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3 bedsNew constructionWith a pool
5 Bedroom Homes in Winter Haven, FL
11 listings

5 Bedroom Homes in Winter Haven, FL

5 Bedroom Homes in Winter Haven, FL

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11 Listings
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5 Bedroom Homes in Winter Haven, FL

11 Listings

  1. 9504 Waterford Oaks Blvd — photo66Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$725,000

5 bd · 3 ba · 2,916 sqft

9504 Waterford Oaks Blvd, Winter Haven, FL

Brooke Boyette · KELLER WILLIAMS TAMPA PROPERTIES

  • 9513 Waterford Oaks Blvd — photo66Active

    $750,000

    5 bd · 4 ba · 3,611 sqft

    9513 Waterford Oaks Blvd, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  • 1020 Lena Run Ct — photo44Active

    $598,000

    5 bd · 3 ba · 3,068 sqft

    1020 Lena Run Ct, Winter Haven, FL

    Sarah Garner · COLDWELL BANKER REALTY

  • 1016 S Lake Mariam Dr — photoPrice Reduced92Active

    $750,000

    5 bd · 4 ba · 3,694 sqft

    1016 S Lake Mariam Dr, Winter Haven, FL

    Kelly Jones · KELLER WILLIAMS REALTY SMART 1

  • 25 Lakewood Cswy — photo52Active

    $849,900

    5 bd · 4 ba · 4,108 sqft

    25 Lakewood Cswy, Winter Haven, FL

    Melissa Meyer · KEENE'S POINTE REALTY

  • 328 Hamilton Shores Dr NE — photo80Active

    $765,000

    5 bd · 4 ba · 3,812 sqft

    328 Hamilton Shores Dr NE, Winter Haven, FL

    Michael Stone · THE STONES REAL ESTATE FIRM

  • 445 Talamone Dr — photoPrice Reduced57Active

    $519,990

    5 bd · 3 ba · 2,653 sqft

    445 Talamone Dr, Winter Haven, FL

    Jimmy Aguilar · 3D TEAM REALTY LLC

  • 3097 Buckeye Pointe Dr — photoPrice Reduced59Active

    $430,000

    5 bd · 3 ba · 2,577 sqft

    3097 Buckeye Pointe Dr, Winter Haven, FL

    Desiree Carlson · RE/MAX HERITAGE PROFESSIONALS

  • 250 Brigham Rd NW — photo67Active

    $1,195,000

    5 bd · 6 ba · 3,235 sqft

    250 Brigham Rd NW, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  • 1450 W Lake Cannon Dr NW — photoPrice Reduced15Active

    $299,000

    5 bd · 2 ba · 4,053 sqft

    1450 W Lake Cannon Dr NW, Winter Haven, FL

    Veronica Davis · EXP REALTY LLC

  • 1818 6th St SE — photoPrice Reduced69Active

    $479,000

    5 bd · 3 ba · 2,006 sqft

    1818 6th St SE, Winter Haven, FL

    Washington Costa · GARCIA REALTY GROUP

  • Explore Winter Haven homes

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    • With a pool
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Listing data & MLS disclosures

    Stellar MLS
    Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. 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. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

    Winter Haven, FL community profile

    Population
    58,351
    Median income
    $56,564
    Housing units
    26,800
    People per sq. mi.
    605.3
    Area
    96.4 sq. mi.

    Source: HJN community data

    Winter Haven housing market

    August 2026

    Winter Haven 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 187 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 31, 2026

    Median sale price
    $280,000$204,200–$384,975 typical range
    Price per sq. ft.
    $154
    Sales
    290
    Paid in cash
    45.2%

    Homes on the market · MLS, as of Aug 31, 2026

    Median days on market
    34 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    -5.1%