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For sale
    • Price cut: $5.1K (8/7)
    $299,900

    5445 CHANDLER DRIVE, WINTER HAVEN, FL 33884

    4beds
    3,010sqft
    : 
    $2,013/mo
    Get pre-qualified
    Single Family Residence
    Built in 2006
    5,772 Square Feet Lot
    $298,400 Zestimate®
    $100/sqft
    $48/mo HOA

    What's special

    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!
    149 days
    |
    497
    |
    35
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Jacob Hara 407-933-5478,

    TRANSCEND REALTY 407-518-7653

    Source: Stellar MLS,MLS#: S5146003MLS LogoOriginating MLS: Osceola

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 3
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: Second
      • Area: 247 Square Feet
      • Dimensions: 13x19
      Bedroom 2
      • Features: Coat Closet
      • Level: Second
      • Area: 140 Square Feet
      • Dimensions: 10x14
      Bedroom 3
      • Features: Coat Closet
      • Level: Second
      • Area: 168 Square Feet
      • Dimensions: 12x14
      Bedroom 4
      • Features: Coat Closet
      • Level: Second
      • Area: 208 Square Feet
      • Dimensions: 13x16
      Family room
      • Level: First
      • Area: 247 Square Feet
      • Dimensions: 13x19
      Kitchen
      • Level: First
      • Area: 221 Square Feet
      • Dimensions: 13x17
      Living room
      • Level: First
      • Area: 169 Square Feet
      • Dimensions: 13x13
      Heating
      • Central, Electric
      Cooling
      • Central Air
      Appliances
      • Included: Oven, Cooktop, Microwave
      • Laundry: Inside
      Features
      • Eating Space In Kitchen, High Ceilings, Thermostat, Walk-In Closet(s)
      • Flooring: Carpet, Ceramic Tile, Laminate
      • Doors: Sliding Doors
      • Has fireplace: No
      Interior area
      • Total structure area: 3,010
      • Total interior livable area: 3,010 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage - Attached
      • Attached garage spaces: 2
      Features
      • Levels: Two
      • Stories: 2
      • Exterior features: Sidewalk
      Lot
      • Size: 5,772 Square Feet
      Details
      • Parcel number: 262901663574000330
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Block, Stucco, Wood Frame
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 2006

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: BB/HS Internet Available, Electricity Available, Sewer Available, Water Available

      Community & HOA

      Community
      • Pet fee: $0 monthly
      • Subdivision: BENTLEY PLACE
      HOA
      • Has HOA: Yes
      • HOA fee: $48 monthly
      • HOA name: Garrison Property Services
      • HOA phone: 863-353-2558
      Location
      • Region: Winter Haven

      Financial & listing details

      • Price per square foot: $100/sqft
      • Tax assessed value: $323,858
      • Annual tax amount: $5,826
      • Date on market: 3/17/2026
      • Cumulative days on market: 146 days
      • Listing terms: Cash,Conventional,FHA,VA Loan
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Asphalt

        Estimated market value

        $298,400

        $283,000 - $313,000

        $2,402/mo

        Price history

        DateEventPrice
        8/7/2026Price change$299,900-1.7%$100/sqft
        Source: Stellar MLS #S5146003 Report a problem
        6/11/2026Price change$305,000-3%$101/sqft
        Source: Stellar MLS #S5146003 Report a problem
        5/21/2026Price change$314,500-1.6%$104/sqft
        Source: Stellar MLS #S5146003 Report a problem
        4/20/2026Price change$319,500-1.7%$106/sqft
        Source: Stellar MLS #S5146003 Report a problem
        3/17/2026Listed for sale$325,000-13.3%$108/sqft
        Source: Stellar MLS #S5146003 Report a problem
        8/15/2024Listing removed--
        Source: Stellar MLS #O6179191 Report a problem
        7/31/2024Listed for rent$2,675+91.1%$1/sqft
        Source: Stellar MLS #O6179193 Report a problem
        2/15/2024Listed for sale$375,000+64.5%$125/sqft
        Source: Stellar MLS #O6179191 Report a problem
        2/20/2012Listing removed$1,400
        Source: STAR REALTY OF WINTER HAVEN, I #P4618710 Report a problem
        11/17/2011Listed for rent$1,400
        Source: Star Realty of Winter Haven, Inc. Report a problem
        3/30/2006Sold$227,900$76/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$5,827 +4.8%$306,792 +10%
        2024$5,560 +7.3%$278,902 +10%
        2023$5,183 +13.8%$253,547 +10%
        2022$4,556 +10%$230,497 +10%
        2021$4,143 +8.9%$209,543 +9.5%
        2020$3,806 +3.3%$191,333 +5.5%
        2019$3,685 $181,401 +4.6%
        2018$3,685 +3.7%$173,388 +7.8%
        2017$3,553 +20%$160,803 +7.6%
        2016$2,961 +3.9%$149,402 +10%
        2015$2,849 +18.4%$135,820 +10%
        2014$2,407 +4.2%$123,473 +10%
        2013$2,311 +9.3%$112,248 +9.1%
        2012$2,114 -5.2%$102,927 -4.4%
        2011$2,230 -4.3%$107,616 -3%
        2010$2,331 -30.2%$110,911 -27.2%
        2009$3,339 -17%$152,382 -21%
        2008$4,021 $192,770
        2007-- --
        2006$642 --
        2005-- --
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 33880

        Getting around

        29 / 100
        Car-Dependent
        52 / 100
        Bikeable

        Nearby schools

        GreatSchools rating

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