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Homes with a Pool in Winter Haven, FL
71 listings

Homes with a Pool in Winter Haven, FL

Homes with a Pool in Winter Haven, FL

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24 of 71 Listings
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Homes with a Pool in Winter Haven, FL

24 of 71 Listings

  1. 1325 Lake Shipp Dr N — photoNew51

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$224,900

3 bd · 1 ba · 1,733 sqft

1325 Lake Shipp Dr N, Winter Haven, FL

Denise Jones · CENTURY 21 MYERS REALTY

  • 815 Lake Jessie Dr — photoNew30Active

    $595,000

    4 bd · 4 ba · 4,128 sqft

    815 Lake Jessie Dr, Winter Haven, FL

    Aline Oliveira · META ONE REALTY GROUP LLC

  • 117 Homewood Dr — photo51Active

    $350,000

    3 bd · 2 ba · 1,762 sqft

    117 Homewood Dr, Winter Haven, FL

    Lisa Matheny · ENGEL & VOELKERS LAKELAND

  • 7002 Summit Cir — photo25Active

    $340,000

    3 bd · 2 ba · 1,888 sqft

    7002 Summit Cir, Winter Haven, FL

    Angela Fowler · ANGELA FOWLER REAL ESTATE, LLC

  • 281 Gerber Dairy Rd — photo93Active

    $700,000

    3 bd · 4 ba · 2,690 sqft

    281 Gerber Dairy Rd, Winter Haven, FL

    Melissa Mariano, LLC · EXP REALTY LLC

  • 119 Sunfish Dr — photo51Active

    $419,000

    3 bd · 3 ba · 2,613 sqft

    119 Sunfish Dr, Winter Haven, FL

    Carlos DeJesus · EXIT REALTY 4CORNERS

  • 9 Winterset Dr — photo8Active

    $430,000

    4 bd · 2 ba · 2,489 sqft

    9 Winterset Dr, Winter Haven, FL

    Jennifer Perez Mojica · LPT REALTY, LLC

  • 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

  • 822 17th Ter NE — photo31Active

    $379,900

    4 bd · 3 ba · 2,189 sqft

    822 17th Ter NE, Winter Haven, FL

    Jason Stone · BHHS FLORIDA PROPERTIES GROUP

  • 304 Corso Loop — photo12Active

    $220,000

    3 bd · 2 ba · — sqft

    304 Corso Loop, Winter Haven, FL

    Soreina Del Valle Gonzalez Medina PA · United Realty Group Inc.

  • 44 Brevard Dr — photoPrice Reduced28Active

    $495,500

    3 bd · 2 ba · 2,269 sqft

    44 Brevard Dr, Winter Haven, FL

    Kurt Schleicher · SCHLEICHER SELECT PROPERTIES

  • 543 Terranova Cir — photo42Active

    $385,000

    3 bd · 2 ba · 2,118 sqft

    543 Terranova Cir, Winter Haven, FL

    Michael Huculak · PREFERRED RE BROKERS III

  • 333 Lake Howard Dr NW #302B — photoPrice Reduced12Active

    $99,000

    2 bd · 2 ba · 1,030 sqft

    333 Lake Howard Dr NW #302B, Winter Haven, FL

    Karen Myers · UNITED REALTY GROUP INC

  • 437 Broward Ter — photoPrice Reduced32Active

    $379,000

    4 bd · 2 ba · 1,687 sqft

    437 Broward Ter, Winter Haven, FL

    Laura Schmidt · BHHS FLORIDA PROPERTIES GROUP

  • 1380 S Lake Roy Dr — photo46Active

    $395,000

    4 bd · 3 ba · 2,468 sqft

    1380 S Lake Roy Dr, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  • 276 18th St NE — photo27Active

    $279,900

    3 bd · 2 ba · 1,218 sqft

    276 18th St NE, Winter Haven, FL

    Marcelo Garrido · AGENT TRUST REALTY CORPORATION

  • 204 Lake Mariam Ct — photoPrice Reduced16Active

    $399,999

    3 bd · 2 ba · 2,117 sqft

    204 Lake Mariam Ct, Winter Haven, FL

    Langley Gault · POLK REALTY ADVISORS LLC

  • 405 Valley Ct — photoPrice Reduced88Active

    $465,000

    4 bd · 2 ba · 2,463 sqft

    405 Valley Ct, Winter Haven, FL

    Cannon Kirby · ROOST REALTY GROUP LLC

  • 318 Hamilton Shores Dr NE — photoPrice Reduced58Active

    $533,000

    4 bd · 2 ba · 2,806 sqft

    318 Hamilton Shores Dr NE, Winter Haven, FL

    Dani Borow · KELLER WILLIAMS REALTY

  • 215 Santa Rosa Dr — photoPrice Reduced25Active

    $304,900

    4 bd · 2 ba · 2,355 sqft

    215 Santa Rosa Dr, Winter Haven, FL

    Cynthia Fernandez · XCLUSIVE HOMES LLC

  • 153 Browning Cir — photo48Active

    $269,000

    3 bd · 2 ba · 1,144 sqft

    153 Browning Cir, Winter Haven, FL

    Kimberly Jones · RE/MAX HERITAGE PROFESSIONALS

  • 5888 Windridge Dr — photo30Active

    $330,000

    4 bd · 3 ba · 2,836 sqft

    5888 Windridge Dr, Winter Haven, FL

    Danique Haywood · MARK SPAIN REAL ESTATE

  • 506 Clayton Cir — photoPrice Reduced26Active

    $309,900

    4 bd · 3 ba · 2,004 sqft

    506 Clayton Cir, Winter Haven, FL

    Anne Halbert · LIVE FLORIDA REALTY

  • 280 Santa Rosa Dr — photoPrice Reduced44Active

    $415,000

    3 bd · 2 ba · 2,251 sqft

    280 Santa Rosa Dr, Winter Haven, FL

    Ashley James · KELLER WILLIAMS REALTY SMART 1

  • 123
    Realty.com

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    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Listing data & MLS disclosures

    MIAMI REALTORS MLS
    The multiple listing information is provided by MIAMI Association of Realtors® from a copyrighted compilation of listings. The compilation of listings and each individual listingare ©2026 MIAMI Association of Realtors®. All Rights Reserved.
    The information provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Last Updated: 2026-09-17 17:50:51 UTC
    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%