$305,000
5445 Chandler Drive
Winter Haven, FL 33884
Listing updated: June 11, 2026 at 3:38 PM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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!
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history86 days on market
- Status: ActiveMar 17, 2026
- Listed$325,000Mar 17, 2026
- Price reduced$305,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 86
- Subdivision
- Bentley Place
- County
- Polk
- Year built
- 2006
- Living area
- 3,010 sq ft
- Price/sq ft
- $101
- Lot size
- 5,772 sq ft
- Lot category
- 0 to less than 1/4
- Flood zone
- X (12105C0535H)
- Garage
- 2 spaces
- Annual taxes
- $5,827 (2025)
- Parcel #
- 26-29-01-663574-000330
- MLS #
- S5146003
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Interior Details
- Bedrooms
- 4
- Full bathrooms
- 3
- Flooring
- Carpet, Ceramic Tile, Laminate
- Appliances
- Built-In Oven, Cooktop, Microwave
- Interior features
- Eat-in Kitchen, High Ceilings, Thermostat, Walk-In Closet(s)
- Laundry
- Inside
- Stories / Levels
- Two
- Direction faces
- Southwest
Heating & Cooling
- Heating
- Central, Electric
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
HOA & Financial
- HOA fee
- $575 / Annually
- Monthly HOA
- $48/mo
- Total monthly fees
- $48/mo
- Total annual fees
- $575
- HOA name
- Garrison Property Services
- CDD
- No
- Min lease term
- 1-2 Years
- Listing terms
- Cash, Conventional, FHA, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Must verify all restrictions with the HOA
- Approval process
- Must verify all restrictions with the HOA
Exterior & Construction
- Exterior features
- Sidewalk, Sliding Doors
- Construction materials
- Block, Stucco, Frame
- Roof
- Shingle
- Foundation
- Slab
- Road surface
- Asphalt
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- BB/HS Internet Available, Electricity Available, Sewer Available, Water Available
Community
- Pets allowed
- Breed Restrictions, Cats OK, Dogs OK
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Bedroom 2 | Second | 10x14 |
| Bedroom 3 | Second | 12x14 |
| Bedroom 4 | Second | 13x16 |
| Primary Bedroom | Second | 13x19 |
| Family Room | First | 13x19 |
| Kitchen | First | 13x17 |
| Living Room | First | 13x13 |
Listing Details
- Listing date
- 2026-03-17
- On market date
- 2026-03-17
- Original list price
- $325,000
- Occupant type
- Vacant
- MLS area
- 33884 - Winter Haven / Cypress Gardens
- Listing AOR
- Osceola
- Status changed
- 2026-03-17
- Tax legal description
- BENTLEY PLACE PB 130 PGS 26-27 LOT 33
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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).
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 11, 2026 at 3:38 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA