To schedule a showing of 5445 Chandler Drive, Winter Haven, Florida, Call David Shippey at 863-521-4517 TODAY!

$314,500 Reduced -$5,000
5445 Chandler Drive
Winter Haven, FL 33884
  • 4Beds
  • 3.00Total Baths
  • 3 Full, 0 HalfBaths
  • 3,010SqFt
  • 2006Year Built
  • 0.13Acres
  • MLS# S5146003
  • Residential
  • SingleFamilyResidence
  • Active

  • Approx Time on Market2 months, 20 days
  • Area33884 - Winter Haven / Cypress Gardens
  • CountyPolk
  • Subdivision Bentley Place

Overview

Welcome to 5445 Chandler in Winter Havena 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, youll 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 Havens beautiful lakes, this property offers both space and opportunity. If youre looking for a home with room to grow and the ability to add value, this is one you wont want to miss!



Agriculture / Farm

Association Fees / Info

Community Features:  Sidewalks

Pets Allowed:  BreedRestrictions, CatsOk, DogsOk

Hoa Frequency Rate:  575

Association:  Yes

Hoa Fees Frequency:  Annually

Bathroom Info

Total Baths:  3.00

Fullbaths:  3

Building Info

Roof:  Shingle

Building Area Source:  PublicRecords

Buyer Compensation

Exterior Features

Fees / Restrictions

Financial

Original Price:  $325,000

Garage / Parking

Attached Garage:  Yes

Garage:  Yes

Green / Env Info

Interior Features

Floors:  Carpet, CeramicTile, Laminate

Levels:  Two

Laundry Features:  Inside

Interior Features:  EatInKitchen, HighCeilings, WalkInClosets

Appliances:  BuiltInOven, Cooktop, Microwave

Lot Info

Direction Remarks:  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 property5445 Chandler will be on the left (southwest side of the road).

Lot Size Units:  Acres

Lot Size Acres:  0.13

Lot Sqft:  5,772

Misc

Other

Special Conditions:  None

Other Rooms Info

Property Info

Section:  01

Class Type:  SingleFamilyResidence

Property Sub Type:  SingleFamilyResidence

Construction Materials:  Block, Stucco, WoodFrame

Stories:  2

Total Stories:  2

Foundation:  Slab

Human Modified:  Yes

Room Info

Total Rooms:  7

Sqft Info

Sqft:  3,010

Bulding Area Sqft:  3,010

Living Area Units:  SquareFeet

Living Area Source:  PublicRecords

Tax Info

Tax Year:  2,025

Tax Lot:  33

Tax Legal Description:  BENTLEY PLACE PB 130 PGS 26-27 LOT 33

Tax Annual Amount:  5826.64

Tax Book Number:  130-26-27

Unit Info

Utilities / Hvac

Heating:  Central, Electric

Water Source:  Public

Sewer:  PublicSewer

Cool System:  CentralAir

Cooling:  Yes

Heating:  Yes

Utilities:  ElectricityAvailable, HighSpeedInternetAvailable, SewerAvailable, WaterAvailable

Waterfront / Water

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 property5445 Chandler will be on the left (southwest side of the road).

This listing courtesy of Transcend Realty 

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Price & Status History (on davidshippey.com since Tue, Mar 17th 2026)
  • Original Price: $325,000
  • Current Price: $314,500
  • Price Reduced: $10,500
Date ChangedFromTo
05/21/2026$319,500 $314,500 Reduced by $5,000
04/20/2026$325,000 $319,500 Reduced by $5,500

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If you have any questions on 5445 Chandler Drive, Winter Haven, Florida, please call David Shippey at 863-521-4517.


MLS# S5146003 located at 5445 Chandler Drive, Winter Haven, Florida is brought to you by David Shippey REALTOR®

5445 Chandler Drive, Winter Haven, Florida has 4 Beds, 3 Full Bath, and 0 Half Bath.
The MLS Number for 5445 Chandler Drive, Winter Haven, Florida is S5146003.
The price for 5445 Chandler Drive, Winter Haven, Florida is $314,500.
The status of 5445 Chandler Drive, Winter Haven, Florida is Active.
The subdivision of 5445 Chandler Drive, Winter Haven, Florida is Bentley Place.
The home located at 5445 Chandler Drive, Winter Haven, Florida was built in 2026.