc. Name: Garrison Property Services
  • Pet Restrictions: Must verify all restrictions with the HOA

Heating & Cooling

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

Utilities

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

Structural Information

  • Exterior Const.: Block, Stucco, Wood Frame
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 3,010
  • Sq. Ft. Source: Public Records
  • Year Built: 2006

Lot Features

  • Lot Size (Acres): 0.13
  • Lot Size (Sq. Ft.): 5,772
  • Lot Size: 5772
  • Street/Road Desc.: Asphalt

Financial Considerations

  • Association Fee: $575
  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $5,826.64
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: BENTLEY PLACE PB 130 PGS 26-27 LOT 33
  • Flood Zone Info: X
  • APN: 262901663574000330
  • Property ID: 262901663574000330

Listed by Transcend Realty

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Listing agent

— 5445 Chandler Dr —

  • Transcend Realty

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 5445 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 5445 Chandler Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/17/2026
Listed
$325,000
42.61%
MLS
3/24/2006
Sold
$227,900
—
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 5445 Chandler Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,827
5%
$323,858
-6%
2024
$5,560
7%
$343,408
5%
2023
$5,183
25%
$326,477
56%
2021
$4,143
-9%
$209,543
-20%
2022
$4,556
10%
$261,394
37%
2021
$4,143
33%
$191,333
10%
2017
$3,119
—
$173,388
8%
2017
$3,119
5%
$160,803
6%
2016
$2,961
4%
$151,965
12%
2015
$2,849
-23%
$135,820
-25%
2019
$3,685
47%
$181,401
47%
2014
$2,507
8%
$123,473
10%
2013
$2,311
—
$112,248
—
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.

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NMLS#: 1598647

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Listed by Transcend Realty

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5445 Chandler Drive, Winter Haven, FL 33884 (MLS# S5146003) is a Single Family property with 4 bedrooms and 3 full bathrooms. 5445 Chandler Drive is currently listed for $325,000 and was received on March 17, 2026. Want to learn more about 5445 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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